1-monooleoyl-rac-glycerol profile

1-Monooleoyl-rac-glycerol, also known as **monoolein**, is a monoglyceride, specifically the glycerol monoester of oleic acid. It's a simple lipid molecule that has gained significant attention in research for various reasons:

**Properties and Applications:**

* **Self-Assembly and Membrane Mimicry:** Monoolein has a unique ability to self-assemble into various structures, including micelles, vesicles (liposomes), and lamellar phases. This property makes it a valuable tool for mimicking biological membranes in research.
* **Lipid Nanoparticle Formation:** Monoolein is widely used in the development of lipid nanoparticles (LNPs) for drug delivery. LNPs formulated with monoolein can encapsulate and deliver therapeutic molecules, such as nucleic acids (e.g., mRNA and siRNA), to specific cells and tissues.
* **Biocompatibility and Safety:** Monoolein is generally considered biocompatible and safe, making it suitable for pharmaceutical and biomedical applications.
* **Crystallization and Phase Behavior:** Monoolein exhibits complex phase behavior, forming different crystalline and liquid phases depending on temperature and water content. This makes it useful for studying lipid crystallization and membrane phase transitions.
* **Food Industry:** Monoolein is also used as an emulsifier in the food industry, helping to stabilize mixtures of oil and water.

**Importance for Research:**

* **Drug Delivery and Therapeutics:** As mentioned earlier, monoolein is crucial for developing LNPs for drug delivery, enabling the targeted delivery of therapies like mRNA vaccines and gene therapies. This has significant implications for treating diseases like cancer, genetic disorders, and infectious diseases.
* **Membrane Biology and Biophysics:** Monoolein's ability to form membrane-like structures allows researchers to study membrane properties, including lipid bilayer formation, protein-lipid interactions, and membrane fluidity.
* **Nanotechnology and Materials Science:** Monoolein's self-assembly properties make it a valuable material for creating various nanostructures with potential applications in fields like biosensors, drug delivery, and tissue engineering.
* **Food Science and Technology:** Monoolein's emulsifying properties contribute to the development of stable and appealing food products, affecting their texture, shelf life, and overall quality.

In conclusion, 1-monooleoyl-rac-glycerol (monoolein) is a versatile molecule with a wide range of applications in research, spanning drug delivery, membrane biology, nanotechnology, and food science. Its ability to self-assemble, mimic membranes, and interact with other molecules makes it an essential tool for understanding and manipulating biological systems.

Peceol: lipid excipient containing readily dispersible mixture of mono- & diglycerides of oleic acid [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1-oleoylglycerol : A 1-monoglyceride where the acyl group is oleoyl. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

monooleoylglycerol : A monoglyceride in which the acyl group is oleoyl with the position of acylation unspecified. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Products

ID Source	ID
PubMed CID	5283468
CHEMBL ID	428593
CHEBI ID	75342
SCHEMBL ID	15603
MeSH ID	M0445887

Synonym
25496-72-4
9-octadecenoic acid (z)-, monoester with 1,2,3-propanetriol
2,3-dihydroxypropyl (z)-octadec-9-enoate
monoglyceryl oleate
edenor gmo
emery oleic acid ester 2221
excel o 95f
dur-em 204
emalsy mo
arlacel 129
emalsy ol
glycolube 100
monomuls 90018
s 1096
mazol gmo
supeol
excel o 95r
aldo mo-fg
monooleoylglycerol
kemester 2000
dimodan lsqk
glycerine monooleate
gmo 8903
glyceryl oleate
olein, mono-
oleic acid monoglyceride
ol 100
glycerol, 1-mono (9-octa-decenoate)
oleic acid glycerol monoester
atmer 1007
emerest 2421
alkamuls gmo 45lg
oleic acid, monoester with glycerol
rikemal o 71d
oleylmonoglyceride
aldo 40
dimodan gmo 90
adchem gmo
oleic monoglyceride
glycerol oleate
glycerin monooleate
sunsoft o 30b
kessco gmo
ajax gmo
rikemal ol 100
peceol
emcol o
emuldan rylo-mg 90
emasol mo 50
einecs 247-038-6
emrite 6009
canamex glicepol 182
glycerol monooleate
s 1097
sinnoester ogc
excel o 95n
olicine
dur-em 114
1,2,3-propanetriol mono((z)-9-octadecenoate)
nikkol mgo
s 1096r
hsdb 493
loxiol g 10
LMGL01010005
1-oleoyl-rac-glycerol
oleoyl glycerol
mg(18:1(9z)/0:0/0:0)[rac]
1-(9z-octadecenoyl)-rac-glycerol
1-glyceryl oleate
aldo hmo
glycerol .alpha.-cis-9-octadecenate
1-oleylglycerol
aldo mo
1-monoolein
glycerin 1-monooleate
glyceryl monooleate
nsc-406285
olein, 1-mono-
glycerol 1-monooleate
1-monooleoylglycerol
nsc406285
glycerol .alpha.-monooleate
111-03-5
1-oleoylglycerol
monoolein
9-octadecenoic acid (z)-,3-dihydroxypropyl ester
.alpha.-monoolein
2,3-dihydroxypropyl oleate
monoolein (van)
alpha-monoolein
dl-a-monoolein
glyceryl cis-9-octadecenoate
rac-1-monoolein
9-octadecenoic acid, monoester with 1,2,3-propanetriol
dimodan mo 90
danisco mo 90
9-octadecenoic acid, 2,3-dihydroxypropyl ester, (9z)-
fema no. 2526
rylo mg 19
9-octadecenoic acid (9z)-, 2,3-dihydroxypropyl ester (9ci)
rac-glycerol 1-monooleate
glycerol alpha-monooleate
glyceryl monooleate (van)
glycerol alpha-cis-9-octadecenate
9-octadecenoic acid (z)-, 2,3-dihydroxypropyl ester (9ci)
9-octadecenoic acid (z)-, 2,3-dihydroxypropyl ester
1-monooleoyl-rac-glycerol
glycerol 1-oleate
olein, 1-mono- (8ci)
rac-1-monooleoylglycerol
1-mono(cis-9-octacenoyl)glycerol
1-(cis-9-octadecenoyl)-rac-glycerol
1-oleoyl-rac-glycerol, >=99%
67701-32-0
glycerides, c14-18 and c16-18-unsatd. mono- and di-
9-octadecenoic acid (9z)-, monoester with 1,2,3-propanetriol
1-oleoyl-rac-glycerol, technical, ~40% (tlc)
mono-olein
CFF6FE9F-EF1B-4B03-88B1-5421DCF14582
glyceryl 1-oleate
glyceryl monooleate 40%
chebi:75342 ,
monolein
glyceryl monooleate 90
glyceryl monooleate 60
glyceryl monooleate 90%
glyceryl monooleate 40
CHEMBL428593
glyceryl mono-oleate
G0082
1-(9z-octadecenoyl)-glycerol
2,3-dihydroxypropyl (9z)-octadec-9-enoate
AKOS015966695
unii-c4yad5f5g6
c4yad5f5g6 ,
glyceryl monooleate [nf]
9-octadecenoic acid, 2,3-dihydroxypropyl ester
nsc 406285
9-octadecenenoic acid (z)-, 2,3-dihydroxypropyl ester
einecs 203-827-7
d3aef6s35p ,
9-octadecenoic acid (9z)-, 2,3-dihydroxypropyl ester
unii-d3aef6s35p
rac 1-oleoyl glycerol
1-oleoyl glycerol
gtpl5756
glyceryl monooleate [fhfi]
1-glyceryl monooleate
SCHEMBL15603
cis-9-octadecenoic acid 2,3-dihydroxypropyl ester
2,3-dihydroxypropyl (9z)-9-octadecenoate #
glycerol-1-oleate
ablunol gmo
witconol 2421
mazol 300 k (salt/mix)
dl-.alpha.-monoolein
W-110892
W-109408
mfcd00042735
DTXSID3042003
925-14-4
DB13171
mg (18:1/0:0/0:0)
1-(9z)-octadecenoylglycerol
HY-128754
9-octadecenoicacid(z)-,2,3-dihydroxypropylester
Q27071132
oleoyl-glycerol
CS-0102558
bdbm50529937
BS-1088

Excerpt	Reference	Relevance
"There is a need for safe and potent adjuvants capable of delivering vaccine candidates over the mucosal barrier, with good capacity to stimulate both mucosal and systemic cell-mediated and humoral immunity."	( Safety and immunogenicity, after nasal application of HIV-1 DNA gagp37 plasmid vaccine in young mice. Hagbom, M; Hinkula, J; Schroder, U; Wahren, B, 2008)	0.35
"A safe and convenient intranasal mode of HIV-1 DNA plasmid and adjuvant delivery was shown not to interfere with the tissues in close proximity to the central nervous system."	( Safety and immunogenicity, after nasal application of HIV-1 DNA gagp37 plasmid vaccine in young mice. Hagbom, M; Hinkula, J; Schroder, U; Wahren, B, 2008)	0.35
"Lyotropic non-lamellar liquid crystalline (LLC) aqueous nanodispersions hold a great promise in drug solubilization and delivery, but these nanosystems often induce severe hemolysis and complement activation, which limit their applications for safe intravenous administration."	( Citrem modulates internal nanostructure of glyceryl monooleate dispersions and bypasses complement activation: Towards development of safe tunable intravenous lipid nanocarriers. Mat Azmi, ID; Moghimi, SM; Nilsson, C; Wibroe, PP; Yaghmur, A, 2015)	0.42
" Despite a growing interest in their potential use for therapeutic applications, there are surprisingly few literature data concerning the toxic effects of these nanoparticles at high concentrations in vitro and in vivo, and their effects on cell metabolism."	( Evaluation of toxicity of glycerol monooleate nanoparticles on PC12 cell line. Astolfi, L; Boge, L; Bysell, H; Eriksson, M; Martini, A; Simoni, E; Valente, F, 2018)	0.48

Excerpt	Reference	Relevance
"This investigation compared the tumor distribution, efficacy, blood pharmacokinetic parameters and hematological alterations following treatment with chitosan/glyceryl-monooleate (GMO) nanostructures containing paclitaxel (PTX) to a conventional formulation of PTX (Taxol(®)) in BALB/c female mice."	( Antitumor efficacy, tumor distribution and blood pharmacokinetics of chitosan/glyceryl-monooleate nanostructures containing paclitaxel. Dash, AK; Jain, N; Joshi, SS; Munt, DJ; Trickler, WJ, 2011)	0.37
"The tumor and blood concentrations of PTX were evaluated by HPLC and the pharmacokinetic parameters were determined through noncompartmental methods."	( Antitumor efficacy, tumor distribution and blood pharmacokinetics of chitosan/glyceryl-monooleate nanostructures containing paclitaxel. Dash, AK; Jain, N; Joshi, SS; Munt, DJ; Trickler, WJ, 2011)	0.37

Excerpt	Reference	Relevance
" The percent absolute bioavailability of the compound was enhanced from 3-6% (PEG 400 solution) to 15-27% when the emulsion formulations were used."	( Enhancement of nasal delivery of a renin inhibitor in the rat using emulsion formulations. Baron, DA; Belonio, B; Kararli, TT; Katz, B; Needham, TE; Schmidt, RE; Schoenhard, G, 1992)	0.28
" The absolute bioavailability of cyclosporine from two new lipid vehicles was determined in rats after intragastric administration and compared to that of Sandimmun oral solution, which contains non-ionic surface active substances in addition to dietary lipids."	( Bioavailability of cyclosporine in rats after intragastric administration: a comparative study of the L2-phase and two other lipid-based vehicles. Björkman, S; Bojrup, M; Ekberg, H; Landin, B; Ljusberg-Wahren, H; Ostraat, O; Qi, Z, 1996)	0.29
" Bioavailability of a suspension formulation in rats was less than 1%, but increased to approximately 9% when administered as a 20% soybean oil-in-water emulsion."	( Lipid-based delivery systems for improving the bioavailability and lymphatic transport of a poorly water-soluble LTB4 inhibitor. Ficorilli, JV; Fogal, SE; Hauss, DJ; Jayaraj, AA; Keirns, JJ; Price, CA; Roy, T, 1998)	0.3
"Acyclovir is a widely used agent in the treatment of herpes virus infections of the skin, but owing to its poor physicochemical properties in terms of bioavailability and suboptimal formulations, the treatment is far from optimal."	( Release kinetics of acyclovir from a suspension of acyclovir incorporated in a cubic phase delivery system. Helledi, LS; Schubert, L, 2001)	0.31
" The aim was to develop a formula, which has both bioadhesive and sustained release properties of the resultant cubic phase, so that increasing gastric residence time to improve bioavailability of the drug and at the same time obtaining a sustained action."	( Formulation of an oral dosage form utilizing the properties of cubic liquid crystalline phases of glyceryl monooleate. Freij, I; Ibrahim, H; Khalil, E; Sallam, AS, 2002)	0.31
"Microemulsion systems possessing a potentially improved skin bioavailability of lidocaine were designed and explored for some characteristics."	( New microemulsion vehicle facilitates percutaneous penetration in vitro and cutaneous drug bioavailability in vivo. Shapiro, L; Sintov, AC, 2004)	0.32
" The industrial usefulness of the developed SMEDDS was evaluated with regard to bioavailability and chemical stability using the vitamin D analogue, seocalcitol, as model compound."	( Bioavailability of seocalcitol II: development and characterisation of self-microemulsifying drug delivery systems (SMEDDS) for oral administration containing medium and long chain triglycerides. Grove, M; Müllertz, A; Nielsen, JL; Pedersen, GP, 2006)	0.33
" MO-nanoparticles can be an interesting system to increase the oral bioavailability of drugs."	( Evaluation of the enhanced oral effect of omapatrilat-monolein nanoparticles prepared by the emulsification-diffusion method. Ganem-Quintanar, A; Martínez, AL; Navarrete-Rodríguez, M; Quintanar-Guerrero, D; Rodríguez-Romo, S; Tamayo-Esquivel, D, )	0.13
" However, it has a low bioavailability after being administered orally on account of its low solubility in water."	( Formulation and biopharmaceutical evaluation of silymarin using SMEDDS. Chi, SC; Kim, TS; Park, JH; Woo, JS, 2007)	0.34
" Subsequent oral bioavailability studies were conducted in rats, in which a model poorly water soluble drug, cinnarizine (CIN), was administered orally as an aqueous suspension, or as a solution in GMO or OG."	( A lipid-based liquid crystalline matrix that provides sustained release and enhanced oral bioavailability for a model poorly water soluble drug in rats. Boyd, BJ; Davey, G; Khoo, SM; Porter, CJ; Whittaker, DV, 2007)	0.34
" Lipid excipients are increasingly used as drug delivery systems for hydrophobic drugs to increase their bioavailability by overcoming the barrier of low absorption."	( Lipid excipients Peceol and Gelucire 44/14 decrease P-glycoprotein mediated efflux of rhodamine 123 partially due to modifying P-glycoprotein protein expression within Caco-2 cells. Lee, SD; Sachs-Barrable, K; Thamboo, A; Wasan, KM, 2007)	0.34
" The results suggest a new mechanism which may contribute to the improved bioavailability seen for drugs formulated with lipid-based excipients."	( Lipid excipients Peceol and Gelucire 44/14 decrease P-glycoprotein mediated efflux of rhodamine 123 partially due to modifying P-glycoprotein protein expression within Caco-2 cells. Lee, SD; Sachs-Barrable, K; Thamboo, A; Wasan, KM, 2007)	0.34
" The results showed a trend by which the rate of absorption of (14)C-glucose followed that observed in the corresponding in vitro release studies, providing the first indication that the nanostructure of these materials may provide the ability to tailor the absorption kinetics of hydrophilic drugs in vivo, and hence form the basis of a new drug delivery system."	( Nanostructure of liquid crystalline matrix determines in vitro sustained release and in vivo oral absorption kinetics for hydrophilic model drugs. Boyd, BJ; Hanley, T; Lee, KW; Nguyen, TH, 2009)	0.35
"Oral drug development had been hindered by the bioavailability issue despite vast market popularity."	( Effects of monoglycerides on rhodamine 123 accumulation, estradiol 17 beta-D-glucuronide bidirectional transport and MRP2 protein expression within Caco-2 cells. Jia, JX; Wasan, KM, 2008)	0.35
"Glyceryl monooleate (GMO)/poloxamer 407 cubic nanoparticles were investigated as potential oral drug delivery systems to enhance the bioavailability of the water-insoluble model drug simvastatin."	( Glyceryl monooleate/poloxamer 407 cubic nanoparticles as oral drug delivery systems: I. In vitro evaluation and enhanced oral bioavailability of the poorly water-soluble drug simvastatin. Chen, J; Hu, F; Lai, J; Lu, Y; Sun, J; Wu, W; Yin, Z, 2009)	0.35
" Oral bioavailability studies were conducted in rats, and disposition of lipid and drug in segments of the gastrointestinal tract was determined over time."	( Phytantriol and glyceryl monooleate cubic liquid crystalline phases as sustained-release oral drug delivery systems for poorly water-soluble drugs II. In-vivo evaluation. Boyd, BJ; Hanley, T; Larson, I; Nguyen, TH; Porter, CJ, 2010)	0.36
"The oral bioavailability of cinnarizine using the PHY formulation was 41%, compared to 19% for the GMO formulation and 6% for an aqueous suspension."	( Phytantriol and glyceryl monooleate cubic liquid crystalline phases as sustained-release oral drug delivery systems for poorly water-soluble drugs II. In-vivo evaluation. Boyd, BJ; Hanley, T; Larson, I; Nguyen, TH; Porter, CJ, 2010)	0.36
"05) in oral bioavailability (F%=21%) compared to a CZ suspension (9%) and oleic acid emulsion (12%)."	( Nanostructured liquid crystalline particles provide long duration sustained-release effect for a poorly water soluble drug after oral administration. Boyd, BJ; Hanley, T; Nguyen, TH; Porter, CJ, 2011)	0.37
" However, its therapeutic effect is compromised by its poor oral bioavailability due to the poor solubility and low permeability across intestinal epithelia."	( Silymarin glyceryl monooleate/poloxamer 407 liquid crystalline matrices: physical characterization and enhanced oral bioavailability. Guan, P; Hu, F; Lian, R; Lu, Y; Niu, M; Qi, J; Tan, Y; Wu, W, 2011)	0.37
" However, the greatest challenge in the administration of curcumin stems from its low bioavailability and high rate of metabolism."	( Antiglioma activity of curcumin-loaded lipid nanoparticles and its enhanced bioavailability in brain tissue for effective glioblastoma therapy. Kundu, P; Mohanty, C; Sahoo, SK, 2012)	0.38
"Curcumin (CUR) is a well-known natural compound showing antioxidant, anti-inflammatory, and antitumor abilities but characterized by poor bioavailability and chemical instability, which drastically reduce its application in the treatment of chronic diseases such as osteoarthritis."	( Evaluation of monooleine aqueous dispersions as tools for topical administration of curcumin: characterization, in vitro and ex-vivo studies. Caggia, S; Cardile, V; Cortesi, R; Crascì, L; Drechsler, M; Esposito, E; Mariani, P; Offerta, A; Panico, AM; Puglia, C, 2013)	0.39
"Sodium diclofenac (Na-DFC) and celecoxib (CLXB) are common nonsteroidal anti-inflammatory (NSAID) drugs which suffer from poor bioavailability and severe side effects when consumed orally, and their transdermal delivery might present important advantages."	( HIV-TAT enhances the transdermal delivery of NSAID drugs from liquid crystalline mesophases. Aserin, A; Cohen-Avrahami, M; Garti, N; Ottaviani, MF; Shames, AI, 2014)	0.4
"Microemulsions show significant promise for enhancing the oral bioavailability of biopharmaceutics classification system (BCS) class II drugs, but how about class III drugs remains unclear."	( Improving oral bioavailability of metformin hydrochloride using water-in-oil microemulsions and analysis of phase behavior after dilution. Cai, J; Hu, H; Huang, M; Li, Y; Song, J; Tian, N; Wang, Y; Wu, C; Xing, Q, 2014)	0.4
"The design of nanostructured drug delivery systems (DDS) that improve the efficacy of therapeutic principles by enhancing their biocompatibility, bioavailability and targeting, has been the focus of extensive research over the past years."	( Magnetocubosomes for the delivery and controlled release of therapeutics. Baglioni, P; Berti, D; Castroflorio, B; Mendozza, M; Montis, C; Salvatore, A, 2015)	0.42
" Interestingly, it was found that PHY 30 % w/w in GMO provided the highest bioavailability for cinnarizine (CZ) amongst the other combinations, including GMO alone."	( Examining the gastrointestinal transit of lipid-based liquid crystalline systems using whole-animal imaging. Boyd, BJ; Graham, B; Nguyen, TH; Nowell, CJ; Pham, AC, 2015)	0.42
" Thus, a stable, floating, multiparticulate GMO/Eudragit E100 nanostructures having ability to release the drug in sustained manner with enhanced oral bioavailability can prove to be a promising carrier system for poorly water soluble drugs."	( Fabrication of novel GMO/Eudragit E100 nanostructures for enhancing oral bioavailability of carvedilol. Choudhary, B; Mahadik, KR; Patil, SS; Roy, K, 2016)	0.43
"To improve the solubility and bioavailability of oridonin (ORI), glycerol monooleate lipid (GMO)- or phytantriol (PYT)-Poloxamer 407-propylene glycol-water systems were firstly used to develop cubosomes containing ORI for oral delivery."	( Comparative studies on glycerol monooleate- and phytantriol-based cubosomes containing oridonin in vitro and in vivo. Gu, Y; Han, K; Hu, C; Huang, J; Huang, Y; Li, G; Mei, L; Pan, X; Peng, T; Shi, X; Wu, C, 2017)	0.46
" Because phase stability, loading efficiency, and bioavailability are strongly correlated, the interplay between MO phases and entrapped compounds is worthy of investigation."	( Cytochrome-c Affects the Monoolein Polymorphism: Consequences for Stability and Loading Efficiency of Drug Delivery Systems. Barbosa, LR; Funari, SS; Itri, R; Mariani, P; Mazzoni, S, 2016)	0.43
" Furthermore, the in vivo pharmacokinetic results suggested that these cubosomes led to a considerable increase in the systemic oral bioavailability of the drugs compared with pure dispersions of the same materials."	( Enhancing the Solubility and Oral Bioavailability of Poorly Water-Soluble Drugs Using Monoolein Cubosomes. Ali, MA; Itai, S; Iwao, Y; Kataoka, N; Noguchi, S; Oka, T; Ranneh, AH, 2017)	0.46
" The OA bearing hexagonal LCNDs provided a significant enhancement in the intestinal permeation compared to glyceryl monooleate cubical nanodispersion and demonstrated an outstanding in vivo performance by maintaining higher ROS plasma levels up to 8 h and enhancing oral bioavailability compared to commercial tablet."	( Hexagonal Liquid Crystalline Nanodispersions Proven Superiority for Enhanced Oral Delivery of Rosuvastatin: In Vitro Characterization and In Vivo Pharmacokinetic Study. Gabr, MM; Mortada, SM; Sallam, MA, 2017)	0.46
"Present investigation deals with formulation and evaluation of tamoxifen (TMX)-loaded liquid crystalline nanoparticles (TMX-LCNPs) for improving oral bioavailability and safety of the existing treatment."	( Improved Oral Bioavailability, Therapeutic Efficacy, and Reduced Toxicity of Tamoxifen-Loaded Liquid Crystalline Nanoparticles. Heeralal, B; Jain, S; Kushwah, V; Swami, R; Swarnakar, NK, 2018)	0.48
" The novel topical application has many advantages like averting the GI-irritation, preventing the metabolism of drugs in the liver and increasing the bioavailability of the drug over the conventional dosage forms."	( Topical Delivery of Erythromycin Through Cubosomes for Acne. Bhargava, S; Jain, A; Jain, P; Jain, R; Jain, S; Khan, S, 2018)	0.48
"Implication of different dietary specific lipids such as phytantriol (PT) and glyceryl monooleate (GMO) on enhancing the oral bioavailability of amphotericin B (AmB) was examined."	( Lyotropic Liquid Crystalline Nanoparticles of Amphotericin B: Implication of Phytantriol and Glyceryl Monooleate on Bioavailability Enhancement. Jain, S; Katiyar, SS; Kushwah, V; Swami, R; Swarnakar, NK; Yadav, P, 2018)	0.48
"Lipid based-formulations can enhance the bioavailability of poorly water-soluble lipophilic drugs through enhanced solubilisation of drugs in the gastrointestinal (GI) tract during digestion."	( Solubilisation behaviour of poorly water-soluble drugs during digestion of solid SMEDDS. Boyd, BJ; Hawley, A; Jannin, V; Pouton, C; Vithani, K, 2018)	0.48
" In the preliminary formulation development phase 1-oleoyl-rac-glycerol was chosen as the oily lipid phase, based on the high drug solubility and potential bioavailability enhancement capability."	( A redispersible dry emulsion system with simvastatin prepared via fluid bed layering as a means of dissolution enhancement of a lipophilic drug. Dreu, R; Luštrik, M; Pirker, L; Pohlen, M, 2018)	0.48
" The blood circulation time and bioavailability of the enzymes or drugs could be improved by inserting them in nanocarriers, which could decrease and/or avoid the need of frequent intravenous infusions along with the minimization or elimination of associated immunogenic responses."	( Monoolein-based nanoparticles for drug delivery to the central nervous system: A platform for lysosomal storage disorder treatment. Bernardi, A; de Farias, MA; de Sá Coutinho, D; Donida, B; Frozza, R; Immich, MF; Kessler, RG; Machado, AZ; Moura, DJ; Poletto, F; Portugal, RV; Raabe, M; Tauffner, B; Vargas, CR, 2018)	0.48
"Lipid-based formulations (LBF) have shown oral bioavailability enhancement of lipophilic drugs, but not necessarily in the case of hydrophobic drugs."	( Chase Dosing of Lipid Formulations to Enhance Oral Bioavailability of Nilotinib in Rats. Griffin, BT; Holm, R; Koehl, NJ; Kuentz, M, 2020)	0.56
"Nilotinib in vivo bioavailability in rats was determined after administering an aqueous suspension chase dosed with blank olive oil, Captex 1000, Peceol or Capmul MCM, respectively."	( Chase Dosing of Lipid Formulations to Enhance Oral Bioavailability of Nilotinib in Rats. Griffin, BT; Holm, R; Koehl, NJ; Kuentz, M, 2020)	0.56
" Both long chain chase dosed excipients also significantly increased the bioavailability up to 2-fold compared to the aqueous suspension."	( Chase Dosing of Lipid Formulations to Enhance Oral Bioavailability of Nilotinib in Rats. Griffin, BT; Holm, R; Koehl, NJ; Kuentz, M, 2020)	0.56
"Chase dosed LBF enhanced the in vivo bioavailability of nilotinib."	( Chase Dosing of Lipid Formulations to Enhance Oral Bioavailability of Nilotinib in Rats. Griffin, BT; Holm, R; Koehl, NJ; Kuentz, M, 2020)	0.56
"Low bioavailability and poor permeability of the blood-brain barrier are problematic when delivering therapeutic agents and particularly anti-human immunodeficiency virus therapy to the central nervous system."	( Nanosized Cubosomal Thermogelling Dispersion Loaded with Saquinavir Mesylate to Improve Its Bioavailability: Preparation, Optimization, in vitro and in vivo Evaluation. Hosny, KM, 2020)	0.56
"Duloxetine (DLX) is dual serotonin and norepinephrine reuptake inhibitor suffering from limited bioavailability (≈ 40%) due to extensive hepatic metabolism."	( Brain Targeting of Duloxetine HCL via Intranasal Delivery of Loaded Cubosomal Gel: In vitro Characterization, ex vivo Permeation, and in vivo Biodistribution Studies. Abdelbary, GA; Elsayed, I; Elsenosy, FM; Elshafeey, AH; Fares, AR, 2020)	0.56
"Accordingly, intranasal DLX in situ cubo-gel can be considered as an innovative nano-carrier delivery system for bioavailability enhancement and efficient brain targeting of DLX to maximize its effect."	( Brain Targeting of Duloxetine HCL via Intranasal Delivery of Loaded Cubosomal Gel: In vitro Characterization, ex vivo Permeation, and in vivo Biodistribution Studies. Abdelbary, GA; Elsayed, I; Elsenosy, FM; Elshafeey, AH; Fares, AR, 2020)	0.56
"The use of glyceryl monooleate (GMO)-based nanoparticles has not yet been explored in overcoming the low bioavailability of Epigallocatechin-3-gallate (EGCG), a green tea polyphenol with a known anticancer activity."	( Tuning curvature and phase behavior of monoolein bilayers by epigallocatechin-3-gallate: Structural insight and cytotoxicity. Armeni, T; Galeazzi, R; Gerelli, Y; Laudadio, E; Mariani, P; Minnelli, C; Mobbili, G; Moretti, P; Pigozzo, A, 2022)	0.72

Excerpt	Relevance	Reference
"Various monoolein-water systems containing tramadol HCl, a potent analgesic, were formulated to obtain sustained-release dosage forms which could be administered by subcutaneous, intramuscular or intrathecal injections."	( In vitro/in vivo characterization of a tramadol HCl depot system composed of monoolein and water. Fontaine, J; Malonne, H; Moës, A, 2000)	0.31
" The unique properties of the cubic liquid crystalline phase that result upon the presence of excess body fluids at body temperature were utilized to formulate an oral dosage form containing furosemide as the model drug."	( Formulation of an oral dosage form utilizing the properties of cubic liquid crystalline phases of glyceryl monooleate. Freij, I; Ibrahim, H; Khalil, E; Sallam, AS, 2002)	0.31
" Owing to sticky and waxy nature of GMO, preparation of oral solid dosage form utilizing GMO is still a challenge for pharmaceutical researchers."	( Spray dried glyceryl monooleate-magnesium trisilicate dry powder as cubic phase precursor. Biradar, SV; Paradkar, AR; Shah, MH, 2006)	0.33
" The MTT cytotoxicity dose-response studies revealed the placebo at/or below 1 mg/ml has no effect on MIA PaCa-2 or BxPC-3 cells."	( Chitosan and glyceryl monooleate nanostructures containing gemcitabine: potential delivery system for pancreatic cancer treatment. Dash, AK; Khurana, J; Nagvekar, AA; Trickler, WJ, 2010)	0.36
" Pharmacokinetic studies demonstrated that systemic exposure of CsA after intratracheal administration of the DE/CsA-RP at a pharmacologically effective dose (100 μg-CsA/rat) was 50-fold less than that of the oral CsA dosage form at a toxic dose (10 mg/kg)."	( Inhalable dry-emulsion formulation of cyclosporine A with improved anti-inflammatory effects in experimental asthma/COPD-model rats. Aoki, Y; Kawabata, Y; Kojo, Y; Mizumoto, T; Ogawa, K; Onoue, S; Sato, H; Wada, K; Yamada, S, 2012)	0.38
" Single-step and sequential light-triggered release and retention of the embedded dye molecules are demonstrated, thereby achieving exquisite temporal, spatial, and dosage control of the release, opening up the possibility of using such lipidic biomaterials as effective matrices in therapy, when a continuous release of active drugs might be toxic."	( Design of Light-Triggered Lyotropic Liquid Crystal Mesophases and Their Application as Molecular Switches in "On Demand" Release. Aleandri, S; Landau, EM; Mezzenga, R; Speziale, C, 2015)	0.42
" In this study, we investigated the mechanism of paclitaxel absorption after oral administration of DHP107 in mice and rats by changing the dosing interval, and evaluated the influence of bile excretion."	( Absorption mechanism of DHP107, an oral paclitaxel formulation that forms a hydrated lipidic sponge phase. Chung, H; Chung, HJ; Hong, JW; Jang, Y; Yun, CW, 2017)	0.46
" The novel topical application has many advantages like averting the GI-irritation, preventing the metabolism of drugs in the liver and increasing the bioavailability of the drug over the conventional dosage forms."	( Topical Delivery of Erythromycin Through Cubosomes for Acne. Bhargava, S; Jain, A; Jain, P; Jain, R; Jain, S; Khan, S, 2018)	0.48
"Sildenafil citrate (SIL), a type 5-specific phosphodiesterase inhibitor, demonstrates valuable results in the management of infertility in women; however, the absence of vaginal dosage form in addition to the associated oral adverse effects minimize its clinical performance."	( Novel in situ gelling vaginal sponges of sildenafil citrate-based cubosomes for uterine targeting. Abdel-Razik, AH; Aboud, HM; Ali, AA; Hassan, AH, 2018)	0.48
" This study explored the potential of lipid vehicles to improve the bioavailability of the hydrophobic drug nilotinib comparing a chase dosing approach and lipid suspensions."	( Chase Dosing of Lipid Formulations to Enhance Oral Bioavailability of Nilotinib in Rats. Griffin, BT; Holm, R; Koehl, NJ; Kuentz, M, 2020)	0.56
"Nilotinib in vivo bioavailability in rats was determined after administering an aqueous suspension chase dosed with blank olive oil, Captex 1000, Peceol or Capmul MCM, respectively."	( Chase Dosing of Lipid Formulations to Enhance Oral Bioavailability of Nilotinib in Rats. Griffin, BT; Holm, R; Koehl, NJ; Kuentz, M, 2020)	0.56
"Compared to the lipid suspensions, the chase dosed lipids showed a 2- to 7-fold higher bioavailability."	( Chase Dosing of Lipid Formulations to Enhance Oral Bioavailability of Nilotinib in Rats. Griffin, BT; Holm, R; Koehl, NJ; Kuentz, M, 2020)	0.56
"Chase dosed LBF enhanced the in vivo bioavailability of nilotinib."	( Chase Dosing of Lipid Formulations to Enhance Oral Bioavailability of Nilotinib in Rats. Griffin, BT; Holm, R; Koehl, NJ; Kuentz, M, 2020)	0.56
"Adherence to antiretroviral therapy by pediatric patients is difficult because of the lack of dosage forms adequate for children."	( Monoolein-based nanoparticles containing indinavir: a taste-masked drug delivery system. Araújo, BV; Bianchin, MD; Colombo, M; Immich, MF; Koester, LS; Külkamp-Guerreiro, IC; Poletto, F; Prebianca, G; Teixeira, ML, 2021)	0.62

Product Category	Products
Beauty & Personal Care	70
Baby & Kids Products	25
Household Essentials	7
Active Lifestyle & Fitness	1
Herbs, Botanicals & Homeopathy	1

Product	Brand	Category	Compounds Matched from Ingredients	Date Retrieved
Acure Radically Rejuvenating Cleansing Cream -- 4 fl oz	Acure	Beauty & Personal Care	glyceryl oleate, citric acid, gluconolactone, cetearyl alcohol, citric acid, tocopherol, tocopherol, glyceryl stearate, glycerin, glyceryl caprylate, oat, sodium cocoyl glutamate	2024-11-29 10:47:42
Acure Resurfacing Glycolic + Unicorn Root Cleanser -- 4 fl oz	Acure	Beauty & Personal Care	glyceryl oleate, decyl glucoside, ethylhexylglycerin, glycerin, glycolic acid, hemp, lactic acid, glyceryl caprylate, phenethyl alcohol	2024-11-29 10:47:42
Acure Seriously Soothing Cleansing Cream -- 4 fl oz	Acure	Beauty & Personal Care	caprylyl glycol, glyceryl oleate, chamomile, calendula, decyl glucoside, ethylhexylglycerin, glycerin, glyceryl caprylate, phenethyl alcohol	2024-11-29 10:47:42
Acure Ultra Hydrating Green Juice Cleanser -- 4 fl oz	Acure	Beauty & Personal Care	glyceryl oleate, orange, decyl glucoside, ethylhexylglycerin, glycerin, glyceryl caprylate, phenethyl alcohol	2024-11-29 10:47:42
Alba Botanica Hawaiian Detox Body Wash Volcanic Clay -- 32 fl oz	Alba	Beauty & Personal Care	glyceryl oleate, orange, citric acid, allyl caproate, benzyl alcohol, citric acid, cocamidopropyl betaine, glycerin, limonene, sodium benzoate, vanillin	2024-11-29 10:47:42
Alba Botanica Hawaiian Detox Scrub Volcanic Clay -- 4 oz	Alba	Beauty & Personal Care	glyceryl oleate, orange, citric acid, allyl caproate, benzyl alcohol, citric acid, triethyl citrate, glycerin, limonene, glyceryl caprylate, sodium benzoate, sodium cocoyl glutamate	2024-11-29 10:47:42
Alba Botanica More Moisture Shampoo Coconut Milk -- 12 fl oz	Alba	Beauty & Personal Care	glyceryl oleate, citric acid, benzoic acid, benzyl alcohol, benzyl salicylate, citric acid, coumarin, coumarin, dehydroacetic acid, panthenol, glycerin, phenoxyethanol, sodium benzoate	2024-11-29 10:47:42
Alba Botanica Pineapple Enzyme Exfoliating Facial Cleanser -- 8 fl oz	Alba	Beauty & Personal Care	glyceryl oleate, orange, citric acid, benzoic acid, benzyl alcohol, benzyl benzoate, citric acid, dehydroacetic acid, panthenol, glycerine, limonene, maltodextrin, phenoxyethanol, sodium benzoate	2024-11-29 10:47:42
Alba Botanica® More Moisture Shampoo Coconut Milk -- 32 fl oz	Alba	Beauty & Personal Care	glyceryl oleate, citric acid, benzoic acid, benzyl alcohol, benzyl salicylate, citric acid, coumarin, coumarin, dehydroacetic acid, panthenol, glycerin, phenoxyethanol, sodium benzoate	2024-11-29 10:47:42
Alba Botanica® Natural Hawaiian Shampoo Gardenia -- 12 fl oz	Alba	Beauty & Personal Care	glyceryl oleate, amyl cinnamal, citric acid, benzoic acid, benzyl alcohol, benzyl salicylate, citric acid, citronellol, cocamidopropyl betaine, dehydroacetic acid, panthenol, ethylhexylglycerin, geraniol, glycerin, hexyl cinnamal, hydroxycitronellal, hydroxyisohexyl 3-cyclohexene carboxaldehyde, linalool, phenoxyethanol, sodium benzoate, sodium sulfate	2024-11-29 10:47:42
Aquaphor Lip Repair Immediate Relief -- 0.35 fl oz	Aquaphor	Beauty & Personal Care	glyceryl oleate, ascorbyl palmitate, bisabolol, tocopherol, panthenol, tocopherol, glyceryl stearate, glycerin, magnesium sulfate, Octyldodecanol	2024-11-29 10:47:42
Attitude Little Leaves 2 in 1 Shampoo & Body Wash Vanilla & Pear -- 16 fl oz	Attitude	Baby & Kids Products	glyceryl oleate, citric acid, citric acid, triethyl citrate, maltodextrin, sodium benzoate, gamma-undecalactone	2024-11-29 10:47:42
Attitude Little Leaves Bubble Wash - Watermelon & Coco -- 16 fl oz	Attitude	Baby & Kids Products	glyceryl oleate, citric acid, citric acid, decanal, triethyl citrate, maltodextrin, sodium benzoate	2024-11-29 10:47:42
Attitude Sensitive Skin Shampoo - Extra Gentle & Volumizing - Fragrance Free -- 16 fl oz	Attitude	Beauty & Personal Care	glyceryl oleate, citric acid, citric acid, panthenol, glycerin, oat, sodium benzoate	2024-11-29 10:47:42
Attitude Sensitive Skin Shampoo - Soothing & Volumizing - Chamomile -- 16 fl oz	Attitude	Beauty & Personal Care	glyceryl oleate, floral, citric acid, citric acid, panthenol, triethyl citrate, geranyl acetate, glycerin, linalyl acetate, sodium benzoate	2024-11-29 10:47:42
Attitude Sensitive Skin Shower Gel Extra Gentle - Fragrance Free -- 16 fl oz	Attitude	Beauty & Personal Care	glyceryl oleate, citric acid, citric acid, glycerin, oat, sodium benzoate	2024-11-29 10:47:42
Attitude Super Leaves Hand Soap Orange Leaves -- 16 fl oz	Attitude	Household Essentials	glyceryl oleate, orange, citric acid, citric acid, decanal, decyl glucoside, pentadecalactone, maltodextrin, sodium benzoate	2024-11-29 10:47:42
Attitude Super Leaves Moisture Rich Shampoo -- 32 fl oz	Attitude	Beauty & Personal Care	glyceryl oleate, citric acid, citric acid, panthenol, maltodextrin, vitamin B5, sodium benzoate	2024-11-29 10:47:42
Attitude Super Leaves Nourishing & Strengthening Shampoo -- 32 fl oz	Attitude	Beauty & Personal Care	glyceryl oleate, citric acid, citric acid, panthenol, maltodextrin, vitamin B5, sodium benzoate	2024-11-29 10:47:42
Attitude Super Leaves Shampoo - Clarifying -- 16 fl oz	Attitude	Beauty & Personal Care	Glyceryl oleate, Citric acid, Citric acid, Panthenol, Methyl dihydrojasmonate, Maltodextrin, Sodium benzoate	2024-11-29 10:47:42
Attitude Super Leaves Shampoo - Moisture Rich -- 16 fl oz	Attitude	Beauty & Personal Care	Glyceryl oleate, Citric acid, Citric acid, Panthenol, Pentadecalactone, Methyl dihydrojasmonate, Hexyl salicylate, Maltodextrin, Sodium benzoate	2024-11-29 10:47:42
Attitude Super Leaves Shampoo Color Protection -- 16 fl oz	Attitude	Beauty & Personal Care	glyceryl oleate, floral, citric acid, allyl caproate, citric acid, panthenol, maltodextrin, vitamin B5, sodium benzoate, gamma-undecalactone	2024-11-29 10:47:42
Avalon Organics Bath & Shower Gel Nourishing Lavender -- 12 fl oz	Avalon Organics	Beauty & Personal Care	Glyceryl Oleate, Citric Acid, Benzyl Alcohol, Bisabolol, Citric Acid, Coumarin, Coumarin, Decyl Glucoside, Limonene, Sodium Benzoate, Sodium Sulfate, Sorbitol	2024-11-29 10:47:42
Avalon Organics Bath & Shower Gel Refreshing Lemon -- 12 fl oz	Avalon Organics	Beauty & Personal Care	glyceryl oleate, orange, citric acid, benzyl alcohol, bisabolol, citral, citric acid, decyl glucoside, limonene, sodium benzoate, sorbitol	2024-11-29 10:47:42
Avalon Organics Bath & Shower Gel Revitalizing Peppermint -- 12 fl oz	Avalon Organics	Beauty & Personal Care	Glyceryl Oleate, Orange, Citric Acid, Benzyl Alcohol, Bisabolol, Citric Acid, Decyl Glucoside, Sodium Benzoate, Sodium Sulfate, Sorbitol	2024-11-29 10:47:42
Avalon Organics Biotin B-Complex Thickening Shampoo -- 14 fl oz	Avalon Organics	Beauty & Personal Care	Glyceryl oleate, orange, citric acid, biotin, beta-caryophyllene, citric acid, decyl glucoside, glycerin, niacinamide, sodium benzoate, sodium sulfate	2024-11-29 10:47:42
Avalon Organics Scalp Normalizing Shampoo Tea Tree Mint -- 14 fl oz	Avalon Organics	Beauty & Personal Care	Glyceryl Oleate, Citric Acid, Terpineol, Benzyl Alcohol, Bisabolol, Camphor, Citric Acid, Citronellol, Decyl Glucoside, Geranyl Acetate, Limonene, Linalyl Acetate, Menthol, Sodium Benzoate, Sodium Sulfate, Sorbitol	2024-11-29 10:47:42
Avalon Organics Shampoo Nourishing Lavender -- 11 fl oz	Avalon Organics	Beauty & Personal Care	glyceryl oleate, citric acid, benzyl alcohol, bisabolol, citric acid, coumarin, coumarin, decyl glucoside, limonene, sodium benzoate, sodium sulfate, sorbitol	2024-11-29 10:47:42
Avalon Organics Shampoo Smooth Shine Apple Cider Vinegar -- 11 fl oz	Avalon Organics	Beauty & Personal Care	glyceryl oleate, orange, citric acid, benzyl alcohol, camphor, citric acid, decyl glucoside, ethyl acetoacetate, glycerin, sodium sulfate, gamma-undecalactone	2024-11-29 10:47:42
Avalon Organics Shampoo Strengthening Peppermint -- 11 fl oz	Avalon Organics	Beauty & Personal Care	Glyceryl Oleate, Orange, Citric Acid, Benzyl Alcohol, Bisabolol, Citric Acid, Decyl Glucoside, Sodium Benzoate, Sodium Sulfate, Sorbitol	2024-11-29 10:47:42
Avalon Organics Shampoo Volumizing Rosemary -- 11 fl oz	Avalon Organics	Beauty & Personal Care	Glyceryl Oleate, Orange, Citric Acid, Benzyl Alcohol, Bisabolol, Citric Acid, Decyl Glucoside, Limonene, Sodium Benzoate, Sodium Sulfate, Sorbitol	2024-11-29 10:47:42
Avalon Organics Thickening Shampoo Biotin-B-Complex Therapy -- 32 fl oz	Avalon Organics	Beauty & Personal Care	Glyceryl Oleate, Orange, Citric Acid, Benzyl Alcohol, Bisabolol, Beta-Caryophyllene, Citric Acid, Decyl Glucoside, Glycerin, Limonene, Sodium Benzoate, Sodium Sulfate, Sorbitol	2024-11-29 10:47:42
Avalon Organics Vitamin C Cleansing Gel -- 6 fl oz	Avalon Organics	Beauty & Personal Care	glyceryl oleate, orange, citric acid, ascorbyl glucoside, ascorbic acid, benzyl alcohol, bisabolol, calcium ascorbate, citric acid, decyl glucoside, glycerin, calcium carbonate, sodium benzoate, sodium sulfate, squalane	2024-11-29 10:47:42
Avalon Organics Volumizing Rosemary Shampoo -- 32 fl oz	Avalon Organics	Beauty & Personal Care	glyceryl oleate, orange, citric acid, benzyl alcohol, bisabolol, citric acid, decyl glucoside, limonene, sodium benzoate, sodium sulfate	2024-11-29 10:47:42
Aveeno Baby Bathtime Solutions Gift Set -- 1 Set	Aveeno	Baby & Kids Products	butylene glycol, glyceryl oleate, citric acid, allantoin, benzyl alcohol, cetyl alcohol, citric acid, cocamidopropyl betaine, sodium laureth sulfate, glycerin, isopropyl palmitate, myristyl alcohol, oat, quaternium-15, sodium benzoate, sodium hydroxide	2024-11-29 10:47:42
Aveeno Baby Calming Comfort Bath Hair & Body Wash Lavender & Vanilla Scented -- 18 fl oz	Aveeno	Baby & Kids Products	glyceryl oleate, cocamidopropyl betaine, glycerin, oat	2024-11-29 10:47:42
Aveeno Baby Calming Comfort Bath Hair & Body Wash Lavender & Vanilla Scented -- 8 fl oz	Aveeno	Baby & Kids Products	glyceryl oleate, cocamidopropyl betaine, glycerin, oat	2024-11-29 10:47:42
Aveeno Baby Cleansing Therapy Eczema Care Fragrance Free -- 8 fl oz	Aveeno	Baby & Kids Products	glyceryl oleate, citric acid, ceramide NP, citric acid, cocamidopropyl betaine, panthenol, glyceryl stearate, glycerin, oat, sodium benzoate, sodium hydroxide	2024-11-29 10:47:42
Aveeno Baby Wash & Shampoo Lightly Scented -- 12 fl oz	Aveeno	Baby & Kids Products	glyceryl oleate, citric acid, citric acid, cocamidopropyl betaine, glycerin, oat, sodium benzoate	2024-11-29 10:47:42
Aveeno Baby Wash & Shampoo Lightly Scented -- 8 fl oz	Aveeno	Baby & Kids Products	Butylene Glycol, Glyceryl Oleate, Citric Acid, Citric Acid, Cocamidopropyl Betaine, Glycerin, Oat, Sodium Benzoate, Sodium Hydroxide	2024-11-29 10:47:42
Aveeno Kids Face & Body Wash Sensitive Skin Lightly Scented -- 18 fl oz	Aveeno	Baby & Kids Products	glyceryl oleate, citric acid, citric acid, cocamidopropyl betaine, glycerin, oat, sodium benzoate, sodium hydroxide	2024-11-29 10:47:42
Babe Original Densifying Shampoo -- 13.5 fl oz	Babe Original	Beauty & Personal Care	butylene glycol, glyceryl oleate, PCA, alanine, amaranth, arginine, aspartic acid, biotin, caffeine, cocamidopropyl betaine, decyl glucoside, panthenol, ethylhexylglycerin, glycine, histidine, isoleucine, phenoxyethanol, phenylalanine, proline, propanediol, serine, sodium lactate, threonine, valine	2024-11-29 10:47:42
Babo Botanicals Moisturizing Shampoo & Wash Oat & Calendula -- 16 fl oz	Babo Botanicals	Baby & Kids Products	caprylyl glycol, glyceryl oleate, citric acid, ascorbyl palmitate, annatto, vitamin c, gluconolactone, citric acid, tocopherol, tocopherol, vitamin e, sodium gluconate, glycerin, sorbic acid	2024-11-29 10:47:42
Babo Botanicals Smoothing Shampoo & Wash Berry & Primrose -- 16 fl oz	Babo Botanicals	Beauty & Personal Care	glyceryl oleate, citric acid, ascorbyl palmitate, citric acid, tocopherol, tocopherol, sodium gluconate, glycerin, sorbic acid	2024-11-29 10:47:42
Babyganics Baby Wipes Fragrance Free -- 80 Wipes	Babyganics	Baby & Kids Products	glyceryl oleate, citric acid, citric acid, glycerin, sodium benzoate	2024-11-29 10:47:42
Babyganics Baby Wipes Fragrance Free 10 Packs -- 800 Wipes	Babyganics	Baby & Kids Products	glyceryl oleate, citric acid, citric acid, glycerin, sodium benzoate	2024-11-29 10:47:42
Babyganics Baby Wipes Fragrance Free 5 Packs -- 400 Wipes	Babyganics	Baby & Kids Products	glyceryl oleate, citric acid, citric acid, glycerin, sodium benzoate	2024-11-29 10:47:42
Babyganics Tots 2-in-1 Straight Hair Shampoo & Conditioner - Apricot Chamomile -- 11 fl oz	Babyganics	Baby & Kids Products	glyceryl oleate, citric acid, citric acid, glycerin, sodium benzoate, sodium cocoyl glutamate, sodium hydroxide	2024-11-29 10:47:42
Ceramedx Soothing Facial Lotion Fragrance Free -- 4 fl oz	Ceramedx	Beauty & Personal Care	glyceryl oleate, allantoin, linolenic acid, ascorbic acid, ceramide np, cetearyl alcohol, tocopherol, dl-panthenol, ethylhexylglycerin, tocopherol, glyceryl stearate, glycerin, dimethicone, linoleic acid, maltodextrin	2024-11-29 10:47:42
Clearly Natural Essentials - Foaming Glycerin Hand Soap Aloe Vera -- 8 fl oz	Clearly Natural	Household Essentials	glyceryl oleate, tocopherol, decyl glucoside, tocopherol, vitamin E, glycerin, glycine, phenoxyethanol	2024-11-29 10:47:42
Clearly Natural Essentials - Foaming Glycerin Hand Soap Unscented -- 8 fl oz	Clearly Natural	Household Essentials	glyceryl oleate, tocopherol, decyl glucoside, tocopherol, vitamin E, glycerin, glycine, phenoxyethanol	2024-11-29 10:47:42
Clearly Natural Essentials - Foaming Glycerin Hand Soap Vitamin E -- 8 fl oz	Clearly Natural	Household Essentials	glyceryl oleate, annatto, tocopherol, decyl glucoside, tocopherol, vitamin E, glycerin, glycine, phenoxyethanol	2024-11-29 10:47:42
Derma E Purifying Daily Detox Scrub -- 4 oz	Derma E	Beauty & Personal Care	glyceryl oleate, cetyl alcohol, glycerin, menthol, phenoxyethanol	2024-11-29 10:47:42
Dermarest Psoriasis Medicated Shampoo Plus Conditioner -- 8 fl oz	Dermarest	Beauty & Personal Care	Glyceryl Oleate, Citric Acid, Citric Acid, Cocamidopropyl Betaine, Panthenol, Sodium Laureth Sulfate, Propylene Glycol	2024-11-29 10:47:42
Desert Essence Enriching Shampoo Island Mango -- 8 fl oz	Desert Essence	Beauty & Personal Care	glyceryl oleate, citric acid, benzyl alcohol, citric acid, decyl glucoside, dehydroacetic acid, glycerin, limonene, propanediol	2024-11-29 10:47:42
Desert Essence Replenishing Shampoo Tea Tree -- 12.9 fl oz	Desert Essence	Beauty & Personal Care	glyceryl oleate, citric acid, citric acid, glycerin, menthol, glyceryl caprylate	2024-11-29 10:47:42
Desert Essence Revitalizing Shampoo Italian Lemon -- 8 fl oz	Desert Essence	Beauty & Personal Care	glyceryl oleate, citric acid, benzyl alcohol, citral, citric acid, decyl glucoside, dehydroacetic acid, glycerin, hemp, limonene, propanediol	2024-11-29 10:47:42
Earth Mama Baby Lotion Calming Lavender -- 8 fl oz	Earth Mama	Baby & Kids Products	glyceryl oleate, calendula, cetearyl alcohol, glyceryl stearate, vanilla	2024-11-29 10:47:42
Earth Mama Baby Lotion Simply Non-Scents - Unscented -- 8 fl oz	Earth Mama	Baby & Kids Products	glyceryl oleate, calendula, cetearyl alcohol, glyceryl stearate	2024-11-29 10:47:42
Earth Mama Baby Lotion Sweet Orange -- 8 fl oz	Earth Mama	Baby & Kids Products	glyceryl oleate, calendula, cetearyl alcohol, glyceryl stearate, vanilla	2024-11-29 10:47:42
Earth Mama Belly Butter -- 8 fl oz	Earth Mama	Baby & Kids Products	glyceryl oleate, calendula, cetearyl alcohol, glyceryl stearate, vanilla	2024-11-29 10:47:42
Every Man Jack Beard + Face Wash - Sandalwood -- 6.7 fl oz	Every Man Jack	Beauty & Personal Care	glyceryl oleate, bisabolol, cocoamidopropyl betaine, decyl glucoside, ethylhexylglycerin, glycerin, linalool, phenoxyethanol, sodium benzoate	2024-11-29 10:47:42
Every Man Jack Beard + Face Wash - Sea Salt -- 6.7 oz	Every Man Jack	Beauty & Personal Care	glyceryl oleate, benzyl salicylate, citronellol, cocamidopropyl betaine, decyl glucoside, ethylhexylglycerin, glycerin, linalool, phenoxyethanol, sodium benzoate	2024-11-29 10:47:42
Fresh Monster Kids & Baby Gift Set - Shampoo & Conditioner Body Wash + Bubble Bath -- 1 Set	Fresh Monster	Baby & Kids Products	glyceryl oleate, citric acid, chamomile, citric acid, propanediol, sodium benzoate	2024-11-29 10:47:42
Good Clean Love Balance pH Balanced Personal Wash -- 8 fl oz	Good Clean Love	Beauty & Personal Care	glyceryl oleate, goldenseal, glycerin, lactic acid	2024-11-29 10:47:42
Irwin Naturals Forskolin Fat Loss Diet -- 60 Liquid Softgels	Irwin Naturals	Active Lifestyle & Fitness	glyceryl monooleate, glycerin	2024-11-29 10:47:42
Jason Body Wash De-Stress Hemp Seed Oil -- 30 fl oz	Jason	Beauty & Personal Care	glyceryl oleate, citric acid, allantoin, cetyl alcohol, citric acid, triethyl citrate, glycerin, linalyl acetate, oat, phenoxyethanol, heliotropine	2024-11-29 10:47:42
Jason Body Wash Sensitive Skin Fragrance Free -- 16 oz	Jason	Beauty & Personal Care	glyceryl oleate, citric acid, allantoin, cetyl alcohol, citric acid, glycerin, oat, phenoxyethanol	2024-11-29 10:47:42
Jason Body Wash Sensitive Skin Fragrance Free -- 30 fl oz	Jason	Beauty & Personal Care	glyceryl oleate, citric acid, allantoin, cetyl alcohol, citric acid, glycerin, oat, phenoxyethanol	2024-11-29 10:47:42
Jason Dandruff Relief 2 in1 Shampoo + Conditioner -- 12 fl oz	Jason	Beauty & Personal Care	glyceryl oleate, orange, citric acid, terpineol, benzylacetate, cetyl alcohol, citric acid, triethyl citrate, glycerin, limonene, linalool, maltodextrin, phenethyl alcohol, sodium cocoyl glutamate, sodium hydroxide, zinc carbonate	2024-11-29 10:47:42
Kiss My Face De-Stress 2-in-1 Body Wash & Bath Soak - Cedarwood + Bergamot -- 16 fl oz	Kiss My Face	Beauty & Personal Care	glyceryl oleate, allantoin, cocamidopropyl betaine, decyl glucoside, magnesium sulfate, phenoxyethanol	2024-11-29 10:47:42
Kiss My Face De-Stress 2-in-1 Body Wash & Bath Soak - Lavender + Ylang Ylang -- 16 fl oz	Kiss My Face	Beauty & Personal Care	glyceryl oleate, allantoin, cocamidopropyl betaine, decyl glucoside, magnesium sulfate, phenoxyethanol	2024-11-29 10:47:42
Kiss My Face De-Stress 2-in-1 Body Wash & Bath Soak - Lemongrass + Juniper Berry -- 16 fl oz	Kiss My Face	Beauty & Personal Care	glyceryl oleate, citric acid, allantoin, citric acid, cocamidopropyl betaine, decyl glucoside, magnesium sulfate	2024-11-29 10:47:42
Kiss My Face De-Stress 2-in-1 Body Wash & Bath Soak - Peppermint + Clary Sage -- 16 fl oz	Kiss My Face	Beauty & Personal Care	glyceryl oleate, citric acid, allantoin, citric acid, cocamidopropyl betaine, decyl glucoside, magnesium sulfate	2024-11-29 10:47:42
Kiss My Face Goat Milk Body Wash - Fragrance Free -- 16 fl oz	Kiss My Face	Beauty & Personal Care	glyceryl oleate, citric acid, allantoin, citric acid, cocamidopropyl betaine, decyl glucoside, panthenol, maltodextrin	2024-11-29 10:47:42
Kiss My Face Goat Milk Body Wash - Lavender + Jasmine -- 16 fl oz	Kiss My Face	Beauty & Personal Care	glyceryl oleate, citric acid, allantoin, citric acid, cocamidopropyl betaine, decyl glucoside, panthenol, maltodextrin	2024-11-29 10:47:42
Kiss My Face Shower Gel Peaceful Patchouli -- 16 fl oz	Kiss My Face	Beauty & Personal Care	glyceryl oleate, citric acid, allantoin, citric acid, cocamidopropyl betaine, decyl glucoside, phenoxyethanol	2024-11-29 10:47:42
Mad Hippie Blemish Cream -- 0.5 fl oz	Mad Hippie	Beauty & Personal Care	caprylyl glycol, glyceryl oleate, astaxanthin, cetyl alcohol, curcumin, ethylhexyl glycerin, fucoxanthin, glyceryl stearate, glycerin, microcrystalline cellulose, isopropyl palmitate, phenethyl alcohol, squalane, stearyl alcohol	2024-11-29 10:47:42
Mustela Baby-Infant Diaper Rash Sprayable Cream -- 3 fl oz	Mustela	Baby & Kids Products	glyceryl oleate, cetearyl alcohol, glycerin, microcrystalline cellulose, propanediol	2024-11-29 10:47:42
Natracare Organic & Natural Cleansing Make-Up Removal Wipes -- 20 Wipes	NatraCare	Beauty & Personal Care	glyceryl oleate, citric acid, gluconolactone, citric acid, tocopherol, tocopherol, glycerin, microcrystalline cellulose, levulinic acid, sodium benzoate, sodiumcitrate	2024-11-29 10:47:42
Natracare Organic Baby Wipes -- 50 Wipes	NatraCare	Baby & Kids Products	glyceryl oleate, tocopherol, tocopherol, glycerin, maltodextrin	2024-11-29 10:47:42
Natural Care NerveFix Cream -- 4 fl oz	Natural Care	Herbs, Botanicals & Homeopathy	glyceryl oleate, orange, cetyl alcohol, tocopherol, methylsulfonyl-methane, tocopherol, phenoxyethanol, pyridoxine HCI, sodium benzoate, sodium cocoyl glutamate, stearic acid, vitamin B12	2024-11-29 10:47:42
Organyc Intimate Wash -- 8.5 oz	Organyc	Beauty & Personal Care	glyceryl oleate, citric acid, benzyl alcohol, citric acid, glycerin, limonene, sodium benzoate	2024-11-29 10:47:42
Pacha Soap Co Kids Bubble Bath - Berry Grape -- 16 oz	Pacha Soap Co	Baby & Kids Products	glyceryl oleate, glycerin, propanediol	2024-11-29 10:47:42
Pacha Soap Co Kids Bubble Bath - Orange Mango -- 16 oz	Pacha Soap Co	Baby & Kids Products	glyceryl oleate, glycerin, propanediol	2024-11-29 10:47:42
Pacha Soap Co Kids Bubble Bath - Watermelon Lemonade -- 16 oz	Pacha Soap Co	Baby & Kids Products	glyceryl oleate, glycerin, propanediol	2024-11-29 10:47:42
Pacha Soap Co Shower Steamer Rise -- 10 oz	Pacha Soap Co	Beauty & Personal Care	glyceryl oleate, orange, geranium	2024-11-29 10:47:42
Pacha Soap Co Shower Steamer Sleep -- 10 oz	Pacha Soap Co	Beauty & Personal Care	glyceryl oleate, ferric ammonium ferrocyanide, chamomile	2024-11-29 10:47:42
Seventh Generation Liquid Hand Soap Fresh Lemon & Tea Tree -- 12 fl oz	Seventh Generation	Household Essentials	glyceryl oleate, citric acid, chamomile, citric acid, decyl glucoside, glycerin, sodium benzoate	2024-11-29 10:47:42
Seventh Generation Liquid Hand Soap Lavender & Mint -- 12 fl oz	Seventh Generation	Household Essentials	glyceryl oleate, orange, citric acid, citric acid, decyl glucoside, glycerin, sodium benzoate	2024-11-29 10:47:42
Seventh Generation Liquid Hand Soap Mandarin Orange & Grapefruit -- 12 fl oz	Seventh Generation	Household Essentials	glyceryl oleate, orange, citric acid, citric acid, decyl glucoside, glycerin	2024-11-29 10:47:42
SheaMoisture African Black Soap Clarifying Facial Wipes for Oily & Blemish-Prone Skin -- 30 Wipes	SheaMoisture	Beauty & Personal Care	glyceryl oleate, decyl glucoside, gluconic acid, glycerin, oat, phytic acid, propanediol, sodium benzoate, sodium citrate	2024-11-29 10:47:42
SheaMoisture Daily Hydration 100% Virgin Coconut Oil Body Wash Cleanser to Soften All Skin Types -- 13 fl oz	SheaMoisture	Beauty & Personal Care	caprylyl glycol, glyceryl oleate, decyl glucoside, glycerin	2024-11-29 10:47:42
Soothing Touch Hand & Body Soap Lavender Lace -- 32 fl oz	Soothing Touch	Beauty & Personal Care	glyceryl oleate, phenoxyethanol	2024-11-29 10:47:42
Soothing Touch Hand & Body Soap Spring Blossom -- 32 fl oz	Soothing Touch	Beauty & Personal Care	glyceryl oleate, phenoxyethanol	2024-11-29 10:47:42
The Grandpa Soap Co Rosemary Shampoo Purify -- 8 fl oz	The Grandpa Soap Co	Beauty & Personal Care	glyceryl oleate, citric acid, benzoic acid, benzyl alcohol, citric acid, cocamidopropyl betaine, ethylhexylglycerin, phenoxyethanol	2024-11-29 10:47:42
The Grandpa Soap Co Witch Hazel Shampoo Clarify -- 8 fl oz	The Grandpa Soap Co	Beauty & Personal Care	glyceryl oleate, cocamidopropyl betaine, ethylhexylglycerin, glycerin, phenoxyethanol	2024-11-29 10:47:42
Tints of Nature Permanent Hair Colour Ash Blonde 8C -- 4.4 fl oz	Tints of Nature	Beauty & Personal Care	glyceryl oleate, orange, 4-amino-2-hydroxytoluene, citric acid, chamomile, benzyl alcohol, cetyl alcohol, citric acid, cocamidopropyl betaine, comfrey, tocopherol, panthenol, ethanolamine, ethylhexylglycerin, tocopherol, glycerin, glyceryl laurate, oleic acid, phenoxyethanol, propanediol, salicylic acid, sodium cocoyl glutamate, sodium sulfite, sorbic acid, stearyl alcohol, urea	2024-11-29 10:47:42
Tints of Nature Permanent Hair Colour Dark Copper Blonde 6R -- 4.4 fl oz	Tints of Nature	Beauty & Personal Care	glyceryl oleate, orange, 4-amino-2-hydroxytoluene, citric acid, chamomile, benzyl alcohol, cetyl alcohol, citric acid, cocamidopropyl betaine, comfrey, tocopherol, panthenol, ethanolamine, ethylhexylglycerin, tocopherol, glycerin, glyceryl laurate, oleic acid, phenoxyethanol, propanediol, salicylic acid, sodium cocoyl glutamate, sodium sulfite, sorbic acid, stearyl alcohol, urea	2024-11-29 10:47:42
Tints of Nature Permanent Hair Colour Dark Toffee Blonde 6TF -- 4.4 fl oz	Tints of Nature	Beauty & Personal Care	glyceryl oleate, orange, 4-amino-2-hydroxytoluene, citric acid, chamomile, benzyl alcohol, cetyl alcohol, citric acid, cocamidopropyl betaine, comfrey, tocopherol, panthenol, ethanolamine, ethylhexylglycerin, tocopherol, glycerin, glyceryl laurate, oleic acid, phenoxyethanol, propanediol, salicylic acid, sodium cocoyl glutamate, sodium sulfite, sorbic acid, stearyl alcohol, urea	2024-11-29 10:47:42
Tints of Nature Permanent Hair Colour Soft Copper Blonde 7R -- 4.4 fl oz	Tints of Nature	Beauty & Personal Care	glyceryl oleate, orange, 4-amino-2-hydroxytoluene, citric acid, chamomile, benzyl alcohol, cetyl alcohol, citric acid, cocamidopropyl betaine, comfrey, tocopherol, panthenol, ethanolamine, ethylhexylglycerin, tocopherol, glycerin, glyceryl laurate, oleic acid, phenoxyethanol, propanediol, salicylic acid, sodium cocoyl glutamate, sodium sulfite, sorbic acid, stearyl alcohol, urea	2024-11-29 10:47:42
Weleda Baby Nourishing Body Cream - Calendula -- 2.5 fl oz	Weleda	Baby & Kids Products	glyceryl oleate, glycerin, kaolin, lanolin	2024-11-29 10:47:42
Weleda Renewing Lotion Wild Rose -- 1 fl oz	Weleda	Beauty & Personal Care	glyceryl oleate, glycerin	2024-11-29 10:47:42
Zion Health Daily Lotion Mineral Moisture White Rose -- 8 fl oz	Zion Health	Beauty & Personal Care	caprylyl glycol, glyceryl oleate, allantoin, cetyl alcohol, glyceryl stearate, glycerin, dimethicone, sodium citrate, stearyl alcohol	2024-11-29 10:47:42

Role	Description
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
1-acylglycerol 18:1	A 1-monoglyceride in which the acyl group contains 18 carbons and 1 double bond.
monooleoylglycerol	A monoglyceride in which the acyl group is oleoyl with the position of acylation unspecified.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Diacylglycerol kinase alpha	Homo sapiens (human)	Ki	91.0000	2.2600	2.7900	3.3200	AID1613990
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
phosphatidic acid biosynthetic process	Diacylglycerol kinase alpha	Homo sapiens (human)
protein kinase C-activating G protein-coupled receptor signaling pathway	Diacylglycerol kinase alpha	Homo sapiens (human)
platelet activation	Diacylglycerol kinase alpha	Homo sapiens (human)
diacylglycerol metabolic process	Diacylglycerol kinase alpha	Homo sapiens (human)
glycerolipid metabolic process	Diacylglycerol kinase alpha	Homo sapiens (human)
lipid phosphorylation	Diacylglycerol kinase alpha	Homo sapiens (human)
intracellular signal transduction	Diacylglycerol kinase alpha	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
ATP-dependent diacylglycerol kinase activity	Diacylglycerol kinase alpha	Homo sapiens (human)
calcium ion binding	Diacylglycerol kinase alpha	Homo sapiens (human)
ATP binding	Diacylglycerol kinase alpha	Homo sapiens (human)
phospholipid binding	Diacylglycerol kinase alpha	Homo sapiens (human)
lipid binding	Diacylglycerol kinase alpha	Homo sapiens (human)
kinase activity	Diacylglycerol kinase alpha	Homo sapiens (human)
alkylglycerol kinase activity	Diacylglycerol kinase alpha	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
cytosol	Diacylglycerol kinase alpha	Homo sapiens (human)
plasma membrane	Diacylglycerol kinase alpha	Homo sapiens (human)
membrane	Diacylglycerol kinase alpha	Homo sapiens (human)
plasma membrane	Diacylglycerol kinase alpha	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID331221	Inhibition of COX2 at 50 uM	2008	Bioorganic & medicinal chemistry letters, Jun-15, Volume: 18, Issue:12	Monoglycerides from the brown alga Sargassum sagamianum: Isolation, synthesis, and biological activity.
AID331222	Inhibition of sPLA2-2A at 10 uM by coupled enzyme assay	2008	Bioorganic & medicinal chemistry letters, Jun-15, Volume: 18, Issue:12	Monoglycerides from the brown alga Sargassum sagamianum: Isolation, synthesis, and biological activity.
AID1613990	Inhibition of DGKalpha in human erythrocytes using OAG as substrate preincubated for 1 min followed by OAG addition and measured after 8 mins in presence of [gamma-32P]ATP	2019	European journal of medicinal chemistry, Feb-15, Volume: 164	Identification of a novel DGKα inhibitor for XLP-1 therapy by virtual screening.
AID1345261	Human GPR119 (GPR18, GPR55 and GPR119)	2011	The Journal of clinical endocrinology and metabolism, Sep, Volume: 96, Issue:9	2-Oleoyl glycerol is a GPR119 agonist and signals GLP-1 release in humans.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	72 (11.98)	18.7374
1990's	75 (12.48)	18.2507
2000's	156 (25.96)	29.6817
2010's	259 (43.09)	24.3611
2020's	39 (6.49)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	7 (1.15%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	603 (98.85%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
2-keto-4-methylvalerate alpha-ketoisocaproic acid: RN given refers to parent cpd. 4-methyl-2-oxopentanoate : A 2-oxo monocarboxylic acid anion that is the conjugate base of 4-methyl-2-oxopentanoic acid.. 4-methyl-2-oxopentanoic acid : A 2-oxo monocarboxylic acid that is pentanoic acid (valeric acid) substituted with a keto group at C-2 and a methyl group at C-4. A metabolite that has been found to accumulate in maple syrup urine disease.	2.38	2	2-oxo monocarboxylic acid; branched-chain keto acid	algal metabolite; human metabolite
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.	2.42	2	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
aminolevulinic acid Aminolevulinic Acid: A compound produced from succinyl-CoA and GLYCINE as an intermediate in heme synthesis. It is used as a PHOTOCHEMOTHERAPY for actinic KERATOSIS.. 5-aminolevulinic acid : The simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp.	2.73	3	4-oxo monocarboxylic acid; amino acid zwitterion; delta-amino acid	antineoplastic agent; dermatologic drug; Escherichia coli metabolite; human metabolite; mouse metabolite; photosensitizing agent; plant metabolite; prodrug; Saccharomyces cerevisiae metabolite
ethylene glycol Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.	2.46	2	ethanediol; glycol	metabolite; mouse metabolite; solvent; toxin
acetaldehyde Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.	2.06	1	aldehyde	carcinogenic agent; EC 3.5.1.4 (amidase) inhibitor; electron acceptor; Escherichia coli metabolite; human metabolite; mouse metabolite; mutagen; oxidising agent; Saccharomyces cerevisiae metabolite; teratogenic agent
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	1.96	1	azane; gas molecular entity; mononuclear parent hydride	EC 3.5.1.4 (amidase) inhibitor; metabolite; mouse metabolite; neurotoxin; NMR chemical shift reference compound; nucleophilic reagent; refrigerant
carbamates [no description available]	2.15	1	amino-acid anion
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	1.99	1	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	2.49	2	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	2.67	3	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
coumarin 2H-chromen-2-one: coumarin derivative	2.08	1	coumarins	fluorescent dye; human metabolite; plant metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	2.48	2	trihydroxybenzoic acid	antineoplastic agent; antioxidant; apoptosis inducer; astringent; cyclooxygenase 2 inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; geroprotector; human xenobiotic metabolite; plant metabolite
octanoic acid octanoic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #1764. octanoic acid : A straight-chain saturated fatty acid that is heptane in which one of the hydrogens of a terminal methyl group has been replaced by a carboxy group. Octanoic acid is also known as caprylic acid.	2.05	1	medium-chain fatty acid; straight-chain saturated fatty acid	antibacterial agent; Escherichia coli metabolite; human metabolite
3-hydroxybutyric acid 3-Hydroxybutyric Acid: BUTYRIC ACID substituted in the beta or 3 position. It is one of the ketone bodies produced in the liver.. 3-hydroxybutyric acid : A straight-chain 3-hydroxy monocarboxylic acid comprising a butyric acid core with a single hydroxy substituent in the 3- position; a ketone body whose levels are raised during ketosis, used as an energy source by the brain during fasting in humans. Also used to synthesise biodegradable plastics.	2.07	1	(omega-1)-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; hydroxybutyric acid	human metabolite
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	2.05	1	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	2.39	2	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
glycine [no description available]	1.98	1	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
glyceraldehyde Glyceraldehyde: An aldotriose containing the propionaldehyde structure with hydroxy groups at the 2- and 3-positions. It is involved in the formation of ADVANCED GLYCOSYLATION END PRODUCTS.. glyceraldehyde : An aldotriose comprising propanal having hydroxy groups at the 2- and 3-positions. It plays role in the formation of advanced glycation end-products (AGEs), a deleterious accompaniment to ageing.. aldose : Aldehydic parent sugars (polyhydroxy aldehydes H[CH(OH)]nC(=O)H, n >= 2) and their intramolecular hemiacetals.	1.97	1	aldotriose	fundamental metabolite
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	4.07	14	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
dalteparin Dalteparin: A low-molecular-weight fragment of heparin, prepared by nitrous acid depolymerization of porcine mucosal heparin. The mean molecular weight is 4000-6000 daltons. It is used therapeutically as an antithrombotic agent. (From Merck Index, 11th ed)	2.53	2
hydroquinone [no description available]	2.02	1	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	2.42	2	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
inositol Inositol: An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction.. inositol : Any cyclohexane-1,2,3,4,5,6-hexol.. 1D-chiro-inositol : Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.. muco-inositol : An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.	2.89	4	cyclitol; hexol
niacinamide nicotinamide : A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.	2.31	1	pyridine alkaloid; pyridinecarboxamide; vitamin B3	anti-inflammatory agent; antioxidant; cofactor; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; Escherichia coli metabolite; geroprotector; human urinary metabolite; metabolite; mouse metabolite; neuroprotective agent; Saccharomyces cerevisiae metabolite; Sir2 inhibitor
nitroxyl nitroxyl: hydroxamic acid oxidized to nitroxyl free radical. nitroxyl : A nitrogen oxoacid consisting of an oxygen atom double-bonded to an NH group.	2.1	1	nitrogen oxoacid
hydroxide ion [no description available]	1.95	1	oxygen hydride	mouse metabolite
palmitic acid Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.	2.92	4	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor; plant metabolite
phenylacetaldehyde [no description available]	2.06	1	alpha-CH2-containing aldehyde; phenylacetaldehydes	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
phosphorylcholine Phosphorylcholine: Calcium and magnesium salts used therapeutically in hepatobiliary dysfunction.. phosphocholine : The phosphate of choline; and the parent compound of the phosphocholine family.	2.1	1	phosphocholines	allergen; epitope; hapten; human metabolite; mouse metabolite
propylene glycol Propylene Glycol: A clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations.. propane-1,2-diol : The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze.	3.93	12	glycol; propane-1,2-diols	allergen; human xenobiotic metabolite; mouse metabolite; protic solvent
sarcosine cocobetaine: N-alkyl-betaine; cause of shampoo dermatitis	1.99	1	N-alkylglycine zwitterion; N-alkylglycine; N-methyl-amino acid; N-methylglycines	Escherichia coli metabolite; glycine receptor agonist; glycine transporter 1 inhibitor; human metabolite; mouse metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	2.6	1	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	2.51	2	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
1,2-dioctanoylglycerol 1,2-dioctanoylglycerol: functions as bioregulator of protein kinase C in human platelets	1.97	1
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	4.16	16	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
2,4-dichlorophenoxyacetic acid 2,4-Dichlorophenoxyacetic Acid: An herbicide with irritant effects on the eye and the gastrointestinal system.. 2,4-D : A chlorophenoxyacetic acid that is phenoxyacetic acid in which the ring hydrogens at postions 2 and 4 are substituted by chlorines.	2.44	2	chlorophenoxyacetic acid; dichlorobenzene	agrochemical; defoliant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; environmental contaminant; phenoxy herbicide; synthetic auxin
mercaptoethanol Mercaptoethanol: A water-soluble thiol derived from hydrogen sulfide and ethanol. It is used as a reducing agent for disulfide bonds and to protect sulfhydryl groups from oxidation.	1.97	1	alkanethiol; primary alcohol	geroprotector
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	1.95	1	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
azobenzene azobenzene: photosensor molecule known to undergo reversible isomerization from trans to cis on illumination with photons of appropriate wavelength; RN given refers to cpd without isomeric designation; structure. (E)-azobenzene : The (E)-isomer of azobenzene.. (Z)-azobenzene : The (Z)-isomer of azobenzene.. azobenzene : A molecule whose structure comprises two phenyl rings linked by a N=N double bond; the parent compound of the azobenzene class of compounds.	2.11	1	azobenzenes
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	1.97	1	aromatic ether; nitrile; polyether; tertiary amino compound
carvedilol [no description available]	2.13	1	carbazoles; secondary alcohol; secondary amino compound	alpha-adrenergic antagonist; antihypertensive agent; beta-adrenergic antagonist; cardiovascular drug; vasodilator agent
cefuroxime Cefuroxime: Broad-spectrum cephalosporin antibiotic resistant to beta-lactamase. It has been proposed for infections with gram-negative and gram-positive organisms, GONORRHEA, and HAEMOPHILUS.. cefuroxime : A 3-(carbamoyloxymethyl)cephalosporin compound having a 7-(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido side chain.	1.99	1	carbamate ester; cephalosporin
celecoxib [no description available]	3.03	4	organofluorine compound; pyrazoles; sulfonamide; toluenes	cyclooxygenase 2 inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug
cetyltrimethylammonium ion Cetrimonium: Cetyltrimethylammonium compound whose salts and derivatives are used primarily as topical antiseptics.. cetyltrimethylammonium ion : A quaternary ammonium ion in which the substituents on nitrogen are one hexadecyl and three methyl groups.	2.47	2	quaternary ammonium ion
chlorpheniramine Chlorpheniramine: A histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than PROMETHAZINE.. chlorphenamine : A tertiary amino compound that is propylamine which is substituted at position 3 by a pyridin-2-yl group and a p-chlorophenyl group and in which the hydrogens attached to the nitrogen are replaced by methyl groups. A histamine H1 antagonist, it is used to relieve the symptoms of hay fever, rhinitis, urticaria, and asthma.	2.02	1	monochlorobenzenes; pyridines; tertiary amino compound	anti-allergic agent; antidepressant; antipruritic drug; H1-receptor antagonist; histamine antagonist; serotonin uptake inhibitor
clonidine Clonidine: An imidazoline sympatholytic agent that stimulates ALPHA-2 ADRENERGIC RECEPTORS and central IMIDAZOLINE RECEPTORS. It is commonly used in the management of HYPERTENSION.. clonidine (amino form) : A clonidine that is 4,5-dihydro-1H-imidazol-2-amine in which one of the amino hydrogens is replaced by a 2,6-dichlorophenyl group.	2.49	2	clonidine; imidazoline
decanoic acid decanoate : A fatty acid anion 10:0 that is the conjugate base of decanoic acid.. decanoic acid : A C10, straight-chain saturated fatty acid.	2.05	1	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; anti-inflammatory agent; antibacterial agent; human metabolite; plant metabolite; volatile oil component
r 59022 R 59022: diacylglycerol kinase inhibitor; structure given in first source; platelet activator factor antagonist	2.21	1	diarylmethane
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	2.73	3	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
diclofenac Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt.. diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position.	3.67	9	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
dioctanoyl ethylene glycol [no description available]	2.21	1
donepezil Donepezil: An indan and piperidine derivative that acts as a selective and reversible inhibitor of ACETYLCHOLINESTERASE. Donepezil is highly selective for the central nervous system and is used in the management of mild to moderate DEMENTIA in ALZHEIMER DISEASE.. donepezil : A racemate comprising equimolar amounts of (R)- and (S)-donepezil. A centrally acting reversible acetylcholinesterase inhibitor, its main therapeutic use is in the treatment of Alzheimer's disease where it is used to increase cortical acetylcholine.. 2-[(1-benzylpiperidin-4-yl)methyl]-5,6-dimethoxyindan-1-one : A member of the class of indanones that is 5,6-dimethoxyindan-1-one which is substituted at position 2 by an (N-benzylpiperidin-4-yl)methyl group.	2.57	2	aromatic ether; indanones; piperidines; racemate	EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; nootropic agent
ebastine [no description available]	2.21	1	organic molecular entity
erythrosine Fluoresceins: A family of spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one derivatives. These are used as dyes, as indicators for various metals, and as fluorescent labels in immunoassays.	2.08	1
fenofibrate Pharmavit: a polyvitamin product, comprising vitamins A, D2, B1, B2, B6, C, E, nicotinamide, & calcium pantothene; may be a promising agent for application to human populations exposed to carcinogenic and genetic hazards of ionizing radiation; RN from CHEMLINE	2.17	1	aromatic ether; chlorobenzophenone; isopropyl ester; monochlorobenzenes	antilipemic drug; environmental contaminant; geroprotector; xenobiotic
furosemide Furosemide: A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration that is used for EDEMA and chronic RENAL INSUFFICIENCY.. furosemide : A chlorobenzoic acid that is 4-chlorobenzoic acid substituted by a (furan-2-ylmethyl)amino and a sulfamoyl group at position 2 and 5 respectively. It is a diuretic used in the treatment of congestive heart failure.	2.01	1	chlorobenzoic acid; furans; sulfonamide	environmental contaminant; loop diuretic; xenobiotic
gabapentin Gabapentin: A cyclohexane-gamma-aminobutyric acid derivative that is used for the treatment of PARTIAL SEIZURES; NEURALGIA; and RESTLESS LEGS SYNDROME.. gabapentin : A gamma-amino acid that is cyclohexane substituted at position 1 by aminomethyl and carboxymethyl groups. Used for treatment of neuropathic pain and restless legs syndrome.	2.06	1	gamma-amino acid	anticonvulsant; calcium channel blocker; environmental contaminant; xenobiotic
gossypol Gossypol: A dimeric sesquiterpene found in cottonseed (GOSSYPIUM). The (-) isomer is active as a male contraceptive (CONTRACEPTIVE AGENTS, MALE) whereas toxic symptoms are associated with the (+) isomer.	2.25	1
1-(5-isoquinolinesulfonyl)-2-methylpiperazine 1-(5-Isoquinolinesulfonyl)-2-Methylpiperazine: A specific protein kinase C inhibitor, which inhibits superoxide release from human neutrophils (PMN) stimulated with phorbol myristate acetate or synthetic diacylglycerol.. 1-(5-isoquinolinesulfonyl)-2-methylpiperazine : A member of the class of N-sulfonylpiperazines that is 2-methylpiperazine substituted at position 1 by a 5-isoquinolinesulfonyl group.	1.97	1	isoquinolines; N-sulfonylpiperazine	EC 2.7.11.13 (protein kinase C) inhibitor
haloperidol Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.	2.21	1	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
ethidium Ethidium: A trypanocidal agent and possible antiviral agent that is widely used in experimental cell biology and biochemistry. Ethidium has several experimentally useful properties including binding to nucleic acids, noncompetitive inhibition of nicotinic acetylcholine receptors, and fluorescence among others. It is most commonly used as the bromide.. ethidium : The fluorescent compound widely used in experimental cell biology and biochemistry to reveal double-stranded DNA and RNA.	2.04	1	phenanthridines	fluorochrome; intercalator
lidocaine Lidocaine: A local anesthetic and cardiac depressant used as an antiarrhythmia agent. Its actions are more intense and its effects more prolonged than those of PROCAINE but its duration of action is shorter than that of BUPIVACAINE or PRILOCAINE.. lidocaine : The monocarboxylic acid amide resulting from the formal condensation of N,N-diethylglycine with 2,6-dimethylaniline.	2.69	3	benzenes; monocarboxylic acid amide; tertiary amino compound	anti-arrhythmia drug; drug allergen; environmental contaminant; local anaesthetic; xenobiotic
idebenone [no description available]	2.06	1	1,4-benzoquinones; primary alcohol	antioxidant; ferroptosis inhibitor
ifosfamide [no description available]	2.06	1	ifosfamides	alkylating agent; antineoplastic agent; environmental contaminant; immunosuppressive agent; xenobiotic
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	1.95	1	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic
1-methyl-3-isobutylxanthine 1-Methyl-3-isobutylxanthine: A potent cyclic nucleotide phosphodiesterase inhibitor; due to this action, the compound increases cyclic AMP and cyclic GMP in tissue and thereby activates CYCLIC NUCLEOTIDE-REGULATED PROTEIN KINASES. 3-isobutyl-1-methylxanthine : An oxopurine that is xanthine which is substituted at positions 1 and 3 by methyl and isobutyl groups, respectively.	1.97	1	3-isobutyl-1-methylxanthine
ketanserin Ketanserin: A selective serotonin receptor antagonist with weak adrenergic receptor blocking properties. The drug is effective in lowering blood pressure in essential hypertension. It also inhibits platelet aggregation. It is well tolerated and is particularly effective in older patients.. ketanserin : A member of the class of quinazolines that is quinazoline-2,4(1H,3H)-dione which is substituted at position 3 by a 2-[4-(p-fluorobenzoyl)piperidin-1-yl]ethyl group.	2.21	1	aromatic ketone; organofluorine compound; piperidines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; cardiovascular drug; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; serotonergic antagonist
ketoprofen Ketoprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.. ketoprofen : An oxo monocarboxylic acid that consists of propionic acid substituted by a 3-benzoylphenyl group at position 2.	2.11	1	benzophenones; oxo monocarboxylic acid	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
lauric acid dodecanoic acid : A straight-chain, twelve-carbon medium-chain saturated fatty acid with strong bactericidal properties; the main fatty acid in coconut oil and palm kernel oil.	1.99	1	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antibacterial agent; plant metabolite
metformin Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.	2.88	3	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
metronidazole Metronidazole: A nitroimidazole used to treat AMEBIASIS; VAGINITIS; TRICHOMONAS INFECTIONS; GIARDIASIS; ANAEROBIC BACTERIA; and TREPONEMAL INFECTIONS.. metronidazole : A member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death.	2.7	3	C-nitro compound; imidazoles; primary alcohol	antiamoebic agent; antibacterial drug; antimicrobial agent; antiparasitic agent; antitrichomonal drug; environmental contaminant; prodrug; radiosensitizing agent; xenobiotic
minoxidil Minoxidil: A potent direct-acting peripheral vasodilator (VASODILATOR AGENTS) that reduces peripheral resistance and produces a fall in BLOOD PRESSURE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p371). minoxidil : A pyrimidine N-oxide that is pyrimidine-2,4-diamine 3-oxide substituted by a piperidin-1-yl group at position 6.	2.05	1	dialkylarylamine; tertiary amino compound
mitoxantrone Mitoxantrone: An anthracenedione-derived antineoplastic agent.. mitoxantrone : A dihydroxyanthraquinone that is 1,4-dihydroxy-9,10-anthraquinone which is substituted by 6-hydroxy-1,4-diazahexyl groups at positions 5 and 8.	2.13	1	dihydroxyanthraquinone	analgesic; antineoplastic agent
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	2.52	2	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
nitrendipine Nitrendipine: A calcium channel blocker with marked vasodilator action. It is an effective antihypertensive agent and differs from other calcium channel blockers in that it does not reduce glomerular filtration rate and is mildly natriuretic, rather than sodium retentive.. nitrendipine : A dihydropyridine that is 1,4-dihydropyridine substituted by methyl groups at positions 2 and 6, a 3-nitrophenyl group at position 4, a ethoxycarbonyl group at position 3 and a methoxycarbonyl group at position 5. It is a calcium-channel blocker used in the treatment of hypertension.	2.38	2	C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; ethyl ester; methyl ester	antihypertensive agent; calcium channel blocker; geroprotector; vasodilator agent
ofloxacin Ofloxacin: A synthetic fluoroquinolone antibacterial agent that inhibits the supercoiling activity of bacterial DNA GYRASE, halting DNA REPLICATION.. 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid : An oxazinoquinoline that is 2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinolin-7-one substituted by methyl, carboxy, fluoro, and 4-methylpiperazin-1-yl groups at positions 3, 6, 9, and 10, respectively.. ofloxacin : A racemate comprising equimolar amounts of levofloxacin and dextrofloxacin. It is a synthetic fluoroquinolone antibacterial agent which inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication.	2.11	1	3-oxo monocarboxylic acid; N-arylpiperazine; N-methylpiperazine; organofluorine compound; oxazinoquinoline
potassium chloride Potassium Chloride: A white crystal or crystalline powder used in BUFFERS; FERTILIZERS; and EXPLOSIVES. It can be used to replenish ELECTROLYTES and restore WATER-ELECTROLYTE BALANCE in treating HYPOKALEMIA.. potassium chloride : A metal chloride salt with a K(+) counterion.	2.66	3	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
prilocaine Prilocaine: A local anesthetic that is similar pharmacologically to LIDOCAINE. Currently, it is used most often for infiltration anesthesia in dentistry.. prilocaine : An amino acid amide in which N-propyl-DL-alanine and 2-methylaniline have combined to form the amide bond; used as a local anaesthetic.	2.4	2	amino acid amide; monocarboxylic acid amide	anticonvulsant; local anaesthetic
propantheline Propantheline: A muscarinic antagonist used as an antispasmodic, in rhinitis, in urinary incontinence, and in the treatment of ulcers. At high doses it has nicotinic effects resulting in neuromuscular blocking.	2	1	xanthenes
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.	2.05	1	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
protoporphyrin ix protoporphyrin IX: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7685. protoporphyrin : A cyclic tetrapyrrole that consists of porphyrin bearing four methyl substituents at positions 3, 8, 13 and 17, two vinyl substituents at positions 7 and 12 and two 2-carboxyethyl substituents at positions 2 and 18. The parent of the class of protoporphyrins.	2.96	4
1,6-bis(cyclohexyloximinocarbonyl)hexane 1,6-bis(cyclohexyloximinocarbonyl)hexane: selective inhibitor of canine platelet diglyceride lipase	2.02	1	carbamate ester; organonitrogen compound
risperidone Risperidone: A selective blocker of DOPAMINE D2 RECEPTORS and SEROTONIN 5-HT2 RECEPTORS that acts as an atypical antipsychotic agent. It has been shown to improve both positive and negative symptoms in the treatment of SCHIZOPHRENIA.. risperidone : A member of the class of pyridopyrimidines that is 2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one carrying an additional 2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl group at position 2.	2.21	1	1,2-benzoxazoles; heteroarylpiperidine; organofluorine compound; pyridopyrimidine	alpha-adrenergic antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; psychotropic drug; second generation antipsychotic; serotonergic antagonist
ritanserin Ritanserin: A selective and potent serotonin-2 antagonist that is effective in the treatment of a variety of syndromes related to anxiety and depression. The drug also improves the subjective quality of sleep and decreases portal pressure.. ritanserin : A thiazolopyrimidine that is 5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one which is substituted at position 7 by a methyl group and at position 6 by a 2-{4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl}ethyl group. A potent and long-acting seratonin (5-hydroxytryptamine, 5-HT) antagonist of the subtype 5-HT2 (Ki = 0.39 nM), it is used in the treatment of a variety of disorders including anxiety, depression and schizophrenia. It has little sedative action.	2.21	1	organofluorine compound; piperidines; thiazolopyrimidine	antidepressant; antipsychotic agent; anxiolytic drug; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; serotonergic antagonist
stearic acid octadecanoic acid : A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.	3.27	6	long-chain fatty acid; saturated fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; human metabolite; plant metabolite
tolbutamide Tolbutamide: A sulphonylurea hypoglycemic agent with actions and uses similar to those of CHLORPROPAMIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290). tolbutamide : An N-sulfonylurea that consists of 1-butylurea having a tosyl group attached at the 3-position.	2.89	4	N-sulfonylurea	human metabolite; hypoglycemic agent; insulin secretagogue; potassium channel blocker
triacetin Triacetin: A triglyceride that is used as an antifungal agent.. triacetin : A triglyceride obtained by acetylation of the three hydroxy groups of glycerol. It has fungistatic properties (based on release of acetic acid) and has been used in the topical treatment of minor dermatophyte infections.	2.02	1	triglyceride	adjuvant; antifungal drug; food additive carrier; food emulsifier; food humectant; fuel additive; plant metabolite; solvent
urapidil [no description available]	2.21	1	piperazines
zinc chloride zinc chloride: RN given refers to parent cpd. zinc dichloride : A compound of zinc and chloride ions in the ratio 1:2. It exists in four crystalline forms, in each of which the Zn(2+) ions are trigonal planar coordinated to four chloride ions.	2.11	1	inorganic chloride; zinc molecular entity	astringent; disinfectant; EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor; Lewis acid
carbachol Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.	1.98	1	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic
spironolactone Spironolactone: A potassium sparing diuretic that acts by antagonism of aldosterone in the distal renal tubules. It is used mainly in the treatment of refractory edema in patients with congestive heart failure, nephrotic syndrome, or hepatic cirrhosis. Its effects on the endocrine system are utilized in the treatments of hirsutism and acne but they can lead to adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p827). spironolactone : A steroid lactone that is 17alpha-pregn-4-ene-21,17-carbolactone substituted by an oxo group at position 3 and an alpha-acetylsulfanyl group at position 7.	2.15	1	3-oxo-Delta(4) steroid; oxaspiro compound; steroid lactone; thioester	aldosterone antagonist; antihypertensive agent; diuretic; environmental contaminant; xenobiotic
pilocarpine Pilocarpine: A slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma.. (+)-pilocarpine : The (+)-enantiomer of pilocarpine.	2.08	1	pilocarpine	antiglaucoma drug
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	2.31	1	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	2.03	1	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	2.06	1	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	1.99	1	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	2.7	3	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
galactose galactopyranose : The pyranose form of galactose.	2.03	1	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	1.99	1	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
tributyrin tributyrin: structure. tributyrin : A triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by butyric acid.	1.97	1	butyrate ester; triglyceride	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor; prodrug; protective agent
phlorhizin [no description available]	2.07	1	aryl beta-D-glucoside; dihydrochalcones; monosaccharide derivative	antioxidant; plant metabolite
methylene blue Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.	2.88	3	organic chloride salt	acid-base indicator; antidepressant; antimalarial; antimicrobial agent; antioxidant; cardioprotective agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 4.6.1.2 (guanylate cyclase) inhibitor; fluorochrome; histological dye; neuroprotective agent; physical tracer
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	2.06	1	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
lactose Lactose: A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry.. lactose : A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.. beta-lactose : The beta-anomer of lactose.	3.02	4	lactose
1,2-dipalmitoylphosphatidylcholine 1,2-Dipalmitoylphosphatidylcholine: Synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of PULMONARY SURFACTANTS.	2.93	4
cycloheximide Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.	1.96	1	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
ficusin Ficusin: A naturally occurring furocoumarin, found in PSORALEA. After photoactivation with UV radiation, it binds DNA via single and double-stranded cross-linking.. psoralen : The simplest member of the class of psoralens that is 7H-furo[3,2-g]chromene having a keto group at position 7. It has been found in plants like Psoralea corylifolia and Ficus salicifolia.	2.06	1	psoralens	plant metabolite
mannitol [no description available]	2.43	2	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	2	1	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
n-pentanol n-pentanol: RN given refers to parent cpd. pentan-1-ol : A short-chain primary fatty alcohol that is pentane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Melicope ptelefolia.	2.06	1	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	2.39	2	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
propane Propane: A three carbon alkane with the formula H3CCH2CH3.	2.11	1	alkane; gas molecular entity	food propellant
tert-butyl alcohol tert-Butyl Alcohol: An isomer of butanol that contains a tertiary butyl group that consists of three methyl groups, each separately attached to a central (tertiary) carbon.. tert-butanol : A tertiary alcohol alcohol that is isobutane substituted by a hydroxy group at position 2.	2.06	1	tertiary alcohol	human xenobiotic metabolite
perfluoroethane [no description available]	1.98	1	fluoroalkane; fluorocarbon	refrigerant
linalool linalool: RN given refers to parent cpd without isomeric designation; structure. linalool : A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum.	2.06	1	monoterpenoid; tertiary alcohol	antimicrobial agent; fragrance; plant metabolite; volatile oil component
taurocholic acid Taurocholic Acid: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic.. taurocholate : An organosulfonate oxoanion that is the conjugate base of taurocholic acid.. taurocholic acid : A bile acid taurine conjugate of cholic acid that usually occurs as the sodium salt of bile in mammals.	3.78	11	amino sulfonic acid; bile acid taurine conjugate	human metabolite
n-vinyl-2-pyrrolidinone N-vinyl-2-pyrrolidinone: monomer of POVIDONE; structure given in first source	2.74	3	pyrrolidin-2-ones
thymol Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.	2.31	1	monoterpenoid; phenols	volatile oil component
2-naphthylamine 2-Naphthylamine: A naphthalene derivative with carcinogenic action.. 2-naphthylamine : A naphthylamine carrying the amino group at position 2.	2.31	1	naphthylamine	carcinogenic agent
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2.11	1	xanthene
alpha-chlorohydrin alpha-Chlorohydrin: A chlorinated PROPANEDIOL with antifertility activity in males used as a chemosterilant in rodents.. 3-chloropropane-1,2-diol : A chloropropane-1,2-diol that is propane-1,2-diol substituted by a chloro group at position 3.	2.6	1	chloropropane-1,2-diol
pyrrolidonecarboxylic acid Pyrrolidonecarboxylic Acid: A cyclized derivative of L-GLUTAMIC ACID. Elevated blood levels may be associated with problems of GLUTAMINE or GLUTATHIONE metabolism.. 5-oxo-L-proline : An optically active form of 5-oxoproline having L-configuration.	2.88	1	5-oxoproline; L-proline derivative; non-proteinogenic L-alpha-amino acid	algal metabolite
ethyl butyrate ethyl butyrate : A butyrate ester resulting from the formal condensation of the hydroxy group of ethanol with the carboxy group of butyric acid.	1.96	1	butyrate ester	plant metabolite
acrolein [no description available]	2.31	1	enal	herbicide; human xenobiotic metabolite; toxin
hexylene glycol hexylene glycol: RN given refers to parent cpd. 2-methylpentane-2,4-diol : A glycol in which the two hydroxy groups are at positions 2 and 4 of 2-methylpentane (isopentane).	2.03	1	glycol
dimethyldioctadecylammonium dimethyldioctadecylammonium: a cationic lipid analog; RN given refers to parent cpd	4.9	10
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.4	2	alkane
succinic anhydride [no description available]	2.03	1	cyclic dicarboxylic anhydride; tetrahydrofurandione
propylene carbonate 4-methyl-1,3-dioxolan-2-one: structure in first source	2.11	1
pentane Pentanes: Five-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. pentane : A straight chain alkane consisting of 5 carbon atoms.	2.08	1	alkane; volatile organic compound	non-polar solvent; refrigerant
diethylamine [no description available]	2.05	1	secondary aliphatic amine
isopropyl myristate isopropyl myristate: used for microemulsions; structure	2.48	2	fatty acid ester
1,5-pentanediol [no description available]	2.08	1	primary alcohol
nonane iotrochotin: toxin from the Caribbean sponge Iotrochota birotulata, which selectively permeabilizes synaptosomes. nonane : A straight chain alkane composed of 9 carbon atoms.	2.07	1	alkane	plant metabolite; volatile oil component
carbitol carbitol: used as lubricating oil & in braking fluid, structure. diethylene glycol monoethyl ether : A primary alcohol that is ethanol substituted by a 2-ethoxyethoxy group at position 2.	3.16	5	diether; glycol ether; hydroxypolyether; primary alcohol	protic solvent
dodecyltrimethylammonium dodecyltrimethylammonium: used to determine thermal stability of DNA; RN given refers to parent cpd. dodecyltrimethylammonium ion : A quarternary ammonium cation having one dodecyl and three methyl substituents around the central nitrogen.	2.08	1	quaternary ammonium ion
1,4-naphthoquinone naphthoquinone : A polycyclic aromatic ketone metabolite of naphthalene.. 1,4-naphthoquinone : The parent structure of the family of 1,4-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 4 of the naphthalene ring. Derivatives have pharmacological properties.	2.05	1	1,4-naphthoquinones
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	2.03	1	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
isopropyl palmitate isopropyl palmitate : A fatty acid ester obtained by the formal condensation of carboxy group of palmitic acid with propan-2-ol. Metabolite observed in cancer metabolism.	2.11	1	fatty acid ester; isopropyl ester	human metabolite
3-o-methylglucose 3-O-Methylglucose: A non-metabolizable glucose analogue that is not phosphorylated by hexokinase. 3-O-Methylglucose is used as a marker to assess glucose transport by evaluating its uptake within various cells and organ systems. (J Neurochem 1993;60(4):1498-504). 3-O-methyl-D-glucose : A D-aldohexose that is D-glucose in which the hydrogen of the hydroxy group at position 3 has been substituted by a methyl group. It is a non-metabolisable glucose analogue that is not phosphorylated by hexokinase and is used as a marker to assess glucose transport by evaluating its uptake within various cells and organ systems.	1.97	1	D-aldohexose derivative
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	2.41	1	catechin	antioxidant; plant metabolite
benzoxazoles 1,3-benzoxazole : A benzoxazole in which the benzene ring is fused to a 1,3-oxazole ring across positions 4 and 5.. benzoxazole : Compounds based on a fused 1,2- or 1,3-oxazole and benzene bicyclic ring skeleton.	2.38	2	1,3-benzoxazoles; mancude organic heterobicyclic parent
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	1.95	1	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
paraoxon [no description available]	1.96	1	aryl dialkyl phosphate; organophosphate insecticide	EC 3.1.1.7 (acetylcholinesterase) inhibitor; mouse metabolite
lithocholic acid Lithocholic Acid: A bile acid formed from chenodeoxycholate by bacterial action, usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic.. lithocholic acid : A monohydroxy-5beta-cholanic acid with a alpha-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action.. lithocholate : A bile acid anion that is the conjugate base of lithocholic acid.	2.11	1	bile acid; C24-steroid; monohydroxy-5beta-cholanic acid	geroprotector; human metabolite; mouse metabolite
limestone Calcium Carbonate: Carbonic acid calcium salt (CaCO3). An odorless, tasteless powder or crystal that occurs in nature. It is used therapeutically as a phosphate buffer in hemodialysis patients and as a calcium supplement.. calcium carbonate : A calcium salt with formula CCaO3.	2.1	1	calcium salt; carbonate salt; inorganic calcium salt; one-carbon compound	antacid; fertilizer; food colouring; food firming agent
thymoquinone thymoquinone: constituent of cedarwood; can cause dermatitis; structure. thymoquinone : A member of the class of 1,4-benzoquinones that is 1,4-bezoquinone in which the hydrogens at positions 2 and 5 are replaced by methyl and isopropyl groups, respectively. It is a natural compound isolated from Nigella sativa which has demonstrated promising chemotherapeutic activity.	2.21	1	1,4-benzoquinones	adjuvant; anti-inflammatory agent; antidepressant; antineoplastic agent; antioxidant; cardioprotective agent; plant metabolite
carvacrol carvacrol : A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).	2.31	1	botanical anti-fungal agent; p-menthane monoterpenoid; phenols	agrochemical; antimicrobial agent; flavouring agent; TRPA1 channel agonist; volatile oil component
caprolactone hexano-6-lactone : A epsilon-lactone that is oxepane substituted by an oxo group at position 2.	2.03	1	epsilon-lactone
cyanogen bromide Cyanogen Bromide: Cyanogen bromide (CNBr). A compound used in molecular biology to digest some proteins and as a coupling reagent for phosphoroamidate or pyrophosphate internucleotide bonds in DNA duplexes.	1.96	1
chlormethiazole Chlormethiazole: A sedative and anticonvulsant often used in the treatment of alcohol withdrawal. Chlormethiazole has also been proposed as a neuroprotective agent. The mechanism of its therapeutic activity is not entirely clear, but it does potentiate GAMMA-AMINOBUTYRIC ACID receptors response and it may also affect glycine receptors.	2	1	thiazoles
tricaprylin tricaprylin: 13C-labeled trioctanoin used in breath tests to detect fat malabsorption. trioctanoin : A triglyceride obtained by acylation of the three hydroxy groups of glycerol by octanoic acid. Used as an alternative energy source to glucose for patients with mild to moderate Alzheimer's disease.	3.93	12	octanoate ester; triglyceride	anticonvulsant; plant metabolite
cetyl palmitate palmityl palmitate : A palmitate ester resulting from the formal condensation of palmitic acid with palmityl alcohol. It is used as a thickener and emollient in cosmetics.	2.06	1	hexadecanoate ester	metabolite
n-hexadecane n-hexadecane: structure. hexadecane : A straight-chain alkane with 16 carbon atoms. It is a component of essential oil isolated from long pepper.	2.89	4	long-chain alkane	non-polar solvent; plant metabolite; volatile oil component
paeonol paeonol: structure	2.11	1	methoxybenzenes; phenols	metabolite
tristearin tristearoylglycerol : A triglyceride that is glycerol in which all three hydroxy groups have been formally esterified with stearic acid.	2.78	3	triacylglycerol 54:0	Caenorhabditis elegans metabolite; plant metabolite
fluoromethane fluoromethane: RN given refers to parent cpd. fluorocarbon : Compounds consisting wholly of fluorine and carbon.. fluoromethane : A member of the class of fluoromethanes that is methane in which a single hydrogen is substituted by a fluorine atom.	1.99	1	fluorohydrocarbon; fluoromethanes; methyl halides	refrigerant
n-tetradecane tetradecane : A straight chain alkane consisting of 14 carbon atoms.	2.05	1	long-chain alkane	plant metabolite; volatile oil component
erythromycin Erythromycin: A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.. erythromycin : Any of several wide-spectrum macrolide antibiotics obtained from actinomycete Saccharopolyspora erythraea (formerly known as Streptomyces erythraeus).. erythromycin A : An erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively.	2.17	1	cyclic ketone; erythromycin
formal glycol [no description available]	1.99	1	cyclic acetal; dioxolane
mannoheptulose Mannoheptulose: A 7-carbon keto sugar having the mannose configuration.. D-keto-manno-heptulose : The open chain form of D-manno-heptulose.. D-manno-heptulose : A manno-heptulose with a D-configuration. It has been found in avocados.	1.97	1	D-manno-heptulose
amaranth dye Amaranth Dye: A sulfonic acid-based naphthylazo dye used as a coloring agent for foodstuffs and medicines and as a dye and chemical indicator. It was banned by the FDA in 1976 for use in foods, drugs, and cosmetics. (From Merck Index, 11th ed)	2.06	1
lithium citrate lithium citrate: RN given refers to the trilithium salt. lithium citrate (anhydrous) : A lithium salt that is the anhydrous form of the trilithium salt of citric acid. The tetrahydrate form is used as a source of lithium for the treatment of anxiety disorders, bipolar disorder, and depression.	2.13	1	lithium salt
deoxycytidine [no description available]	2.05	1	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
sodium hydroxide Sodium Hydroxide: A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed)	2.01	1	alkali metal hydroxide
monolaurin monolaurin: RN given refers to cpd with unspecified monolaurin locant. 1-monolauroylglycerol : A 1-monoglyceride with dodecanoyl (lauroyl) as the acyl group.. rac-1-monolauroylglycerol : A rac-1-monoacylglycerol comprising equal amounts of 1-lauroyl-sn-glycerol and 3-lauroyl-sn-glycerol	2.07	1	1-monoglyceride; dodecanoate ester; rac-1-monoacylglycerol
vancomycin Vancomycin: Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to RISTOCETIN that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear.. vancomycin : A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.	2.21	1	glycopeptide	antibacterial drug; antimicrobial agent; bacterial metabolite
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	3.77	10	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
tocopherols [no description available]	2.03	1
bromoxynil octanoate [no description available]	2.21	1
decane decane : A straight-chain alkane with 10 carbon atoms.	1.96	1	alkane
fluorescein Fluorescein: A phthalic indicator dye that appears yellow-green in normal tear film and bright green in a more alkaline medium such as the aqueous humor.. fluorescein (lactone form) : A xanthene dye that is highly fluorescent, detectable even when present in minute quantities. Used forensically to detect traces of blood, in analytical chemistry as an indicator in silver nitrate titrations and in microscopy.	2.51	2	2-benzofurans; gamma-lactone; organic heteropentacyclic compound; oxaspiro compound; polyphenol; xanthene dye	fluorescent dye; radioopaque medium
tricosanoic acid tricosanoic acid : A very long-chain fatty acid that is tricosane in which one of the methyl groups has been oxidised to the corresponding carboxylic acid.	2.03	1	straight-chain saturated fatty acid; very long-chain fatty acid	Daphnia magna metabolite; human metabolite; plant metabolite
benzophenoneidum Benzophenoneidum: An aniline dye used as a disinfectant and an antiseptic agent. It is weakly fluorescing and binds specifically to certain proteins.. auramine O : A hydrochloride obtained by combining 4,4'-carbonimidoylbis(N,N-dimethylaniline) with one molar equivalent of hydrogen chloride. A fluorescent stain for demonstrating acid fast organisms in a method similar to the Ziehl Neelsen. It also can be used to make a fluorescent Schiff reagent.	2.52	2	hydrochloride	fluorochrome; histological dye
didodecyldimethylammonium didodecyldimethylammonium: RN given refers to parent cpd	2.07	1
fluorescein-5-isothiocyanate Fluorescein-5-isothiocyanate: Fluorescent probe capable of being conjugated to tissue and proteins. It is used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.. fluorescein 5-isothiocyanate : The 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.	2.98	4	fluorescein isothiocyanate
iridium Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.	2.15	1	cobalt group element atom; platinum group metal atom
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	2.44	2	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	2.17	1	copper group element atom; elemental silver	Escherichia coli metabolite
technetium Technetium: The first artificially produced element and a radioactive fission product of URANIUM. Technetium has the atomic symbol Tc, and atomic number 43. All technetium isotopes are radioactive. Technetium 99m (m=metastable) which is the decay product of Molybdenum 99, has a half-life of about 6 hours and is used diagnostically as a radioactive imaging agent. Technetium 99 which is a decay product of technetium 99m, has a half-life of 210,000 years.	2.07	1	manganese group element atom
gadolinium Gadolinium: An element of the rare earth family of metals. It has the atomic symbol Gd, atomic number 64, and atomic weight 157.25. Its oxide is used in the control rods of some nuclear reactors.	2.42	2	f-block element atom; lanthanoid atom
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	2.54	2	copper group element atom; elemental gold
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	2.03	1	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
potassium sulfate potassium sulfate: RN given refers to cpd with MF of K2-H2SO4	2.11	1	inorganic potassium salt; potassium salt
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	2.42	2	dihydrogen
fluorine Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.	1.99	1	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
chlorine Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	1.99	1	diatomic chlorine; gas molecular entity	bleaching agent
deuterium oxide Deuterium Oxide: The isotopic compound of hydrogen of mass 2 (deuterium) with oxygen. (From Grant & Hackh's Chemical Dictionary, 5th ed) It is used to study mechanisms and rates of chemical or nuclear reactions, as well as biological processes.	2.45	2	deuterated compound; water	NMR solvent
glycerol 1-stearate glycerol 1-stearate: isolated from the young fronds of the bracken fern Pteridium aquilinum; structure in first source. rac-1-monostearoylglycerol : A rac-1-monoacylglycerol composed of equal amounts of 3-stearoyl-sn-glycerol and 1-stearoyl-sn-glycerol.. 1-monostearoylglycerol : A 1-monoglyceride that has stearoyl as the acyl group.	3.4	7	1-acylglycerol 18:0; rac-1-monoacylglycerol	algal metabolite; Caenorhabditis elegans metabolite
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	2.77	3
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	2.02	1
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	3.23	6	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
bromocriptine Bromocriptine: A semisynthetic ergotamine alkaloid that is a dopamine D2 agonist. It suppresses prolactin secretion.	2.07	1	indole alkaloid	antidyskinesia agent; antiparkinson drug; dopamine agonist; hormone antagonist
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.5	2	benzenes; phenyl acetates
pyrene pyrene: structure in Merck Index, 9th ed, #7746. pyrene : An ortho- and peri-fused polycyclic arene consisting of four fused benzene rings, resulting in a flat aromatic system.	2.07	1	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
alkenes [no description available]	2.39	2
cefazolin Cefazolin: A semisynthetic cephalosporin analog with broad-spectrum antibiotic action due to inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine.. cefazolin : A first-generation cephalosporin compound having [(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl and (1H-tetrazol-1-ylacetyl)amino side-groups at positions 3 and 7 respectively.	1.99	1	beta-lactam antibiotic allergen; cephalosporin; tetrazoles; thiadiazoles	antibacterial drug
allura red ac dye Allura Red AC Dye: new monoazo dye proposed as color additive in various food products; RN given refers to di-Na salt; structure	2.05	1
tramadol Tramadol: A narcotic analgesic proposed for severe pain. It may be habituating.. tramadol : A racemate consisting of equal amounts of (R,R)- and (S,S)-tramadol. A centrally acting synthetic opioid analgesic, used (as the hydrochloride salt) to treat moderately severe pain. The (R,R)-enantiomer exhibits ten-fold higher analgesic potency than the (S,S)-enantiomer. Originally developed by Gruenenthal GmbH and launched in 1977, it was subsequently isolated from the root bark of the South African tree Nauclea latifolia.. (R,R)-tramadol : A 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol in which both stereocentres have R-configuration; the (R,R)-enantiomer of the racemic opioid analgesic tramadol, it exhibits ten-fold higher analgesic potency than the (S,S)-enantiomer.	2	1	2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol	adrenergic uptake inhibitor; antitussive; capsaicin receptor antagonist; delta-opioid receptor agonist; kappa-opioid receptor agonist; metabolite; mu-opioid receptor agonist; muscarinic antagonist; nicotinic antagonist; NMDA receptor antagonist; opioid analgesic; serotonergic antagonist; serotonin uptake inhibitor
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	3.44	7	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
phorbol 12,13-dibutyrate Phorbol 12,13-Dibutyrate: A phorbol ester found in CROTON OIL which, in addition to being a potent skin tumor promoter, is also an effective activator of calcium-activated, phospholipid-dependent protein kinase (protein kinase C). Due to its activation of this enzyme, phorbol 12,13-dibutyrate profoundly affects many different biological systems.	2.38	2	butyrate ester; phorbol ester; tertiary alpha-hydroxy ketone
colforsin Colforsin: Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant COLEUS FORSKOHLII. Has antihypertensive, positive inotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland.	2.38	2	acetate ester; cyclic ketone; labdane diterpenoid; organic heterotricyclic compound; tertiary alpha-hydroxy ketone; triol	adenylate cyclase agonist; anti-HIV agent; antihypertensive agent; plant metabolite; platelet aggregation inhibitor; protein kinase A agonist
simvastatin Simvastatin: A derivative of LOVASTATIN and potent competitive inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It may also interfere with steroid hormone production. Due to the induction of hepatic LDL RECEPTORS, it increases breakdown of LDL CHOLESTEROL.. simvastatin : A member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group. It is used as a cholesterol-lowering and anti-cardiovascular disease drug.	3.05	4	delta-lactone; fatty acid ester; hexahydronaphthalenes; statin (semi-synthetic)	EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor; EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor; ferroptosis inducer; geroprotector; prodrug
finasteride Finasteride: An orally active 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE inhibitor. It is used as a surgical alternative for treatment of benign PROSTATIC HYPERPLASIA.. finasteride : An aza-steroid that is a synthetic drug for the treatment of benign prostatic hyperplasia.	2.1	1	3-oxo steroid; aza-steroid; delta-lactam	androgen antagonist; antihyperplasia drug; EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor
gemcitabine gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.	2.05	1	organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; environmental contaminant; immunosuppressive agent; photosensitizing agent; prodrug; radiosensitizing agent; xenobiotic
duloxetine hydrochloride Duloxetine Hydrochloride: A thiophene derivative and selective NEUROTRANSMITTER UPTAKE INHIBITOR for SEROTONIN and NORADRENALINE (SNRI). It is an ANTIDEPRESSIVE AGENT and ANXIOLYTIC, and is also used for the treatment of pain in patients with DIABETES MELLITUS and FIBROMYALGIA.. (S)-duloxetine hydrochloride : A duloxetine hydrochloride in which the duloxetine moiety has S configuration.	2.25	1	duloxetine hydrochloride	antidepressant
irinotecan [no description available]	2.03	1	carbamate ester; delta-lactone; N-acylpiperidine; pyranoindolizinoquinoline; ring assembly; tertiary alcohol; tertiary amino compound	antineoplastic agent; apoptosis inducer; EC 5.99.1.2 (DNA topoisomerase) inhibitor; prodrug
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	2.15	1	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
octyl gallate [no description available]	2.07	1	gallate ester	food antioxidant; hypoglycemic agent; plant metabolite
octyl glucoside octyl-beta-D-glucoside: RN given refers to (beta)-isomer. octyl beta-D-glucopyranoside : An beta-D-glucoside in which the anomeric hydrogen of beta-D-glucopyranose is substituted by an octyl group.	3.13	5	beta-D-glucoside	plant metabolite
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	3.42	7	D-glucopyranose	epitope; mouse metabolite
baicalin [no description available]	2.11	1	dihydroxyflavone; glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative	antiatherosclerotic agent; antibacterial agent; anticoronaviral agent; antineoplastic agent; antioxidant; cardioprotective agent; EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; ferroptosis inhibitor; neuroprotective agent; non-steroidal anti-inflammatory drug; plant metabolite; prodrug
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	2.41	1	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
cholesteryl sulfate cholesteryl sulfate: component of human seminal plasma & spermatozoa; RN given refers to (3beta)-isomer. cholesterol sulfate : A steroid sulfate that is cholesterol substituted by a sulfoxy group at position 3.	1.98	1	steroid sulfate	human metabolite
1,2-dipalmitoyl-3-phosphatidylethanolamine 1,2-dipalmitoyl-3-phosphatidylethanolamine: RN given refers to parent cpd without isomeric designation	2.38	2
distearoyl phosphatidylglycerol distearoyl phosphatidylglycerol: a surface-active agent. distearoyl phosphatidylglycerol : A phosphatidylglycerol in which the phosphatidyl acyl groups are both stearoyl.	2.7	3	phosphatidylglycerol
nile red nile red : An organic heterotetracyclic compound that is 5H-benzo[a]phenoxazin-5-one substituted at position 9 by a diethylamino group.	2.15	1	aromatic amine; cyclic ketone; organic heterotetracyclic compound; tertiary amino compound	fluorochrome; histological dye
lissamine rhodamine b lissamine rhodamine B: RN given refers to parent cpd; Lissamine Rhodamine B refers to Na salt	2.04	1
rhodamine 110 rhodamine 110: RN given refers to chloride	2.11	1
cephalosporin c cephalosporin C: RN given refers to parent cpd; structure in Merck, 9th ed, #1937. cephalosporin C : A cephalosporin antibiotic carrying a 3-acetoxymethyl substituent and a 6-oxo-N(6)-L-lysino group at position 7.	3.5	2	cephalosporin	fungal metabolite
methacycline [no description available]	2.38	2	1,2-diglyceride
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	2.05	1	1,2,3-triazole
tocophersolan tocophersolan: RN given refers to parent cpd	2.52	2	tocol
ontazolast ontazolast: inhibits arachidonate release that blocks leukotriene B4 and platelet-activating factor biosynthesis in human neutrophils	1.99	1
6-carboxyfluorescein 6-carboxyfluorescein: originally sold as 6-carboxyfluorescein, but commercial product is a mixture of two isomers; correct name is 5(6)-carboxyfluorescein	2.08	1	monocarboxylic acid
4-phenylbutylamine 4-phenylbutylamine: used as a drug partition into lipid bilayers in a cubic liquid-crystalline phase. 4-phenylbutylamine : A phenylalkylamine that is benzene in which one of the hydrogens is substituted by a 4-aminobutyl group.	2	1	benzenes; phenylalkylamine; primary amino compound
ketorolac tromethamine Ketorolac Tromethamine: A pyrrolizine carboxylic acid derivative structurally related to INDOMETHACIN. It is a non-steroidal anti-inflammatory agent used for analgesia for postoperative pain and inhibits cyclooxygenase activity.. ketorolac tromethamine : An organoammonium salt resulting from the mixture of equimolar amounts of ketorolac and tromethamine (tris). It has potent non-sedating analgesic and moderate anti-inflammatory effects. It is used in the short-term management of post-operative pain, and in eye drops to relieve the ocular itching associated with seasonal allergic conjunctivitis.	2.02	1	organoammonium salt	analgesic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor
we 201 We 201: synthetic lysolecithin analog; RN given refers to hydroxide inner salt; structure	2.01	1
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	2	1	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
fibrinogen Fibrinogen: Plasma glycoprotein clotted by thrombin, composed of a dimer of three non-identical pairs of polypeptide chains (alpha, beta, gamma) held together by disulfide bonds. Fibrinogen clotting is a sol-gel change involving complex molecular arrangements: whereas fibrinogen is cleaved by thrombin to form polypeptides A and B, the proteolytic action of other enzymes yields different fibrinogen degradation products.. D-iditol : The D-enantiomer of iditol.	2.05	1	iditol	fungal metabolite
glucuronic acid Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.	3.2	5	D-glucuronic acid	algal metabolite
cremophor el cremophor EL: solvent for Althesin & Propanidid implicated as possible cause of similar adverse effects polyethoxylated castor oil; RN given refers to cpd with unknown MF; see also records for cremophor & cremophor A	2.5	2
laurdan laurdan: RN from CA Index Guide	2.31	1
1-hexadecyl-2-acetyl-glycero-3-phosphocholine Platelet Activating Factor: A phospholipid derivative formed by PLATELETS; BASOPHILS; NEUTROPHILS; MONOCYTES; and MACROPHAGES. It is a potent platelet aggregating agent and inducer of systemic anaphylactic symptoms, including HYPOTENSION; THROMBOCYTOPENIA; NEUTROPENIA; and BRONCHOCONSTRICTION.. 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine : A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.	1.97	1	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
dodecyl-beta-d-maltoside dodecyl beta-D-maltoside : A glycoside resulting from attachment of a dodecyl group to the reducing-end anomeric centre of a beta-maltose molecule.	2.05	1	disaccharide derivative; glycoside	detergent
caprylates Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.	4.25	17	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
hydroxypropylmethylcellulose acetate succinate hydroxypropylmethylcellulose acetate succinate: structure given in first source	2.05	1
dansylsarcosine [no description available]	1.99	1
hydronium ion [no description available]	2.37	2	onium cation; oxygen hydride
magnesium octaethylporphyrin [no description available]	1.95	1
polytrimethylene carbonate trimethylene carbonate: structure in first source	2.03	1
htr composite HTR composite: biocampatible composite of patented technology combining polymethylmethacrylate & polyhydroxyethyl methacrylate without addition of catalysts, inducers or impurities	1.98	1
n-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)phosphatidylethanolamine N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)phosphatidylethanolamine: fluorescent probe for membrane lipids	2.4	2
solutol hs 15 Solutol HS 15: multidrug resistance modification agent in tumor cells; polyoxyethylene esters of 12-hydroxystearic acid; previous RN 105109-85-1	2.11	1	aliphatic alcohol
n-4-nitrobenzo-2-oxa-1,3-diazoledipalmitoyl phosphatidylethanolamine [no description available]	1.99	1
fpl 67047xx FPL 67047XX: inhibits phospholipase A2; structure in first source	1.99	1
2-(9-anthroyloxy)stearic acid [no description available]	2.03	1
bis-q Bis-Q: photochromic activator of acetylcholine receptors; RN given refers to parent cpd without isomeric designation; structure	1.95	1	azobenzenes
xylose xylopyranose: structure in first source	1.99	1	D-xylose
docetaxel anhydrous Docetaxel: A semisynthetic analog of PACLITAXEL used in the treatment of locally advanced or metastatic BREAST NEOPLASMS and NON-SMALL CELL LUNG CANCER.. docetaxel anhydrous : A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group.	2.21	1	secondary alpha-hydroxy ketone; tetracyclic diterpenoid	antimalarial; antineoplastic agent; photosensitizing agent
naproxen Naproxen: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout.. naproxen : A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.	2.5	2	methoxynaphthalene; monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
methyl 5-aminolevulinate methyl 5-aminolevulinate: esterified form of aminolevulinic acid used as PHOTOCHEMOTHERAPY. methyl 5-aminolevulinate : The methyl ester of 5-aminolevulinic acid. A prodrug, it is metabolised to protoporphyrin IX, a photosensitizer, and is used in the photodynamic treatment of non-melanoma skin cancer (including basal cell carcinoma). Topical application (often as the hydrochloride salt) results in an accumulation of protoporphyrin IX in the skin lesions to which the cream has been applied. Subsequent illumination with red light results in the generation of toxic singlet oxygen that destroys cell membranes and thereby kills the tumour cells.	2.08	1	delta-amino acid ester	antineoplastic agent; dermatologic drug; photosensitizing agent; prodrug
cochlioquinone a cochlioquinone A: from Helminthosporium sativum; competitive inhibitor of ivermectin binding; RN from Chem Abstract Index Guide 1990; structure given in first source	2.21	1	oxanes
beta-solamarine beta-solamarine: RN given refers to (3beta,22beta,25S)-isomer; structure given in first source	2.1	1	steroid saponin
monactin monactin: marcrotetrolide antibiotic produced by cycloheximide producing species of Streptomyces; it is homolog of nonactin from the same species; minor descriptor (75-86); on-line & INDEX MEDICUS search ANTIBIOTICS (75-86)	1.96	1
trinactin trinactin: homolog of nonactin	1.96	1
1,2-diphytanoylphosphatidylcholine [no description available]	2.4	2
biotin vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.	1.99	1	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
isofuranodiene isofuranodiene: structure	2.41	1
neurotensin (1-8) neurotensin (1-8) : An 8 amino acid peptide fragment of neurotensin.	2.88	1	peptide zwitterion; peptide	human metabolite
yh 1885 YH 1885: proton pump inhibitor; structure in first source	2.17	1
sorafenib [no description available]	2.25	1	(trifluoromethyl)benzenes; aromatic ether; monochlorobenzenes; phenylureas; pyridinecarboxamide	angiogenesis inhibitor; anticoronaviral agent; antineoplastic agent; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; ferroptosis inducer; tyrosine kinase inhibitor
cholic acid Cholic Acid: A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.. cholic acid : A bile acid that is 5beta-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12.	3.03	4	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
deoxycholic acid Deoxycholic Acid: A bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent.. deoxycholic acid : A bile acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 12 respectively.	3.33	2	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human blood serum metabolite
gossypol acetic acid [no description available]	2.25	1
taurochenodeoxycholic acid Taurochenodeoxycholic Acid: A bile salt formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. It acts as detergent to solubilize fats in the small intestine and is itself absorbed. It is used as a cholagogue and choleretic.. taurochenodeoxycholate : An organosulfonate oxoanion that is the conjugate base of taurochenodeoxycholic acid arising from deprotonation of the sulfonate OH group; major species at pH 7.3.. taurochenodeoxycholic acid : A bile acid taurine conjugate of chenodeoxycholic acid.	2.36	2	bile acid taurine conjugate	human metabolite; mouse metabolite
lithium chloride Lithium Chloride: A salt of lithium that has been used experimentally as an immunomodulator.. lithium chloride : A metal chloride salt with a Li(+) counterion.	1.97	1	inorganic chloride; lithium salt	antimanic drug; geroprotector
tetranactin tetranactin: from Streptomyces strain S-3466; miticidal; structure	1.96	1	macrotetrolide
saquinavir Saquinavir: An HIV protease inhibitor which acts as an analog of an HIV protease cleavage site. It is a highly specific inhibitor of HIV-1 and HIV-2 proteases, and also inhibits CYTOCHROME P-450 CYP3A.. saquinavir : An aspartic acid derivative obtained by formal condensation of the primary amino group of (2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-3-hydroxy-1-phenylbutan-2-ylamine with the carboxy group of N(2)(-quinolin-2-ylcarbonyl)-L-asparagine. An inhibitor of HIV-1 protease.	2.25	1	L-asparagine derivative; quinolines	antiviral drug; HIV protease inhibitor
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.5	2	cyclodextrin
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	2.21	1	cinnamic acid	plant metabolite
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	2.39	2	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	3.23	5	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
retinol Vitamin A: Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of CAROTENOIDS found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.. vitamin A : Any member of a group of fat-soluble retinoids produced via metabolism of provitamin A carotenoids that exhibit biological activity against vitamin A deficiency. Vitamin A is involved in immune function, vision, reproduction, and cellular communication.. all-trans-retinol : A retinol in which all four exocyclic double bonds have E- (trans-) geometry.. retinol : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraen-1-ol substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).	2.9	4	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
oleic acid Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.	6.23	53	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
tacrolimus Tacrolimus: A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.. tacrolimus (anhydrous) : A macrolide lactam containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis.	2.1	1	macrolide lactam	bacterial metabolite; immunosuppressive agent
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	2.07	1	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
clindamycin Clindamycin: An antibacterial agent that is a semisynthetic analog of LINCOMYCIN.. clindamycin : A carbohydrate-containing antibiotic that is the semisynthetic derivative of lincomycin, a natural antibiotic.	2.11	1
lycopene [no description available]	2.07	1	acyclic carotene	antioxidant; plant metabolite
azaserine Azaserine: Antibiotic substance produced by various Streptomyces species. It is an inhibitor of enzymatic activities that involve glutamine and is used as an antineoplastic and immunosuppressive agent.. azaserine : A carboxylic ester resulting from the formal condensation of the carboxy group of diazoacetic acid with the alcoholic hydroxy group of L-serine. An antibiotic produced by a Streptomyces species.	1.97	1	carboxylic ester; diazo compound; L-serine derivative; non-proteinogenic L-alpha-amino acid	antifungal agent; antimetabolite; antimicrobial agent; antineoplastic agent; glutamine antagonist; immunosuppressive agent; metabolite
enkephalin, leucine Enkephalin, Leucine: One of the endogenous pentapeptides with morphine-like activity. It differs from MET-ENKEPHALIN in the LEUCINE at position 5. Its first four amino acid sequence is identical to the tetrapeptide sequence at the N-terminal of BETA-ENDORPHIN.. Leu-enkephalin : A pentapeptide comprising L-tyrosine, glycine, glycine, L-phenylalanine and L-leucine residues joined in sequence by peptide linkages. It is an endogenous opioid peptide produced in vertebrate species, including rodents, primates and humans that results from decomposition of proenkephalin or dynorphin and exhibits antinociceptive properties.	2	1	pentapeptide; peptide zwitterion	analgesic; delta-opioid receptor agonist; human metabolite; mu-opioid receptor agonist; neurotransmitter; rat metabolite
cinnamaldehyde 3-phenylprop-2-enal : A member of the class of cinnamaldehydes that is prop-2-enal in which a hydrogen at position 3 has been replaced by a phenyl group. The configuration of the double bond is not specified; the name "cinnamaldehyde" is widely used to refer to the E (trans) isomer.. (E)-cinnamaldehyde : The E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes.	2.31	1	3-phenylprop-2-enal; cinnamaldehydes	antifungal agent; EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor; flavouring agent; hypoglycemic agent; plant metabolite; sensitiser; vasodilator agent
elaidic acid [no description available]	2.07	1	octadec-9-enoic acid	food component
citral citral: Xref geranial: geraniol is also available; Xref neral: nerol is also available; vitamin A antagonist; oxygenated monoterpene; inhibits cytosolic dehydrogenases; structure. citral : An enal that consists of octa-2,6-dienal bearing methyl substituents at positions 3 and 7. A mixture of the two geometric isomers geranial and neral, it is the major constituent (75-85%) of oil of lemon grass, the volatile oil of Cymbopogon citratus, or of C. flexuosus. It also occurs in oils of verbena, lemon, and orange.	2.31	1	enal; monoterpenoid; polyprenal	plant metabolite; volatile oil component
retinaldehyde Retinaldehyde: A diterpene derived from the carotenoid VITAMIN A which functions as the active component of the visual cycle. It is the prosthetic group of RHODOPSIN (i.e., covalently bonded to ROD OPSIN as 11-cis-retinal). When stimulated by visible light, rhodopsin transforms this cis-isomer of retinal to the trans-isomer (11-trans-retinal). This transformation straightens-out the bend of the retinal molecule and causes a change in the shape of rhodopsin triggering the visual process. A series of energy-requiring enzyme-catalyzed reactions convert the 11-trans-retinal back to the cis-isomer.. all-trans-retinal : A retinal in which all four exocyclic double bonds have E- (trans-) geometry.	2.4	2	retinal; vitamin A	gap junctional intercellular communication inhibitor; human metabolite; mouse metabolite
piperine piperine : A N-acylpiperidine that is piperidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum.	2.11	1	benzodioxoles; N-acylpiperidine; piperidine alkaloid; tertiary carboxamide	food component; human blood serum metabolite; NF-kappaB inhibitor; plant metabolite
squalene Addavax: an oil-water nanoemulsion and adjuvant containing squalene, Tween 80, and sorbitane trioleate	3.35	7	triterpene	human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	2.79	3	stilbene
ricinoleic acid ricinoleic acid: RN given refers to (R-(Z))-isomer; structure in Merck Index, 9th ed, #8005. ricinoleic acid : A (9Z)-12-hydroxyoctadec-9-enoic acid in which the 12-hydroxy group has R-configuration..	1.95	1	(9Z)-12-hydroxyoctadec-9-enoic acid
palmitoyl coenzyme a Palmitoyl Coenzyme A: A fatty acid coenzyme derivative which plays a key role in fatty acid oxidation and biosynthesis.. palmitoyl-CoA : A long-chain fatty acyl-CoA resulting from the formal condensation of the carboxy group of hexadecanoic acid with the thiol group of coenzyme A.	1.98	1	11,12-saturated fatty acyl-CoA; 3-substituted propionyl-CoA; long-chain fatty acyl-CoA; palmitoyl bioconjugate	Escherichia coli metabolite; mouse metabolite
s 1033 [no description available]	2.25	1	(trifluoromethyl)benzenes; imidazoles; pyridines; pyrimidines; secondary amino compound; secondary carboxamide	anticoronaviral agent; antineoplastic agent; tyrosine kinase inhibitor
r 59949 R 59949: diacylglycerol kinase inhibitor	2.52	2	diarylmethane
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	3.8	10	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
urb 597 cyclohexyl carbamic acid 3'-carbamoylbiphenyl-3-yl ester: a fatty acid amide hydrolase inhibitor; structure in first source	2.15	1	biphenyls
cinnarizine Cinnarizine: A piperazine derivative having histamine H1-receptor and calcium-channel blocking activity with vasodilating and antiemetic properties but it induces PARKINSONIAN DISORDERS.	3.46	7	diarylmethane; N-alkylpiperazine; olefinic compound	anti-allergic agent; antiemetic; calcium channel blocker; geroprotector; H1-receptor antagonist; histamine antagonist; muscarinic antagonist
capsaicin ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.	2.11	1	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
D-fructopyranose [no description available]	1.99	1	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
brij-58 Cetomacrogol: Non-ionic surfactant of the polyethylene glycol family. It is used as a solubilizer and emulsifying agent in foods, cosmetics, and pharmaceuticals, often as an ointment base, and also as a research tool.	2.06	1
5-doxylstearate [no description available]	2.06	1	aminoxyls
digoxin Digoxin: A cardiotonic glycoside obtained mainly from Digitalis lanata; it consists of three sugars and the aglycone DIGOXIGENIN. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in ATRIAL FIBRILLATION and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small. (From Martindale, The Extra Pharmacopoeia, 30th ed, p666). digoxin : A cardenolide glycoside that is digitoxin beta-hydroxylated at C-12. A cardiac glycoside extracted from the foxglove plant, Digitalis lanata, it is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation, but the margin between toxic and therapeutic doses is small.	2.1	1	cardenolide glycoside; steroid saponin	anti-arrhythmia drug; cardiotonic drug; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; epitope
tamoxifen [no description available]	2.17	1	stilbenoid; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; bone density conservation agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; estrogen antagonist; estrogen receptor antagonist; estrogen receptor modulator
sodium taurodeoxycholate Taurodeoxycholic Acid: A bile salt formed in the liver by conjugation of deoxycholate with taurine, usually as the sodium salt. It is used as a cholagogue and choleretic, also industrially as a fat emulsifier.. taurodeoxycholic acid : A bile acid taurine conjugate of deoxycholic acid.. taurodeoxycholate : An organosulfonate oxoanion that is the conjugate base of taurodeoxycholic acid.	3.59	3	bile acid taurine conjugate	human metabolite
valinomycin Valinomycin: A cyclododecadepsipeptide ionophore antibiotic produced by Streptomyces fulvissimus and related to the enniatins. It is composed of 3 moles each of L-valine, D-alpha-hydroxyisovaleric acid, D-valine, and L-lactic acid linked alternately to form a 36-membered ring. (From Merck Index, 11th ed) Valinomycin is a potassium selective ionophore and is commonly used as a tool in biochemical studies.. valinomycin : A twelve-membered cyclodepsipeptide composed of three repeating D-alpha-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl units joined in sequence. An antibiotic found in several Streptomyces strains.	2.89	4	cyclodepsipeptide; macrocycle	antimicrobial agent; antiviral agent; bacterial metabolite; potassium ionophore
laccase Laccase: A copper-containing oxidoreductase enzyme that catalyzes the oxidation of 4-benzenediol to 4-benzosemiquinone. It also has activity towards a variety of O-quinols and P-quinols. It primarily found in FUNGI and is involved in LIGNIN degradation, pigment biosynthesis and detoxification of lignin-derived products.	2.42	2
3,7,11,15-tetramethyl-1,2,3-hexadecanetriol 3,7,11,15-tetramethyl-1,2,3-hexadecanetriol: structure in first source. phytantriol : A triol that consists of 3,7,11,15-tetramethylhexadecane bearing three hydroxy substituents at positions 1, 2 and 3.	4.97	35	triol
lithium Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.	1.97	1	alkali metal atom
monooctanoin monooctanoin: dissolution agent for retained cholesterol bile duct stones; RN in Chemline for octanoic acid, ester with 1,2,3-propanetriol, MF unknown: 11140-04-8; RN for octanoic acid, 2,3-dihydroxypropyl ester (1-monooctanoin): 502-54-5; RN in 9th CI Form Index for (+-)-1-monooctanoin: 19670-49-6. rac-1-monooctanoylglycerol : A rac-1-monoacylglycerol comprising equal amounts of 1-octanoyl-sn-glycerol and 3-octanoyl-sn-glycerol.. 1-monooctanoylglycerol : A 1-monoglyceride that has octanoyl as the acyl group.	2.76	3	1-monoglyceride; octanoate ester; rac-1-monoacylglycerol
orlistat Orlistat: A lactone derivative of LEUCINE that acts as a pancreatic lipase inhibitor to limit the absorption of dietary fat; it is used in the management of obesity.. orlistat : A carboxylic ester resulting from the formal condensation of the carboxy group of N-formyl-L-leucine with the hydroxy group of (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug.	1.99	1	beta-lactone; carboxylic ester; formamides; L-leucine derivative	anti-obesity agent; bacterial metabolite; EC 2.3.1.85 (fatty acid synthase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor
quinine [no description available]	2.02	1	cinchona alkaloid	antimalarial; muscle relaxant; non-narcotic analgesic
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	2.78	3
sodium dodecyl sulfate Sodium Dodecyl Sulfate: An anionic surfactant, usually a mixture of sodium alkyl sulfates, mainly the lauryl; lowers surface tension of aqueous solutions; used as fat emulsifier, wetting agent, detergent in cosmetics, pharmaceuticals and toothpastes; also as research tool in protein biochemistry.. sodium dodecyl sulfate : An organic sodium salt that is the sodium salt of dodecyl hydrogen sulfate.	2.07	1	organic sodium salt	detergent; protein denaturant
crocin crocin: a free radical scavenger	2.15	1
galactomannan galactomannan: a galectin inhibitor. galactomannan : A heteroglycan consisting of a mannan backbone with galactose side groups.	2.03	1	oligosaccharide
alpha-chymotrypsin Chymotrypsin: A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.	2.03	1
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	2.05	1
hydroxyethylcellulose hydroxyethylcellulose: component of contact lens wetting solutions; aldiamed is an artificial saliva; RN given refers to parent cpd. hydroxyethylcellulose : A polysaccharide derivative that is cellulose in which hydroxyethyl groups are bound to some of the hydroxyl groups of the glucopyranose monomers.	2.1	1
rhodamine 123 Rhodamine 123: A fluorescent probe with low toxicity which is a potent substrate for ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1 and the bacterial multidrug efflux transporter. It is used to assess mitochondrial bioenergetics in living cells and to measure the efflux activity of ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1 in both normal and malignant cells. (Leukemia 1997;11(7):1124-30). rhodamine 123(1+) : A cationic fluorescent dye derived from 9-phenylxanthene.	2.44	2	organic cation; xanthene dye	fluorochrome
quercetin [no description available]	2.8	3	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
ubiquinone q2 Ubiquinone Q2: interacts with iron atom to form acceptor quinone complex; RN given refers to cpd with unspecified isomeric designation	2	1	ubiquinones
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	2.42	2	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
calcitriol dihydroxy-vitamin D3: as a major in vitro metabolite of 1alpha,25-dihydroxyvitamin D3, produced in primary cultures of neonatal human keratinocytes	2.03	1	D3 vitamins; hydroxycalciol; triol	antineoplastic agent; antipsoriatic; bone density conservation agent; calcium channel agonist; calcium channel modulator; hormone; human metabolite; immunomodulator; metabolite; mouse metabolite; nutraceutical
vitamin k semiquinone radical vitamin K semiquinone radical: found in active preparations of vitamin K-dependent carboxylase. vitamin K : Any member of a group of fat-soluble 2-methyl-1,4-napthoquinones that exhibit biological activity against vitamin K deficiency. Vitamin K is required for the synthesis of prothrombin and certain other blood coagulation factors.	2.03	1
beta carotene beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.	2.41	2	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
11-cis-retinal Rhodopsin: A purplish-red, light-sensitive pigment found in RETINAL ROD CELLS of most vertebrates. It is a complex consisting of a molecule of ROD OPSIN and a molecule of 11-cis retinal (RETINALDEHYDE). Rhodopsin exhibits peak absorption wavelength at about 500 nm.. 11-cis-retinal : A retinal having 2E,4Z,6E,8E-double bond geometry.	2.07	1	retinal	chromophore; human metabolite; mouse metabolite
leukotriene b4 Leukotriene B4: The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene B4 : A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway.	1.99	1	dihydroxy monocarboxylic acid; hydroxy polyunsaturated fatty acid; leukotriene; long-chain fatty acid	human metabolite; mouse metabolite; plant metabolite; vasoconstrictor agent
hymecromone Hymecromone: A coumarin derivative possessing properties as a spasmolytic, choleretic and light-protective agent. It is also used in ANALYTICAL CHEMISTRY TECHNIQUES for the determination of NITRIC ACID.	2.08	1	hydroxycoumarin	antineoplastic agent; hyaluronic acid synthesis inhibitor
vitamin d 2 Ergocalciferols: Derivatives of ERGOSTEROL formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. They differ from CHOLECALCIFEROL in having a double bond between C22 and C23 and a methyl group at C24.. vitamin D2 : A vitamin D supplement and has been isolated from alfalfa.	1.96	1	hydroxy seco-steroid; seco-ergostane; vitamin D	bone density conservation agent; nutraceutical; plant metabolite; rodenticide
amphotericin b Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.	3.42	7	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
fucoxanthin fucoxanthin: RN given refers to (3S,3'S,5R,5'R,6S,6'R)-isomer. fucoxanthin : An epoxycarotenol that is found in brown seaweed and which exhibits anti-cancer, anti-diabetic, anti-oxidative and neuroprotective properties.	2.11	1
7-hydroxycoumarin 7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.	2.08	1	hydroxycoumarin	fluorescent probe; food component; plant metabolite
glyceryl 2-arachidonate glyceryl 2-arachidonate: binds to cannabinoid receptors; structure in first source. 2-arachidonoylglycerol : An endocannabinoid and an endogenous agonist of the cannabinoid receptors (CB1 and CB2). It is an ester formed from omega-6-arachidonic acid and glycerol.	2.02	1	2-acylglycerol 20:4; endocannabinoid	human metabolite
1-arachidonyl monoglyceride 1-arachidonyl monoglyceride: causes platelet aggregation	1.95	1	1-acylglycerol 20:4
selachyl alcohol selachyl alcohol: RN given refers to (Z-(+-))-isomer; structure	2.71	3	alkylglycerol
(2e)-decenal (2E)-decenal: structure in first source. (2E)-dec-2-enal : A dec-2-enal in which the olefinic double bond has E configuration.	2.06	1	2-decenal	alarm pheromone; mutagen; nematicide
oleylamide oleylamide: plastic additive; can cause contact urticaria; RN given refers to (Z)-isomer; a sleep inducing factor. aliphatic amide : A carboxamide in which the amide linkage is bonded directly to an aliphatic system.. oleamide : A fatty amide derived from oleic acid.	2.01	1	primary fatty amide	human metabolite; plant metabolite
monolinolein monolinolein: inactivates or inhibits African Swine Fever virus. rac-1-monolinoleoylglycerol : A rac-1-monoacylglycerol that is composed of equal amounts of 1-linoleoyl-sn-glycerol and 3-linoleoyl-sn-glycerol.	3.14	5	1-acylglycerol 18:2; rac-1-monoacylglycerol	antiviral agent; human metabolite; plant metabolite
cholesteryl oleate cholesteryl oleate: RN given refers to ((Z)-isomer). cholesteryl oleate : The (Z)-stereoisomer of cholesteryl octadec-9-enoate.	2.02	1	CE(18:1); cholesteryl octadec-9-enoate	mouse metabolite
oleyl alcohol oleyl alcohol: structure; RN given refers to cpd without isomeric designation	1.97	1	fatty alcohol 18:1; long-chain primary fatty alcohol	metabolite; nonionic surfactant
seocalcitol seocalcitol: structure given in first source	2.03	1
deamino arginine vasopressin Deamino Arginine Vasopressin: A synthetic analog of the pituitary hormone, ARGININE VASOPRESSIN. Its action is mediated by the VASOPRESSIN receptor V2. It has prolonged antidiuretic activity, but little pressor effects. It also modulates levels of circulating FACTOR VIII and VON WILLEBRAND FACTOR.	2.06	1	heterodetic cyclic peptide	diagnostic agent; renal agent; vasopressin receptor agonist
lysophosphatidylcholines lysophosphatidylcholine : An acylglycerophosphocholine resulting from partial hydrolysis of a phosphatidylcholine, which removes one of the fatty acyl groups. The structure is depicted in the image where R1 = acyl, R2 = H or where R1 = H, R2 = acyl.	3.49	8	1-O-acyl-sn-glycero-3-phosphocholine
magnesium trisilicate magnesium trisilicate: RN given refers to parent cpd	2.03	1
1,2-oleoylphosphatidylcholine 1,2-oleoylphosphatidylcholine: RN given refers to (Z,Z)-isomer. dioleoyl phosphatidylcholine : A phosphatidylcholine in which the phosphatidyl acyl groups are both oleoyl.	3.74	10	phosphatidylcholine(1+)
2-oleoylglycerol 2-oleoylglycerol : A 2-monoglyceride where the acyl group is (9Z)-octadecenoyl.	2.06	1	2-acylglycerol 18:1; monooleoylglycerol
cesium Cesium: A member of the alkali metals. It has an atomic symbol Cs, atomic number 50, and atomic weight 132.91. Cesium has many industrial applications, including the construction of atomic clocks based on its atomic vibrational frequency.	1.96	1	alkali metal atom
oleylamine oleylamine: promotes fusion of mouse A(9) fibroblasts; RN given refers to parent cpd with unspecified isomeric designation; structure	2.46	2
rubidium Rubidium: An element that is an alkali metal. It has an atomic symbol Rb, atomic number 37, and atomic weight 85.47. It is used as a chemical reagent and in the manufacture of photoelectric cells.	2.38	2	alkali metal atom
indinavir sulfate Indinavir: A potent and specific HIV protease inhibitor that appears to have good oral bioavailability.	2.31	1	dicarboxylic acid diamide; N-(2-hydroxyethyl)piperazine; piperazinecarboxamide	HIV protease inhibitor
ethyl oleate [no description available]	2.47	2	long-chain fatty acid ethyl ester	acaricide; plant metabolite
methyl oleate [no description available]	2.07	1	fatty acid methyl ester
dimyristoylphosphatidylcholine 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine : A 1,2-diacyl-sn-glycero-3-phosphocholine where the two phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).. dimyristoyl phosphatidylcholine : A phosphatidylcholine where the phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).	2.02	1	1,2-diacyl-sn-glycero-3-phosphocholine; phosphatidylcholine 28:0; tetradecanoate ester	antigen; mouse metabolite
silicon Silicon: A trace element that constitutes about 27.6% of the earth's crust in the form of SILICON DIOXIDE. It does not occur free in nature. Silicon has the atomic symbol Si, atomic number 14, and atomic weight [28.084; 28.086].	2.39	2	carbon group element atom; metalloid atom; nonmetal atom
phytochlorin phytochlorin: RN given refers to (2S-trans)-isomer; structure given in the first source	2.17	1
triolein Triolein: (Z)-9-Octadecenoic acid 1,2,3-propanetriyl ester.. triolein : A triglyceride formed by esterification of the three hydroxy groups of glycerol with oleic acid. Triolein is one of the two components of Lorenzo's oil.	3.77	11	triglyceride	Caenorhabditis elegans metabolite; plant metabolite
carbocyanines Carbocyanines: Compounds that contain three methine groups. They are frequently used as cationic dyes used for differential staining of biological materials.	2.15	1	cyanine dye; organic iodide salt	fluorochrome
25-hydroxyvitamin d 2 25-Hydroxyvitamin D 2: 9,10-Secoergosta-5,7,10(19),22-tetraene-3,25-diol. Biologically active metabolite of vitamin D2 which is more active in curing rickets than its parent. The compound is believed to attach to the same receptor as vitamin D2 and 25-hydroxyvitamin D3.	1.96	1	hydroxycalciol; seco-ergostane; vitamin D	bone density conservation agent; human xenobiotic metabolite; nutraceutical
1,2-dielaidoylphosphatidylethanolamine 1,2-dielaidoylphosphatidylethanolamine: RN given refers to (E,E)-isomer; member of a class of cationic lipid formulations called cytofectins	2.38	2
tellurium Tellurium: An element that is a member of the chalcogen family. It has the atomic symbol Te, atomic number 52, and atomic weight 127.60. It has been used as a coloring agent and in the manufacture of electrical equipment. Exposure may cause nausea, vomiting, and CNS depression.	1.96	1	chalcogen; metalloid atom
1-palmitoyl-2-oleoylphosphatidylcholine 1-palmitoyl-2-oleoylphosphatidylcholine: RN given refers to (Z)-isomer	2.72	3
linolenyl alcohol linolenyl alcohol: RN given refers to (Z,Z,Z)-isomer. (9Z,12Z,15Z)-octadecatrien-1-ol : A long chain fatty primary alcohol that is octadecanol containing three double bonds located at positions 9, 12 and 15.	1.96	1	long-chain primary fatty alcohol	antibacterial agent
neo-gambogic acid neo-gambogic acid: from Gamboge (Garcinia hanburryi); structure given in first source	2.11	1
1,2-dioleoylphosphatidylserine 1,2-dioleoylphosphatidylserine: RN given in first source; RN given refers to (R-(Z,Z))-isomer; RN for cpd without isomeric designation not available 6/90. 1,2-dioleoyl-sn-glycero-3-phospho-L-serine : A 3-sn-phosphatidyl L-serine in which the phosphatidyl acyl groups are both oleoyl.. phosphatidylserine(18:1/18:1) : A 3-sn-phosphatidyl-L-serine in which the 1- and 2-acyl groups are octadecenoyl groups.	2.99	4	phosphatidylserine(18:1/18:1)	mouse metabolite
stemphone stemphone: structure given in first source	2.21	1
enkephalin, leucine-2-alanine Enkephalin, Leucine-2-Alanine: A delta-selective opioid (ANALGESICS, OPIOID). It can cause transient depression of mean arterial blood pressure and heart rate.	2.7	3
staurosporine staurosporinium : Conjugate acid of staurosporine.	2.67	3	ammonium ion derivative
dioleoylphosphatidic acid dioleoylphosphatidic acid: RN given refers to (Z)-isomer. dioleoyl phosphatidic acid : A phosphatidic acid in which the phosphatidyl acyl groups are both oleoyl.	2.42	2	1,2-bis(octadec-9-enoyl)phosphatidic acid
chlorhexidine Chlorhexidine: A disinfectant and topical anti-infective agent used also as mouthwash to prevent oral plaque.. chlorhexidine : A bisbiguanide compound with a structure consisting of two (p-chlorophenyl)guanide units linked by a hexamethylene bridge.	2.17	1	biguanides; monochlorobenzenes	antibacterial agent; antiinfective agent
ursodoxicoltaurine tauroursodeoxycholate : An organosulfonate oxoanion that is the conjugate base of tauroursodeoxycholic acid arising from deprotonation of the sulfonate OH group; major species at pH 7.3.. tauroursodeoxycholic acid : A bile acid taurine conjugate derived from ursoodeoxycholic acid.	1.96	1	bile acid taurine conjugate	anti-inflammatory agent; apoptosis inhibitor; bone density conservation agent; cardioprotective agent; human metabolite; neuroprotective agent
psd 502 Lidocaine, Prilocaine Drug Combination: A topical local anesthetic preparation that is composed of a mixture of lidocaine and prilocaine. It is used to provide anesthesia during minor surgery and for the treatment of PREMATURE EJACULATION.	1.99	1
sorbitan monooleate [no description available]	2.1	1	fatty acid ester
zeolites [no description available]	2.21	1
trans-sodium crocetinate trans-sodium crocetinate: vitamin A-analog that increases diffusivity of oxygen in aqueous solutions, including plasma	2.17	1
quininone quininone: RN given refers to cpd without isomeric designation; converted from quinidine by resting cells of Hansenula anomala	2.02	1
acebutolol alpha-D-glucosyl-(1->4)-alpha-D-mannose : An alpha-D-glucosyl-(1->4)-D-mannopyranose in which the anomeric hydroxy group has alpha configuration.	2.69	3	alpha-D-glucosyl-(1->4)-D-mannopyranose
sepharose agarose : A linear polysaccharide made up from alternating D-galactose and 3,6-anhydro-alpha-L-galactopyranose residues joined by alpha-(1->3)- and beta-(1->4)-linkages.	2.03	1
pituitrin Pituitrin: A substance or extract from the neurohypophysis (PITUITARY GLAND, POSTERIOR).	1.97	1
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	1.97	1	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	2.98	4
cholecystokinin Cholecystokinin: A peptide, of about 33 amino acids, secreted by the upper INTESTINAL MUCOSA and also found in the central nervous system. It causes gallbladder contraction, release of pancreatic exocrine (or digestive) enzymes, and affects other gastrointestinal functions. Cholecystokinin may be the mediator of satiety.	2.38	2
alamethicin Alamethicin: A cyclic nonadecapeptide antibiotic that can act as an ionophore and is produced by strains of Trichoderma viride. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	1.99	1
gramicidin a Gramicidin: A group of peptide antibiotics from BACILLUS brevis. Gramicidin C or S is a cyclic, ten-amino acid polypeptide and gramicidins A, B, D are linear. Gramicidin is one of the two principal components of TYROTHRICIN.	4.28	19
glucagon Glucagon: A 29-amino acid pancreatic peptide derived from proglucagon which is also the precursor of intestinal GLUCAGON-LIKE PEPTIDES. Glucagon is secreted by PANCREATIC ALPHA CELLS and plays an important role in regulation of BLOOD GLUCOSE concentration, ketone metabolism, and several other biochemical and physiological processes. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1511). glucagon : A 29-amino acid peptide hormone consisting of His, Ser, Gln, Gly, Thr, Phe, Thr, Ser, Asp, Tyr, Ser, Lys, Tyr, Leu, Asp, Ser, Arg, Arg, Ala, Gln, Asp, Phe, Val, Gln, Trp, Leu, Met, Asn and Thr residues joined in sequence.	1.97	1	peptide hormone
oligonucleotides [no description available]	2.43	2
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	3.46	7	glycoside
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	5.13	45	1,2-diacyl-sn-glycero-3-phosphocholine
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	2.43	2
chitosan [no description available]	4.09	14
esterastin esterastin: inhibitor of esterases; structure	1.96	1
bucladesine Bucladesine: A cyclic nucleotide derivative that mimics the action of endogenous CYCLIC AMP and is capable of permeating the cell membrane. It has vasodilator properties and is used as a cardiac stimulant. (From Merck Index, 11th ed). bucladesine : A 3',5'-cyclic purine nucleotide that is the 2'-butanoate ester and 6-N-butanoyl derivative of 3',5'-cyclic AMP.	2	1	3',5'-cyclic purine nucleotide
osteum [no description available]	2.98	4	organic molecular entity
stearates Stearates: Salts and esters of the 18-carbon saturated, monocarboxylic acid--stearic acid.	1.97	1
merocyanine dye merocyanine dye: fluorescent dye used for studying axons 2 position on pyrimidine ring may be S or O; RN given refers to Na salt; structure	1.95	1
phosphatidylcholines 1-stearoyl-2-oleoyl-sn-glycero-3-phosphocholine: RN given refers to (Z)-isomer. 1-stearoyl-2-oleoyl-sn-glycero-3-phosphocholine : A phosphatidylcholine 36:1 in which the phosphatidyl acyl groups at positions 1 and 2 are stearoyl and oleoyl respectively.	2	1	1-acyl-2-oleoyl-sn-glycero-3-phosphocholine betaine; 1-octadecanoyl-2-octadecenoyl-sn-glycero-3-phosphocholine
ethyl cellulose [no description available]	2.49	2	glycoside
neurotensin neurotensin, Tyr(11)-: RN given refers to parent cpd & (D)-isomer; RN for cpd without isomeric designation not avail 5/91	3.29	2	peptide hormone	human metabolite; mitogen; neurotransmitter; vulnerary
mannans [no description available]	2.03	1
piperidines Piperidines: A family of hexahydropyridines.	2.79	3
methylcellulose Methylcellulose: Methylester of cellulose. Methylcellulose is used as an emulsifying and suspending agent in cosmetics, pharmaceutics and the chemical industry. It is used therapeutically as a bulk laxative.	2.05	1
1,2-dioleoyl-sn-glycero-3-phosphoglycerol 1,2-dioleoyl-sn-glycero-3-phospho-(1'-sn-glycerol) : A 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) in which both acyl groups are specified as oleoyl.	2.49	2	1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol)
chondroitin Chondroitin: A mucopolysaccharide constituent of chondrin. (Grant & Hackh's Chemical Dictionary, 5th ed)	2.25	1
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	2.75	3	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
tetracycline Tetracycline: A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.. tetracycline : A broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.	2.02	1
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	2.08	1	benzenes; hydroxycoumarin; methyl ketone
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	3.31	6
sorbitan monolaurate sorbitan monolaurate: span type materials are artificial esters of the common fatty acids & hexitol anhydrides derived from sorbitol	2.47	2
caseins Caseins: A mixture of related phosphoproteins occurring in milk and cheese. The group is characterized as one of the most nutritive milk proteins, containing all of the common amino acids and rich in the essential ones.	3.29	6
phthalocyanine phthalocyanine : A tetrapyrrole fundamental parent that consists of four isoindole-type units, with the connecting carbon atoms in the macrocycle replaced by nitrogen.	2.06	1	phthalocyanines; tetrapyrrole fundamental parent
oridonin [no description available]	2.15	1
nonactin nonactin: macrolide tetrolide antibiotic isolated from cycloheximide-producing species of Streptomyces; minor descriptor (75-86); on-line & INDEX MEDICUS search ANTIBIOTICS (75-86)	2.36	2
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	3.83	11
silybin Silybin: The major active component of silymarin flavonoids extracted from seeds of the MILK THISTLE, Silybum marianum; it is used in the treatment of HEPATITIS; LIVER CIRRHOSIS; and CHEMICAL AND DRUG INDUCED LIVER INJURY, and has antineoplastic activity; silybins A and B are diastereomers.	2.51	2
lactoferrin Lactoferrin: An iron-binding protein that was originally characterized as a milk protein. It is widely distributed in secretory fluids and is found in the neutrophilic granules of LEUKOCYTES. The N-terminal part of lactoferrin possesses a serine protease which functions to inactivate the TYPE III SECRETION SYSTEM used by bacteria to export virulence proteins for host cell invasion.	2.25	1
muramidase Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.	3.27	6
acyclovir Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.	2	1	2-aminopurines; oxopurine	antimetabolite; antiviral drug
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	2.17	1	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor
sildenafil citrate Sildenafil Citrate: A PHOSPHODIESTERASE TYPE-5 INHIBITOR; VASODILATOR AGENT and UROLOGICAL AGENT that is used in the treatment of ERECTILE DYSFUNCTION and PRIMARY PULMONARY HYPERTENSION.. sildenafil citrate : The citrate salt of sildenafil.	2.17	1	citrate salt	EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; vasodilator agent
maltodextrin maltodextrin : A dextrin in which the D-glucose units are linked by alpha-(1->4) glycosidic bonds.	2.52	2
dinactin dinactin: homolog of the above minor; a macrotetrolide	1.96	1
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	2.4	2

Condition	Relationship Strength	Studies
Duncan Disease [description not available]	2.21	1
Lymphoproliferative Disorders Disorders characterized by proliferation of lymphoid tissue, general or unspecified.	2.21	1
Breast Cancer [description not available]	2.79	3
Breast Neoplasms Tumors or cancer of the human BREAST.	2.79	3
Candida Infection [description not available]	2.08	1
Candidiasis Infection with a fungus of the genus CANDIDA. It is usually a superficial infection of the moist areas of the body and is generally caused by CANDIDA ALBICANS. (Dorland, 27th ed)	2.08	1
Aspergillus Infection [description not available]	2.03	1
Aspergillosis Infections with fungi of the genus ASPERGILLUS.	2.03	1
Benign Neoplasms [description not available]	3.04	4
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	3.04	4
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	4.52	8
Malignant Melanoma [description not available]	3.08	4
Cancer of Skin [description not available]	2.61	2
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	3.08	4
Skin Neoplasms Tumors or cancer of the SKIN.	2.61	2
Benign Neoplasms, Brain [description not available]	2.53	2
Astrocytoma, Grade IV [description not available]	2.53	2
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	2.53	2
Glioblastoma A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.	2.53	2
Cancer of Lung [description not available]	2.25	1
Lung Neoplasms Tumors or cancer of the LUNG.	2.25	1
Cornea Injuries [description not available]	2.31	1
Burns, Chemical Burns caused by contact with or exposure to CAUSTICS or strong ACIDS.	2.31	1
Corneal Angiogenesis [description not available]	2.31	1
Eye Burns Injury to any part of the eye by extreme heat, chemical agents, or ultraviolet radiation.	2.31	1
Corneal Neovascularization New blood vessels originating from the corneal blood vessels and extending from the limbus into the adjacent CORNEAL STROMA. Neovascularization in the superficial and/or deep corneal stroma is a sequel to numerous inflammatory diseases of the ocular anterior segment, such as TRACHOMA, viral interstitial KERATITIS, microbial KERATOCONJUNCTIVITIS, and the immune response elicited by CORNEAL TRANSPLANTATION.	2.31	1
Corneal Injuries Damage or trauma inflicted to the CORNEA by external means.	2.31	1
Weight Gain Increase in BODY WEIGHT over existing weight.	2.31	1
Acute Liver Injury, Drug-Induced [description not available]	2.17	1
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	2.17	1
Anasarca [description not available]	2.77	3
Innate Inflammatory Response [description not available]	2.81	3
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	2.77	3
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	2.81	3
Acne [description not available]	2.17	1
Acne Vulgaris A chronic disorder of the pilosebaceous apparatus associated with an increase in sebum secretion. It is characterized by open comedones (blackheads), closed comedones (whiteheads), and pustular nodules. The cause is unknown, but heredity and age are predisposing factors.	2.17	1
Dysplastic Nevus Syndrome, Hereditary [description not available]	2.17	1
Lysosomal Enzyme Disorders [description not available]	2.17	1
Infection, Wound [description not available]	2.21	1
Infections, Staphylococcal Skin [description not available]	2.21	1
Staphylococcal Skin Infections Infections to the skin caused by bacteria of the genus STAPHYLOCOCCUS.	2.21	1
Infectious Endophthalmitis Infectious condition of the internal eye.	2.21	1
Endophthalmitis Suppurative inflammation of the tissues of the internal structures of the eye frequently associated with an infection.	2.21	1
Airflow Obstruction, Chronic [description not available]	2.48	2
Asthma, Bronchial [description not available]	2.48	2
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	2.48	2
Pulmonary Disease, Chronic Obstructive A disease of chronic diffuse irreversible airflow obstruction. Subcategories of COPD include CHRONIC BRONCHITIS and PULMONARY EMPHYSEMA.	2.48	2
Arthritis, Degenerative [description not available]	2.5	2
Osteoarthritis A progressive, degenerative joint disease, the most common form of arthritis, especially in older persons. The disease is thought to result not from the aging process but from biochemical changes and biomechanical stresses affecting articular cartilage. In the foreign literature it is often called osteoarthrosis deformans.	2.5	2
Burns Injuries to tissues caused by contact with heat, steam, chemicals (BURNS, CHEMICAL), electricity (BURNS, ELECTRIC), or the like.	2.1	1
Intraocular Pressure The pressure of the fluids in the eye.	2.08	1
Parodontosis [description not available]	2.42	2
Periodontal Diseases Pathological processes involving the PERIODONTIUM including the gum (GINGIVA), the alveolar bone (ALVEOLAR PROCESS), the DENTAL CEMENTUM, and the PERIODONTAL LIGAMENT.	2.42	2
Arthritides, Bacterial [description not available]	2.11	1
Fungal Diseases [description not available]	2.11	1
Mycoses Diseases caused by FUNGI.	2.11	1
Embolism, Pulmonary [description not available]	2.1	1
Pulmonary Embolism Blocking of the PULMONARY ARTERY or one of its branches by an EMBOLUS.	2.1	1
Pleuropneumonia Inflammation of the lung parenchyma that is associated with PLEURISY, inflammation of the PLEURA.	2.1	1
Swine Diseases Diseases of domestic swine and of the wild boar of the genus Sus.	2.1	1
Actinobacillus Infections Infections with bacteria of the genus ACTINOBACILLUS.	2.1	1
Phlegmon [description not available]	2.11	1
Cellulitis An acute, diffuse, and suppurative inflammation of loose connective tissue, particularly the deep subcutaneous tissues, and sometimes muscle, which is most commonly seen as a result of infection of a wound, ulcer, or other skin lesions.	2.11	1
Acute Confusional Senile Dementia [description not available]	2.52	2
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	2.52	2
Candidiasis, Invasive An important nosocomial fungal infection with species of the genus CANDIDA, most frequently CANDIDA ALBICANS. Invasive candidiasis occurs when candidiasis goes beyond a superficial infection and manifests as CANDIDEMIA, deep tissue infection, or disseminated disease with deep organ involvement.	2.13	1
Infectious Skin Diseases [description not available]	2.15	1
Skin Diseases, Infectious Skin diseases caused by bacteria, fungi, parasites, or viruses.	2.15	1
Cancer of Pancreas [description not available]	2.4	2
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	2.4	2
Electrolytes Substances that dissociate into two or more ions, to some extent, in water. Solutions of electrolytes thus conduct an electric current and can be decomposed by it (ELECTROLYSIS). (Grant & Hackh's Chemical Dictionary, 5th ed)	2.67	3
Linear Skull Fracture [description not available]	2.07	1
Autosomal Dominant Juvenile Parkinson Disease [description not available]	2.07	1
Parkinsonian Disorders A group of disorders which feature impaired motor control characterized by bradykinesia, MUSCLE RIGIDITY; TREMOR; and postural instability. Parkinsonian diseases are generally divided into primary parkinsonism (see PARKINSON DISEASE), secondary parkinsonism (see PARKINSON DISEASE, SECONDARY) and inherited forms. These conditions are associated with dysfunction of dopaminergic or closely related motor integration neuronal pathways in the BASAL GANGLIA.	2.07	1
Invasiveness, Neoplasm [description not available]	2.44	2
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	2.07	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.07	1
Cardiometabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components not only include metabolic dysfunctions of METABOLIC SYNDROME but also HYPERTENSION, and ABDOMINAL OBESITY.	2.07	1
Metabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components of metabolic syndrome include ABDOMINAL OBESITY; atherogenic DYSLIPIDEMIA; HYPERTENSION; HYPERGLYCEMIA; INSULIN RESISTANCE; a proinflammatory state; and a prothrombotic (THROMBOSIS) state.	2.07	1
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	2.07	1
Extravascular Hemolysis [description not available]	2.07	1
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.07	1
Polyarthritis [description not available]	2.08	1
Arthritis Acute or chronic inflammation of JOINTS.	2.08	1
Palmoplantaris Pustulosis [description not available]	2.1	1
Dermatitis Any inflammation of the skin.	2.1	1
Psoriasis A common genetically determined, chronic, inflammatory skin disease characterized by rounded erythematous, dry, scaling patches. The lesions have a predilection for nails, scalp, genitalia, extensor surfaces, and the lumbosacral region. Accelerated epidermopoiesis is considered to be the fundamental pathologic feature in psoriasis.	2.1	1
Pericementitis [description not available]	2.4	2
Periodontitis Inflammation and loss of connective tissues supporting or surrounding the teeth. This may involve any part of the PERIODONTIUM. Periodontitis is currently classified by disease progression (CHRONIC PERIODONTITIS; AGGRESSIVE PERIODONTITIS) instead of age of onset. (From 1999 International Workshop for a Classification of Periodontal Diseases and Conditions, American Academy of Periodontology)	2.4	2
Cancer of Prostate [description not available]	2.02	1
Hormone-Dependent Neoplasms [description not available]	2.02	1
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2.02	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.44	2
Bladder Cancer [description not available]	2.02	1
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.02	1
Bleeding [description not available]	2.04	1
Blood Loss, Surgical Loss of blood during a surgical procedure.	2.04	1
Hemorrhage Bleeding or escape of blood from a vessel.	2.04	1
HIV Coinfection [description not available]	2.04	1
HIV Infections Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).	2.04	1
Pocket, Periodontal [description not available]	1.98	1
Periodontal Pocket An abnormal extension of a gingival sulcus accompanied by the apical migration of the epithelial attachment and bone resorption.	1.98	1
Adenocarcinoma, Basal Cell [description not available]	1.98	1
Cancer of Colon [description not available]	1.98	1
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	1.98	1
Colonic Neoplasms Tumors or cancer of the COLON.	1.98	1
Infections, Staphylococcal [description not available]	1.98	1
Abscess Accumulation of purulent material in tissues, organs, or circumscribed spaces, usually associated with signs of infection.	1.98	1
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	1.98	1
Infections, Plasmodium [description not available]	2	1
Malaria A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.	2	1
Colitis Gravis [description not available]	2	1
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	2	1
Allergy, Drug [description not available]	1.97	1
Drug Hypersensitivity Immunologically mediated adverse reactions to medicinal substances used legally or illegally.	1.97	1
Diabetic Angiopathies VASCULAR DISEASES that are associated with DIABETES MELLITUS.	1.97	1
Carcinoma, Epidermoid [description not available]	1.97	1
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	1.97	1
Middle Ear Inflammation [description not available]	1.97	1
Otitis Media Inflammation of the MIDDLE EAR including the AUDITORY OSSICLES and the EUSTACHIAN TUBE.	1.97	1
Goldblatt Syndrome [description not available]	1.97	1
Hypertension, Renovascular Hypertension due to RENAL ARTERY OBSTRUCTION or compression.	1.97	1
Experimental Leukemia [description not available]	1.97	1

1-monooleoyl-rac-glycerol

Description

Cross-References

Synonyms (171)

Research Excerpts

Toxicity

Pharmacokinetics

Bioavailability

Dosage Studied

Occurs in Manufacturing (104 Product(s))

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Roles (1)

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Protein Targets (1)

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Biological Processes (7)

Molecular Functions (7)

Ceullar Components (3)

Bioassays (4)

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Studies (601)

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Research Demand Index: 8.40

Study Types

1-monooleoyl-rac-glycerol

Description

Cross-References

Synonyms (171)

Research Excerpts

Toxicity

Pharmacokinetics

Bioavailability

Dosage Studied

Occurs in Manufacturing (104 Product(s))

Product Categories

Products

Roles (1)

Drug Classes (2)

Protein Targets (1)

Inhibition Measurements

Biological Processes (7)

Molecular Functions (7)

Ceullar Components (3)

Bioassays (4)

Research

Studies (601)

Market Indicators

Research Demand Index: 8.40

Study Types

Related Drugs (419)

Related Conditions (123)