methylformamide profile

Methylformamide (N-methylformamide, HCONHCH3) is a colorless, hygroscopic liquid that is miscible with water and most organic solvents. It is a versatile chemical used in various applications, including as a solvent, a reagent in organic synthesis, and a component in formulations for textiles, plastics, and pharmaceuticals. Methylformamide can be synthesized through the reaction of formamide with methanol in the presence of a catalyst. It has been shown to exhibit various biological effects, including cytotoxicity and genotoxicity. Its importance lies in its role as a versatile solvent and reagent, particularly in the synthesis of pharmaceuticals, pesticides, and other fine chemicals. Research into methylformamide is ongoing due to its potential applications in diverse fields, including materials science, nanotechnology, and green chemistry. Studies focus on its synthesis, properties, reactivity, and biological effects, aiming to optimize its use and explore its potential for new applications.'

N-methylformamide : A member of the class of formamides having a N-methyl substituent. [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]

ID Source	ID
PubMed CID	31254
CHEMBL ID	9240
CHEBI ID	7438
MeSH ID	M0043801

Synonym
x 188
nsc 3051
wln: vhm1
monomethylformamide
nsc-3051
formamide, n-methyl-
ek 7011
nsc3051
methylformamide
formamide, n-methyl- ( )
NCI60_002574
methanimidic acid, methyl-
(e)-methylimidoformic acid
formamide, methyl-
n-methyl-formimidic acid
methylimidoformic acid
n-methyl-formic acid-amide
(z)-methylimidoformic acid
formic acid amide, n-methyl-
hsdb 100
ai3-26076
einecs 204-624-6
n-methyl formamide
brn 1098352
123-39-7
NMF ,
n-methylformamide
n-methylformamide, 99%
AKOS000118787
n-formylmethylamine
CHEMBL9240
FT-0652807
F0059
n-monomethylformamide
hconhch3
n-methyl-formamide
chebi:7438 ,
n-methylmethanamide
A805066
STL146549
xpe4g7y986 ,
unii-xpe4g7y986
4-04-00-00170 (beilstein handbook reference)
ec 204-624-6
FT-0638572
n-methylformamide [hsdb]
n-methylformamide [mi]
n-methyl-d3-formamide
BBL027430
n-methylcarboxamide
87955-92-8
DTXSID0025608
mfcd00003280
J-004934
F0001-0365
methyl-methanimidic acid
n-methyl formic acid amide
Q138742
863653-47-8
SB85388
EN300-19419
Z104473766

Excerpt	Reference	Relevance
"N-methylformamide (NMF) is an anti-proliferative, differentiating agent studied in several cell lines as well as in preclinical and clinical trials, whose mechanisms of action are still unclear. "	( N-methylformamide and 9-hydroxystearic acid: two anti-proliferative and differentiating agents with different modes of action in colon cancer cells. Boga, C; Calonghi, N; Masotti, L; Pagnotta, E, 2006)	1.78
"N-Methylformamide is an antitumour drug with hepatotoxic properties. "	( Investigation of the mechanism of hepatotoxicity of N-methylformamide in mice: effects on calcium sequestration in hepatic microsomes and mitochondria and on hepatic plasma membrane potential. Chahwala, SB; Gescher, A; Whitby, H, 1984)	1.24
"N-Methylformamide (NMF) is a metabolite of dimethylformamide (DMF), a solvent with wide applications in the chemical industry. "	( Developmental toxicity of N-methylformamide administered by gavage to CD rats and New Zealand white rabbits. Kelich, SL; Mercieca, MD; Pohland, RC, 1995)	1.31
"N-Methylformamide (NMF) is a polar solvent with maturational activity, i.e., it induces malignant cells to form more differentiated phenotypes. "	( The effect of N-methylformamide on radiocurability of murine tumors. Iwakawa, M; Milas, L, 1988)	1.34
"N-methylformamide (NMF) is a polar-planar solvent with both cytotoxic and differentiating activity in preclinical models; it also acts as a radiosensitizer. "	( Phase I trial of N-methylformamide (NMF, NSC 3051). Aisner, J; Donehower, M; Fortner, CL; O'Dwyer, PJ; Sigman, LM; Van Echo, DA, 1985)	1.32

Excerpt	Reference	Relevance
"N-Methylformamide has been identified as a crucial promoter of C-CF(3) bond formation from the Pd center."	( Pd(II)-catalyzed ortho trifluoromethylation of arenes and insights into the coordination mode of acidic amide directing groups. Dai, HX; Wasa, M; Yu, JQ; Zhang, XG, 2012)	0.94
"N-Methylformamide has no influence on the NAD-synthesis induced by nicotinamide or tryptophan."	( Influence of N-methylformamide on the development, the NAD synthesis, and the activity of the ADPR transferase of rat embryos. Grahn, H; Grätz, R; Kröger, H, 1983)	1.18
"N-Methylformamide (NMF) has been reported to cause liver damage in animals and man. "	( An investigation of the mechanism of hepatotoxicity of the antitumour agent N-methylformamide in mice. Gescher, A; Levy, L; Whitby, H, 1984)	1.22
"N-Methylformamide (NMF) has been an agent of considerable interest to oncologists because of its broad spectrum of preclinical antitumor activity, tumor-differentiating abilities, and radiosensitizing and chemosensitizing properties. "	( Clinical pharmacology of oral and i.v. N-methylformamide: a pharmacologic basis for lack of clinical antineoplastic activity. Donehower, RC; Ettinger, DS; Grochow, LB; Noe, DA; Orr, DW; Rowinsky, EK, 1988)	1.26
"Dimethylformamide has been used as a model inducer in carcinoma and fibroblastic models."	( Alkylformamides as inducers of tumour cell differentiation--a mini-review. Hickman, JA; Langdon, SP, 1987)	0.83

Excerpt	Reference	Relevance
" To study the mechanism of this toxicity, suspensions of mouse hepatocytes were tested as an in vitro model system suitable for the study of the relationship between (i) the toxic potential of formamides, (ii) their metabolism to N-alkylcarbamoylating species, and (iii) their ability to deplete hepatic glutathione pools."	( Cytotoxicity and metabolism of the hepatotoxin N-methylformamide and related formamides in mouse hepatocytes. Gescher, A; Mráz, J; Shaw, AJ, 1988)	0.53
" A mild granulocytosis was seen in this strain after administration of the LD50 (2300 mg/kg) dosage."	( Studies on the toxicity of the antitumour agent N-methylformamide in mice. Chubb, D; Gescher, A; Hickman, JA; Langdon, SP; Stevens, MF, 1985)	0.52
" Comparison of the acute toxicity of DMF, DMF-OH and NMF shows that NMF is more toxic than DMF-OH, which is itself more toxic than DMF."	( In vivo metabolism of dimethylformamide and relationship to toxicity in the male rat. Lauwerys, R; Scailteur, V, 1984)	0.57
" HMF is considerably less toxic to tumour-bearing BDF1 mice than NMF and, unlike NMF, does not reduce hepatic glutathione levels in vivo."	( The formation and metabolism of N-hydroxymethyl compounds--IV. Cytotoxicity and antitumour activity of N-hydroxymethylformamide, a putative metabolite of N-methylformamide (NSC 3051). Cooksey, PG; Gate, EN; Gescher, A; Hickman, JA; Langdon, SP; Stevens, MF, 1983)	0.48
"7 mmol/kg DMF, HMMF, or NMF showed i) that DMF is more toxic than HMMF or NMF, and ii) that hepatotoxicity occurs later for DMF than for HMMF or NMF."	( Metabolism and hepatotoxicity of N,N-dimethylformamide, N-hydroxymethyl-N-methylformamide, and N-methylformamide in the rat. Belpaire, FM; Buylaert, W; Rosseel, MT; Van den Bulcke, M; Wijnants, P, 1994)	0.56
" First convincingly introduced by Baxter and Lathe in 1971, the concept that certain amides can block toxic effects of dimethyl sulfoxide (Me(2)SO) was contradicted by direct experiments in 1990."	( Cryoprotectant toxicity neutralization. Fahy, GM, 2010)	0.36

Excerpt	Reference	Relevance
"The effect of N-methylformamide (NMF) in combination with Adriamycin (ADM) and cis-diamminedichloroplatinum (DDP) on the cell survival and cell cycle kinetics of two human tumour lines was assessed: HT29 colon carcinoma and M14 melanoma cells were exposed to ADM and DDP alone or in combination with a non-cytotoxic dose of NMF, according to different schedules."	( Importance of cell cycle perturbations on the effectiveness of N-methylformamide and anti-neoplastic drugs in combination. Candiloro, A; Cucco, C; D'Agnano, I; Marangolo, M; Zupi, G, 1991)	0.87

Excerpt	Reference	Relevance
" The bioavailability with oral administration is 90% to 95%."	( N-methylformamide: cytotoxic, radiosensitizer, or chemosensitizer. Clagett-Carr, K; Hoth, DF; Leyland-Jones, B; Plowman, J; Sarosy, G, 1988)	1
" Parallel bioavailability studies confirmed excellent absorption of the drug."	( Phase I trial of N-methylformamide. Dubbelman, R; McVie, JG; Simonetti, G; ten Bokkel Huinink, WW, 1984)	0.6

Excerpt	Relevance	Reference
"The S-(N-methylcarbamoyl) derivatives of glutathione, cysteine and N-acetylcysteine, the S-linked conjugates derived from a reactive metabolite of N-methylformamide (NMF), were studied in mice dosed with an equimolar mixture of NMF and deuterium-labelled NMF."	( The use of mass spectrometry in the study of chemically-reactive drug metabolites. Application of MS/MS and LC/MS to the analysis of glutathione- and related S-linked conjugates of N-methylformamide. Baillie, TA; Howald, WN; Pearson, PG; Rashed, MS, 1989)	0.67
" Further evidence that methylamine was a metabolite of N-methylformamide was provided by ion pair HPLC analysis of urine from mice dosed with [14C]methyl-labeled N-methylformamide."	( The fate of N-methylformamide in mice. Routes of elimination and characterization of metabolites. Gescher, A; Kestell, P; Slack, JA, )	0.74
" After injection of NMF at its LD10 (800 mg/kg) dosage the total peripheral white blood cell and platelet counts were unchanged in BALB/c mice."	( Studies on the toxicity of the antitumour agent N-methylformamide in mice. Chubb, D; Gescher, A; Hickman, JA; Langdon, SP; Stevens, MF, 1985)	0.52
" Pregnant rats and rabbits were dosed once daily by gavage on Gestation Days 6-15 and 6-18, respectively."	( Developmental toxicity of N-methylformamide administered by gavage to CD rats and New Zealand white rabbits. Kelich, SL; Mercieca, MD; Pohland, RC, 1995)	0.59
" Motility parameters were related to urinary NMF in a dose-response manner but were not related to airborne DMF."	( Sperm function in workers exposed to N,N-dimethylformamide in the synthetic leather industry. Chang, HY; Guo, YL; Hsu, PC; Shih, TS; Tsai, CY, 2004)	0.59
" One approach for improving the predictive success of compound toxicity has been to compare the gene expression profile in preclinical models dosed with novel compounds to a gene expression database generated from compounds with known toxicity."	( Identification of potential genomic biomarkers of hepatotoxicity caused by reactive metabolites of N-methylformamide: Application of stable isotope labeled compounds in toxicogenomic studies. Atherton, J; Jiang, P; Kostrubsky, S; Madore, S; Mutlib, A; Nelson, S; Obert, L, 2006)	0.55
" Few studies have assessed the dose-response relationships between internal exposure biomarkers and liver injury in DMF exposed populations."	( A Comparative Benchmark Dose Study for N, N-Dimethylformamide Induced Liver Injury in a Chinese Occupational Cohort. Cheng, J; Guan, M; Jiang, H; Jiang, X; Leng, S; Liu, Q; Wang, C; Wu, Z; Xu, B; Ye, M; Zhang, M; Zhao, W; Zheng, M, 2017)	0.71
" Specific degradation rates of NMF and MDG under both aerobic and anoxic conditions decreased in the matrix of full-scale wastewater, and high copper dosage would further reduce the degradation rates."	( Effects of copper on biological treatment of NMF- and MDG-containing wastewater from TFT-LCD industry. Cheng, HH; Lee, YC; Lu, IC; Pien, TT; Whang, LM, 2020)	0.56

Class	Description
formamides	Amides with the general formula R(1)R(2)NCHO (R(1) and R(2) can be H).
[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]

Assay ID	Title	Year	Journal	Article
AID1079947	Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079935	Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID122376	Antitumor activity was evaluated for the compound against the M5076 reticulum cell sarcoma in mice and the % T/C(treated/control) value was calculated at optimal dose of 200 mg/kg	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID110148	Antitumor activity was evaluated against the M5076 reticulum cell sarcoma in mice measured as Control tumor volume for the treated at the optimal dose 25 mg/Kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID110147	Antitumor activity was evaluated against the M5076 reticulum cell sarcoma in mice measured as Control tumor volume for the treated at the optimal dose 200 mg/Kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID110029	Antitumor activity was evaluated against the TLX5 lymphoma in mice measured for control as death day at a optimal dose of 800 mg/Kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID1079937	Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079948	Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID116889	Antitumor activity was evaluated against the M5076 reticulum cell sarcoma in mice at dose of 400-6.25 mg/kg per day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID122260	Antitumor activity was evaluated against the TLX5 lymphoma in mice measured as treated to control at a optimal dose of 400 mg/Kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID110031	Antitumor activity was evaluated against the TLX5 lymphoma in mice measured for control as death day at the below optimal dose 400 mg/Kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID110146	Antitumor activity was evaluated against the M5076 reticulum cell sarcoma in mice measured as Control tumor volume for the treated at the optimal dose 100 mg/kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID118238	Antitumor activity was evaluated against the TLX5 lymphoma measured as mean death day for the treated at a optimal dose of 200 mg/Kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID118810	Antitumor activity was evaluated against the M5076 reticulum cell sarcoma in mice measured as mean tumor volume for the treated at the optimal dose 50 mg/Kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID1079942	Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079940	Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID122258	Antitumor activity was evaluated against the TLX5 lymphoma in mice measured as treated to control at a optimal dose of 100 mg/Kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID118239	Antitumor activity was evaluated against the TLX5 lymphoma measured as mean death day for the treated at a optimal dose of 400 mg/Kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID110028	Antitumor activity was evaluated against the TLX5 lymphoma in mice measured for control as death day at a optimal dose of 200 mg/Kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID1079932	Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079936	Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079938	Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID110151	Antitumor activity was evaluated against the M5076 reticulum cell sarcoma in mice measured as Control tumor volume for the treated at the optimal dose 50 mg/kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID118806	Antitumor activity was evaluated against the M5076 reticulum cell sarcoma in mice measured as mean tumor volume for the treated at the optimal dose 100 mg/Kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID1079931	Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079949	Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID122379	Antitumor activity was evaluated for the compound against the M5076 reticulum cell sarcoma in mice and the % T/C(treated/control) value was calculated at optimal dose of 50 mg/kg	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID118808	Antitumor activity was evaluated against the M5076 reticulum cell sarcoma in mice measured as mean tumor volume for the treated at the optimal dose 25 mg/Kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID1079943	Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID116705	Antitumor activity was evaluated against the M5076 reticulum cell sarcoma in mice at dose of 400-6.25 mg/kg per day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID118237	Antitumor activity was evaluated against the TLX5 lymphoma measured as mean death day for the treated at a optimal dose of 100 mg/Kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID118240	Antitumor activity was evaluated against the TLX5 lymphoma measured as mean death day for the treated at a optimal dose of 800 mg/Kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID1079944	Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID122377	Antitumor activity was evaluated for the compound against the M5076 reticulum cell sarcoma in mice and the % T/C(treated/control) value was calculated at optimal dose of 25 mg/kg	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID1079945	Animal toxicity known. [column 'TOXIC' in source]
AID1079933	Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079941	Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID122266	Antitumor activity was evaluated for the compound against the M5076 reticulum cell sarcoma in mice and the % T/C(treated/control) value was calculated at optimal dose of 100 mg/kg	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID1079934	Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID122259	Antitumor activity was evaluated against the TLX5 lymphoma in mice measured as treated to control at a optimal dose of 200 mg/Kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID1079939	Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID122261	Antitumor activity was evaluated against the TLX5 lymphoma in mice measured as treated to control at a optimal dose of 800 mg/Kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
AID1079946	Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID110027	Antitumor activity was evaluated against the TLX5 lymphoma in mice measured for control as death day at a optimal dose of 100 mg/Kg/day	1986	Journal of medicinal chemistry, Jun, Volume: 29, Issue:6	Structural studies on bioactive compounds. 4. A structure-antitumor activity study on analogues of N-methylformamide.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	116 (45.31)	18.7374
1990's	50 (19.53)	18.2507
2000's	54 (21.09)	29.6817
2010's	30 (11.72)	24.3611
2020's	6 (2.34)	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	7 (2.55%)	5.53%
Reviews	7 (2.55%)	6.00%
Case Studies	1 (0.36%)	4.05%
Observational	0 (0.00%)	0.25%
Other	260 (94.55%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
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.	1.99	1	0	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.	2.93	4	0	ethanediol; glycol	metabolite; mouse metabolite; solvent; toxin
acetamide acetimidic acid : A carboximidic acid that is acetic acid in which the carbonyl oxygen is replaced by an imino group.	7.48	2	0	acetamides; carboximidic acid; monocarboxylic acid amide; N-acylammonia
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	1.98	1	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
benzene [no description available]	7.01	1	0	aromatic annulene; benzenes; volatile organic compound	carcinogenic agent; environmental contaminant; non-polar solvent
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	2.74	3	0	halide anion; monoatomic bromine
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	2.02	1	0	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
butyric acid Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.	3.35	7	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
carbamates [no description available]	2.69	3	0	amino-acid anion
carbon monoxide Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.	2.06	1	0	carbon oxide; gas molecular entity; one-carbon compound	biomarker; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; human metabolite; ligand; metabolite; mitochondrial respiratory-chain inhibitor; mouse metabolite; neurotoxin; neurotransmitter; P450 inhibitor; probe; signalling molecule; vasodilator agent
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	3.04	5	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	2.02	1	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
cytosine [no description available]	1.98	1	0	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae 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.	1.97	1	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
dimethylglycine dimethylglycine: metabolic product of calcium pangamate; mutagen when mixed with nitrite; RN given refers to parent cpd. N,N-dimethylglycine : An N-methylglycine that is glycine carrying two N-methyl substituents.	2.1	1	0	amino acid zwitterion; N-methyl-amino acid; N-methylglycines	Daphnia magna metabolite; human metabolite; mouse metabolite
dimethylamine [no description available]	1.96	1	0	methylamines; secondary aliphatic amine	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.	4.18	17	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	2.03	1	0	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
formamide formimidic acid : A carboximidic acid that is formic acid in which the carbonyl oxygen is replaced by an imino group.. primary carboxamide : A carboxamide resulting from the formal condensation of a carboxylic acid with ammonia; formula RC(=O)NH2.	4.07	15	0	carboximidic acid; formamides; monocarboxylic acid amide; one-carbon compound	solvent
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	8.92	12	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	2.74	3	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	2	1	0	imidazole
pyruvaldehyde Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.. methylglyoxal : A 2-oxo aldehyde derived from propanal.	2.42	2	0	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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.	8.42	7	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.05	1	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	2.05	1	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
4-aminobenzoic acid 4-Aminobenzoic Acid: An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.. 4-ammoniobenzoate : A zwitterion obtained by transfer of a proton from the carboxy to the amino group of 4-aminobenzoic acid.. 4-aminobenzoic acid : An aminobenzoic acid in which the amino group is para to the carboxy group.	2	1	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant 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.	2.41	2	0	glycol; propane-1,2-diols	allergen; human xenobiotic metabolite; mouse metabolite; protic solvent
1-propanol 1-Propanol: A colorless liquid made by oxidation of aliphatic hydrocarbons that is used as a solvent and chemical intermediate.. propan-1-ol : The parent member of the class of propan-1-ols that is propane in which a hydrogen of one of the methyl groups is replaced by a hydroxy group.	2.02	1	0	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
pteridines [no description available]	1.96	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; pteridines
pyridoxal [no description available]	6.97	1	0	hydroxymethylpyridine; methylpyridines; monohydroxypyridine; pyridinecarbaldehyde; vitamin B6	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
sarcosine cocobetaine: N-alkyl-betaine; cause of shampoo dermatitis	2.1	1	0	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.	2.42	2	0	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.	2.03	1	0	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
mandelic acid SAMMA: mandelic acid condensation polymer	1.99	1	0	2-hydroxy monocarboxylic acid; benzenes	antibacterial agent; human xenobiotic metabolite
1,2-dimethylhydrazine 1,2-Dimethylhydrazine: A DNA alkylating agent that has been shown to be a potent carcinogen and is widely used to induce colon tumors in experimental animals.. 1,2-dimethylhydrazine : A member of the class of hydrazines that is hydrazine in which one of the hydrogens attached to each nitrogen is replaced by a methyl group. A powerful DNA alkylating agent and carcinogen, it is used to induce colon cancer in laboratory rats and mice.	1.97	1	0	hydrazines	alkylating agent; carcinogenic agent
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.	2	1	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
altretamine Altretamine: A hexamethyl-2,4,6-triamine derivative of 1,3,5-triazine.	1.96	1	0	triamino-1,3,5-triazine
amifostine anhydrous Amifostine: A phosphorothioate proposed as a radiation-protective agent. It causes splenic vasodilation and may block autonomic ganglia.. amifostine : An organic thiophosphate that is the S-phospho derivative of 2-[(3-aminopropyl)amino]ethanethiol. A prodrug for the free thiol, WR-1065, which is used as a cytoprotectant in cancer chemotherapy and radiotherapy.	1.97	1	0	diamine; organic thiophosphate	antioxidant; prodrug; radiation protective agent
amlodipine Amlodipine: A long-acting dihydropyridine calcium channel blocker. It is effective in the treatment of ANGINA PECTORIS and HYPERTENSION.. amlodipine : A fully substituted dialkyl 1,4-dihydropyridine-3,5-dicarboxylate derivative, which is used for the treatment of hypertension, chronic stable angina and confirmed or suspected vasospastic angina.	2.25	1	0	dihydropyridine; ethyl ester; methyl ester; monochlorobenzenes; primary amino compound	antihypertensive agent; calcium channel blocker; vasodilator agent
benzamide benzamide : An aromatic amide that consists of benzene bearing a single carboxamido substituent. The parent of the class of benzamides.	2.07	1	0	benzamides
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.	1.98	1	0	aromatic ether; nitrile; polyether; tertiary amino compound
carmustine Carmustine: A cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p462) This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (From Merck Index, 11th ed). carmustine : A member of the class of N-nitrosoureas that is 1,3-bis(2-chloroethyl)urea in which one of the nitrogens is substituted by a nitroso group.	1.96	1	0	N-nitrosoureas; organochlorine compound	alkylating agent; antineoplastic agent
chlorzoxazone Chlorzoxazone: A centrally acting central muscle relaxant with sedative properties. It is claimed to inhibit muscle spasm by exerting an effect primarily at the level of the spinal cord and subcortical areas of the brain. (From Martindale, The Extra Pharmacopoea, 30th ed, p1202). chlorzoxazone : A member of the class of 1,3-benzoxazoles that is 1,3-benzoxazol-2-ol in which the hydrogen atom at position 5 is substituted by chlorine. A centrally acting muscle relaxant with sedative properties, it is used for the symptomatic treatment of painful muscle spasm.	1.98	1	0	1,3-benzoxazoles; heteroaryl hydroxy compound; organochlorine compound	muscle relaxant; sedative
desipramine Desipramine: A tricyclic dibenzazepine compound that potentiates neurotransmission. Desipramine selectively blocks reuptake of norepinephrine from the neural synapse, and also appears to impair serotonin transport. This compound also possesses minor anticholinergic activity, through its affinity to muscarinic receptors.. desipramine : A dibenzoazepine consisting of 10,11-dihydro-5H-dibenzo[b,f]azepine substituted on nitrogen with a 3-(methylamino)propyl group.	2	1	0	dibenzoazepine; secondary amino compound	adrenergic uptake inhibitor; alpha-adrenergic antagonist; antidepressant; cholinergic antagonist; drug allergen; EC 3.1.4.12 (sphingomyelin phosphodiesterase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; serotonin uptake inhibitor
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	3.22	6	0	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
hexamethylene bisacetamide N,N'-diacetyl-1,6-diaminohexane: chemical name obtained from Acta Biol Hung 1990;41(1-3):199-208	2.66	3	0	acetamides
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	2	1	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; radical scavenger; xenobiotic
imipramine Imipramine: The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.. imipramine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom.	2	1	0	dibenzoazepine	adrenergic uptake inhibitor; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
vitamin k 3 Vitamin K 3: A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.	1.97	1	0	1,4-naphthoquinones; vitamin K	angiogenesis inhibitor; antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human urinary metabolite; nutraceutical
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	1.96	1	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
primaquine Primaquine: An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404). primaquine : An N-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at the N(4) position. It is a drug used in the treatment of malaria and Pneumocystis pneumonia.	2.25	1	0	aminoquinoline; aromatic ether; N-substituted diamine	antimalarial
procarbazine Procarbazine: An antineoplastic agent used primarily in combination with mechlorethamine, vincristine, and prednisone (the MOPP protocol) in the treatment of Hodgkin's disease.. procarbazine : A benzamide obtained by formal condensation of the carboxy group of 4-[(2-methylhydrazino)methyl]benzoic acid with the amino group of isopropylamine. An antineoplastic chemotherapy drug used for treatment of Hodgkin's lymphoma. Metabolism yields azo-procarbazine and hydrogen peroxide, which results in the breaking of DNA strands.	3.06	1	0	benzamides; hydrazines	antineoplastic agent
temozolomide [no description available]	1.97	1	0	imidazotetrazine; monocarboxylic acid amide; triazene derivative	alkylating agent; antineoplastic agent; prodrug
urethane [no description available]	7.85	4	0	carbamate ester	fungal metabolite; mutagen
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	1.97	1	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	2.04	1	0	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
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.	6.93	1	0	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
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.	2.02	1	0	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
cyanides Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.	2	1	0	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	1.96	1	0	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
aminopyrine Aminopyrine: A pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of AGRANULOCYTOSIS. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of CYTOCHROME P-450 metabolic activity in LIVER FUNCTION TESTS.. aminophenazone : A pyrazolone that is 1,2-dihydro-3H-pyrazol-3-one substituted by a dimethylamino group at position 4, methyl groups at positions 1 and 5 and a phenyl group at position 2. It exhibits analgesic, anti-inflammatory, and antipyretic properties.	1.96	1	0	pyrazolone; tertiary amino compound	antipyretic; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
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.	2.39	2	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
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.	1.93	1	0	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
dimethylnitrosamine Dimethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties. It causes serious liver damage and is a hepatocarcinogen in rodents.	2.73	3	0	nitrosamine	geroprotector; mutagen
methionine Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.	1.96	1	0	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	2.04	1	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
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.	2.38	2	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
chloroform Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.	2.02	1	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
dimethyl sulfone [no description available]	2.37	2	0	sulfone
dimethylformamide Dimethylformamide: A formamide in which the amino hydrogens are replaced by methyl groups.. N,N-dimethylformamide : A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.	9.15	70	1	formamides; volatile organic compound	geroprotector; hepatotoxic agent; polar aprotic solvent
cytarabine [no description available]	2.67	3	0	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent
valine Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.	2.02	1	0	L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid; valine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae 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.	1.96	1	0	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
methylamine methyl group : An alkyl group that is the univalent group derived from methane by removal of a hydrogen atom.	2.4	2	0	methylamines; one-carbon compound; primary aliphatic amine	mouse metabolite
propane Propane: A three carbon alkane with the formula H3CCH2CH3.	2.42	2	0	alkane; gas molecular entity	food propellant
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	2.41	2	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
ethanethiol ethanethiol: RN given refers to parent cpd; structure. ethanethiol : An alkanethiol that is ethane substituted by a thiol group at position 1. It is added to odorless gaseous products such as liquefied petroleum gas (LPG) to provide a garlic scent which helps warn of gas leaks.	7.42	2	0	alkanethiol	rodenticide
methylethyl ketone methylethyl ketone: solvent; colorless synthetic resins, smokeless powders; may be irritating to eyes, mucous membranes; may be toxic in high concentrations; structure. butanone : Any ketone that is butane substituted by an oxo group at unspecified position.. butan-2-one : A dialkyl ketone that is a four-carbon ketone carrying a single keto- group at position C-2.	2.02	1	0	butanone; dialkyl ketone; methyl ketone; volatile organic compound	bacterial metabolite; polar aprotic solvent
acrylamide [no description available]	2.03	1	0	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
n-methylacetamide N-methylacetamide: RN given refers to parent cpd. N-methylacetamide : A monocarboxylic acid amide that is the N-methyl derivative of acetamide.	9.8	10	0	acetamides; monocarboxylic acid amide	metabolite
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	1.96	1	0	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
styrene Styrene: A colorless, toxic liquid with a strong aromatic odor. It is used to make rubbers, polymers and copolymers, and polystyrene plastics.. styrene : A vinylarene that is benzene carrying a vinyl group. It has been isolated from the benzoin resin produced by Styrax species.	1.99	1	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
propylene carbonate 4-methyl-1,3-dioxolan-2-one: structure in first source	2	1	0
thiophenol thiophenol : A thiol in which the sulfanyl group is attached to a phenyl group.	2	1	0	aryl thiol
2,5-hexanedione 2,5-hexanedione: metabolite of methyl-n-butyl ketone. 2,5-hexanedione : A diketone that is hexane substituted by oxo groups at positions 2 and 5. It is a toxic metabolite of hexane and of 2-hexanone	7.39	2	0	diketone; methyl ketone	human xenobiotic metabolite; neurotoxin
diethylhexyl phthalate Diethylhexyl Phthalate: An ester of phthalic acid. It appears as a light-colored, odorless liquid and is used as a plasticizer for many resins and elastomers.. bis(2-ethylhexyl) phthalate : A phthalate ester that is the bis(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	1.96	1	0	diester; phthalate ester	androstane receptor agonist; apoptosis inhibitor; plasticiser
4-nitrosodimethylaniline 4-nitrosodimethylaniline: structure; RN given refers to parent cpd. N,N-dimethyl-4-nitrosoaniline : A member of the class of dimethylanilines that is N,N-dimethylaniline having a nitroso group at the 4-position.	2	1	0	dimethylaniline; nitroso compound; tertiary amino compound
ditiocarb Ditiocarb: A chelating agent that has been used to mobilize toxic metals from the tissues of humans and experimental animals. It is the main metabolite of DISULFIRAM.. diethyldithiocarbamic acid : A member of the class of dithiocarbamic acids that is diethylcarbamic acid in which both of the oxygens are replaced by sulfur.	1.96	1	0	dithiocarbamic acids	chelator; copper chelator
12-crown-4 12-crown-4: structure in first source. 12-crown-4 : A crown ether that is cyclododecane in which the carbon atoms at positions 1, 4, 7 and 10 have been replaced by oxygen atoms.	2.6	1	0	crown ether; saturated organic heteromonocyclic parent
azacitidine Azacitidine: A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.. 5-azacytidine : An N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-ribofuranosyl residue via an N-glycosidic linkage. An antineoplastic agent, it is used in the treatment of myeloid leukaemia.	1.97	1	0	N-glycosyl-1,3,5-triazine; nucleoside analogue	antineoplastic agent
hydantoins Hydantoins: Compounds based on imidazolidine dione. Some derivatives are ANTICONVULSANTS.. imidazolidine-2,4-dione : An imidazolidinone with oxo groups at position 2 and 4.	2.13	1	0	imidazolidine-2,4-dione
cdta CDTA: RN given refers to parent cpd; structure	2.03	1	0	organooxygen compound
3-pyridinaldehyde pyridine-3-carbaldehyde : A pyridinecarbaldehyde that is pyridine substituted by a formyl group at position 3.	2.03	1	0	pyridinecarbaldehyde
1-naphthylisothiocyanate 1-Naphthylisothiocyanate: A tool for the study of liver damage which causes bile stasis and hyperbilirubinemia acutely and bile duct hyperplasia and biliary cirrhosis chronically, with changes in hepatocyte function. It may cause skin and kidney damage.	2.04	1	0	isothiocyanate	insecticide
docusate Dioctyl Sulfosuccinic Acid: All-purpose surfactant, wetting agent, and solubilizer used in the drug, cosmetics, and food industries. It has also been used in laxatives and as cerumenolytics. It is usually administered as either the calcium, potassium, or sodium salt.	2.01	1	0	diester; organosulfonic acid
n-methylbenzamide N-methylbenzamide: RN given refers to parent cpd	1.96	1	0
2-pyrrolidone 2-pyrrolidone: RN given refers to parent cpd. pyrrolidin-2-one : The simplest member of the class of pyrrolidin-2-ones, consisting of pyrrolidine in which the hydrogens at position 2 are replaced by an oxo group. The lactam arising by the formal intramolecular condensation of the amino and carboxy groups of gamma-aminobutyric acid (GABA).	1.97	1	0	pyrrolidin-2-ones	metabolite; polar solvent
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	9.25	18	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
methyl isocyanate methyl isocyanate: structure. methyl isocyanate : The isocyanate that is methane modified by a single isocyanato substituent.	2.02	1	0	isocyanates	allergen; apoptosis inducer
n-ethylacetamide N-ethylacetamide : A member of the class of acetamides that is the N-ethyl derivative of acetamide.	2.02	1	0	acetamides	metabolite
n-ethylformamide [no description available]	4.17	5	0
n-methylpyrrolidone 1-methylpyrrolidin-2-one: structure in first source. N-methylpyrrolidin-2-one : A member of the class of pyrrolidine-2-ones that is pyrrolidin-2-one in which the hydrogen attached to the nitrogen is replaced by a methyl group.	1.97	1	0	lactam; N-alkylpyrrolidine; pyrrolidin-2-ones	polar aprotic solvent
methionine sulfoximine methionine sulfoximine : A non-proteinogenic alpha-amino acid that is the sulfoximine derivative of methionine .	2.66	3	0	methionine derivative; non-proteinogenic alpha-amino acid; sulfoximide
dithiothreitol 1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.	1.98	1	0	1,4-dimercaptobutane-2,3-diol; butanediols; dithiol; glycol; thiol	chelator; human metabolite; reducing agent
carbonates Carbonates: Salts or ions of the theoretical carbonic acid, containing the radical CO2(3-). Carbonates are readily decomposed by acids. The carbonates of the alkali metals are water-soluble; all others are insoluble. (From Grant & Hackh's Chemical Dictionary, 5th ed). carbonates : Organooxygen compounds that are salts or esters of carbonic acid, H2CO3.	2	1	0	carbon oxoanion
propanoldiaminetetracetic acid [no description available]	2.03	1	0
buthionine sulfoximine Buthionine Sulfoximine: A synthetic amino acid that depletes glutathione by irreversibly inhibiting gamma-glutamylcysteine synthetase. Inhibition of this enzyme is a critical step in glutathione biosynthesis. It has been shown to inhibit the proliferative response in human T-lymphocytes and inhibit macrophage activation. (J Biol Chem 1995;270(33):1945-7). 2-amino-4-(S-butylsulfonimidoyl)butanoic acid : A non-proteinogenic alpha-amino acid that is homocysteine in which the thiol group carries an oxo, imino and butyl groups.. S-butyl-DL-homocysteine (S,R)-sulfoximine : A sulfoximide that is the sulfoximine derivative of an analogue of DL-methionine in which the S-methyl group is replaced by S-butyl.	2.66	3	0	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
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.	1.99	1	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
molybdenum Molybdenum: A metallic element with the atomic symbol Mo, atomic number 42, and atomic weight 95.95. It is an essential trace element, being a component of the enzymes xanthine oxidase, aldehyde oxidase, and nitrate reductase.	2.37	2	0	chromium group element atom	micronutrient
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	2.07	1	0	metal allergen; nickel group element atom; platinum group metal atom
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	1.99	1	0	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
ferric chloride ferric chloride: RN given refers to cpd with MF of Fe-Cl3; used to induce experimental arterial thrombosis to evaluate antithrombotic agents	2.02	1	0	iron coordination entity	astringent; Lewis acid
ferrous chloride ferrous chloride: induces convulsions; RN given refers to parent cpd	2.02	1	0	iron coordination entity
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	6.97	1	0	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.	1.97	1	0	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
silver chloride [no description available]	2.47	2	0	inorganic chloride; silver salt
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.	2.11	1	0	deuterated compound; water	NMR solvent
ozone Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.	2.03	1	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
misonidazole Misonidazole: A nitroimidazole that sensitizes normally radio-resistant hypoxic cells to radiation. It may also be directly cytotoxic to hypoxic cells and has been proposed as an antineoplastic.	6.96	1	0
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.	2.37	2	0	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
18-crown-6 18-crown-6 : A crown ether that is cyclooctadecane in which the carbon atoms at positions 1, 4, 7, 10, 13 and 16 have been replaced by oxygen atoms.	2.6	1	0	crown ether; saturated organic heteromonocyclic parent	phase-transfer catalyst
1,4-dioxane 1,4-dioxane: dehydrating agent; polar solvent miscible both with water & most organic solvents. dioxane : Any member of the class of dioxanes that is a cyclohexane in which two carbon atoms are replaced by oxygen atoms.. 1,4-dioxane : A dioxane with oxygen atoms at positions 1 and 4.	2.6	1	0	dioxane; volatile organic compound	carcinogenic agent; metabolite; NMR chemical shift reference compound; non-polar solvent
dimethylacetamide hallucinogen : Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.. N,N-dimethylacetamide : A member of the class of acetamides that is acetamide in which the hydrogens attached to the N atom have been replaced by two methyl groups respectively. Metabolite observed in cancer metabolism.	9.02	4	0	acetamides; monocarboxylic acid amide	human metabolite
transferrin Transferrin: An iron-binding beta1-globulin that is synthesized in the LIVER and secreted into the blood. It plays a central role in the transport of IRON throughout the circulation. A variety of transferrin isoforms exist in humans, including some that are considered markers for specific disease states.	2.13	1	0
15-crown-5 15-crown-5 : A saturated organic heteromonocyclic parent that is cyclopentadecane in which the carbon atoms at positions 1, 4, 7, 10 and 13 have been replaced by oxygen atoms to give a crown ether.	2.6	1	0	crown ether; saturated organic heteromonocyclic parent
etoposide [no description available]	2.91	4	0	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
spirogermanium spirogermanium: RN given refers to parent cpd	4.32	2	2
idarubicin Idarubicin: An orally administered anthracycline antineoplastic. The compound has shown activity against BREAST NEOPLASMS; LYMPHOMA; and LEUKEMIA.	3.36	1	1	anthracycline antibiotic; deoxy hexoside; monosaccharide derivative
caracemide [no description available]	1.96	1	0
dimethylhydrazines Dimethylhydrazines: Hydrazines substituted with two methyl groups in any position.	1.97	1	0
8-amino-1,3,6-naphthalenetrisulfonic acid 8-amino-1,3,6-naphthalenetrisulfonic acid: RN given refers to parent cpd	1.99	1	0
glutathione disulfide Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.	1.97	1	0	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
imipramine n-oxide imipramine N-oxide: RN given refers to parent cpd; structure	2	1	0	dibenzooxazepine
silver bromide [no description available]	2.47	2	0
n-hydroxymethylformamide N-hydroxymethylformamide: structure given in first source	1.96	1	0
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.	2.03	1	0	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.	1.99	1	0	iditol	fungal metabolite
benzoylphenylalanine N-benzoyl-L-phenylalanine : An N-acyl-L-phenylalanine that is L-phenylalanine in which one of the hydrogens of the amino group has been replaced by a benzoyl group.	2.04	1	0	2-(benzoylamino)-3-phenylpropanoic acid; N-acyl-L-phenylalanine
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	1.96	1	0	cobalt group element atom; metal allergen	micronutrient
cyanates Cyanates: Organic salts of cyanic acid containing the -OCN radical.. cyanates : Salts and esters of cyanic acid, HOC#N; compounds carrying the cyanate functional group -O-C#N.. isocyanates : Organonitrogen compounds that are derivatives of isocyanic acid; compounds containing the isocyanate functional group -N=C=O (as opposed to the cyanate group, -O-C#N).	2.02	1	0
n-hydroxymethyl-n-methylformamide N-hydroxymethyl-N-methylformamide: metabolite of dimethylformamide	3.6	9	0	tertiary carboxamide
n-acetyl-s-(n-methylcarbamoyl)cysteine N-acetyl-S-(N-methylcarbamoyl)cysteine: human metabolite of N,N-dimethylformamide & N-methylformamide; structure given in first source	4.14	16	0	N-acyl-amino acid
icrf 193 4,4'-(1,2-dimethyl-1,2-ethanediyl)bis-2,6-piperazinedione: structure given in first source; RN given refers to cpd without isomeric designation. ICRF-193 : An N-alkylpiperazine that is butane which is substituted by a 3,5-dioxopiperazin-1-yl group at positions 2 and 3. The meso isomer.	1.99	1	0
s-(n-methylcarbamoyl)glutathione S-(N-methylcarbamoyl)glutathione: metabolite of N-methylformamide	2.66	3	0
3,5-dibromo-4-nitrosobenzenesulfonate 3,5-dibromo-4-nitrosobenzenesulfonate: structure given in first source	1.99	1	0
s-lactoylglutathione [no description available]	1.97	1	0
1-aminoindan [no description available]	2.25	1	0
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	2.38	2	0	oxygen hydride; oxygen radical; reactive oxygen species
fe(iii)-edta Fe(III)-EDTA: iron fortifying agent; RN given refers to parent cpd	1.96	1	0	iron coordination entity
potassium bromide potassium bromide : A metal bromide salt with a K(+) counterion.	2.03	1	0	potassium salt
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.43	2	0	cyclodextrin
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid 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).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	3.22	6	0	retinoic acid; vitamin A	anti-inflammatory agent; antineoplastic agent; antioxidant; AP-1 antagonist; human metabolite; keratolytic drug; retinoic acid receptor agonist; retinoid X receptor agonist; signalling molecule
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).	1.96	1	0	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
aphidicolin Aphidicolin: An antiviral antibiotic produced by Cephalosporium aphidicola and other fungi. It inhibits the growth of eukaryotic cells and certain animal viruses by selectively inhibiting the cellular replication of DNA polymerase II or the viral-induced DNA polymerases. The drug may be useful for controlling excessive cell proliferation in patients with cancer, psoriasis or other dermatitis with little or no adverse effect upon non-multiplying cells.. aphidicolin : A tetracyclic diterpenoid that has an tetradecahydro-8,11a-methanocyclohepta[a]naphthalene skeleton with two hydroxymethyl substituents at positions 4 and 9, two methyl substituents at positions 4 and 11b and two hydroxy substituents at positions 3 and 9. An antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication.	2.37	2	0	tetracyclic diterpenoid	antimicrobial agent; antimitotic; antineoplastic agent; antiviral drug; apoptosis inducer; Aspergillus metabolite; DNA synthesis inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; fungal 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.	6.93	1	0	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
melphalan Melphalan: An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.. melphalan : A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.	2.39	2	0	L-phenylalanine derivative; nitrogen mustard; non-proteinogenic L-alpha-amino acid; organochlorine compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent
tolfenamic acid tolfenamic acid: structure. tolfenamic acid : An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 3-chloro-2-methylphenyl group. Tolfenamic acid is used specifically for relieving the pain of migraine. It also shows anticancer activity.	2	1	0	aminobenzoic acid; organochlorine compound; secondary amino compound	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; EC 2.7.1.33 (pantothenate kinase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
retinol acetate retinol acetate: structure given in first source	1.96	1	0	acetate ester
flavin-adenine dinucleotide Flavin-Adenine Dinucleotide: A condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972)	1.96	1	0	flavin adenine dinucleotide; vitamin B2	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; prosthetic group
mercaptopurine Mercaptopurine: An antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia.. purine-6-thiol : A thiol that is the tautomer of mercaptopurine.. mercaptopurine : A member of the class of purines that is 6,7-dihydro-1H-purine carrying a thione group at position 6. An adenine analogue, it is used in the treatment of acute lymphocytic leukemia (ALL), chronic myeloid leukemia (CML), Crohn's disease, and ulcerative colitis.	2.37	2	0	aryl thiol; purines; thiocarbonyl compound	anticoronaviral agent; antimetabolite; antineoplastic agent
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	2.03	1	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
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.	2.01	1	0	bile acid taurine conjugate	human metabolite
nadp [no description available]	1.97	1	0
cobaltous chloride cobaltous chloride: RN given refers to unlabeled cpd; RN in Chemline for cobalt trichloride: 10241-04-0; RN for 60-labeled cpd: 14543-09-0; RN for 57-labeled cpd: 164113-89-1; RN for 58-labeled cpd: 29377-09-1; structure. cobalt dichloride : A cobalt salt in which the cobalt metal is in the +2 oxidation state and the counter-anion is chloride. It is used as an indicator for water in desiccants.	1.96	1	0	cobalt salt; inorganic chloride	allergen; calcium channel blocker; sensitiser; two-colour indicator
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.	2.01	1	0	organic sodium salt	detergent; protein denaturant
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.	2.03	1	0
diethyl maleate diethyl maleate : A maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with ethanol. A colourless liquid at room temperature (m.p. -10degreeC) with boiling point 220degreeC at 1 atm., it is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis.	1.97	1	0	ethyl ester; maleate ester	glutathione depleting agent
bilirubin [no description available]	1.96	1	0	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
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.	1.97	1	0
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	1.99	1	0	carbon group element atom; elemental lead; metal atom	neurotoxin
arsenic Arsenic: A shiny gray element with atomic symbol As, atomic number 33, and atomic weight 75. It occurs throughout the universe, mostly in the form of metallic arsenides. Most forms are toxic. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), arsenic and certain arsenic compounds have been listed as known carcinogens. (From Merck Index, 11th ed)	7.05	1	0	metalloid atom; pnictogen	micronutrient
indium Indium: A metallic element, atomic number 49, atomic weight 114.818, symbol In. It is named from its blue line in the spectrum.. indium atom : A metallic element first identified and named from the brilliant indigo (Latin indicum) blue line in its flame spectrum.	7.05	1	0	boron group element atom
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	7.88	4	0	cysteinium	fundamental metabolite
germanium Germanium: A rare metal element with a blue-gray appearance and atomic symbol Ge, atomic number 32, and atomic weight 72.63.	8.36	1	1	carbon group element atom; metalloid atom; nonmetal atom
10(9)-hydroxystearic acid 10(9)-hydroxystearic acid: structure; RN given refers to parent cpd; see also records for 9-hydroxystearic acid & 10-hydroxystearic acid. 9-hydroxyoctadecanoic acid : A hydroxyoctadecanoic acid that is octadecanoic acid (stearic acid) which has been substituted by a hydroxy group at position 9.	2.03	1	0	hydroxyoctadecanoic acid
phytosterols Phytosterols: A class of organic compounds known as sterols or STEROIDS derived from plants.. phytosterols : Sterols similar to cholesterol which occur in plants and vary only in carbon side chains and/or presence or absence of a double bond.	2.08	1	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	6.96	1	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
oligonucleotides [no description available]	7.03	1	0
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	2.03	1	0	glycoside
n-methylcarbamate N-methylcarbamate: RN given refers to parent cpd	7.69	3	0	amino-acid anion
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	2.02	1	0
echinomycin Echinomycin: A cytotoxic polypeptide quinoxaline antibiotic isolated from Streptomyces echinatus that binds to DNA and inhibits RNA synthesis.	6.96	1	0	cyclodepsipeptide
nitrogenase Nitrogenase: An enzyme system that catalyzes the fixing of nitrogen in soil bacteria and blue-green algae (CYANOBACTERIA). EC 1.18.6.1.	3.08	5	0
peptones Peptones: Derived proteins or mixtures of cleavage products produced by the partial hydrolysis of a native protein either by an acid or by an enzyme. Peptones are readily soluble in water, and are not precipitable by heat, by alkalis, or by saturation with ammonium sulfate. (Dorland, 28th ed)	2.05	1	0
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.	2.37	2	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
gamithromycin gamithromycin: an antibiotic used in cattle. gamithromycin : A macrolide antibiotic with formula C40H76N2O12. It is used for the treatment of of bovine respiratory disease caused by Mannheimia haemolytica, Pasteurella multocida, Histophilus somni and Mycoplasma bovis in beef and non-lactating dairy cattle. The compound is also licensed in Europe for the treatment of footrot in sheep caused by Dichelobacter nodosus and Fusobacterium nodosus.	2.25	1	0	macrolide antibiotic; monosaccharide derivative	antibacterial drug; protein synthesis inhibitor
levoleucovorin Levoleucovorin: A folate analog consisting of the pharmacologically active isomer of LEUCOVORIN.. (6S)-5-formyltetrahydrofolic acid : The pharmacologically active (6S)-stereoisomer of 5-formyltetrahydrofolic acid.	1.97	1	0	5-formyltetrahydrofolic acid	antineoplastic agent; metabolite
hypoxanthine [no description available]	1.96	1	0	nucleobase analogue; oxopurine; purine nucleobase	fundamental metabolite
dacarbazine (E)-dacarbazine : A dacarbazine in which the N=N double bond adopts a trans-configuration.	3.47	2	0	dacarbazine
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	1.96	1	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
bropirimine [no description available]	6.98	1	0	pyrimidines
molybdopterin cytosine dinucleotide molybdopterin cytosine dinucleotide: pterin of carbon monoxide dehydrogenase from Pseudomonas carboxydoflava; structure has been determined	1.96	1	0	molybdopterin dinucleotide; molybdopterins; thiol
molybdenum cofactor molybdenum cofactor: also see records for molybdopterin cytosine dinucleotide and molybdopterin guanine dinucleotide. MoO2-molybdopterin cofactor(2-) : An organophosphate oxoanion obtained by deprotonation of the phosphate OH groups of MoO2-molybdopterin cofactor.. MoO2-molybdopterin cofactor : An Mo-molybdopterin cofactor in which the coordinated molybdenum species is MoO2.	1.96	1	0	Mo-molybdopterin cofactor; organophosphate oxoanion
concanavalin a Concanavalin A: A MANNOSE/GLUCOSE binding lectin isolated from the jack bean (Canavalia ensiformis). It is a potent mitogen used to stimulate cell proliferation in lymphocytes, primarily T-lymphocyte, cultures.	1.96	1	0
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	2.02	1	0

Condition	Relationship Strength	Studies	Trials
Germinoblastoma [description not available]	2.88	4	0
Cancer of Ovary [description not available]	2.66	3	0
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	7.88	4	0
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	2.66	3	0
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)	2.74	3	0
Acute Liver Injury, Drug-Induced [description not available]	5.37	14	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.	5.37	14	1
Alcohol-Induced Disorders Disorders stemming from the misuse and abuse of alcohol.	2.13	1	0
Diseases, Occupational [description not available]	3.81	4	0
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	2.4	2	0
Sarcoma 180 An experimental sarcoma of mice.	6.93	1	0
Experimental Leukemia [description not available]	2.62	3	0
Viral Diseases [description not available]	1.93	1	0
Hepatitis INFLAMMATION of the LIVER.	6.93	1	0
Virus Diseases A general term for diseases caused by viruses.	1.93	1	0
Benign Neoplasms [description not available]	3.46	8	0
Experimental Neoplasms [description not available]	3.65	10	0
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.	3.46	8	0
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.	2.35	2	0
Liver Dysfunction [description not available]	2.89	4	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.02	1	0
Liver Diseases Pathological processes of the LIVER.	2.89	4	0
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)	2.93	4	0
Cancer of Colon [description not available]	6.06	29	1
Colonic Neoplasms Tumors or cancer of the COLON.	6.06	29	1
Fetal Growth Restriction [description not available]	1.96	1	0
Fetal Resorption The disintegration and assimilation of the dead FETUS in the UTERUS at any stage after the completion of organogenesis which, in humans, is after the 9th week of GESTATION. It does not include embryo resorption (see EMBRYO LOSS).	1.96	1	0
Fetal Growth Retardation Failure of a FETUS to attain expected GROWTH.	1.96	1	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	3.81	4	0
Bilirubinemia [description not available]	1.96	1	0
Peripheral Nerve Diseases [description not available]	1.96	1	0
Anorexia The lack or loss of APPETITE accompanied by an aversion to food and the inability to eat. It is the defining characteristic of the disorder ANOREXIA NERVOSA.	2.37	2	0
Nausea An unpleasant sensation in the stomach usually accompanied by the urge to vomit. Common causes are early pregnancy, sea and motion sickness, emotional stress, intense pain, food poisoning, and various enteroviruses.	3.22	6	0
Peripheral Nervous System Diseases Diseases of the peripheral nerves external to the brain and spinal cord, which includes diseases of the nerve roots, ganglia, plexi, autonomic nerves, sensory nerves, and motor nerves.	1.96	1	0
Diffuse Mixed Small and Large Cell Lymphoma [description not available]	1.96	1	0
Lymphoma, Non-Hodgkin Any of a group of malignant tumors of lymphoid tissue that differ from HODGKIN DISEASE, being more heterogeneous with respect to malignant cell lineage, clinical course, prognosis, and therapy. The only common feature among these tumors is the absence of giant REED-STERNBERG CELLS, a characteristic of Hodgkin's disease.	1.96	1	0
EHS Tumor [description not available]	3.21	6	0
ATLL [description not available]	1.98	1	0
Leukemia-Lymphoma, Adult T-Cell Aggressive T-Cell malignancy with adult onset, caused by HUMAN T-LYMPHOTROPIC VIRUS 1. It is endemic in Japan, the Caribbean basin, Southeastern United States, Hawaii, and parts of Central and South America and sub-Saharan Africa.	1.98	1	0
Bone Cancer [description not available]	1.98	1	0
Osteogenic Sarcoma [description not available]	2.38	2	0
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	1.98	1	0
Osteosarcoma A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)	7.38	2	0
Malignant Melanoma [description not available]	4.05	3	1
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)	4.05	3	1
Acute Promyelocytic Leukemia [description not available]	2.38	2	0
Leukemia, Promyelocytic, Acute An acute myeloid leukemia in which abnormal PROMYELOCYTES predominate. It is frequently associated with DISSEMINATED INTRAVASCULAR COAGULATION.	2.38	2	0
Invasiveness, Neoplasm [description not available]	1.98	1	0
Rhabdomyosarcoma A malignant solid tumor arising from mesenchymal tissues which normally differentiate to form striated muscle. It can occur in a wide variety of sites. It is divided into four distinct types: pleomorphic, predominantly in male adults; alveolar (RHABDOMYOSARCOMA, ALVEOLAR), mainly in adolescents and young adults; embryonal (RHABDOMYOSARCOMA, EMBRYONAL), predominantly in infants and children; and botryoidal, also in young children. It is one of the most frequently occurring soft tissue sarcomas and the most common in children under 15. (From Dorland, 27th ed; Holland et al., Cancer Medicine, 3d ed, p2186; DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, pp1647-9)	7.89	4	0
Birth Weight The mass or quantity of heaviness of an individual at BIRTH. It is expressed by units of pounds or kilograms.	1.98	1	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	3.36	7	0
Fetal Death Death of the developing young in utero. BIRTH of a dead FETUS is STILLBIRTH.	1.98	1	0
Abnormalities, Drug-Induced Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.	3.59	3	0
Weight Gain Increase in BODY WEIGHT over existing weight.	2.39	2	0
Experimental Hepatoma [description not available]	3.36	7	0
Cancer of Lung [description not available]	5.88	9	3
B16 Melanoma [description not available]	2.39	2	0
Metastase [description not available]	7.89	4	0
Lung Neoplasms Tumors or cancer of the LUNG.	5.88	9	3
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.89	4	0
Carcinoma, Epidermoid [description not available]	4.06	3	1
Cancer of Cervix [description not available]	3.78	2	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)	4.06	3	1
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	3.78	2	1
Carcinoma, Non-Small Cell Lung [description not available]	4.32	2	2
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	4.32	2	2
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	1.98	1	0
Acute Disease Disease having a short and relatively severe course.	1.98	1	0
Colorectal Cancer [description not available]	1.97	1	0
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	1.97	1	0
Adenocarcinoma, Basal Cell [description not available]	5.15	11	1
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	10.15	11	1
Carcinoma, Oat Cell [description not available]	3.36	1	1
Carcinoma, Small Cell An anaplastic, highly malignant, and usually bronchogenic carcinoma composed of small ovoid cells with scanty neoplasm. It is characterized by a dominant, deeply basophilic nucleus, and absent or indistinct nucleoli. (From Stedman, 25th ed; Holland et al., Cancer Medicine, 3d ed, p1286-7)	3.36	1	1
Di Guglielmo Disease [description not available]	2.37	2	0
Leukemia, Erythroblastic, Acute A myeloproliferative disorder characterized by neoplastic proliferation of erythroblastic and myeloblastic elements with atypical erythroblasts and myeloblasts in the peripheral blood.	2.37	2	0
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	3.58	3	0
Dysembryoma [description not available]	1.97	1	0
Teratoma A true neoplasm composed of a number of different types of tissue, none of which is native to the area in which it occurs. It is composed of tissues that are derived from three germinal layers, the endoderm, mesoderm, and ectoderm. They are classified histologically as mature (benign) or immature (malignant). (From DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, p1642)	1.97	1	0
Adenocarcinoma Of Kidney [description not available]	2.66	3	0
Cancer of Kidney [description not available]	2.66	3	0
Carcinoma, Renal Cell A heterogeneous group of sporadic or hereditary carcinoma derived from cells of the KIDNEYS. There are several subtypes including the clear cells, the papillary, the chromophobe, the collecting duct, the spindle cells (sarcomatoid), or mixed cell-type carcinoma.	2.66	3	0
Kidney Neoplasms Tumors or cancers of the KIDNEY.	2.66	3	0
Experimental Mammary Neoplasms [description not available]	2.66	3	0
Acute Myelogenous Leukemia [description not available]	4.14	6	0
Leukemia, Myeloid, Acute Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.	4.14	6	0
Fibrosarcoma A sarcoma derived from deep fibrous tissue, characterized by bundles of immature proliferating fibroblasts with variable collagen formation, which tends to invade locally and metastasize by the bloodstream. (Stedman, 25th ed)	1.97	1	0
Female Genital Neoplasms [description not available]	1.97	1	0
Genital Neoplasms, Female Tumor or cancer of the female reproductive tract (GENITALIA, FEMALE).	1.97	1	0
Cancer of Gastrointestinal Tract [description not available]	1.97	1	0
Carcinoma, Anaplastic [description not available]	2.37	2	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	2.37	2	0
Blood Poisoning [description not available]	3.35	1	1
Cancer of Rectum [description not available]	4.27	4	1
Rectal Neoplasms Tumors or cancer of the RECTUM.	4.27	4	1
Sepsis Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.	3.35	1	1
Cancer of Head [description not available]	1.97	1	0
Head and Neck Neoplasms Soft tissue tumors or cancer arising from the mucosal surfaces of the LIP; oral cavity; PHARYNX; LARYNX; and cervical esophagus. Other sites included are the NOSE and PARANASAL SINUSES; SALIVARY GLANDS; THYROID GLAND and PARATHYROID GLANDS; and MELANOMA and non-melanoma skin cancers of the head and neck. (from Holland et al., Cancer Medicine, 4th ed, p1651)	1.97	1	0
Leucocythaemia [description not available]	1.97	1	0
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	6.97	1	0
Glial Cell Tumors [description not available]	1.96	1	0
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	1.96	1	0
Leukemia P388 An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.	1.97	1	0
Bone Marrow Diseases Diseases involving the BONE MARROW.	1.96	1	0
Preleukemia Conditions in which the abnormalities in the peripheral blood or bone marrow represent the early manifestations of acute leukemia, but in which the changes are not of sufficient magnitude or specificity to permit a diagnosis of acute leukemia by the usual clinical criteria.	1.96	1	0
Symptom Cluster [description not available]	1.96	1	0
Syndrome A characteristic symptom complex.	1.96	1	0
Granulocytic Leukemia [description not available]	1.96	1	0
Leukemia, Myeloid Form of leukemia characterized by an uncontrolled proliferation of the myeloid lineage and their precursors (MYELOID PROGENITOR CELLS) in the bone marrow and other sites.	1.96	1	0
Myeloproliferative Disorders Conditions which cause proliferation of hemopoietically active tissue or of tissue which has embryonic hemopoietic potential. They all involve dysregulation of multipotent MYELOID PROGENITOR CELLS, most often caused by a mutation in the JAK2 PROTEIN TYROSINE KINASE.	1.96	1	0
Leukocytopenia [description not available]	1.96	1	0
Leukopenia A decrease in the number of LEUKOCYTES in a blood sample below the normal range (LEUKOCYTE COUNT less than 4000).	1.96	1	0
Emesis [description not available]	1.96	1	0
Vomiting The forcible expulsion of the contents of the STOMACH through the MOUTH.	1.96	1	0
Lassitude [description not available]	1.96	1	0
Fatigue The state of weariness following a period of exertion, mental or physical, characterized by a decreased capacity for work and reduced efficiency to respond to stimuli.	1.96	1	0
Plasma Cell Tumor [description not available]	1.96	1	0
Plasmacytoma Any discrete, presumably solitary, mass of neoplastic PLASMA CELLS either in BONE MARROW or various extramedullary sites.	1.96	1	0
Abnormalities, Autosome [description not available]	1.96	1	0

methylformamide

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Research Demand Index: 49.81

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