pulegone profile

pulegone: component of peppermint oil; RN given refers to cpd without isomeric designation; structure in Merck [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

(+)-pulegone : The (5R)-enantiomer of p-menth-4(8)-en-3-one. [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	442495
CHEMBL ID	2924219
CHEBI ID	35596
SCHEMBL ID	38305
MeSH ID	M0118596

Synonym
cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (r)-
1beta-p-menth-4(8)-en-3-one
(r)-pulegone
CHEBI:35596 ,
(1r)-(+)-p-menth-4(8)-en-3-one
(5r)-2-isopropylidene-5-methylcyclohexanone
(5r)-5-methyl-2-(propan-2-ylidene)cyclohexan-1-one
1-isopropylidene-4-methyl-2-cyclohexanone
d-pulegone
1-methyl-4-isopropylidene-3-cyclohexanone
pulegone, (d)
(+)-(r)-pulegone
3-methyl-6-isopropylidenecyclohexanone
p-menth-4(8)-en-3-one, (r)-(+)-
(r)-(+)-pulegone
nsc-15334
5-methyl-2-(1-methylethylidene)cyclohexanone, (r)-
ai3-11218
pulegone, d-
pulegon
4(8)-p-menthen-3-one, delta-
fema no. 2963
ccris 5746
einecs 201-943-2
cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (theta)-
pulegone (natural)
nsc 15334
cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (5r)-
(+)-pulegone
89-82-7
C09893
pulegone
(r)-(+)-pulegone, 85%, technical grade
(r)-(+)-pulegone, >=90%
(r)-(+)-pulegone, 97%
r-(+)-pulegone
LMPR0102090025
(5r)-5-methyl-2-propan-2-ylidenecyclohexan-1-one
(+)-1-methyl-4-isopropylidene-3-cyclohexanone
STK801810
(5r)-5-methyl-2-(propan-2-ylidene)cyclohexanone
AKOS005622693
hsdb 8146
4lf2673r3g ,
unii-4lf2673r3g
(r)-p-menth-4(8)-en-3-one
BMSE000839
(r)-2-isopropylidene-5-methylcyclohexanone
NCGC00257760-01
dtxcid405975
dtxsid2025975 ,
cas-89-82-7
tox21_200206
CHEMBL2924219
S9140
(5r)-2-isopropylidene-5-methyl-cyclohexanone
FT-0604434
pulegone [mi]
(1r)-pulegone
(r)-(+)-p-menth-4(8)-en-3-one
pulegone [iarc]
pulegone [fhfi]
BBL033995
SCHEMBL38305
DTXSID3051757 ,
W-100358
4(8)-p-menthen-3-one, (r)-(+)-
(+)-4(8)-para-menthen-3-one
P2331
mfcd00063000
(+)-pulegone, analytical standard
(+)-pulegone, primary pharmaceutical reference standard
dtxcid6030312
pulegone (iarc)
fema 2963
pulegone,(s)
(r)-5-methyl-2-(propan-2-ylidene)cyclohexanone
AS-18103
Q413816
A14353
(r)-(+)-pulegone 1000 microg/ml in hexane
HY-N1500
CS-0017045
CCG-266234
(r)-pulegone - 90%
XP164793
10.14272/NZGWDASTMWDZIW-MRVPVSSYSA-N.1
doi:10.14272/nzgwdastmwdziw-mrvpvssysa-n.1
EN300-220670
Z1255364872

Excerpt	Reference	Relevance
"R(+)-pulegone is a ketone monoterpene and it is the main constituent of essential oils in several plants. "	( Pharmacological evaluation of R(+)-pulegone on cardiac excitability: role of potassium current blockage and control of action potential waveform. Cruz, JS; Gondim, AN; Menezes-Filho, JE; Roman-Campos, D; Santos-Miranda, A; Vasconcelos, CM, 2014)	1.19
"Pulegone is a component of these oils."	( Mode of action of pulegone on the urinary bladder of F344 rats. Adams, BR; Adams, TB; Anwar, MM; Arnold, LL; Cohen, SM; Da Rocha, MS; Dodmane, PR; Pennington, KL; Taylor, SV; Wermes, C, 2012)	1.43
"Pulegone is a monoterpene ketone that is usually associated with the herb pennyroyal but is also found in the essential oils from many other mint species. "	( Comparative disposition of (R)-(+)-pulegone in B6C3F1 mice and F344 rats. Burka, LT; Chen, LJ; Lebetkin, EH, 2003)	2.04
"(+)-Pulegone is a central intermediate in the biosynthesis of (-)-menthol, the most significant component of peppermint essential oil. "	( Menthofuran regulates essential oil biosynthesis in peppermint by controlling a downstream monoterpene reductase. Croteau, RB; Mahmoud, SS, 2003)	0.88
"Pulegone is a major constituent of pennyroyal oil and a minor component of peppermint oil. "	( 14C-labeled pulegone and metabolites binding to alpha2u-globulin in kidneys of male F-344 rats. Borghoff, SJ; Burka, LT; Ferguson, LJ; Lebetkin, EH; Lih, FB; Parkinson, HD; Tomer, KB, 2007)	2.16

Excerpt	Reference	Relevance
"Pulegone has negative reinforcing properties and seems to possess anxiolytic-like actions unrelated to the benzodiazepine site of the γ-aminobutyric acid type A (GABAA) receptor."	( The aversive, anxiolytic-like, and verapamil-sensitive psychostimulant effects of pulegone. Bispo-da-Silva, LB; da Silveira, NS; de Oliveira-Silva, GL; Lamanes, Bde F; Prado, LC, 2014)	1.35

Excerpt	Reference	Relevance
"Treatment with pulegone also improved the vascular response to acetylcholine."	( Pulegone Prevents Hypertension through Activation of Muscarinic Receptors and Cyclooxygenase Pathway in L-NAME-Induced Hypertensive Rats. Alsahli, TG; Bashir, A; Ehsan, R; Gasparotto Junior, A; Jahan, S; Malik, MNH; Razzaq, MA; Younis, W, 2023)	2.69

Excerpt	Reference	Relevance
" Simple dose-toxicity studies of a metabolite will help to elucidate its toxic effect, but it is not possible to quantify its role in the toxicity produced by the parent compound unless the disposition of the preformed and endogenously formed metabolite is taken into account."	( Contribution of menthofuran to the hepatotoxicity of pulegone: assessment based on matched area under the curve and on matched time course. Nelson, SD; Slattery, JT; Thomassen, D, 1988)	0.52
" One patient died, one received N-acetylcysteine, and two ingested minimally toxic amounts of pennyroyal and were not treated with N-acetylcysteine."	( Pennyroyal toxicity: measurement of toxic metabolite levels in two cases and review of the literature. Anderson, IB; Blanc, PD; Meeker, JE; Mullen, WH; Nelson, SD; Oishi, S, 1996)	0.29
" Data on human metabolites may provide new insights into the toxic mechanisms and treatment of pennyroyal poisoning, including the potential role of N-acetylcysteine."	( Pennyroyal toxicity: measurement of toxic metabolite levels in two cases and review of the literature. Anderson, IB; Blanc, PD; Meeker, JE; Mullen, WH; Nelson, SD; Oishi, S, 1996)	0.29
" Peppermint Oil was minimally toxic in acute oral studies."	( Final report on the safety assessment of Mentha Piperita (Peppermint) Oil, Mentha Piperita (Peppermint) Leaf Extract, Mentha Piperita (Peppermint) Leaf, and Mentha Piperita (Peppermint) Leaf Water. Nair, B, 2001)	0.31
" The primary constituent, R-(+)-pulegone, is metabolized via hepatic cytochrome P450 to toxic intermediates."	( Mitigation of pennyroyal oil hepatotoxicity in the mouse. Bond, GR; Goetz, RJ; Lindsell, CJ; Otten, EJ; Sztajnkrycer, MD, 2003)	0.6
" A simple linear regression analysis showed statistically significant relationships between the studied toxic effects and viscosity of the monoterpenoids (p < 0."	( Comparative toxicity of oxygenated monoterpenoids in experimental hydroalcoholic lotions to permethrin-resistant adult head lice. Gallardo, A; Gonzalez-Audino, P; Mougabure-Cueto, G; Picollo, MI; Toloza, A; Vassena, C, 2011)	0.37
"55 µg per adult respectively) and was more toxic than menthone (7 day LD(50)=33."	( Toxicity of Schizonpeta multifida essential oil and its constituent compounds towards two grain storage insects. Chu, SS; Jiang, GH; Liu, ZL, 2011)	0.37
" There was no mortality, adverse effects on general conditions or changes in body weight, food consumption and feed conversion efficiency throughout the study in male and female rats."	( Safety assessment of essential oil from Minthostachys verticillata (Griseb.) Epling (peperina): 90-days oral subchronic toxicity study in rats. Bagnis, G; Cariddi, LN; Cavaglieri, LR; Cristofolini, A; Escobar, FM; Gallucci, MN; Mañas, F; Sabini, LI; Sabini, MC, 2015)	0.42

Excerpt	Relevance	Reference
"Pulegone was given orally by gavage to groups of 28 SPF Wistar rats at dosage levels of 0 or 160 mg/kg body weight per day for 28 days."	( Lack of histological cerebellar changes in Wistar rats given pulegone for 28 days. Comparison of immersion and perfusion tissue fixation. Mølck, AM; Olsen, P; Poulsen, M; Tindgard Lauridsen, S, 1998)	1.98
" The following metabolites were isolated and identified from the urine of rats dosed with I: 3-methyl-5-(1-methylethylidene)-cyclopent-2-enone (Ie), Z-4-methyl-2-(1-hydroxymethylethylidene)-cyclopentanone (Ib), E-4-methyl-2-(1-hydroxymethylethylidene)-cyclopentanone (Ia), 3-hydroxy-4-methyl-2-(1-methylethylidene)-cyclopentanone (If), 4-hydroxy-4-methyl-2-(1-methylethylidene)-cyclopentanone (Ic), and E-4-methyl-2-(1-carboxyethylidene)-cyclopentanone (Id)."	( Effect of ring size in R-(+)-pulegone-mediated hepatotoxicity: studies on the metabolism of R-(+)-4-methyl-2-(1-methylethylidene)-cyclopentanone and DL-camphorone in rats. Bhat, VB; Madyastha, MK; Thulasiram, HV, 2001)	0.6
" Repeated intradermal dosing with Peppermint Oil produced moderate and severe reactions in rabbits, although Peppermint Oil did not appear to be phototoxic."	( Final report on the safety assessment of Mentha Piperita (Peppermint) Oil, Mentha Piperita (Peppermint) Leaf Extract, Mentha Piperita (Peppermint) Leaf, and Mentha Piperita (Peppermint) Leaf Water. Nair, B, 2001)	0.31
" To test this hypothesis, male and female rats were dosed orally with 14C-labeled pulegone (80 mg/kg, 120 microCi/kg) or menthofuran (60 mg/kg, 120 microCi/kg) or menthones (80 mg/kg, 120 microCi/kg) in corn oil, and the kidney cytosol was prepared 24 h after dosing."	( 14C-labeled pulegone and metabolites binding to alpha2u-globulin in kidneys of male F-344 rats. Borghoff, SJ; Burka, LT; Ferguson, LJ; Lebetkin, EH; Lih, FB; Parkinson, HD; Tomer, KB, 2007)	0.94
" Liver and kidney weights of dosed groups of females were generally significantly greater than those of the vehicle control group."	( Toxicology and carcinogenesis studies of pulegone (CAS No. 89-82-7) in F344/N rats and B6C3F1 mice (gavage studies). , 2011)	0.64
" The inhibitory activities were analysed by dose-response curves and the ED 50 were estimated."	( Allelopathic potential of Artemisia arborescens: isolation, identification and quantification of phytotoxic compounds through fractionation-guided bioassays. Abenavoli, MR; Araniti, F; Conforti, F; Lupini, A; Marrelli, M; Menichini, F; Sorgonà, A; Statti, GA, 2013)	0.39
" Firstly, the hypotensive dose-response relationship of pulegone was evaluated in normotensive anesthetized rats using the invasive method."	( Pulegone Prevents Hypertension through Activation of Muscarinic Receptors and Cyclooxygenase Pathway in L-NAME-Induced Hypertensive Rats. Alsahli, TG; Bashir, A; Ehsan, R; Gasparotto Junior, A; Jahan, S; Malik, MNH; Razzaq, MA; Younis, W, 2023)	2.6

Class	Description
p-menth-4(8)-en-3-one	A p-menthane monoterpenoid that is cyclohexan-1-one substituted by a methyl group at position 5 and a propan-2-ylidene group at position 2.
[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]

Pathway	Proteins	Compounds
menthol biosynthesis	8	21

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
RAR-related orphan receptor gamma	Mus musculus (house mouse)	Potency	27.3338	0.0060	38.0041	19,952.5996	AID1159521
AR protein	Homo sapiens (human)	Potency	13.3723	0.0002	21.2231	8,912.5098	AID743036; AID743040; AID743042; AID743053
glucocorticoid receptor [Homo sapiens]	Homo sapiens (human)	Potency	17.1091	0.0002	14.3764	60.0339	AID720691; AID720692
pregnane X nuclear receptor	Homo sapiens (human)	Potency	30.6690	0.0054	28.0263	1,258.9301	AID1346982
estrogen nuclear receptor alpha	Homo sapiens (human)	Potency	39.7527	0.0002	29.3054	16,493.5996	AID743075; AID743079; AID743080
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a	Homo sapiens (human)	Potency	27.3338	0.0017	23.8393	78.1014	AID743083
nuclear factor of kappa light polypeptide gene enhancer in B-cells 1 (p105), isoform CRA_a	Homo sapiens (human)	Potency	0.0062	19.7391	45.9784	64.9432	AID1159509
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Assay ID	Title	Year	Journal	Article
AID1081541	Nematicidal activity against Meloidogyne javanica J2 (root-knot nematode) larvae immersed in compound solution for 48 hr assessed as reduction in larval motility	2010	Journal of agricultural and food chemistry, Jul-14, Volume: 58, Issue:13	Phytochemistry and nematicidal activity of the essential oils from 8 Greek Lamiaceae aromatic plants and 13 terpene components.
AID1081539	Nematicidal activity against Meloidogyne incognita J2 (root-knot nematode) larvae immersed in compound solution for 48 hr assessed as reduction in larval motility	2010	Journal of agricultural and food chemistry, Jul-14, Volume: 58, Issue:13	Phytochemistry and nematicidal activity of the essential oils from 8 Greek Lamiaceae aromatic plants and 13 terpene components.
AID1112564	Bird repellent activity against Columba livia f. domestica fed with compound treated maize seeds assessed as feeding deterrence activity at 1.4 ml/kg measured for 4 days by aviary food choice trials	2013	Pest management science, Mar, Volume: 69, Issue:3	Assessing the effects of three potential chemical repellents to prevent bird damage to corn seeds and seedlings.
AID1112560	Bird repellent activity against Columba livia f. domestica assessed as decrease in damage of maize seedlings grown from compound-treated seeds at 1.4 ml/kg measured in the field at 2 to 16 days after germination during field trials	2013	Pest management science, Mar, Volume: 69, Issue:3	Assessing the effects of three potential chemical repellents to prevent bird damage to corn seeds and seedlings.
AID1112558	Phytotoxicity against Zea mays (maize) seeds assessed as germination rate at 25 degC after 5-6 days by standard vigour method	2013	Pest management science, Mar, Volume: 69, Issue:3	Assessing the effects of three potential chemical repellents to prevent bird damage to corn seeds and seedlings.
AID1105270	Insecticidal activity against Frankliniella occidentalis (western flower thrips) assessed as mortality at 1 ul/45mL	2011	Molecules (Basel, Switzerland), Mar-15, Volume: 16, Issue:3	Fungicidal properties of the essential oil of Hesperozygis marifolia on Aspergillus flavus link.
AID1112518	Displacement of [3H]TBOB binding to GABA receptor in Musca domestica (house fly) heads homogenates assessed as [3H]TBOB binding at 500 uM incubated for 90 min by scintillation counting method	2012	Pest management science, Aug, Volume: 68, Issue:8	Quantitative structure-activity relationships of monoterpenoid binding activities to the housefly GABA receptor.
AID1112559	Phytotoxicity against Zea mays (maize) seeds assessed as germination rate at 10 degC after 7 days by standard vigour method	2013	Pest management science, Mar, Volume: 69, Issue:3	Assessing the effects of three potential chemical repellents to prevent bird damage to corn seeds and seedlings.
AID1112517	Toxicity to Musca domestica (house fly) applied to pronotum assessed as compound level per fly causing insect mortality measured after 24 hr	2012	Pest management science, Aug, Volume: 68, Issue:8	Quantitative structure-activity relationships of monoterpenoid binding activities to the housefly GABA receptor.
AID1105271	Antifungal activity against Aspergillus flavus assessed as inhibition of mycelial growth measured after 72 hr at 0.8 mg/mL at 28 +/- 1 degC	2011	Molecules (Basel, Switzerland), Mar-15, Volume: 16, Issue:3	Fungicidal properties of the essential oil of Hesperozygis marifolia on Aspergillus flavus link.
AID1112562	Bird repellent activity against Columba livia f. domestica assessed as decrease in damage of maize seedlings grown from compound-treated seeds at 1.4 ml/kg measured after 3 days exposure during aviary trials	2013	Pest management science, Mar, Volume: 69, Issue:3	Assessing the effects of three potential chemical repellents to prevent bird damage to corn seeds and seedlings.
AID1081540	Nematicidal activity against Meloidogyne incognita J2 (root-knot nematode) larvae immersed in compound solution for 96 hr assessed as reduction in larval motility	2010	Journal of agricultural and food chemistry, Jul-14, Volume: 58, Issue:13	Phytochemistry and nematicidal activity of the essential oils from 8 Greek Lamiaceae aromatic plants and 13 terpene components.
AID1081538	Nematicidal activity against Meloidogyne incognita J2 (root-knot nematode) larvae immersed in compound solution for 24 hr assessed as reduction in larval motility	2010	Journal of agricultural and food chemistry, Jul-14, Volume: 58, Issue:13	Phytochemistry and nematicidal activity of the essential oils from 8 Greek Lamiaceae aromatic plants and 13 terpene components.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	13 (7.78)	18.7374
1990's	19 (11.38)	18.2507
2000's	48 (28.74)	29.6817
2010's	73 (43.71)	24.3611
2020's	14 (8.38)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	8 (4.52%)	6.00%
Case Studies	2 (1.13%)	4.05%
Observational	0 (0.00%)	0.25%
Other	167 (94.35%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
dinitrochlorobenzene Dinitrochlorobenzene: A skin irritant that may cause dermatitis of both primary and allergic types. Contact sensitization with DNCB has been used as a measure of cellular immunity. DNCB is also used as a reagent for the detection and determination of pyridine compounds.. 1-chloro-2,4-dinitrobenzene : A C-nitro compound that is chlorobenzene carrying a nitro substituent at each of the 2- and 4-positions.	7.47	2	C-nitro compound; monochlorobenzenes	allergen; epitope; sensitiser
adenine [no description available]	2.13	1	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
coumarin 2H-chromen-2-one: coumarin derivative	7.74	3	coumarins	fluorescent dye; human metabolite; plant metabolite
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	2.13	1	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
bupropion Bupropion: A propiophenone-derived antidepressant and antismoking agent that inhibits the uptake of DOPAMINE.. bupropion : An aromatic ketone that is propiophenone carrying a tert-butylamino group at position 2 and a chloro substituent at position 3 on the phenyl ring.	2.05	1	aromatic ketone; monochlorobenzenes; secondary amino compound	antidepressant; environmental contaminant; xenobiotic
creatine [no description available]	1.99	1	glycine derivative; guanidines; zwitterion	geroprotector; human metabolite; mouse metabolite; neuroprotective agent; nutraceutical
phenol [no description available]	2.03	1	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
pyrogallol benzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.	2.48	2	benzenetriol; phenolic donor	plant metabolite
vanillin Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).	2.07	1	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
huperzine a huperzine A: RN given refers to 5R-(5alpha,9beta,11E)-isomer; structure given in first source. huperzine A : A sesquiterpene alkaloid isolated from a club moss Huperzia serrata that has been shown to exhibit neuroprotective activity. It is also an effective inhibitor of acetylcholinesterase and has attracted interest as a therapeutic candidate for Alzheimer's disease.	2.49	2	quinolone
menthol Menthol: A monoterpene cyclohexanol produced from mint oils.	7.64	78	p-menthane monoterpenoid; secondary alcohol	volatile oil component
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	2.37	2	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
acetaminophen Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.	8.83	3	acetamides; phenols	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; cyclooxygenase 3 inhibitor; environmental contaminant; ferroptosis inducer; geroprotector; hepatotoxic agent; human blood serum metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
aristolochic acid i aristolochic acid I: phospholipase A inhibitor. aristolochic acid A : An aristolochic acid that is phenanthrene-1-carboxylic acid that is substituted by a methylenedioxy group at the 3,4 positions, by a methoxy group at position 8, and by a nitro group at position 10. It is the most abundant of the aristolochic acids and is found in almost all Aristolochia (birthworts or pipevines) species. It has been tried in a number of treatments for inflammatory disorders, mainly in Chinese and folk medicine. However, there is concern over their use as aristolochic acid is both carcinogenic and nephrotoxic.	3.12	1	aristolochic acids; aromatic ether; C-nitro compound; cyclic acetal; monocarboxylic acid; organic heterotetracyclic compound	carcinogenic agent; metabolite; mutagen; nephrotoxin; toxin
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.	7.47	2	aromatic ether; nitrile; polyether; tertiary amino compound
camphor, (+-)-isomer [no description available]	2.73	3	bornane monoterpenoid; cyclic monoterpene ketone	plant metabolite
chlorpheniramine Chlorpheniramine: A histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than PROMETHAZINE.. chlorphenamine : A tertiary amino compound that is propylamine which is substituted at position 3 by a pyridin-2-yl group and a p-chlorophenyl group and in which the hydrogens attached to the nitrogen are replaced by methyl groups. A histamine H1 antagonist, it is used to relieve the symptoms of hay fever, rhinitis, urticaria, and asthma.	1.97	1	monochlorobenzenes; pyridines; tertiary amino compound	anti-allergic agent; antidepressant; antipruritic drug; H1-receptor antagonist; histamine antagonist; serotonin uptake inhibitor
cimetidine Cimetidine: A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output.. cimetidine : A member of the class of guanidines that consists of guanidine carrying a methyl substituent at position 1, a cyano group at position 2 and a 2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl group at position 3. It is a H2-receptor antagonist that inhibits the production of acid in stomach.	2.01	1	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
eucalyptol [no description available]	3.47	7
4-cresol 4-cresol: RN given refers to parent cpd. p-cresol : A cresol that consists of toluene substituted by a hydroxy group at position 4. It is a metabolite of aromatic amino acid metabolism produced by intestinal microflora in humans and animals.	2.42	2	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
diclofenac Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt.. diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position.	2.05	1	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
disulfiram [no description available]	2.01	1	organic disulfide; organosulfur acaricide	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 3.1.1.1 (carboxylesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; ferroptosis inducer; fungicide; NF-kappaB inhibitor
flumazenil Flumazenil: A potent benzodiazepine receptor antagonist. Since it reverses the sedative and other actions of benzodiazepines, it has been suggested as an antidote to benzodiazepine overdoses.. flumazenil : An organic heterotricyclic compound that is 5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted at positions 3, 5, 6, and 8 by ethoxycarbonyl, methyl, oxo, and fluoro groups, respectively. It is used as an antidote to benzodiazepine overdose.	2.1	1	ethyl ester; imidazobenzodiazepine; organofluorine compound	antidote to benzodiazepine poisoning; GABA antagonist
haloperidol Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.	2.1	1	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	2.1	1	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
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	2.6	1	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic
kinetin Kinetin: A furanyl adenine found in PLANTS and FUNGI. It has plant growth regulation effects.. cytokinin : A phytohormone that promote cell division, or cytokinesis, in plant roots and shoots.. kinetin : A member of the class of 6-aminopurines that is adenine carrying a (furan-2-ylmethyl) substituent at the exocyclic amino group.	2.13	1	6-aminopurines; furans	cytokinin; geroprotector
methyl salicylate methyl salicylate: used in over-the-counter liniments, ointments, lotions for relief of musculoskeletal aches and pains; has hemolytic effect on human & sheep erythrocytes; RN given refers to parent cpd; structure in Merck Index, 9th ed, #5990. methyl salicylate : A benzoate ester that is the methyl ester of salicylic acid.	2.07	1	benzoate ester; methyl ester; salicylates	flavouring agent; insect attractant; metabolite
metyrapone Metyrapone: An inhibitor of the enzyme STEROID 11-BETA-MONOOXYGENASE. It is used as a test of the feedback hypothalamic-pituitary mechanism in the diagnosis of CUSHING SYNDROME.. metyrapone : An aromatic ketone that is 3,3-dimethylbutan-2-one in which the methyl groups at positions 1 and 4 are replaced by pyridin-3-yl groups. A steroid 11beta-monooxygenase (EC 1.14.15.4) inhibitor, it is used in the diagnosis of adrenal insufficiency.	1.97	1	aromatic ketone	antimetabolite; diagnostic agent; EC 1.14.15.4 (steroid 11beta-monooxygenase) inhibitor
myristicin myristicin: asaricin is an isomer; structure; a methylene dioxy version of elemicin;	2.48	2	organic molecular entity	metabolite
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	2.02	1	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
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.	2.66	3	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
potassium chloride Potassium Chloride: A white crystal or crystalline powder used in BUFFERS; FERTILIZERS; and EXPLOSIVES. It can be used to replenish ELECTROLYTES and restore WATER-ELECTROLYTE BALANCE in treating HYPOKALEMIA.. potassium chloride : A metal chloride salt with a K(+) counterion.	2.46	2	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
pyrilamine Pyrilamine: A histamine H1 antagonist. It has mild hypnotic properties and some local anesthetic action and is used for allergies (including skin eruptions) both parenterally and locally. It is a common ingredient of cold remedies.. mepyramine : An ethylenediamine derivative that is ethylenediamine in which one of the amino nitrogens is substituted by two methyl groups and the remaining amino nitrogen is substituted by a 4-methoxybenzyl and a pyridin-2-yl group.	1.97	1	aromatic ether; ethylenediamine derivative	H1-receptor antagonist
safrole Safrole: A member of the BENZODIOXOLES that is a constituent of several VOLATILE OILS, notably SASSAFRAS oil. It is a precursor in the synthesis of the insecticide PIPERONYL BUTOXIDE and the drug N-methyl-3,4-methylenedioxyamphetamine (MDMA).. safrole : A member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted by an allyl group at position 5. It is found in several plants, including black pepper, cinnamon and nutmeg, and is present in several essential oils, notably that of sassafras. It has insecticidal properties and has been used as a topical antiseptic. Although not thought to pose a significant carcinogenic risk to humans, findings of weak carcinogenicity in rats have resulted in the banning of its (previously widespread) use in perfumes and soaps, and as a food additive.	7.4	2	benzodioxoles	flavouring agent; insecticide; metabolite; plant metabolite
troglitazone Troglitazone: A chroman and thiazolidinedione derivative that acts as a PEROXISOME PROLIFERATOR-ACTIVATED RECEPTORS (PPAR) agonist. It was formerly used in the treatment of TYPE 2 DIABETES MELLITUS, but has been withdrawn due to hepatotoxicity.	2.05	1	chromanes; thiazolidinone	anticoagulant; anticonvulsant; antineoplastic agent; antioxidant; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; hypoglycemic agent; platelet aggregation inhibitor; vasodilator agent
reserpine Reserpine: An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use.. reserpine : An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.	2.05	1	alkaloid ester; methyl ester; yohimban alkaloid	adrenergic uptake inhibitor; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; first generation antipsychotic; plant metabolite; xenobiotic
piperonyl butoxide [no description available]	2.37	2	benzodioxoles	pesticide synergist
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.	7.4	2	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
bromodeoxyuridine Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.	2.07	1	pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent
carbon disulfide Carbon Disulfide: A colorless, flammable, poisonous liquid, CS2. It is used as a solvent, and is a counterirritant and has local anesthetic properties but is not used as such. It is highly toxic with pronounced CNS, hematologic, and dermatologic effects.	2.4	2	one-carbon compound; organosulfur compound
linalool linalool: RN given refers to parent cpd without isomeric designation; structure. linalool : A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum.	3.47	7	monoterpenoid; tertiary alcohol	antimicrobial agent; fragrance; plant metabolite; volatile oil component
alpha-pinene [no description available]	2.79	3	pinene	plant metabolite
9,10-anthraquinone 9,10-anthraquinone : An anthraquinone that is anthracene in which positions 9 and 10 have been oxidised to carbonyls.	2.08	1	anthraquinone
piperitone piperitone: from Mentha longifolia var. chorodictya Rech F; structure in first source. piperitone : A p-menthane monoterpenoid that is cyclohex-2-en-1-one substituted by a methyl group at position 3 and an isopropyl group at position 6.	3.25	5	cyclic terpene ketone; p-menthane monoterpenoid	plant metabolite; volatile oil component
thymol Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.	3.18	5	monoterpenoid; phenols	volatile oil component
methyleugenol methyleugenol: structure	2.59	2	phenylpropanoid
furfuryl alcohol furfuryl alcohol: structure. furfuryl alcohol : A furan bearing a hydroxymethyl substituent at the 2-position.	2.03	1	furans; primary alcohol	Maillard reaction product
carveol carveol: structure given in first source; prolongs tumor latency and decreases tumor yield. carveol : A limonene monoterpenoid that is cyclohex-2-en-1-ol substituted by a methyl group at position 2 and a prop-1-en-2-yl group at position 5.	2.51	2	limonene monoterpenoid	plant metabolite; volatile oil component
carvone carvone: an oxidized derivative of limonene; RN given refers to cpd without isomeric designation; L-carvone has spearmint flavor, D-carvone has dill/caraway flavor. carvone : A p-menthane monoterpenoid that consists of cyclohex-2-enone having methyl and isopropenyl substituents at positions 2 and 5, respectively.	2.86	3	botanical anti-fungal agent; carvones	allergen
4-cymene 4-cymene: structure. p-cymene : A monoterpene that is toluene substituted by an isopropyl group at position 4.	2.47	2	monoterpene; toluenes	human urinary metabolite; plant metabolite; volatile oil component
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.06	1	alkane
cyclohexanol Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.	2.99	4	cyclohexanols; secondary alcohol	solvent
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2.11	1	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
piperonal piperonal: has been used as a pediculicide; structure. piperonal : An arenecarbaldehyde that is 1,3-benzodioxole substituted by a formyl substituent at position 5. It has been isolated from Piper nigrum.	7.44	2	arenecarbaldehyde; benzodioxoles	fragrance; insect repellent; plant metabolite
methyl anthranilate methyl anthranilate : A benzoate ester that is the methyl ester of anthranilic acid.	2.08	1	benzoate ester	flavouring agent; metabolite
estragole estragole : A phenylpropanoid that is chavicol in which the hydroxy group is replaced by a methoxy group.	3.02	4	alkenylbenzene; monomethoxybenzene; phenylpropanoid	carcinogenic agent; flavouring agent; genotoxin; insect attractant; plant metabolite
citronellol citronellol: alcohol form of citronellal; found in rose oil; RN given refers to parent cpd without isomeric designation; structure. citronellol : A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7.. insect repellent : An insecticide that acts as a repellent to insects.	2.42	2	monoterpenoid	plant metabolite
sodium cyanide Sodium Cyanide: A highly poisonous compound that is an inhibitor of many metabolic processes and is used as a test reagent for the function of chemoreceptors. It is also used in many industrial processes.. sodium cyanide : A cyanide salt containing equal numbers of sodium cations and cyanide anions.	2.05	1	cyanide salt; one-carbon compound; sodium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	2	1	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
pyrazines Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.	2.03	1	diazine; pyrazines	Daphnia magna metabolite
1,4-cineole 1,4-cineole: monoterpene; flavor component of lime Citrus medica L. var acida; structure given in first source. 1,4-cineole : An oxabicycloalkane consisting of p-menthane with an epoxy bridge across positions 1 and 4.	2.48	2
carvacrol carvacrol : A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).	3.15	5	botanical anti-fungal agent; p-menthane monoterpenoid; phenols	agrochemical; antimicrobial agent; flavouring agent; TRPA1 channel agonist; volatile oil component
citronellic acid citronellic acid: structure in first source. citronellic acid : A monounsaturated fatty acid that is oct-6-enoic acid carrying methyl groups at positions 3 and 7.	2.07	1	medium-chain fatty acid; monoterpenoid; monounsaturated fatty acid	flavouring agent; plant metabolite
elemene elemene: a sclerosing and antineoplastic agent isolated from Curcuma wenyujin & Rhizoma zedoariae; beta- and delta- elemene are also available	2.03	1
4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol 4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol: structure in first source. 4-terpineol : A terpineol that is 1-menthene carrying a hydroxy substituent at position 4.	2.05	1	terpineol; tertiary alcohol	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiparasitic agent; apoptosis inducer; plant metabolite; volatile oil component
dansyl chloride dansyl chloride: RN given refers to unlabeled cpd	2.02	1	aminonaphthalene; sulfonic acid derivative
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	3.09	1	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
zinc oxide Zinc Oxide: A mild astringent and topical protectant with some antiseptic action. It is also used in bandages, pastes, ointments, dental cements, and as a sunblock.	2.11	1	zinc molecular entity
beta-pinene beta-pinene: alpha-pinene is also available. beta-pinene : An isomer of pinene with an exocyclic double bond. It is a component of essential oils from many plants.	2.11	1	pinene	plant metabolite
methionine sulfoximine methionine sulfoximine : A non-proteinogenic alpha-amino acid that is the sulfoximine derivative of methionine .	1.97	1	methionine derivative; non-proteinogenic alpha-amino acid; sulfoximide
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.	1.97	1	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
limonene Limonene: A naturally-occurring class of MONOTERPENES which occur as a clear colorless liquid at room temperature. Limonene is the major component in the oil of oranges which has many uses, including as flavor and fragrance. It is recognized as safe in food by the Food and Drug Administration (FDA).. limonene : A monoterpene that is cyclohex-1-ene substituted by a methyl group at position 1 and a prop-1-en-2-yl group at position 4 respectively.	3.99	12	cycloalkene; p-menthadiene	human metabolite
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	2.04	1	elemental platinum; nickel group element atom; platinum group metal atom
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	2.7	3	dihydrogen
3-carene 3-carene: RN given refers to cpd without isomeric designation	2.11	1	monoterpene
menthone menthone : The trans-stereoisomer of p-menthan-3-one.. (-)-menthone : A menthone that is cyclohexanone substituted by a methyl and an isopropyl group at positions 5 and 2 respectively (the 2S,5R-stereoisomer).	4.92	34	menthone
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	3.62	9
verbenone verbenone: platelet aggregation inhibitor; RN given refers to cpd without isomeric designation. 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one : A carbobicyclic compound that is bicyclo[3.1.1]heptane which is substituted by an oxo group at position 2 and by methyl groups at positions 4, 6 and 6, and which contains a double bond between positions 3 and 4.. (S)-(-)-verbenone : A 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one in which both chiral centres have S configuration.	1.98	1	carbobicyclic compound; cyclic ketone; enone
myrcene myrcene: structure in first source. beta-myrcene : A monoterpene that is octa-1,6-diene bearing methylene and methyl substituents at positions 3 and 7 respectively.	2.53	2	monoterpene	anabolic agent; anti-inflammatory agent; flavouring agent; fragrance; plant metabolite; volatile oil component
alkenes [no description available]	2.53	2
diltiazem Diltiazem: A benzothiazepine derivative with vasodilating action due to its antagonism of the actions of CALCIUM ion on membrane functions.. diltiazem : A 5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate in which both stereocentres have S configuration. A calcium-channel blocker and vasodilator, it is used as the hydrochloride in the management of angina pectoris and hypertension.	2.1	1	5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate	antihypertensive agent; calcium channel blocker; vasodilator agent
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	2.6	1	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
permethrin hemoglobin Atlanta-Coventry: Leu replaced by Pro at beta75 and Leu deleted at beta141	2.06	1	cyclopropanecarboxylate ester; cyclopropanes	agrochemical; ectoparasiticide; pyrethroid ester acaricide; pyrethroid ester insecticide; scabicide
simvastatin Simvastatin: A derivative of LOVASTATIN and potent competitive inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It may also interfere with steroid hormone production. Due to the induction of hepatic LDL RECEPTORS, it increases breakdown of LDL CHOLESTEROL.. simvastatin : A member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group. It is used as a cholesterol-lowering and anti-cardiovascular disease drug.	2.1	1	delta-lactone; fatty acid ester; hexahydronaphthalenes; statin (semi-synthetic)	EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor; EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor; ferroptosis inducer; geroprotector; prodrug
verbenol verbenol: RN given refers to cpd with unspecified isomeric designation; structure	1.98	1	monoterpenoid
efavirenz efavirenz: HIV-1 reverse transcriptase inhibitor. efavirenz : 1,4-Dihydro-2H-3,1-benzoxazin-2-one substituted at the 4 position by cyclopropylethynyl and trifluoromethyl groups (S configuration) and at the 6 position by chlorine. A non-nucleoside reverse transcriptase inhibitor with activity against HIV, it is used with other antiretrovirals for combination therapy of HIV infection.	2.1	1	acetylenic compound; benzoxazine; cyclopropanes; organochlorine compound; organofluorine compound	antiviral drug; HIV-1 reverse transcriptase inhibitor
glutathione disulfide Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.	2.02	1	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
citronellal, (r)-isomer (R)-(+)-citronellal : The (3R)-stereoisomer of 3,7-dimethyloct-6-enal (citronellal).	2.07	1	citronellal
isopiperitenone isopiperitenone: structure given in first source	6.96	1	p-menthadien-3-one
beta-thujone [no description available]	7.4	2	beta-thujone
friedelin 3-friedelanone: from the stem bark of Irvingia gabonensis; structure in first source. friedelin : A pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork.	1.98	1	cyclic terpene ketone; pentacyclic triterpenoid	anti-inflammatory drug; antipyretic; non-narcotic analgesic; plant metabolite
zingiberene zingiberene: in wild tomato; structure in first source. zingiberene : 2-Methylcyclohexa-1,3-diene in which a hydrogen at the 5 position is substituted (R configuration) by a 6-methyl-hept-5-en-2-yl group (S configuration). It is a sesquiterpene found in the dried rhizomes of Indonesian ginger, Zingiber officinale.	2.08	1	cyclohexadiene; sesquiterpene
triptolide [no description available]	2	1	diterpenoid; epoxide; gamma-lactam; organic heteroheptacyclic compound	antispermatogenic agent; plant metabolite
ezetimibe Ezetimibe: An azetidine derivative and ANTICHOLESTEREMIC AGENT that inhibits intestinal STEROL absorption. It is used to reduce total CHOLESTEROL; LDL CHOLESTEROL, and APOLIPOPROTEINS B in the treatment of HYPERLIPIDEMIAS.. ezetimibe : A beta-lactam that is azetidin-2-one which is substituted at 1, 3, and 4 by p-fluorophenyl, 3-(p-fluorophenyl)-3-hydroxypropyl, and 4-hydroxyphenyl groups, respectively (the 3R,3'S,4S enantiomer).	2.1	1	azetidines; beta-lactam; organofluorine compound	anticholesteremic drug; antilipemic drug; antimetabolite
camphora camphora: a component of Guanxingao, a kind of traditional Chinese rubber electuary medicine which is able to either cure or guard against coronary heart disease and angina pectoris. (R)-camphor : The (R)- enantiomer of camphor.	2.07	1	camphor
3-octanone 3-octanone : A dialkyl ketone that is octane in which the two methylene protons at position 3 have been replaced by an oxo group.	2.03	1	dialkyl ketone	antifeedant; biomarker; fungal metabolite; human urinary metabolite; insect attractant; plant metabolite; toxin
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	2.39	2
menthofuran menthofuran: RN given refers to cpd without isomeric designation; derives from cyclization of pulegone. menthofuran : A monoterpenoid that is 4,5,6,7-tetrahydro-1-benzofuran substituted by methyl groups at positions 3 and 6.	5.97	20	1-benzofurans; monoterpenoid	nematicide; plant metabolite
piperitenone piperitenone: structure given in first source	8.3	6	p-menthadien-3-one
(+)-limonene (4R)-limonene : An optically active form of limonene having (4R)-configuration.	2.47	2	limonene	plant metabolite
ryanodine Ryanodine: A methylpyrrole-carboxylate from RYANIA that disrupts the RYANODINE RECEPTOR CALCIUM RELEASE CHANNEL to modify CALCIUM release from SARCOPLASMIC RETICULUM resulting in alteration of MUSCLE CONTRACTION. It was previously used in INSECTICIDES. It is used experimentally in conjunction with THAPSIGARGIN and other inhibitors of CALCIUM ATPASE uptake of calcium into SARCOPLASMIC RETICULUM.. ryanodine : An insecticide alkaloid isolated from South American plant Ryania speciosa.	2.13	1
patchouli alcohol patchouli alcohol: major component of the essential oil of patchouli; perfumery raw material. patchouli alcohol : A carbotricyclic compound and sesquiterpenoid tertiary alcohol that is tricyclo[5.3.1.0(3,8)]undecan-3-ol which is substituted at positions 2, 2, 6 and 8 by methyl groups (the 1R,3R,6S,7S,8S-diastereoisomer).	2.05	1
naringin [no description available]	1.98	1	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; neohesperidoside	anti-inflammatory agent; antineoplastic agent; metabolite
phenylpropanolamine fawcettimine: from Lyopodium; structure in first source	2.04	1	azaspiro compound
1-alpha-terpineol (S)-(-)-alpha-terpineol : The (S)-enantiomer of alpha-terpineol.	2.07	1	alpha-terpineol	plant metabolite
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	2.07	1	cinnamic acid	plant metabolite
spathulenol spathulenol: sesquiterpene alcohol isolated from essential oils of Artemisia vulgaris L. & Artemisia dracunculus L.. spathulenol : A tricyclic sesquiterpenoid that is 4-methylidenedecahydro-1H-cyclopropa[e]azulene carrying three methyl substituents at positions 1, 1 and 7 as well as a hydroxy substituent at position 7.	2.08	1
alpha-asarone asarone: structure in Merck Index, 9th ed, #847. asarone : A phenylpropanoid that is benzene substituted by methoxy groups at positions 1, 2 and 4 and a propen-1-yl group at position 5. It has been isolated from Acorus.. alpha-asarone : The trans-isomer of asarone.	1.96	1	asarone	anticonvulsant; GABA modulator
anethole anethole: an isomer of estragole; structurally similar to CAPSAICIN; has some neurological and insecticidal and skin absorption effects; RN given refers to unspecified stereoisomer. anethole : A monomethoxybenzene that is methoxybenzene substituted by a prop-1-en-1-yl group at position 4.. trans-anethole : The trans-stereoisomer of anethole.	2.96	4	anethole	flavouring agent
geraniol [no description available]	2.46	2	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
citral citral: Xref geranial: geraniol is also available; Xref neral: nerol is also available; vitamin A antagonist; oxygenated monoterpene; inhibits cytosolic dehydrogenases; structure. citral : An enal that consists of octa-2,6-dienal bearing methyl substituents at positions 3 and 7. A mixture of the two geometric isomers geranial and neral, it is the major constituent (75-85%) of oil of lemon grass, the volatile oil of Cymbopogon citratus, or of C. flexuosus. It also occurs in oils of verbena, lemon, and orange.	2.42	2	enal; monoterpenoid; polyprenal	plant metabolite; volatile oil component
beta-ionone beta-ionone: stimulator of carotenogenesis; carotenoid inhibitor; intermediate in synthesis of Vit A; RN given refers to cpd without isomeric designation; structure. beta-ionone : An ionone that is but-3-en-2-one substituted by a 2,6,6-trimethylcyclohex-1-en-1-yl group at position 4.	2.21	1	ionone	antioxidant; fragrance
mintlactone mintlactone: isolated from Mentha cardiaca structure in first source	2.48	2
sesquiterpenes [no description available]	3.79	10
caryophyllene oxide caryophyllene oxide: has butyrylcholinesterase inhibitory activity; structure in first source. epoxide : Any cyclic ether in which the oxygen atom forms part of a 3-membered ring.	2.84	3	epoxide	metabolite
nadp [no description available]	2.67	3
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	2.02	1	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
caryophyllene (-)-beta-caryophyllene : A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of beta-caryophyllene, occurring in many essential oils, particularly oil of cloves.. beta-caryophyllene : A sesquiterpene with a [7.2.0]-bicyclic structure comprising fused 9- and 4-membered rings, with a trans-ring junction, a trans-double bond between the 4- and 5-positions of the 9-membered ring, a methylidene group at position 9, and methyl groups at positions 3, 11, and 11. The most commonly occurring form is the (1R,9S)-(-)-enantiomer, which is found in many essential oils, particularly clove oil.. cannabinoid : A diverse group of pharmacologically active secondary metabolite characteristic to Cannabis plant as well as produced naturally in the body by humans and animals. Cannabinoids contain oxygen as a part of the heterocyclic ring or in the form of various functional groups. They are subdivided on the basis of their origin.	2.05	1	beta-caryophyllene	fragrance; insect attractant; metabolite; non-steroidal anti-inflammatory drug
cinnamyl alcohol cinnamyl alcohol: RN given refers to parent cpd without isomeric designation. (E)-cinnamyl alcohol : The E (trans) stereoisomer of cinnamyl alcohol.. cinnamyl alcohol : A primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C=C bond unspecified).	2.03	1	cinnamyl alcohol	plant metabolite
methyl-p-coumarate methyl-p-coumarate: structure in first source. 4-coumaric acid methyl ester : A cinnamate ester that is the methyl ester of 4-coumaric acid.	2.13	1	4-coumaric acid methyl ester
nerolidol nerolidol: sesquiterpene; RN given refers to cpd without isomeric designation; nerol is also available. nerolidol : A farnesane sesquiterpenoid that is dodeca-1,6,10-triene which carries methyl groups at positions 3, 7 and 11 and a hydroxy group at position 3. It is a natural product that is present in various flowers and plants with a floral odor. Chemically, it exists in two geometric isomers, trans and cis forms. It is widely used in cosmetics (e.g. shampoos and perfumes), in non-cosmetic products (e.g. detergents and cleansers) and also as a food flavoring agent.. (6Z)-nerolidol : A nerolidol in which the double bond at position 6 adopts a cis-configuration.	2.17	1	nerolidol
caryophyllene caryophyllene: RN given refers to cpd without isomeric designation; structure given in first source	2.78	3
methyl ferulate methyl ferulate: inhibits LDL oxidation; isolated from Chrysanthemum coronarium; structure in first source. trans-methylferulate : A cinnamate ester that is the methyl ester of ferulic acid. It has been isolated from Pisonia aculeata.	7.13	1	cinnamate ester; guaiacols; methyl ester	plant metabolite
germacrene d germacrene D: RN in 9th CI Form Index for unspecified stereoisomer: 37839-63-7	2.08	1
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.	2.05	1	cysteinium	fundamental metabolite
huperzine b huperzine B: Chinese drug isolated from Huperzia serrata; structure given in first source; also isolated from Phlegmariurus fordii	2.1	1	phenanthrol
cadinol cadinol: from callus cultures of Chamomilla recutita (Asteraceae)	2.17	1
isomenthone isomenthone: from the essential oil of rose-scented geranium (Pelargonium spp.)	2.8	3	isomenthone
isoborneol isoborneol: RN given refers to cpd without isomeric designation; structure	2.17	1	borneol
picrotoxin Picrotoxin: A noncompetitive antagonist at GABA-A receptors and thus a convulsant. Picrotoxin blocks the GAMMA-AMINOBUTYRIC ACID-activated chloride ionophore. Although it is most often used as a research tool, it has been used as a CNS stimulant and an antidote in poisoning by CNS depressants, especially the barbiturates.. picrotoxin : A mixture consisting of equimolar amounts of picrotoxinin and picrotin found in the climbing plant Anamirta cocculus.	2.1	1
heme Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.	1.97	1
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	2.93	4	benzenes; hydroxycoumarin; methyl ketone
clozapine Clozapine: A tricylic dibenzodiazepine, classified as an atypical antipsychotic agent. It binds several types of central nervous system receptors, and displays a unique pharmacological profile. Clozapine is a serotonin antagonist, with strong binding to 5-HT 2A/2C receptor subtype. It also displays strong affinity to several dopaminergic receptors, but shows only weak antagonism at the dopamine D2 receptor, a receptor commonly thought to modulate neuroleptic activity. Agranulocytosis is a major adverse effect associated with administration of this agent.. clozapine : A benzodiazepine that is 5H-dibenzo[b,e][1,4]diazepine substituted by a chloro group at position 8 and a 4-methylpiperazin-1-yl group at position 11. It is a second generation antipsychotic used in the treatment of psychiatric disorders like schizophrenia.	2.46	2	benzodiazepine; N-arylpiperazine; N-methylpiperazine; organochlorine compound	adrenergic antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; GABA antagonist; histamine antagonist; muscarinic antagonist; second generation antipsychotic; serotonergic antagonist; xenobiotic
aprepitant Aprepitant: A morpholine neurokinin-1 (NK1) receptor antagonist that is used in the management of nausea and vomiting caused by DRUG THERAPY, and for the prevention of POSTOPERATIVE NAUSEA AND VOMITING.. aprepitant : A morpholine-based antiemetic, which is or the prevention of acute and delayed nausea and vomiting associated with initial and repeat courses of highly emetogenic cancer chemotherapy. Aprepitant is a selective high-affinity antagonist of human substance P/neurokinin 1 (NK1) receptors.	2.1	1	(trifluoromethyl)benzenes; cyclic acetal; morpholines; triazoles	antidepressant; antiemetic; neurokinin-1 receptor antagonist; peripheral nervous system drug; substance P receptor antagonist
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	2	1

Condition	Relationship Strength	Studies
Malignant Melanoma [description not available]	2.6	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)	2.6	1
Blood Pressure, High [description not available]	2.6	1
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	7.6	1
Acute Liver Injury, Drug-Induced [description not available]	4.28	7
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.	4.28	7
Allergic Contact Dermatitis [description not available]	2.17	1
Eczema, Atopic [description not available]	2.17	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.46	2
Itching [description not available]	2.17	1
Dermatitis, Atopic A chronic inflammatory genetically determined disease of the skin marked by increased ability to form reagin (IgE), with increased susceptibility to allergic rhinitis and asthma, and hereditary disposition to a lowered threshold for pruritus. It is manifested by lichenification, excoriation, and crusting, mainly on the flexural surfaces of the elbow and knee. In infants it is known as infantile eczema.	2.17	1
Pruritus An intense itching sensation that produces the urge to rub or scratch the skin to obtain relief.	2.17	1
Dermatitis, Allergic Contact A contact dermatitis due to allergic sensitization to various substances. These substances subsequently produce inflammatory reactions in the skin of those who have acquired hypersensitivity to them as a result of prior exposure.	2.17	1
Caliciviridae Infections Virus diseases caused by CALICIVIRIDAE. They include HEPATITIS E; VESICULAR EXANTHEMA OF SWINE; acute respiratory infections in felines, rabbit hemorrhagic disease, and some cases of gastroenteritis in humans.	2.17	1
Fish Diseases Diseases of freshwater, marine, hatchery or aquarium fish. This term includes diseases of both teleosts (true fish) and elasmobranchs (sharks, rays and skates).	2.21	1
Bacterial Infections, Gram-Negative [description not available]	2.21	1
Gram-Negative Bacterial Infections Infections caused by bacteria that show up as pink (negative) when treated by the gram-staining method.	2.21	1
Weight Gain Increase in BODY WEIGHT over existing weight.	2.11	1
Empyema, Gall Bladder [description not available]	2.11	1
Gallstone Disease [description not available]	2.11	1
Cholecystitis Inflammation of the GALLBLADDER; generally caused by impairment of BILE flow, GALLSTONES in the BILIARY TRACT, infections, or other diseases.	2.11	1
Cholelithiasis Presence or formation of GALLSTONES in the BILIARY TRACT, usually in the gallbladder (CHOLECYSTOLITHIASIS) or the common bile duct (CHOLEDOCHOLITHIASIS).	2.11	1
Extravascular Hemolysis [description not available]	2.13	1
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.13	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.05	1
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	3.34	2
Pediculosis [description not available]	2.06	1
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.06	1
Lice Infestations Parasitic attack or subsistence on the skin by members of the order Phthiraptera, especially on humans by Pediculus humanus of the family Pediculidae. The hair of the head, eyelashes, and pubis is a frequent site of infestation. (From Dorland, 28th ed; Stedman, 26th ed)	2.06	1
Atopic Hypersensitivity [description not available]	2.06	1
Bladder Cancer [description not available]	2.06	1
Bone Cancer [description not available]	2.06	1
Cancer of Liver [description not available]	2.06	1
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.06	1
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	2.06	1
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.06	1
Liver Neoplasms Tumors or cancer of the LIVER.	2.06	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.4	2
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.	2.07	1
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	2.07	1
Liver Dysfunction [description not available]	2.9	4
Liver Diseases Pathological processes of the LIVER.	2.9	4
Acute Hepatic Failure [description not available]	2.41	2
Liver Failure, Acute A form of rapid-onset LIVER FAILURE, also known as fulminant hepatic failure, caused by severe liver injury or massive loss of HEPATOCYTES. It is characterized by sudden development of liver dysfunction and JAUNDICE. Acute liver failure may progress to exhibit cerebral dysfunction even HEPATIC COMA depending on the etiology that includes hepatic ISCHEMIA, drug toxicity, malignant infiltration, and viral hepatitis such as post-transfusion HEPATITIS B and HEPATITIS C.	2.41	2
Infectious Endophthalmitis Infectious condition of the internal eye.	1.98	1
Endophthalmitis Suppurative inflammation of the tissues of the internal structures of the eye frequently associated with an infection.	1.98	1
Uveitis, Posterior Inflammation of the choroid as well as the retina and vitreous body. Some form of visual disturbance is usually present. The most important characteristics of posterior uveitis are vitreous opacities, choroiditis, and chorioretinitis.	1.98	1
Plant Poisoning Poisoning by the ingestion of plants or its leaves, berries, roots or stalks. The manifestations in both humans and animals vary in severity from mild to life threatening. In animals, especially domestic animals, it is usually the result of ingesting moldy or fermented forage.	2.9	1
Brain Disorders [description not available]	1.99	1
Brain Swelling [description not available]	1.99	1
Aura [description not available]	1.99	1
MODS [description not available]	1.99	1
Brain Diseases Pathologic conditions affecting the BRAIN, which is composed of the intracranial components of the CENTRAL NERVOUS SYSTEM. This includes (but is not limited to) the CEREBRAL CORTEX; intracranial white matter; BASAL GANGLIA; THALAMUS; HYPOTHALAMUS; BRAIN STEM; and CEREBELLUM.	1.99	1
Brain Edema Increased intracellular or extracellular fluid in brain tissue. Cytotoxic brain edema (swelling due to increased intracellular fluid) is indicative of a disturbance in cell metabolism, and is commonly associated with hypoxic or ischemic injuries (see HYPOXIA, BRAIN). An increase in extracellular fluid may be caused by increased brain capillary permeability (vasogenic edema), an osmotic gradient, local blockages in interstitial fluid pathways, or by obstruction of CSF flow (e.g., obstructive HYDROCEPHALUS). (From Childs Nerv Syst 1992 Sep; 8(6):301-6)	1.99	1
Epilepsy A disorder characterized by recurrent episodes of paroxysmal brain dysfunction due to a sudden, disorderly, and excessive neuronal discharge. Epilepsy classification systems are generally based upon: (1) clinical features of the seizure episodes (e.g., motor seizure), (2) etiology (e.g., post-traumatic), (3) anatomic site of seizure origin (e.g., frontal lobe seizure), (4) tendency to spread to other structures in the brain, and (5) temporal patterns (e.g., nocturnal epilepsy). (From Adams et al., Principles of Neurology, 6th ed, p313)	1.99	1
Multiple Organ Failure A progressive condition usually characterized by combined failure of several organs such as the lungs, liver, kidney, along with some clotting mechanisms, usually postinjury or postoperative.	1.99	1
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.4	2
Weight Reduction [description not available]	1.99	1
Weight Loss Decrease in existing BODY WEIGHT.	1.99	1
Dermatitis, Contact, Phototoxic [description not available]	2.92	1
Dermatoses [description not available]	2.92	1
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	2.92	1

pulegone

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Research Demand Index: 47.81

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