Thymol - Compound Card

Thymol

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Thymol

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Monoaromatic
Canonical Smiles Cc1ccc(c(c1)O)C(C)C
InChI InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h4-7,11H,1-3H3
InChIKey MGSRCZKZVOBKFT-UHFFFAOYSA-N
Formula C10H14O
HBA 1
HBD 1
MW 150.22
Rotatable Bonds 1
TPSA 20.23
LogP 2.82
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 11
Formal Charge 0
Fraction CSP3 0.4
Exact Mass 150.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Chenopodium ambrosioides Chenopodiaceae Plantae 330163
2 Artemisia herba-alba Asteraceae Plantae 72329
3 Thymus maroccanus Lamiaceae Plantae 49990
4 Thymus broussonetii Lamiaceae Plantae 751869
5 Cupressus arizonica Cupressaceae Plantae 49011
6 Chrysanthemum viscidehirtum Asteraceae Plantae 13422
7 Chrysanthemum macrocarpum Asteraceae Plantae 13422
8 Pyrethrum santolinoides Asteraceae Plantae 2072400
9 Pyrethrum santolinoides Asteraceae Plantae 2072400
10 Pulicaria arabica Asteraceae Plantae 119185

Showing of synonyms

  • Mahmoud AA, Ahmed AA, et al. (1994). 2,3-secogermacranolides and germacranolides from Pyrethrum santolionoides. Phytochemistry,1994,36(2),393-398. [View]
  • Khallouki F, Hmamouchi MH, et al. (2000). Antibacterial and molluscicidal activities of the essential oil of Chrysanthemum viscidehirtum. Fitoterapia,2000,71,544-546. [View] [PubMed]
  • Saad A, Fadli M, et al. (2010). Anticandidal activity of the essential oils of Thymus maroccanus and Thymus broussonetii and their synergism with amphotericin B and fluconazol. Phytomedicine,2010,17(13),1057-1060. [View] [PubMed]
  • Hafez S, Sarg TM, et al. (1987). Caryophyllene derivatives from Pulicaria arabica. Phytochemistry,1987,26(12),3356-3358. [View]
  • Cheraif I, Jannet HB, et al. (2007). Chemical composition and antimicrobial activity of essential oils of Cupressus arizonica Greene. Biochemical Systematics and Ecology,2007,35,813 -820. [View]
  • Boutaghane N, Kabouche A, et al. (2008). Composition of the essential oil of Chrysanthemum macrocarpum from Algeria. Chemistry of Natural Compounds,2008,44(6),817-818. [View]
  • Ahmed AA (2000). Highly oxygenated monoterpenes from Chenopodium ambrosioides. Journal of Natural Products,2000,63(7),989-991. [View] [PubMed]
  • Gordon MM, Van Derveer D, et al. (1981). New germacranolides from Artemisia herba alba. X-ray crystal structures of 3beta,8alpha-dihydroxy-6betaH,7alphaH,11betaH-germacran-4(14),9(10)-dien-6,12-olide and the corresponding 3-oxo-olide.. Journal of Natural Products,1981,44(4),432-440. [View]
  • Abdel-Mogib M, Jakupovic J, et al. (1989). Sesquiterpene lactones from Pyrethrum santolinoides. Phytochemistry,1989,28(1),268-271. [View]
Pubchem: 6989
Kegg Ligand: C09908
Chebi: 27607
Nmrshiftdb2: 10008971
Metabolights: MTBLC27607
Drugbank: DB02513
Pdb Ligand: IPB
Bindingdb: 50240432
CPRiL: 16227
Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 150.22 g/mol

Antibacterial
Molluscicidal

Absorption

Caco-2 (logPapp)
-4.44
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.99
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.45
Plasma Protein Binding
34.28
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.67
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.33
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Toxic
Eye Irritation
Toxic
Maximum Tolerated Dose
0.89
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.57
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
3.81
Rat (Acute)
2.07
Rat (Chronic Oral)
2.03
Fathead Minnow
3.96
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
231.17
Hydration Free Energy
-4.82
Log(D) at pH=7.4
3.35
Log(P)
3.18
Log S
-2.23
Log(Vapor Pressure)
-1.7
Melting Point
18.93
pKa Acid
10.56
pKa Basic
7.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.9345
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.9345
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.8861
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.8861
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8855
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8855
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8792
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8792
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8328
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8328
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8261
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8261
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.8217
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.8217
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.8123
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.8123
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8082
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8082
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 4 0.8055
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 4 0.8055
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7934
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7934
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7913
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7913
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7814
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7814
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7778
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7778
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7705
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7705
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7699
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7699
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7643
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7643
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7612
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7612
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7609
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7609
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7578
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7578
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7569
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7569
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7558
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7558
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7552
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7552
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7525
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7525
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7501
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7501
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7493
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7493
Fructose-1,6-bisphosphatase 1 P00636 F16P1_PIG Sus scrofa 3 0.7480
Fructose-1,6-bisphosphatase 1 P00636 F16P1_PIG Sus scrofa 3 0.7480
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7427
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7427
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7426
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7426
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7388
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7388
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7358
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7358
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7357
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7357
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7325
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7325
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7276
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7276
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7273
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7273
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7268
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7268
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7255
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7255
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7248
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7248
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7236
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7236
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7209
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7209
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7197
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7197
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7177
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7177
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7158
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7158
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7150
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7150
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 2 0.7141
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 2 0.7141
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7125
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7125
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7118
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7118
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7116
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7116
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7116
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7116
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7104
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7104
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7092
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7092
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7086
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7086
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7077
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7077
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7070
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7070
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7066
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7066
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7059
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7059
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7048
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7048
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7046
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7046
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7044
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7044
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7021
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7021
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7010
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7010
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7008
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7008
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7005
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7005
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7000
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7000

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