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(2R*,3R*,4R*)-menth-1(7)-en-2,3-diol
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Monoterpene
| Canonical Smiles | CC([C@H]1CCC(=C)[C@H]([C@@H]1O)O)C |
|---|---|
| InChI | InChI=1S/C10H18O2/c1-6(2)8-5-4-7(3)9(11)10(8)12/h6,8-12H,3-5H2,1-2H3/t8-,9-,10-/m1/s1 |
| InChIKey | YLLPOUNPAFCEFB-OPRDCNLKSA-N |
| Formula | C10H18O2 |
| HBA | 2 |
| HBD | 2 |
| MW | 170.25 |
| Rotatable Bonds | 1 |
| TPSA | 40.46 |
| LogP | 1.33 |
| Number Rings | 1 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 12 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.8 |
| Exact Mass | 170.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Artemisia hugueti | Asteraceae | Plantae | 4219 |
Showing of synonyms
(2R*,3R*,4R*)-menth-1(7)-en-2,3-diol
- Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones from North African Artemisia species.. Phytochemistry,1994,37(2),477-485. [View]
Pubchem:
21630990
No compound-protein relationship available.
SMILES: C=C1CCCCC1
Level: 0
Mol. Weight: 170.25 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.75
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -3.45
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.78
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.33
- Plasma Protein Binding
- 34.67
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.07
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.24
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.25
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 2.62
- 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
- -0.32
- Rat (Acute)
- 1.86
- Rat (Chronic Oral)
- 2.02
- Fathead Minnow
- 3.37
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 266.53
- Hydration Free Energy
- -8.8
- Log(D) at pH=7.4
- 1.27
- Log(P)
- 2.14
- Log S
- -1.65
- Log(Vapor Pressure)
- -3.34
- Melting Point
- 92.49
- pKa Acid
- 10.19
- pKa Basic
- 7.08
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.9492 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.9492 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 3 | 0.8987 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 3 | 0.8987 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.8626 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.8626 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8597 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8597 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8546 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8546 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.8504 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.8504 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 3 | 0.8414 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 3 | 0.8414 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8117 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8117 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7986 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7986 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7864 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7864 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7848 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7848 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7834 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7834 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7786 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7786 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7667 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7667 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7640 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7640 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7573 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7573 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7497 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7497 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7478 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7478 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7468 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7468 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7402 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7402 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7399 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7399 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7362 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7362 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7361 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7361 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7355 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7355 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7340 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7340 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7339 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7339 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7328 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7328 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 2 | 0.7317 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 2 | 0.7317 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7306 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7306 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7305 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7305 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7288 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7288 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 2 | 0.7279 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 2 | 0.7279 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7276 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7276 |
| Epoxide hydrolase | Q41415 | Q41415_SOLTU | Solanum tuberosum | 3 | 0.7275 |
| Epoxide hydrolase | Q41415 | Q41415_SOLTU | Solanum tuberosum | 3 | 0.7275 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7270 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7270 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7266 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7266 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7264 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7264 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7262 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7262 |
| Corticosteroid-binding globulin | P31211 | CBG_RAT | Rattus norvegicus | 3 | 0.7251 |
| Corticosteroid-binding globulin | P31211 | CBG_RAT | Rattus norvegicus | 3 | 0.7251 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7249 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7249 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7249 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7249 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7246 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7246 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7245 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7245 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7243 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7243 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7237 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7237 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7210 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7210 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 3 | 0.7209 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 3 | 0.7209 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7208 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7208 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7208 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7208 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7207 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7207 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7206 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7206 |
| Androgen receptor | P19091 | ANDR_MOUSE | Mus musculus | 3 | 0.7196 |
| Androgen receptor | P19091 | ANDR_MOUSE | Mus musculus | 3 | 0.7196 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7184 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7184 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7179 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7179 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7173 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7173 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7170 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7170 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7167 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7167 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7163 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7163 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7159 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7159 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 2 | 0.7159 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 2 | 0.7159 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7158 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7158 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7153 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7153 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7153 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7153 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7145 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7145 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7115 |
| Alcohol dehydrogenase 1C | P00326 | ADH1G_HUMAN | Homo sapiens | 2 | 0.7115 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7115 |
| Alcohol dehydrogenase 1C | P00326 | ADH1G_HUMAN | Homo sapiens | 2 | 0.7115 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7114 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7114 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7108 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7108 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7106 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7106 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7100 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7100 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7074 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7074 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7072 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7072 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7068 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7068 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 2 | 0.7046 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 2 | 0.7046 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7037 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7037 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7034 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7034 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7020 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7020 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7002 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7002 |
| Steroid 21-hydroxylase | P08686 | CP21A_HUMAN | Homo sapiens | 2 | 0.7001 |
| Steroid 21-hydroxylase | P08686 | CP21A_HUMAN | Homo sapiens | 2 | 0.7001 |