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(3aR,9aR)-3a,4,9,9a-tetrahydro-5,8-dimethyl-3-methylenenaphtho[2,3-b]furan-2(3H)-one
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | C=C1C(=O)O[C@H]2[C@@H]1Cc1c(C)ccc(c1C2)C |
|---|---|
| InChI | InChI=1S/C15H16O2/c1-8-4-5-9(2)12-7-14-13(6-11(8)12)10(3)15(16)17-14/h4-5,13-14H,3,6-7H2,1-2H3/t13-,14-/m1/s1 |
| InChIKey | GTRAODQPIPVSKC-ZIAGYGMSSA-N |
| Formula | C15H16O2 |
| HBA | 2 |
| HBD | 0 |
| MW | 228.29 |
| Rotatable Bonds | 0 |
| TPSA | 26.3 |
| LogP | 2.5 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 17 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.4 |
| Exact Mass | 228.12 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Artemisia reptans | Asteraceae | Plantae | 72350 |
Showing of synonyms
(3aR,9aR)-3a,4,9,9a-tetrahydro-5,8-dimethyl-3-methylenenaphtho[2,3-b]furan-2(3H)-one
- Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones and acetylenes from Artemisia reptans.. Phytochemistry,1994,37(4),1055-1099. [View]
No compound-protein relationship available.
SMILES: C=C1C(=O)OC(C12)Cc3c(C2)cccc3
Level: 0
Mol. Weight: 228.29 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.93
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.15
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.56
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.86
- Plasma Protein Binding
- 63.55
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Non-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
- 9.25
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.33
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.37
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.36
- 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
- 3.51
- Rat (Acute)
- 1.78
- Rat (Chronic Oral)
- 1.89
- Fathead Minnow
- 4.11
- 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
- 333.95
- Hydration Free Energy
- -4.93
- Log(D) at pH=7.4
- 3.09
- Log(P)
- 2.99
- Log S
- -4.03
- Log(Vapor Pressure)
- -5.03
- Melting Point
- 129.5
- pKa Acid
- 11.52
- pKa Basic
- 5.45
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.9551 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.9551 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 3 | 0.9465 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 3 | 0.9465 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 3 | 0.9184 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 3 | 0.9184 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8759 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8759 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8750 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8750 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.8715 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.8715 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8695 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8695 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8599 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8599 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.8486 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.8486 |
| Odorant-binding protein | P81245 | OBP_PIG | Sus scrofa | 3 | 0.8415 |
| Odorant-binding protein | P81245 | OBP_PIG | Sus scrofa | 3 | 0.8415 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8408 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8408 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8403 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8403 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8399 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8399 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8354 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8354 |
| 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase | Q84HC8 | NCSB1_STRCZ | Streptomyces carzinostaticus | 3 | 0.8344 |
| 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase | Q84HC8 | NCSB1_STRCZ | Streptomyces carzinostaticus | 3 | 0.8344 |
| Aldo-keto reductase family 1 member B10 | O60218 | AK1BA_HUMAN | Homo sapiens | 4 | 0.8208 |
| Aldo-keto reductase family 1 member B10 | O60218 | AK1BA_HUMAN | Homo sapiens | 4 | 0.8208 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.8049 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.8049 |
| 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase | Q84HC8 | NCSB1_STRCZ | Streptomyces carzinostaticus | 3 | 0.8025 |
| 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase | Q84HC8 | NCSB1_STRCZ | Streptomyces carzinostaticus | 3 | 0.8025 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7905 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7905 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7863 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7863 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 4 | 0.7851 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 4 | 0.7851 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7820 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7820 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7808 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7808 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7707 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7707 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7685 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7685 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7658 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7658 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.7655 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.7655 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7585 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7585 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7502 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7502 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 2 | 0.7446 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 2 | 0.7446 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7424 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7424 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7399 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7399 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7372 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7372 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7282 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7282 |
| Abscisic acid receptor PYL10 | Q8H1R0 | PYL10_ARATH | Arabidopsis thaliana | 3 | 0.7279 |
| Abscisic acid receptor PYL10 | Q8H1R0 | PYL10_ARATH | Arabidopsis thaliana | 3 | 0.7279 |
| Beta-2 adrenergic receptor | P07550 | ADRB2_HUMAN | Homo sapiens | 3 | 0.7255 |
| Beta-2 adrenergic receptor | P07550 | ADRB2_HUMAN | Homo sapiens | 3 | 0.7255 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7243 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7243 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7242 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7242 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 2 | 0.7217 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 2 | 0.7217 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7146 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7146 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7146 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7146 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 3 | 0.7140 |
| Aromatase | P11511 | CP19A_HUMAN | Homo sapiens | 3 | 0.7140 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7122 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7122 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 2 | 0.7118 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 2 | 0.7118 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7096 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 2 | 0.7096 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7061 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7061 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7054 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7054 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.7044 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.7044 |
| Cytochrome P450 2A6 | P11509 | CP2A6_HUMAN | Homo sapiens | 3 | 0.7028 |
| Cytochrome P450 2A6 | P11509 | CP2A6_HUMAN | Homo sapiens | 3 | 0.7028 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7026 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7026 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7023 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7023 |