Select a section from the left sidebar
Aulacocarpin B
- Family: Plantae - Loganiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene
| Canonical Smiles | COC(=O)/C(=C/C[C@H]1[C@]2(CO2)C[C@H]([C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)O)/C1CO1 |
|---|---|
| InChI | InChI=1S/C21H32O6/c1-19(2)16(23)7-8-20(3)15(21(11-27-21)9-13(22)17(19)20)6-5-12(14-10-26-14)18(24)25-4/h5,13-17,22-23H,6-11H2,1-4H3/b12-5+/t13-,14?,15-,16+,17+,20-,21-/m1/s1 |
| InChIKey | OCZNPNYYEDNTIA-ZCZREUOKSA-N |
| Formula | C21H32O6 |
| HBA | 6 |
| HBD | 2 |
| MW | 380.48 |
| Rotatable Bonds | 4 |
| TPSA | 91.82 |
| LogP | 1.83 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.86 |
| Exact Mass | 380.22 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Aframomum escapum | Loganiaceae | Plantae | 188478 |
Showing of synonyms
Aulacocarpin B
Methyl (E)-4-((1R,2S,4R,4aR,6S,8aS)-4,6-dihydroxy-5,5,8a-trimethylspiro(3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane)-1-yl)-2-(oxiran-2-yl)but-2-enoate
Methyl (E)-4-[(1R,2S,4R,4aR,6S,8aS)-4,6-dihydroxy-5,5,8a-trimethylspiro[3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane]-1-yl]-2-(oxiran-2-yl)but-2-enoate
157878-19-8
CHEMBL461902
- Ayimele G, Tane P, et al. (2004). Aulacocarpin A and B, nerolidol and β-sitosterol glucoside from Aframomum escapum. Biochemical Systematics and Ecology, 2004, 32(12), 1205-1207. [View]
No compound-protein relationship available.
SMILES: O1CC1C=CCC(C23CO3)C4C(CC2)CCCC4
Level: 1
Mol. Weight: 380.48 g/mol
SMILES: O1CC12CC3C(CC2)CCCC3
Level: 0
Mol. Weight: 380.48 g/mol
SMILES: C1CO1
Level: 0
Mol. Weight: 380.48 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.08
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.740
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.26
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.260
- Plasma Protein Binding
- 34.02
- 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
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 12.200
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.190
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.300
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.070
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -10.870
- Rat (Acute)
- 4.210
- Rat (Chronic Oral)
- 1.770
- Fathead Minnow
- 3.940
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 437.360
- Hydration Free Energy
- -5.930
- Log(D) at pH=7.4
- 2.110
- Log(P)
- 2.05
- Log S
- -3.29
- Log(Vapor Pressure)
- -6.8
- Melting Point
- 110.91
- pKa Acid
- 5.33
- pKa Basic
- 3.33
No predicted protein targets found for this compound.