Select a section from the left sidebar
Zoapatanolide A
- Family: Plantae - Anacardiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene
| Canonical Smiles | C/C=C(/C(=O)OC1C(O)/C(=C\CC(/C(=C\C2[C@@H]1C(=C)C(=O)O2)/C)O)/C)\C |
|---|---|
| InChI | InChI=1S/C20H26O6/c1-6-10(2)19(23)26-18-16-13(5)20(24)25-15(16)9-12(4)14(21)8-7-11(3)17(18)22/h6-7,9,14-18,21-22H,5,8H2,1-4H3/b10-6+,11-7-,12-9-/t14?,15?,16-,17?,18?/m0/s1 |
| InChIKey | BXFQVBKJGJTIAT-CGSFVSGYSA-N |
| Formula | C20H26O6 |
| HBA | 6 |
| HBD | 2 |
| MW | 362.42 |
| Rotatable Bonds | 2 |
| TPSA | 93.06 |
| LogP | 1.98 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 362.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Anacardium occidentale | Anacardiaceae | Plantae | 171929 |
Showing of synonyms
Zoapatanolide A
BRN 4764017
84886-38-4
2-Butenoic acid, 2-methyl-, 2,3,3a,4,5,8,9,11a-octahydro-5,9-dihydroxy-6,10-dimethyl-3-methylene-2-oxocyclodeca(b)furan-4-yl ester, (3aS-(3aR*,4S*(Z),5S*,6E,9S*,10Z,11aS*))-
((3aS,4R,5R,6E,9R,10Z,11aR)-5,9-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca(b)furan-4-yl) (Z)-2-methylbut-2-enoate
(3AR,4S,5S,9S,11ar)-5,9-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca(b)furan-4-yl (2E)-2-methylbut-2-enoic acid
(3AR,4S,5S,9S,11ar)-5,9-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-4-yl (2E)-2-methylbut-2-enoic acid
[(3aS,4R,5R,6E,9R,10Z,11aR)-5,9-dihydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (Z)-2-methylbut-2-enoate
- Taiwo Bamigboye J, Fatokun Amos A, et al. (2017). Identification of compounds with cytotoxic activity from the leaf of the Nigerian medicinal plant, Anacardium occidentale L. (Anacardiaceae). Bioorganic & Medicinal Chemistry, 2017, 25(8), 2327-2335. [View]
Pubchem:
6448268
Cas:
84886-38-4
No compound-protein relationship available.
SMILES: C=C1C(=O)OC(C12)C=CCCC=CCC2
Level: 0
Mol. Weight: 362.42 g/mol
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.65
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.65
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.45
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.47
- Plasma Protein Binding
- 40.75
- 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
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.2
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.37
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.18
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.53
- 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
- Safe
- T. Pyriformis
- -0.57
- Rat (Acute)
- 2.89
- Rat (Chronic Oral)
- 2.2
- Fathead Minnow
- 4.51
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 366.6
- Hydration Free Energy
- -8.22
- Log(D) at pH=7.4
- 1.66
- Log(P)
- 1.72
- Log S
- -2.86
- Log(Vapor Pressure)
- -7.15
- Melting Point
- 130.78
- pKa Acid
- 7.42
- pKa Basic
- 3.34
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.9262 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8074 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7030 |