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3-O-acetyloleanolic acid
- Family: Plantae - Euphorbiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Pentacyclic Triterpene
| Canonical Smiles | CC(=O)OC1CCC2(C(C1(C)C)CCC3(C2CC=C4C3(CCC5(C4CC(CC5)(C)C)C(=O)O)C)C)C |
|---|---|
| InChI | InChI=1S/C32H50O4/c1-20(33)36-25-12-13-29(6)23(28(25,4)5)11-14-31(8)24(29)10-9-21-22-19-27(2,3)15-17-32(22,26(34)35)18-16-30(21,31)7/h9,22-25H,10-19H2,1-8H3,(H,34,35) |
| InChIKey | RIXNFYQZWDGQAE-UHFFFAOYSA-N |
| Formula | C32H50O4 |
| HBA | 3 |
| HBD | 1 |
| MW | 498.75 |
| Rotatable Bonds | 2 |
| TPSA | 63.6 |
| LogP | 7.8 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 36 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.88 |
| Exact Mass | 498.37 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Alchornea laxiflora | Euphorbiaceae | Plantae | 316698 |
Showing of synonyms
3-O-acetyloleanolic acid
4339-72-4
Oleanolic acid 3-acetate
Acetyl oleanolic acid
3-?O-?Acetyloleanolic acid
(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-acetyloxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid
Olean-12-en-28-oic acid, 3-(acetyloxy)-, (3beta)-
(4AS,6AS,6BR,8AR,10S,12AR,12BR,14BS)-10-(ACETYLOXY)-2,2,6A,6B,9,9,12A-HEPTAMETHYL-1,3,4,5,6,7,8,8A,10,11,12,12B,13,14B-TETRADECAHYDROPICENE-4A-CARBOXYLIC ACID
MFCD09752429
3--cetyloleanolic acid
3-O-Acetyloleanolicacid
SCHEMBL828971
CHEMBL486822
DTXSID20963002
3beta-acetoxyolean-12-en-28-acid
HY-N2618
BDBM50102741
AKOS016036262
3-(Acetyloxy)olean-12-en-28-oic acid
AC-34649
BS-16825
DA-70502
CS-0023022
C75167
(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
- Siwe-Noundou X, Ndinteh D, et al. (2019). Biological activity of plant extracts and isolated compounds from Alchornea laxiflora: Anti-HIV, antibacterial and cytotoxicity evaluation. South African Journal of Botany, 2019, 122, 498-503. [View]
Pubchem:
151202
Cas:
4339-72-4
Gnps:
CCMSLIB00006436478
Zinc:
ZINC000003964583
Nmrshiftdb2:
60029393
Chembl:
CHEMBL486822
Bindingdb:
50102741
CPRiL:
102563
SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CCCC5
Level: 0
Mol. Weight: 498.75 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.4
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.9
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.37
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 2.24
- Plasma Protein Binding
- 31.85
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- 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
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 2.11
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.2
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.5
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 2.93
- Micronucleos
- Safe
- 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
- -286.13
- Rat (Acute)
- 2.25
- Rat (Chronic Oral)
- 1.87
- Fathead Minnow
- 4.58
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 463.69
- Hydration Free Energy
- -2.84
- Log(D) at pH=7.4
- 5.12
- Log(P)
- 7.77
- Log S
- -6.61
- Log(Vapor Pressure)
- -8.62
- Melting Point
- 257.61
- pKa Acid
- 7.18
- pKa Basic
- 8.55
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8219 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7705 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7669 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7369 |
| Retinol-binding protein 2 | P50120 | RET2_HUMAN | Homo sapiens | 3 | 0.7109 |