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3-epioleanolic acid
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpenoid
| Canonical Smiles | O[C@@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)O)C)C |
|---|---|
| InChI | InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23+,27-,28+,29+,30-/m0/s1 |
| InChIKey | MIJYXULNPSFWEK-KDQGZELNSA-N |
| Formula | C30H48O3 |
| HBA | 2 |
| HBD | 2 |
| MW | 456.71 |
| Rotatable Bonds | 1 |
| TPSA | 57.53 |
| LogP | 7.23 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.9 |
| Exact Mass | 456.36 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ekebergia capensis | Meliaceae | Plantae | 124949 |
| 2 | Ekebergia capensis | Meliaceae | Plantae | 124949 |
Showing of synonyms
3-epioleanolic acid
Epi-Oleanolic Acid
(20R)-3alpha-Hydroxyolean-12-en-28-oic acid
3-alpha-Hydroxyolean-12-en-28-oate
3-alpha-Hydroxyolean-12-en-28-oic acid
Epi-oleanolate
3-Epioleanolate
25499-90-5
3-epi-Oleanolic Acid
CHEMBL486382
CHEBI:68103
(4aS,6aR,6aS,6bR,8aR,10R,12aR,14bS)-10-hydroxy-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
SCHEMBL26940985
DTXSID201316135
BDBM50241532
AKOS037515061
LMPR0106150020
3alpha-Hydroxyolean-12-en-28-oic Acid
DA-69094
PD200026
XE180444
(3alpha)-3-hydroxyolean-12-en-28-oic acid
G13570
Q27136594
(4aS,6aS,6bR,8aR,10R,12aR,12bR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
- Murata T, Miyase T, et al. (2008). Antiplasmodial triterpenoids from Ekebergia capensis.. Journal of Natural Products,2008,71(2),167-174. [View] [PubMed]
- Irungu BN, Orwa JA, et al. (2014). Constituents of the roots and leaves of Ekebergia capensis and their potential antiplasmodial and cytotoxic activities.. Molecules,2014,19(9),14235-14246. [View] [PubMed]
Pubchem:
11869658
Cas:
25499-90-5
Gnps:
CCMSLIB00006516304
Zinc:
ZINC000003881983
Chebi:
68103
Nmrshiftdb2:
60060988
Metabolights:
MTBLC68103
Chembl:
CHEMBL486382
Bindingdb:
50241532
CPRiL:
414884
SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CCCC5
Level: 0
Mol. Weight: 456.71 g/mol
Anti-plasmodial
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -5.47
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.65
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.97
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.98
- Plasma Protein Binding
- 90.17
- 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
- 3.14
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.57
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.72
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 3.91
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- 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
- -79.82
- Rat (Acute)
- 2.4
- Rat (Chronic Oral)
- 2.17
- Fathead Minnow
- 3.94
- 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
- 461.12
- Hydration Free Energy
- -3.23
- Log(D) at pH=7.4
- 5.21
- Log(P)
- 7.03
- Log S
- -6.49
- Log(Vapor Pressure)
- -8.89
- Melting Point
- 266.89
- pKa Acid
- 5.99
- pKa Basic
- 8.53
No predicted protein targets found for this compound.