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Oleanonic acid
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpenoid
| Canonical Smiles | OC(=O)[C@]12CC[C@@]3(C(=CC[C@H]4[C@@]3(C)CC[C@@H]3[C@]4(C)CCC(=O)C3(C)C)[C@@H]2CC(CC1)(C)C)C |
|---|---|
| InChI | InChI=1S/C30H46O3/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/h8,20-22H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,27-,28+,29+,30-/m0/s1 |
| InChIKey | FMIMFCRXYXVFTA-FUAOEXFOSA-N |
| Formula | C30H46O3 |
| HBA | 2 |
| HBD | 1 |
| MW | 454.7 |
| Rotatable Bonds | 1 |
| TPSA | 54.37 |
| LogP | 7.44 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.87 |
| Exact Mass | 454.34 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Lantana montevidensis | Verbenaceae | Plantae | 1241423 |
| 2 | Ekebergia capensis | Meliaceae | Plantae | 124949 |
| 3 | Ekebergia capensis | Meliaceae | Plantae | 124949 |
Showing of synonyms
Oleanonic acid
17990-42-0
Olean-12-en-28-oic acid, 3-oxo-
3-OXOOLEANOLIC ACID
3-oxo-olean-12-en-28-oic acid
3-Oxoolean-12-en-28-oic Acid
(4aS,6aR,6aS,6bR,8aR,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid
CHEMBL470029
3-Ketooleanolic Acid
Oleanonicacid
3-Oxooleanolicacid
(4AS,6AS,6BR,8AR,12AR,12BR,14BS)-2,2,6A,6B,9,9,12A-HEPTAMETHYL-10-OXO-3,4,5,6,7,8,8A,11,12,12B,13,14B-DODECAHYDRO-1H-PICENE-4A-CARBOXYLIC ACID
MFCD09752411
Oleoside 11-methylester
Oleanonic acid (Standard)
JV79HC9A5B
SCHEMBL246220
3-Oxo-olean-12-en28-saure
STX-50
HY-N1487R
DTXSID90939279
HY-N1487
SAA99042
BDBM50346613
BLE-99006
MSK183267
S9505
AKOS032948921
CS-5795
AC-33969
AS-76428
DA-49628
F16163
(4aS,6aR,6aS,6bR,8aR,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylicacid
3-Oxo-olean-12-en-28-oic acidOlean-12-en-28-oic acid, 3-oxo-
- 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]
- Mohamed NM, Makboul MA, et al. (2015). New pentacyclic triterpenoid from the roots of Lantana montevidensis (spreng.) briq. cultivated in Egypt. Planta Medica,2015,81-PC22. [View]
Pubchem:
12313704
Cas:
17990-42-0
Gnps:
CCMSLIB00010129510
Zinc:
ZINC000013558220
Nmrshiftdb2:
60024000
Chembl:
CHEMBL470029
Bindingdb:
50346613
CPRiL:
84213
SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CC(=O)CC5
Level: 0
Mol. Weight: 454.7 g/mol
Anti-plasmodial
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -5.47
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.67
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.67
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 2.28
- Plasma Protein Binding
- 93.61
- 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
- Non-Inhibitor
Excretion
- Clearance
- 3.79
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.54
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.76
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 3.46
- 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
- -78.22
- Rat (Acute)
- 2.27
- Rat (Chronic Oral)
- 2.12
- Fathead Minnow
- 3.92
- 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
- 476.88
- Hydration Free Energy
- -3.24
- Log(D) at pH=7.4
- 5.02
- Log(P)
- 6.63
- Log S
- -6.3
- Log(Vapor Pressure)
- -8.59
- Melting Point
- 262.66
- pKa Acid
- 5.92
- pKa Basic
- 8.23