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3-O-acetyloleanolic acid
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpenoid
| Canonical Smiles | CC(=O)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/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)/t22-,23-,24+,25-,29-,30+,31+,32-/m0/s1 |
| InChIKey | RIXNFYQZWDGQAE-DFHVBEEKSA-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 | Neoboutonia macrocalyx | Euphorbiaceae | Plantae | 1260343 |
| 2 | Rauvolfia caffra | Apocynaceae | Plantae | 947877 |
| 3 | Drypetes molunduana | Euphorbiaceae | Plantae | 20145 |
| 4 | Coffea canephora | Rubiaceae | Plantae | 49390 |
| 5 | Ormocarpum sennoides | Leguminosae/Fabaceae | Plantae | 77289 |
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
- Mewaba S, Happi E, et al. (2022). Antibacterial compounds of the cultivated Robusta coffee: Coffea canephora Pierre ex A. Froehner. Scientific African, 2022, 16, e01274. [View]
- Bitombo AN, Zintchem AAA, et al. (2022). Antimicrobial and cytotoxic activities of indole alkaloids and other constituents from the stem barks of Rauvolfia caffra Sond (Apocynaceae). Natural product research,2022, 36(6), 1467-1475. [View] [PubMed]
- Chalo DM, Kakudidi E, et al. (2021). Chemical constituents of the roots of Ormocarpum sennoides subsp. Zanzibaricum. Biochemical Systematics and Ecology, 2021, 97,104277. [View]
- Wandji J, Wansi JD, et al. (2000). Sesquiterpene lactone and friedelane derivative from drypetes molunduana.. Phytochemistry,2000, 54(8), 811-815. [View] [PubMed]
- Maffo T, Wafo P, et al. (2015). Terpenoids from the stem bark of Neoboutonia macrocalyx (Euphorbiaceae). Phytochemistry Letters, 2015, 12, 328-331. [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
Antimicrobial
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -5.33
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.89
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.38
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 2.21
- Plasma Protein Binding
- 97.01
- 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
- 2.17
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.4
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.57
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 3.19
- 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
- -291.77
- Rat (Acute)
- 2.3
- Rat (Chronic Oral)
- 1.97
- Fathead Minnow
- 3.99
- 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
- 485.25
- Hydration Free Energy
- -2.86
- Log(D) at pH=7.4
- 5.13
- Log(P)
- 7.39
- Log S
- -6.62
- Log(Vapor Pressure)
- -9.26
- Melting Point
- 251.39
- pKa Acid
- 7.1
- pKa Basic
- 8.57
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7480 |