Select a section from the left sidebar
Oleanolic acid
- Family: Plantae - Araliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpenoid
| Canonical Smiles | O[C@H]1CC[C@]2(C(C1(C)C)CC[C@@]1(C2CC=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-YOQSOQNOSA-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 | Dizygotheca kerchoveana | Araliaceae | Plantae | — |
Showing of synonyms
Oleanolic acid
508-02-1
Oleanic acid
Caryophyllin
Astrantiagenin C
Giganteumgenin C
Virgaureagenin B
Oleanol
Oleonolic acid
3beta-Hydroxyolean-12-en-28-oic acid
3-beta-Hydroxyolean-12-en-28-oic acid
CCRIS 6493
NSC-114945
UNII-6SMK8R7TGJ
6SMK8R7TGJ
Gledigenin 1
EINECS 208-081-6
(3-beta)-3-Hydroxyolean-12-en-28-oic acid
NSC 114945
CHEBI:37659
Olean-12-en-28-oic acid, 3beta-hydroxy-
Olean-12-en-28-oic acid, 3-beta-hydroxy-
DTXSID50858790
Olean-12-en-28-oic acid, 3-hydroxy-, (3-beta)-
OLEANOLIC ACID (USP-RS)
OLEANOLIC ACID [USP-RS]
DTXCID701474453
(3beta)-3-hydroxyolean-12-en-28-oic acid
OLEANOLIC ACID (CONSTITUENT OF BANABA LEAF)
OLEANOLIC ACID (CONSTITUENT OF HOLY BASIL LEAF)
208-081-6
(4aS,6aR,6aS,6bR,8aR,10S,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
OleanolicAcid
NSC114945
Olean-12-en-28-oic acid, 3-hydroxy-, (3beta)-
MFCD00064914
(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-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
(4aS,5S,6aS,6bR,8R,8aR,10S,12aR,12bR,14bS)-10-Hydroxy-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-octadecahydro-2H-picene-4a-carboxylic acid
SMR000445561
OLEANOLIC_ACID
CHEMBL168
(3.beta.)-3-Hydroxyolean-12-en-28-oic acid
Olean-12-en-28-oic acid, 3-hydroxy-, (3.beta.)-
Oleanolic-acid
OleanolsA currencyure
Oleanoic Acid Hydrate
Olean-12-en-28-oic acid, 3.beta.-hydroxy-
Oleanolic acid (Standard)
Oleanolic acid, >=97%
OLEANOLIC ACID [MI]
SCHEMBL71070
MLS000697656
MLS002207133
GTPL3306
OLEANOLIC ACID [WHO-DD]
HY-N0156R
GLXC-06699
HMS2232D15
Oleanolic acid (OA)(Compound 1)
Oleanolic acid, analytical standard
EX-A1991
HY-N0156
MSK40102
BDBM50346601
3-beta-Hydroxyolean-12-en-28-oate
3beta-hydroxy-Olean-12-en-28-oate
AKOS015951416
AC-8026
CCG-208530
CS-3800
FO71102
LMPR0106150004
3.beta.-hydroxy-Olean-12-en-28-oate
3beta-hydroxy-Olean-12-en-28-oic acid
NCGC00017222-10
NCGC00017222-13
(2S,5S,10S,18S,1R,14R,15R,20R)-18-hydroxy-1,2,8,8,15,19,19-heptamethylpentacyc lo[12.8.0.0<2,11>.0<5,10>.0<15,20>]docos-11-ene-5-carboxylic acid
1ST40102
AS-35338
BP-25410
(3-beta)-3-Hydroxyolean-12-en-28-oate
3.beta.-hydroxy-Olean-12-en-28-oic acid
NS00019728
(3.beta.)-3-hydroxy-Olean-12-en-28-oate
C17148
EN300-342251
(3.beta.)-3-hydroxy-Olean-12-en-28-oic acid
(3.beta.)-3-beta-hydroxy-Olean-12-en-28-oate
3.BETA.-HYDROXYOLEAN-12-EN-28-OIC ACID
Q418628
(3.beta.)-3-beta-hydroxy-Olean-12-en-28-oic acid
BRD-K90647725-001-06-5
BRD-K90647725-001-07-3
Oleanolic acid, primary pharmaceutical reference standard
C7EE6ACC-7175-4947-B524-FF8479525DA1
OLEANOLIC ACID (CONSTITUENT OF BANABA LEAF) [DSC]
OLEANOLIC ACID (CONSTITUENT OF HOLY BASIL LEAF) [DSC]
Oleanolic acid, United States Pharmacopeia (USP) Reference Standard
(4aS,6aR,6aS,6bR,8aR,10S,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-carboxylicacid
(4aS,6aS,6bR,8aR,10S,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
Pubchem:
10494
Cas:
508-02-1
Gnps:
CCMSLIB00006413532
Zinc:
ZINC000003785416
Kegg Ligand:
C17148
Chebi:
37659
Nmrshiftdb2:
60018521
Metabolights:
MTBLC37659
Chembl:
CHEMBL168
Comptox:
DTXSID50858790
Bindingdb:
50346601
CPRiL:
54985
SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CCCC5
Level: 0
Mol. Weight: 456.71 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.41
- 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
- -2.01
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.98
- Plasma Protein Binding
- 85.62
- 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
- 2.95
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.43
- 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
- Safe
- 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
- -78.88
- Rat (Acute)
- 2.39
- Rat (Chronic Oral)
- 2.17
- Fathead Minnow
- 3.95
- 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
- 458.43
- Hydration Free Energy
- -3.24
- Log(D) at pH=7.4
- 5.16
- Log(P)
- 7.18
- Log S
- -6.52
- Log(Vapor Pressure)
- -8.63
- Melting Point
- 275.01
- pKa Acid
- 5.97
- pKa Basic
- 8.58
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Vitamin D(3) 25-hydroxylase | C4B644 | CPVDH_PSEAH | Pseudonocardia autotrophica | 3 | 0.8287 |
| Vitamin D(3) 25-hydroxylase | C4B644 | CPVDH_PSEAH | Pseudonocardia autotrophica | 3 | 0.8287 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7841 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7841 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7541 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7541 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7421 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7421 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7195 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7195 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7175 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7175 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7024 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7024 |