Oleanolic acid






Names

    • CCRIS 6493
    • NSC114945
    • (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
    • OLEANOLIC ACID (CONSTITUENT OF BANABA LEAF) [DSC]
    • OleanolsA currencyure
    • CHEMBL168
    • NSC 114945
    • SMR000445561
    • OLEANOLIC ACID [MI]
    • (3.beta.)-3-hydroxy-Olean-12-en-28-oate
    • DTXCID701474453
    • Olean-12-en-28-oic acid, 3beta-hydroxy-
    • oleonolic acid
    • 1ST40102
    • CCG-208530
    • Olean-12-en-28-oic acid, 3-hydroxy-, (3beta)-
    • BRD-K90647725-001-06-5
    • 508-02-1
    • (3-beta)-3-Hydroxyolean-12-en-28-oate
    • Oleanoic Acid Hydrate
    • Olean-12-en-28-oic acid, 3-hydroxy-, (3.beta.)-
    • (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
    • UNII-6SMK8R7TGJ
    • (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
    • Oleanolic acid, primary pharmaceutical reference standard
    • OLEANOLIC ACID (USP-RS)
    • Oleanolic acid, analytical standard
    • (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
    • (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
    • Oleanolic acid (OA)(Compound 1)
    • Oleanolic acid, >=97%
    • CHEBI:37659
    • 3beta-Hydroxyolean-12-en-28-oic acid
    • NCGC00017222-13
    • AC-8026
    • HY-N0156
    • OLEANOLIC ACID (CONSTITUENT OF HOLY BASIL LEAF)
    • Olean-12-en-28-oic acid, 3.beta.-hydroxy-
    • oleanolic-acid
    • 3.beta.-hydroxy-Olean-12-en-28-oic acid
    • NCGC00017222-10
    • OLEANOLIC_ACID
    • NSC-114945
    • 3beta-hydroxy-Olean-12-en-28-oic acid
    • Oleanolic acid, United States Pharmacopeia (USP) Reference Standard
    • Olean-12-en-28-oic acid, 3-hydroxy-, (3-beta)-
    • C17148
    • MLS002207133
    • 3beta-hydroxy-Olean-12-en-28-oate
    • HY-N0156R
    • Q-100572
    • NS00019728
    • 6SMK8R7TGJ
    • 3-beta-Hydroxyolean-12-en-28-oic acid
    • Oleanol
    • Virgaureagenin B
    • Oleanolic acid
    • 3.beta.-hydroxy-Olean-12-en-28-oate
    • LMPR0106150004
    • (3.beta.)-3-Hydroxyolean-12-en-28-oic acid
    • Olean-12-en-28-oic acid, 3-beta-hydroxy-
    • (3.beta.)-3-beta-hydroxy-Olean-12-en-28-oate
    • OLEANOLIC ACID (CONSTITUENT OF HOLY BASIL LEAF) [DSC]
    • Oleanic acid
    • GTPL3306
    • Giganteumgenin C
    • Oleanolic acid, European Pharmacopoeia (EP) Reference Standard
    • (3.beta.)-3-beta-hydroxy-Olean-12-en-28-oic acid
    • (3beta)-3-hydroxyolean-12-en-28-oic acid
    • (3.beta.)-3-hydroxy-Olean-12-en-28-oic acid
    • 3-beta-Hydroxyolean-12-en-28-oate
    • BDBM50346601
    • Q418628
    • OleanolicAcid
    • OLEANOLIC ACID
    • CS-3800
    • EX-A1991
    • Astrantiagenin C
    • (3-beta)-3-Hydroxyolean-12-en-28-oic acid
    • OLEANOLIC ACID [WHO-DD]
    • 3.BETA.-HYDROXYOLEAN-12-EN-28-OIC ACID
    • AS-35338
    • AKOS015951416
    • OLEANOLIC ACID (CONSTITUENT OF BANABA LEAF)
    • Caryophyllin
    • OLEANOLIC ACID [USP-RS]
    • DTXSID50858790
    • Oleanolic acid (Standard)
    • EINECS 208-081-6
    • BRD-K90647725-001-07-3
    • BP-25410
    • MLS000697656
    • C7EE6ACC-7175-4947-B524-FF8479525DA1
    • HMS2232D15
    • (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
    • SCHEMBL71070
    • EN300-342251
    • Gledigenin 1
    • MFCD00064914

Attributes

  • Canonical SMILES

    C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)C)(C)C)O

  • 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

  • Molecule Class: Minor compounds
  • TPSA: 57.53
  • #RotBonds: 1
  • MW: 456.7110000000003
  • HBD: 2
  • HBA: 2
  • logP: 7.233600000000009
  • Chemical Formula: C30H48O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. catharinensis Brazil 403124 UEC117862

External Databases


References

  • Chromatographic analysis and antioxidant capacity of Tabernaemontana catharinensis. Nat Prod Commun, 2014 (PMID 24660464).

Compound-Protein Relationships


Compound Activities

    • Antioxidant

Predicted NMR Spectral Data


Predicted MS Fragmentation Pattern

    N.B.: It is recommended to zoom in on a specific area of an MS plot before hovering on a peak.

Predicted ADMET Properties

    Property Model Name Predicted Value
    Absorption Caco-2 (logPaap) -5.49
    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 (Central Nervous System) -2.03
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.98
    Plasma Protein Binding 90.31
    Steady State Volume of Distribution 0.65
    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 3.15
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.54
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I 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 -79.75
    Rat (Acute) 2.4
    Rat (Chronic Oral) 2.17
    Fathead Minnow 3.94
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 461.46
    Hydration Free Energy -3.22
    Log(D) at pH=7.4 5.2
    Log(P) 7.36
    Log S -6.5
    Log(Vapor Pressure) -8.87
    Melting Point 270.7
    pKa Acid 5.99
    pKa Basic 8.54