Olean-12-en-3-yl acetate






Names

    • Olean-12-en-3-yl acetate
    • BAA61693
    • (4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl) acetate
    • D85204
    • beta-Amyrin acetate
    • AKOS032948308
    • .beta.-Amyrenyl acetate
    • O-Acetyl-.beta.-amyrin
    • 3-O-Acetyl-.beta.-amyrin
    • DTXSID50936562
    • Olean-12-en-3.beta.-ol, acetate
    • beta-AMYRIN ACETATE_major
    • AMYRIN, B-
    • NSC403166

Attributes

  • Canonical SMILES

    C[C@]15[C@H]([C@@](C)(C)[C@H](OC(C)=O)CC5)CC[C@]2(C)[C@@H]1CC=C3[C@](C)2CC[C@]4(C)[C@H]3CC(C)(C)CC4

  • InChI

    InChI=1S/C32H52O2/c1-21(33)34-26-13-14-30(7)24(28(26,4)5)12-15-32(9)25(30)11-10-22-23-20-27(2,3)16-17-29(23,6)18-19-31(22,32)8/h10,23-26H,11-20H2,1-9H3/t23-,24-,25+,26+,29+,30-,31+,32+/m0/s1

  • Molecule Class: Terpenoids
  • TPSA: 26.3
  • #RotBonds: 1
  • MW: 468.76600000000036
  • HBD: 0
  • HBA: 2
  • logP: 8.739700000000004
  • Chemical Formula: C32H52O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. coronaria Malaysia 52861 11429

External Databases


References

  • Antituberculosis activity, phytochemical identification of Costus speciosus (J. Koenig) Sm., Cymbopogon citratus (DC. Ex Nees) Stapf., and Tabernaemontana coronaria (L.) Willd. and their effects on the growth kinetics and cellular integrity of Mycobacterium tuberculosis H37Rv. BMC Complement Altern Med, 2018 (PMID 29310671).

Compound-Protein Relationships


Compound Activities

    • Cidal
    • Antituberculosis

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) -4.79
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.59
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.2
    Distribution Blood-Brain Barrier (Central Nervous System) -1.99
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 2.01
    Plasma Protein Binding 90.6
    Steady State Volume of Distribution 1.7
    Metabolism Breast Cancer Resistance Protein Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate 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 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 7.52
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.23
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 1.36
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.64
    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 Safe
    T. Pyriformis -116.28
    Rat (Acute) 2.05
    Rat (Chronic Oral) 1.38
    Fathead Minnow 4.04
    Respiratory Disease Safe
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 455.16
    Hydration Free Energy -2.63
    Log(D) at pH=7.4 7.7
    Log(P) 9.07
    Log S -7.46
    Log(Vapor Pressure) -7.61
    Melting Point 216.84
    pKa Acid 12.66
    pKa Basic 6.9