Lupeol acetate






Names

    • WJ3A89G0H6
    • ODSSDTBFHAYYMD-YOJQYFTNSA-N
    • CLERODOL ACETATE
    • 3BETA-OAC-20(29)-LUPENE
    • Lup-20(29)-en-3beta-ol, acetate
    • CHEMBL453802
    • EINECS 216-575-8
    • LUPEOL ACETATE [MI]
    • Acetyllupeol
    • CS-0090571
    • 20(29)-Lupenol acetate
    • AKOS040760532
    • SCHEMBL936136
    • [(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl] acetate
    • LUPENYL ACETATE
    • Lup-20(29)-en-3.beta.-ol, acetate
    • C08630
    • [(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl] acetate
    • LMPR0106130002
    • Acetic acid (1R,3aR,4S,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-eicosahydro-cyclopenta[a]chrysen-9-yl ester
    • NSC 281806
    • Q27104976
    • 3-O-Acetyllupeol
    • NS00045939
    • MS-28664
    • Lupeol acetic acid
    • LUP-20(30)-EN-3BETA-OL, ACETATE
    • Lupeyl acetic acid
    • UNII-WJ3A89G0H6
    • NSC-281806
    • CHEBI:69744
    • LUP-20(30)-EN-3.BETA.-OL, ACETATE
    • 1617-68-1
    • Lupeol acetate
    • LUP-20(29)-EN-3.BETA.-YL ACETATE
    • Lup-20(29)-en-3-ol, acetate, (3.beta.)-
    • LUP-20(29)-EN-3BETA-YL ACETATE
    • HY-126114
    • 3.BETA.-OAC-20(29)-LUPENE
    • Lupeyl acetate
    • MFCD00017362
    • Lup-20(29)-en-3-ol, acetate, (3beta)-
    • 3-Acetyllupeol

Attributes

  • Canonical SMILES

    CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)OC(=O)C)C)C

  • InChI

    InChI=1S/C32H52O2/c1-20(2)22-12-15-29(6)18-19-31(8)23(27(22)29)10-11-25-30(7)16-14-26(34-21(3)33)28(4,5)24(30)13-17-32(25,31)9/h22-27H,1,10-19H2,2-9H3/t22-,23+,24-,25+,26-,27+,29+,30-,31+,32+/m0/s1

  • Molecule Class: Terpenoids
  • TPSA: 26.3
  • #RotBonds: 2
  • MW: 468.76600000000036
  • HBD: 0
  • HBA: 2
  • logP: 8.595600000000006
  • Chemical Formula: C32H52O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. catharinensis Brazil 403124 UEC117862
    T. cymosa Colombia 761066 JBC3243

External Databases


References

  • Antiviral effect of compounds derived from the seeds of Mammea americana and Tabernaemontana cymosa on Dengue and Chikungunya virus infections. BMC Complement Altern Med, 2017 (PMID 28100218).
  • Chromatographic analysis and antioxidant capacity of Tabernaemontana catharinensis. Nat Prod Commun, 2014 (PMID 24660464).

Compound-Protein Relationships


Compound Activities

    • Antioxidant
    • Cytotoxicity
    • Antiviral

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 -4.58
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.21
    Distribution Blood-Brain Barrier (Central Nervous System) -2.07
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 2.01
    Plasma Protein Binding 92.44
    Steady State Volume of Distribution 1.5
    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 7.68
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.9
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 1.65
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.59
    Micronucleos Safe
    NR-AhR Safe
    NR-AR Toxic
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Safe
    NR-PPAR-gamma Safe
    NR-TR Safe
    T. Pyriformis -156.97
    Rat (Acute) 2.04
    Rat (Chronic Oral) 1.49
    Fathead Minnow 3.92
    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 462.0
    Hydration Free Energy -2.78
    Log(D) at pH=7.4 8.01
    Log(P) 8.82
    Log S -7.44
    Log(Vapor Pressure) -8.1
    Melting Point 204.9
    pKa Acid 12.86
    pKa Basic 7.23