Bauerenol acetate






Names

    • Bauerel acetate
    • NSC-741684
    • Bauerenol (7-bauerenenol) acetate
    • (4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,7,8,9,10,11,12,12a,13,14,14a-tetradecahydro-1H-picen-3-yl) acetate
    • (3S,4AR,6BS,8AR,11R,12S,12AR,12BS,14AR,14BR)-4,4,6B,8A,11,12,12B,14B-OCTAMETHYL-2,3,4A,5,7,8,9,10,11,12,12A,13,14,14A-TETRADECAHYDRO-1H-PICEN-3-YL ACETATE
    • CHEBI:179066
    • 4,4,6b,8a,11,12,12b,14b-octamethyl-1,2,3,4,4a,5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicen-3-yl acetate
    • Bauerenol acetate
    • 17020-04-1
    • Bauerenyl acetate
    • AKOS040761405
    • NSC741684
    • [(3S,4aR,6aS,6bS,8aR,11R,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,7,8,9,10,11,12,12a,13,14,14a-tetradecahydro-1H-picen-3-yl] acetate
    • 26-Norurs-7-en-3-ol, 13-methyl-, 3-acetate, (3b,13a,14b)-
    • 26-Norurs-7-en-3-ol, 13-methyl-, acetate, (3,13,14)- ; Bauerenol acetate ; D:C-Friedours-7-en-3-ol, acetate, (3)-; D:C-Friedours-7-en-3-ol, acetate; Bauerenyl acetate
    • DTHUXXMWYWKQKX-QXZXTIJDSA-N
    • ((3S,4aR,6aS,6bS,8aR,11R,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,7,8,9,10,11,12,12a,13,14,14a-tetradecahydro-1H-picen-3-yl) acetate
    • FS-10473
    • Ilexol, acetate
    • DTXSID00937746
    • NSC 741684

Attributes

  • Canonical SMILES

    C[C@@H]1CC[C@]2(C)CC[C@]3(C)C4=CC[C@@H]5[C@@](CC[C@H](OC(C)=O)C5(C)C)(C)[C@H]4CC[C@@]3(C)[C@@H]2[C@H]1C

  • InChI

    InChI=1S/C32H52O2/c1-20-12-15-29(6)18-19-31(8)24-10-11-25-28(4,5)26(34-22(3)33)14-16-30(25,7)23(24)13-17-32(31,9)27(29)21(20)2/h10,20-21,23,25-27H,11-19H2,1-9H3/t20-,21+,23+,25+,26+,27-,29-,30-,31-,32+/m1/s1

  • Molecule Class: Terpenoids
  • TPSA: 26.3
  • #RotBonds: 1
  • MW: 468.7660000000003
  • HBD: 0
  • HBA: 2
  • logP: 8.595600000000006
  • Chemical Formula: C32H52O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. contorta Cameroon 761060 N43440/HNC
    T. longipes Costa Rica - 7104

External Databases


References

  • Bauerenol Acetate, the Pentacyclic Triterpenoid from Tabernaemontana longipes, is an Antitrypanosomal Agent. Molecules, 2018 (PMID 29419735).
  • Contortamide, a new anti-colon cancer cerebroside and other constituents from Tabernaemontana contorta Stapf (Apocynaceae). Nat Prod Res, 2021 (PMID 31274013).

Compound-Protein Relationships


Compound Activities

    • Antitrypanosomal
    • Anticolon cancer

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) -4.92
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.62
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.11
    Distribution Blood-Brain Barrier (Central Nervous System) -2.07
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 2.06
    Plasma Protein Binding 90.77
    Steady State Volume of Distribution 1.63
    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 8.02
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.17
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 1.63
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.49
    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 -136.51
    Rat (Acute) 1.75
    Rat (Chronic Oral) 1.39
    Fathead Minnow 3.94
    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 458.38
    Hydration Free Energy -2.69
    Log(D) at pH=7.4 7.72
    Log(P) 8.63
    Log S -7.47
    Log(Vapor Pressure) -7.77
    Melting Point 184.25
    pKa Acid 12.67
    pKa Basic 6.98