3-Hydroxyvobtusine






Names

    • 3-Hydroxyvobtusine

Attributes

  • Canonical SMILES

    [H][C@]12[C@]34CC(C(OC)=O)=C5NC6=CC=CC=C6[C@@]51CCN2[C@H](O)[C@]7(C[C@@](C[C@@]([C@@H]8CCN9CC%10)(CCO8)[C@@]9([H])[C@@]%11%10C%12=C%13C(OC)=CC=C%12)([H])[C@]%11(O)N%13C7)[C@@H]3OCC4

  • InChI

    InChI=1S/C43H50N4O7/c1-51-29-9-5-7-27-31(29)47-23-40(21-24-20-38-13-18-53-30(38)10-15-45-16-12-42(27,35(38)45)43(24,47)50)36-39(14-19-54-36)22-25(33(48)52-2)32-41(11-17-46(34(39)41)37(40)49)26-6-3-4-8-28(26)44-32/h3-9,24,30,34-37,44,49-50H,10-23H2,1-2H3/t24-,30-,34-,35-,36+,37+,38+,39-,40-,41-,42+,43+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 116.2
  • #RotBonds: 2
  • MW: 734.8940000000001
  • HBD: 3
  • HBA: 11
  • logP: 3.480800000000002
  • Chemical Formula: C43H50N4O7


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. sphaerocarpa Indonesia 761099 AP070902

External Databases


References

  • Biscarpamontamines A and B, an aspidosperma-iboga bisindole alkaloid and an aspidosperma-aspidosperma bisindole alkaloid, from Tabernaemontana sphaerocarpa. J Nat Prod, 2009 (PMID 19711971).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cytotoxicity

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) -5.91
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 173.02
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 23366.23
    Distribution Blood-Brain Barrier (Central Nervous System) -3.02
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.93
    Plasma Protein Binding 78.48
    Steady State Volume of Distribution 4.43
    Metabolism Breast Cancer Resistance Protein Non-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 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 2.14
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -546.7
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.26
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.38
    Micronucleos Toxic
    NR-AhR Safe
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Safe
    NR-PPAR-gamma Safe
    NR-TR Toxic
    T. Pyriformis -42409410.18
    Rat (Acute) 3.35
    Rat (Chronic Oral) 2.61
    Fathead Minnow 53533.41
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 4766799.88
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.57
    Log(P) 2.83
    Log S -4.47
    Log(Vapor Pressure) -156852.51
    Melting Point 339.86
    pKa Acid -1087.14
    pKa Basic 9.2