3R and 3S-Hydroxyvoacamine






Names

    • 3R and 3S-Hydroxyvoacamine

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@H]2C[C@]3(C(OC)=O)[C@H]1[N@@](CCC4=C3NC5=CC([C@H]6C[C@@H]7C(C(OC)=O)[C@H](N(C)C/C7=C/C)CC8=C6NC9=CC=CC=C89)=C(OC)C=C45)C2O

  • InChI

    InChI=1S/C43H52N4O6/c1-7-22-15-24-20-43(42(50)53-6)38-26(13-14-47(39(22)43)40(24)48)28-19-35(51-4)29(17-33(28)45-38)30-16-27-23(8-2)21-46(3)34(36(27)41(49)52-5)18-31-25-11-9-10-12-32(25)44-37(30)31/h8-12,17,19,22,24,27,30,34,36,39-40,44-45,48H,7,13-16,18,20-21H2,1-6H3/b23-8-/t22-,24-,27-,30+,34+,36?,39-,40?,43+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 120.12
  • #RotBonds: 5
  • MW: 720.9110000000003
  • HBD: 3
  • HBA: 8
  • logP: 5.807300000000007
  • Chemical Formula: C43H52N4O6


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. chippii Ivory Coast - Lg12291

External Databases


References

  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antimicrobial

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) -5.99
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 28.54
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 4499.61
    Distribution Blood-Brain Barrier (Central Nervous System) -3.59
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.07
    Plasma Protein Binding 82.67
    Steady State Volume of Distribution 4.86
    Metabolism Breast Cancer Resistance Protein Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate 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 Inhibitor
    Excretion Clearance 11.54
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -109.58
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.61
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.25
    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 Safe
    T. Pyriformis -8164649.51
    Rat (Acute) 2.88
    Rat (Chronic Oral) 2.74
    Fathead Minnow 10308.43
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 914594.68
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.19
    Log(P) 5.68
    Log S -5.6
    Log(Vapor Pressure) -30052.35
    Melting Point 282.91
    pKa Acid -176.5
    pKa Basic 4.77