(19′S) Hydroxytabernaelegantine A






Names

    • (19′S) Hydroxytabernaelegantine A

Attributes

  • Canonical SMILES

    CC[C@@H]3[C@@H]4C[C@@H]([C@]5=C(NC7=C6CCN(C9)C8C(C(OC)=O)7C[C@@H]9CC8[C@@H](O)C)C6=CC=C5OC)C2=C(C[C@@H]([C@@H]4C(OC)=O)N(C)C3)C1=CC=CC=C1N2

  • InChI

    InChI=1S/C43H54N4O6/c1-7-24-21-46(3)33-18-30-25-10-8-9-11-32(25)44-37(30)31(17-29(24)35(33)41(49)52-5)36-34(51-4)13-12-26-27-14-15-47-20-23-16-28(22(2)48)40(47)43(19-23,42(50)53-6)39(27)45-38(26)36/h8-13,22-24,28-29,31,33,35,40,44-45,48H,7,14-21H2,1-6H3/t22-,23-,24-,28?,29-,31-,33-,35+,40?,43?/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 120.12
  • #RotBonds: 6
  • MW: 722.9270000000001
  • HBD: 3
  • HBA: 8
  • logP: 5.5396000000000045
  • Chemical Formula: C43H54N4O6


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. elegans Mozambique, South Africa, Indonesia 761068 23/SM

External Databases


References

  • Vobasinyl-Iboga Alkaloids from Tabernaemontana elegans: Cell Cycle Arrest and Apoptosis-Inducing Activity in HCT116 Colon Cancer Cells. J Nat Prod, 2016 (PMID 27704811).

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) -6.07
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 27.64
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 4390.84
    Distribution Blood-Brain Barrier (Central Nervous System) -3.65
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.11
    Plasma Protein Binding 76.53
    Steady State Volume of Distribution 4.85
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-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 8.42
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -106.47
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.31
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.25
    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 -7966072.75
    Rat (Acute) 2.85
    Rat (Chronic Oral) 2.39
    Fathead Minnow 10057.94
    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 892049.96
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.18
    Log(P) 4.6
    Log S -5.29
    Log(Vapor Pressure) -29315.27
    Melting Point 275.89
    pKa Acid -172.1
    pKa Basic 6.53