Gabunamine






Names

    • Q15410966
    • 66086-99-5
    • CHEBI:5238
    • methyl (1S,15S,17S,18S)-17-ethyl-7-[(1R,12R,14R,15E)-15-ethylidene-18-methoxycarbonyl-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraen-12-yl]-6-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene-1-carboxylate
    • GABUNAMINE
    • C09193
    • Gabunamine

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=CC(=C(C=C45)[C@H]6C[C@@H]\7C([C@@H](CC8=C6NC9=CC=CC=C89)NC/C7=C/C)C(=O)OC)OC)C(=O)OC

  • InChI

    InChI=1S/C42H50N4O5/c1-6-23-14-22-19-42(41(48)51-5)38-26(12-13-46(21-22)39(23)42)28-16-29(35(49-3)18-33(28)45-38)30-15-27-24(7-2)20-43-34(36(27)40(47)50-4)17-31-25-10-8-9-11-32(25)44-37(30)31/h7-11,16,18,22-23,27,30,34,36,39,43-45H,6,12-15,17,19-21H2,1-5H3/b24-7-/t22-,23-,27-,30+,34+,36?,39-,42+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 108.68000000000002
  • #RotBonds: 5
  • MW: 690.8850000000001
  • HBD: 3
  • HBA: 7
  • logP: 6.146700000000005
  • Chemical Formula: C42H50N4O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. johnstonii Kenya - -

External Databases

    • PubChem CID: 11953928
    • CAS RN: 66086-99-5

References

  • Plant anticancer agents V: new bisindole alkaloids from Tabernaemontana johnstonii stem bark. J Pharm Sci, 1978 (PMID 621649).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Anticancer
    • Reproducible
    • Cytotoxicity
    • Antileukemic

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) -5.92
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 10.21
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 2087.91
    Distribution Blood-Brain Barrier (Central Nervous System) -3.26
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.49
    Plasma Protein Binding 86.09
    Steady State Volume of Distribution 4.63
    Metabolism Breast Cancer Resistance Protein Non-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 Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 11.13
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Safe
    Bioconcentration Factor -51.22
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.21
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 7.93
    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 -3788901.09
    Rat (Acute) 2.7
    Rat (Chronic Oral) 2.38
    Fathead Minnow 4784.91
    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 422515.38
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.58
    Log(P) 5.37
    Log S -5.51
    Log(Vapor Pressure) -13855.81
    Melting Point 317.82
    pKa Acid -64.01
    pKa Basic 5.93