12-Hydroxyakuammicine






Names

    • 12-Hydroxyakuammicine
    • (1R,11S,12E,17S)-12-ethylidene-8,14-diazapentacyclo(9.5.2.01,9.02,7.014,17)octadeca-2,4,6,9-tetraene-10-carboxylic acid
    • UNII-QJ6XQD4UFS
    • (-)-Vinervine
    • Vinervine
    • methyl (1R,11S,12E,17S)-12-ethylidene-6-hydroxy-8,14-diazapentacyclo[9.5.2.01,9.02,7.014,17]octadeca-2(7),3,5,9-tetraene-10-carboxylate
    • 1963-86-6
    • methyl (1R,11S,12E,17S)-12-ethylidene-6-hydroxy-8,14-diazapentacyclo(9.5.2.01,9.02,7.014,17)octadeca-2(7),3,5,9-tetraene-10-carboxylate
    • Curan-17-oic acid, 2,16,19,20-tetradehydro-12-hydroxy-, methyl ester, (19E)-
    • DTXSID301140692
    • (1R,11S,12E,17S)-12-ethylidene-8,14-diazapentacyclo[9.5.2.01,9.02,7.014,17]octadeca-2,4,6,9-tetraene-10-carboxylic acid
    • QJ6XQD4UFS
    • CHEBI:70500
    • Q27138834

Attributes

  • Canonical SMILES

    C/C=C\1/CN2CC[C@@]34[C@@H]2C[C@@H]1C(=C3NC5=C4C=CC=C5O)C(=O)OC

  • InChI

    InChI=1S/C20H22N2O3/c1-3-11-10-22-8-7-20-13-5-4-6-14(23)17(13)21-18(20)16(19(24)25-2)12(11)9-15(20)22/h3-6,12,15,21,23H,7-10H2,1-2H3/b11-3-/t12-,15-,20+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 61.8
  • #RotBonds: 1
  • MW: 338.4070000000001
  • HBD: 2
  • HBA: 5
  • logP: 2.5367000000000006
  • Chemical Formula: C20H22N2O3


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) -5.11
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.93
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.4
    Distribution Blood-Brain Barrier (Central Nervous System) -2.33
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.68
    Plasma Protein Binding 48.17
    Steady State Volume of Distribution 5.35
    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 Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 10.41
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.68
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.32
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.37
    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 -3.71
    Rat (Acute) 2.86
    Rat (Chronic Oral) 2.55
    Fathead Minnow 4.41
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 409.34
    Hydration Free Energy -6.29
    Log(D) at pH=7.4 2.38
    Log(P) 2.43
    Log S -3.51
    Log(Vapor Pressure) -7.48
    Melting Point 207.18
    pKa Acid 7.15
    pKa Basic 7.18