Akuammicine






Names

    • DTXCID701331875
    • Q15079655
    • Akuammicine
    • 639-43-0
    • RG055O00BG
    • CHEBI:70499
    • NS00093684
    • DTXSID30903914
    • UNII-RG055O00BG
    • AKUAMMICINE [MI]
    • (-)-akuammicine
    • methyl (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-carboxylate
    • Methyl 12-ethylidene-8,14-diazapentacyclo(9.5.2.0,.0,.0,)octadeca-2,4,6,9-tetraene-10-carboxylic acid
    • Methyl 12-ethylidene-8,14-diazapentacyclo[9.5.2.0,.0,.0,]octadeca-2,4,6,9-tetraene-10-carboxylic acid
    • methyl (19E)-2,16-didehydrocur-19-en-17-oate
    • Methyl (19E)-2,16,19,20-tetradehydrocuran-17-oate
    • NCGC00488530-01
    • AH-214/21197006
    • methyl (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-carboxylate
    • Curan-17-oic acid, 2,16,19,20-tetradehydro-, methyl ester, (19E)-
    • AKUAMMICINE, (-)-

Attributes

  • Canonical SMILES

    C/C=C\1/CN2CC[C@@]34[C@@H]2C[C@@H]1C(=C3NC5=CC=CC=C45)C(=O)OC

  • InChI

    InChI=1S/C20H22N2O2/c1-3-12-11-22-9-8-20-14-6-4-5-7-15(14)21-18(20)17(19(23)24-2)13(12)10-16(20)22/h3-7,13,16,21H,8-11H2,1-2H3/b12-3-/t13-,16-,20+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 41.57000000000001
  • #RotBonds: 1
  • MW: 322.40800000000013
  • HBD: 1
  • HBA: 4
  • logP: 2.831100000000001
  • Chemical Formula: C20H22N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbosa Malaysia, China 1679252 GK604

External Databases


References

  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).

Compound-Protein Relationships


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) -4.69
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.81
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.71
    Distribution Blood-Brain Barrier (Central Nervous System) -2.18
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.9
    Plasma Protein Binding 56.42
    Steady State Volume of Distribution 5.69
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 7.07
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.02
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.12
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.28
    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 -2.09
    Rat (Acute) 3.38
    Rat (Chronic Oral) 2.27
    Fathead Minnow 4.46
    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 404.9
    Hydration Free Energy -4.46
    Log(D) at pH=7.4 2.62
    Log(P) 2.78
    Log S -3.1
    Log(Vapor Pressure) -7.15
    Melting Point 183.63
    pKa Acid 8.84
    pKa Basic 7.53