Vincadifformine






Names

    • methyl (5S,12R,19S)-2,3-didehydroaspidospermidine-3-carboxylate
    • 3247-10-7
    • NSC815333
    • Aspidospermidine-3-carboxylic acid, 2,3-didehydro-, methyl ester, (5alpha,12beta,19alpha)-
    • NSC-785180
    • GIGFIWJRTMBSRP-ACRUOGEOSA-N
    • 6,7-Dihydrotabersonine
    • NSC785180
    • CHEMBL251690
    • NS00093728
    • Vincadifformine
    • (+/-)-Vincadifformine
    • methyl (5alpha,12beta,19alpha)-2,3-didehydroaspidospermidine-3-carboxylate
    • NSC-815333
    • methyl (1R,12S,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9-tetraene-10-carboxylate
    • Aspidospermidine-3-carboxylic acid, 2,3-didehydro-, methylester, (5alpha,12beta,19alpha)-
    • SCHEMBL4660755
    • DTXSID20954218
    • (-)-Vincadifformine
    • CHEBI:70507
    • (5alpha,12beta,19alpha)-2,3-didehydro-aspidospermidine-3-carboxylic acid methyl ester (vinadifformine)
    • (5alpha,12beta,19alpha)-2,3-didehydroaspidospermidine-3-carboxylic acid methyl ester
    • Methyl 2,3-didehydroaspidospermidine-3-carboxylate
    • EINECS 221-823-3

Attributes

  • Canonical SMILES

    CC[C@@]12CCCN3[C@@H]1[C@@]4(CC3)C5=CC=CC=C5NC4=C(C2)C(=O)OC

  • InChI

    InChI=1S/C21H26N2O2/c1-3-20-9-6-11-23-12-10-21(19(20)23)15-7-4-5-8-16(15)22-17(21)14(13-20)18(24)25-2/h4-5,7-8,19,22H,3,6,9-13H2,1-2H3/t19-,20-,21-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 41.57000000000001
  • #RotBonds: 2
  • MW: 338.45100000000014
  • HBD: 1
  • HBA: 4
  • logP: 3.4452000000000016
  • Chemical Formula: C21H26N2O2


Species

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

External Databases


References

  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • The alkaloids of Tabernaemontana riedelii and T. rigida. J Org Chem, 1968 (PMID 5639341).

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) -4.76
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.86
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.68
    Distribution Blood-Brain Barrier (Central Nervous System) -2.47
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.85
    Plasma Protein Binding 56.51
    Steady State Volume of Distribution 4.49
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor 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 6.37
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.27
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.78
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.64
    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 -4.49
    Rat (Acute) 3.54
    Rat (Chronic Oral) 2.15
    Fathead Minnow 3.97
    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 407.82
    Hydration Free Energy -4.93
    Log(D) at pH=7.4 3.17
    Log(P) 3.42
    Log S -3.13
    Log(Vapor Pressure) -7.33
    Melting Point 179.91
    pKa Acid 9.19
    pKa Basic 7.91