Apovincanmine






Names

    • DA-50650
    • methyl (15S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylate
    • (3alpha,16alpha)-Eburnamenine-14-carboxylic Acid Methyl Ester
    • Apovincanmine
    • Methyl (3alpha,16alpha)-eburnamenine-14-carboxylate
    • Q15410269
    • 504R182ZX7
    • methyl(3a,16a)-eburnamenine-14-carboxylate
    • Methyl eburnamenine-14-carboxylate, (3alpha,16alpha)-
    • VINPOCETINE IMPURITY B (EP IMPURITY)
    • Eburnamenine-14-carboxylic acid, methyl ester, (3.alpha.,16.alpha.)-
    • Apovincaminum [Latin]
    • Apovincaminum
    • Methyl (13aS,13bS)-13a-Ethyl-2,3,5,6,13a,13b-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate (Apovincamine)
    • Apovincamina [Spanish]
    • Methyl eburnamenine-14-carboxylate, (3.alpha.,16.alpha.)-
    • EINECS 225-491-0
    • CHEMBL1163488
    • AKOS040744755
    • C09035
    • VINPOCETINE IMPURITY B [EP IMPURITY]
    • CHEBI:2787
    • Eburnamenine-14-carboxylic acid, methyl ester, (3alpha,16alpha)-
    • METHYL(3.ALPHA.,16.ALPHA.)-EBURNAMENINE-14-CARBOXYLATE
    • Methyl (3.alpha.,16.alpha.)-eburnamenine-14-carboxylate
    • methyl (15S,19S)-15-ethyl-1,11-diazapentacyclo(9.6.2.02,7.08,18.015,19)nonadeca-2,4,6,8(18),16-pentaene-17-carboxylate
    • DTXSID401023598
    • Eburnamenine-14-carboxylic acid, methyl ester, (3-alpha,16-alpha)-
    • UNII-504R182ZX7
    • Apovincamine [INN]
    • Apovincamina
    • Apovincaminum (Latin)
    • NS00045147
    • 1ST10857
    • HY-135743
    • Vinpocetine impurity B
    • Methyl (13aS,13bS)-13a-ethyl-2,3,4,6,13a,14b-hexahydro-1H-indilol(3.2.1-de)pyrido(3,2,1-ij)(1,5)naphthylridin-12-carboxylat
    • CS-0113909
    • cis-Apovincamine
    • Apovincamine
    • (+)-CIS-APOVINCAMINE
    • (+)-apovincamine
    • SCHEMBL194507
    • Methyl(3alpha,16alpha)-eburnamenine-14-carboxylate
    • 4880-92-6

Attributes

  • Canonical SMILES

    CC[C@@]12CCCN3[C@]1([H])C4=C(C5=CC=CC=C5N4C(C(OC)=O)=C2)CC3

  • InChI

    InChI=1S/C21H24N2O2/c1-3-21-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(18(15)19(21)22)17(13-21)20(24)25-2/h4-5,7-8,13,19H,3,6,9-12H2,1-2H3/t19-,21+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 34.47
  • #RotBonds: 2
  • MW: 336.4350000000002
  • HBD: 0
  • HBA: 4
  • logP: 3.758200000000002
  • Chemical Formula: C21H24N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bovina China, Vietnam 3036760 Cai20150423
    T. rigida Brazil - -

External Databases


References

  • The alkaloids of Tabernaemontana riedelii and T. rigida. J Org Chem, 1968 (PMID 5639341).
  • Vincan- and eburnan-type alkaloids from Tabernaemontana bovina and their hypoglycemic activity. Phytochemistry, 2021 (PMID 34218044).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Hypoglycemic

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

    Category Property Name Predicted Value
    Absorption Caco-2 (logPaap) -4.81
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.67
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.17
    Distribution Blood-Brain Barrier (Central Nervous System) -2.6
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.84
    Plasma Protein Binding 54.99
    Steady State Volume of Distribution 4.12
    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 Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 6.54
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.88
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.66
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 8.88
    Micronucleos Toxic
    NR-AhR Toxic
    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 -6.24
    Rat (Acute) 3.11
    Rat (Chronic Oral) 1.72
    Fathead Minnow 4.35
    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 423.04
    Hydration Free Energy -5.78
    Log(D) at pH=7.4 3.29
    Log(P) 3.77
    Log S -2.97
    Log(Vapor Pressure) -7.6
    Melting Point 180.38
    pKa Acid 10.34
    pKa Basic 7.39