Names

    • Vincamina [DCIT]
    • Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3.alpha.,14.beta.,16.alpha.)-
    • Vincamine, analytical reference material
    • Tripervan
    • VINCAMINE [MART.]
    • Devincan
    • Methyl vincaminate
    • 13a-ethyl-2,3,5,6,12,13,13a,13b-octahydro-12-hydroxy-1H-indolo(3,2,1-de)pyrido(3,2,1-ij)(1,5) naphthyridine-12-carboxylic acid methyl ester
    • VINCAMINE (EP MONOGRAPH)
    • vincamine
    • (3alpha, 14beta, 16alpha)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester
    • methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
    • Vincaminum
    • CHEMBL1165342
    • Novicet
    • Vincagil
    • Tox21_301968
    • Vincamina
    • Anasclerol (base)
    • methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo(9.6.2.0^(2,7).0^(8,18).0^(15,19))nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
    • (3.alpha.,14.beta.,16.alpha.)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid, methyl ester
    • Methyl (41S,12S,13aS)-13a-ethyl-12-hydroxy-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate
    • DTXCID7020134
    • NCGC00184983-03
    • BRD-K40902647-001-03-7
    • Vincamine, 98%
    • Equipur
    • Arteriovinca
    • Angiopac
    • BSPBio_000142
    • CS-4536
    • NCGC00255542-01
    • KS-5179
    • DTXSID9040134
    • Vincaminum (INN-Latin)
    • Prestwick3_000271
    • Vincimax
    • Vinkametrin
    • Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3alpha,14beta,16alpha)-
    • Cetal retard
    • Vincaminum [INN-Latin]
    • Vincapan
    • Perval
    • UNII-996XVD0JHT
    • Vincamine base
    • Pervone
    • Vraap
    • Vincamine (INN)
    • SPBio_002361
    • Vinodrel retard
    • EINECS 216-576-3
    • methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
    • Devinkan
    • (3alpha,14beta,16alpha)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester
    • Minorin
    • NSC-91998
    • Vincadar
    • MLS002154249
    • SMR000112509
    • Monorin
    • HMS1568H04
    • s3891
    • NS00006858
    • D08677
    • Decincan
    • Vincachron
    • BCBcMAP01_000080
    • CHEBI:9985
    • BPBio1_000158
    • (3.ALPHA.,14.BETA.,16.ALPHA.)-14,15-DIHYDRO-14-HYDROXYEBURNAMENINE-14-CARBOXYLIC ACID METHYL ESTER
    • AC-22625
    • Vinvasaunier
    • 1617-90-9
    • Vincamidol
    • MFCD00078054
    • Oxygeron
    • Prestwick0_000271
    • Methyl vincaminic acid
    • NCGC00184983-01
    • VINCAMINE [MI]
    • methyl 14beta-hydroxy-14,15-dihydro-3alpha,16alpha-eburnamenine-14alpha-carboxylate
    • Cerebroxine
    • methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo(9.6.2.02,7.08,18.015,19)nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
    • Sostenil
    • cis-Vincamine
    • methyl(15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
    • Vincasaunier
    • SCHEMBL147179
    • Vincalen
    • VINCAMINE (MART.)
    • Anasclerol
    • Vinca-Minor
    • Prestwick_495
    • (+)-Vincamine
    • HMS3712H04
    • Prestwick2_000271
    • HY-B1021
    • methyl (3alpha,14beta,16alpha)-14-hydroxy-14,15-dihydroeburnamenine-14-carboxylate
    • HY-B1021R
    • BCP05837
    • Tox21_111342
    • Vincafolina
    • 996XVD0JHT
    • Q416225
    • NSC 91998
    • VINCAMINE [WHO-DD]
    • Minorine
    • Cetal retard (TN)
    • (+)-cis-Vincamine
    • C04AX07
    • Vincamine [INN:BAN:DCF]
    • CAS-1617-90-9
    • SMP1_000314
    • Methyl(41S,12S,13aS)-13a-ethyl-12-hydroxy-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate
    • Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-,methyl ester, (3alpha,14beta,16alpha)-
    • VINCAMINE [EP MONOGRAPH]
    • CCG-208544
    • Tox21_111342_1
    • Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3alpha,14beta,16.)
    • (3alpha,14beta,16alpha)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid, methyl ester
    • C09251
    • VINCAMINE [HSDB]
    • Vincafor
    • Ocu-vinc
    • Vincamine (Standard)
    • Pervincamine
    • AKOS015896471
    • Vincafarm
    • Vincapront
    • 14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester
    • Prestwick1_000271
    • DB13374
    • Vincamin
    • GTPL349
    • NCGC00094824-01
    • Vinca-Ecobi
    • methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.0?,?.0?,??.0??,??]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
    • Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methylester, (3a,14b,16a)-
    • Alkaloid obtained from Vinca minor
    • HSDB 7150
    • HMS2095H04
    • Q-100193
    • VINCAMINE [INN]
    • HMS2268C20

Attributes

  • Canonical SMILES

  • InChI

  • Molecule Class:
  • TPSA:
  • #RotBonds:
  • MW:
  • HBD:
  • HBA:
  • logP:
  • Chemical Formula:


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. corymbose Malaysia - K667
    T. rigida Brazil - -

External Databases


References

  • Seco-tabersonine alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2009 (PMID 19217125).
  • The alkaloids of Tabernaemontana riedelii and T. rigida. J Org Chem, 1968 (PMID 5639341).

Compound-Protein Relationships


Compound Activities

  • No activity found

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) -4.88
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.79
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.29

    Distribution Blood-Brain Barrier (Central Nervous System) -2.49
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.94
    Plasma Protein Binding 57.25
    Steady State Volume of Distribution 3.12

    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 Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor

    Excretion Clearance 7.89
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs

    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.3
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.16
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.51
    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 -6.52
    Rat (Acute) 2.63
    Rat (Chronic Oral) 1.73
    Fathead Minnow 3.96
    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 429.43
    Hydration Free Energy -5.56
    Log(D) at pH=7.4 2.49
    Log(P) 2.72
    Log S -2.78
    Log(Vapor Pressure) -8.58
    Melting Point 216.28
    pKa Acid 8.15
    pKa Basic 6.9