Tabersonine






Names

    • Methyl (5a,12b,19a)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylic acid
    • HMS3887M03
    • MN955K48NB
    • Aspidospermidine-3-carboxylic acid, 2,3,6,7-tetradehydro-, methyl ester, (5alpha,12beta,19alpha)-
    • methyl (1R,12R,19S)-12-ethyl-8,16-diazapentacyclo(10.6.1.01,9.02,7.016,19)nonadeca-2,4,6,9,13-pentaene-10-carboxylate
    • DA-58232
    • (5a,12b,19a)-2,3,6,7-Tetradehydroaspidospermidine-3-carboxylic acid, methyl ester
    • AKOS015896776
    • methyl(1R,12R,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9,13-pentaene-10-carboxylate
    • s9427
    • EINECS 224-615-0
    • DTXSID30196102
    • CCG-267873
    • Methyl (5alpha,12beta,19alpha)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylic acid
    • methyl (5alpha,12beta,19alpha)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylate
    • 21217-98-1
    • Methyl(5alpha,19alpha)-16-methoxy-8-oxo-2,3,6,7-tetradehydroaspidospermidine-3-carboxylate
    • (5alpha,12beta,19alpha)-2,3,6,7-Tetradehydroaspidospermidine-3-carboxylate, methyl ester
    • Tabersonine
    • NS00031405
    • 3a-Ethyl-3a,4,6,11,12,13a-hexahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylic Acid Methyl Ester
    • Methyl (3aR,3a1S,10bR)-3a-ethyl-3a,3a1,4,6,11,12-hexahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate
    • Tabersonin
    • 1H-INDOLIZINO(8,1-CD)CARBAZOLE-5-CARBOXYLIC ACID, 3A-ETHYL-3A,4,6,11,12,13A-HEXAHYDRO-, METHYL ESTER
    • HY-N1431
    • (-)-Tabersonine
    • ASPIDOSPERMIDINE-3-CARBOXYLIC ACID, 2,3,6,7-TETRADEHYDRO-, METHYL ESTER, (5.ALPHA.,12R,19.ALPHA.)-
    • Aspidospermidine-3-carboxylic acid, 2,3,6,7-tetradehydro-, methyl ester, (5alpha,12R,19alpha)-
    • Q21099578
    • AC-26458
    • NSC815334
    • Aspidospermidine-3-carboxylic acid, 2,3,6,7-tetrahydro-, methyl ester, (5-alpha,12-beta,19-alpha)-
    • Methyl (5I+-,12I2,19I+-)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylic acid
    • FNGGIPWAZSFKCN-ACRUOGEOSA-N
    • methyl (1R,12R,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9,13-pentaene-10-carboxylate
    • CS-0016859
    • (5a,12b,19a)-2,3,6,7-Tetradehydroaspidospermidine-3-carboxylate, methyl ester
    • C09244
    • methyl 2,3,6,7-tetradehydro-5alpha,12beta,19alpha-aspidospermidine-3-carboxylate
    • NCGC00488792-01
    • MFCD28140545
    • Methyl (5I+-,12I2,19I+-)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylate
    • SCHEMBL829379
    • CHEMBL2011511
    • BRN 0050163
    • NSC-815334
    • UNII-MN955K48NB
    • Tabersonine, >=95% (HPLC)
    • 4429-63-4
    • 4-25-00-00997 (Beilstein Handbook Reference)
    • CHEBI:16776
    • DTXCID00118593
    • Methyl (5a,12b,19a)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylate
    • Aspidospermidine-3-carboxylic acid, 2,3,6,7-tetradehydro-, methyl ester, (5.alpha.,12.beta.,19.alpha.)-
    • (5alpha,12beta,19alpha)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylic acid, methyl ester

Attributes

  • Canonical SMILES

    CC[C@]12CC(=C3[C@@]4([C@H]1N(CC4)CC=C2)C5=CC=CC=C5N3)C(=O)OC

  • InChI

    InChI=1S/C21H24N2O2/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/h4-9,19,22H,3,10-13H2,1-2H3/t19-,20-,21-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 41.57000000000001
  • #RotBonds: 2
  • MW: 336.43500000000006
  • HBD: 1
  • HBA: 4
  • logP: 3.2212000000000014
  • Chemical Formula: C21H24N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. arborea Mexico, Costa Rica 681494 132793, 133359, 161424 to 161427
    T. corymbosa Malaysia, China 1679252 GK604
    T. dichotoma Sri Lanka, Malaysia - -
    T. heyneana India 2563820 -

External Databases


References

  • A new alkaloid and other anti-implantation principles from Tabernaemontana heyneana. Planta Med, 2001 (PMID 11509989).
  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • Quantification of Anti-Addictive Alkaloids Ibogaine and Voacangine in In Vivo- and In Vitro-Grown Plants of Two Mexican Tabernaemontana Species. Chem Biodivers, 2016 (PMID 27448833).
  • Tertiary indole alkaloids of Tabernaemontana dichotoma seeds. Planta Med, 1983 (PMID 6635015).

Compound-Protein Relationships


Compound Activities

    • Antiaddictive
    • Uterotrophic
    • Spasmolytic
    • 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) -4.8
    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 Non-Substrate
    Skin Permeability -2.88
    Distribution Blood-Brain Barrier (Central Nervous System) -2.16
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.0
    Plasma Protein Binding 56.1
    Steady State Volume of Distribution 4.5
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor 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 7.88
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.14
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.22
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.65
    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 -4.85
    Rat (Acute) 3.47
    Rat (Chronic Oral) 2.0
    Fathead Minnow 3.95
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Toxic
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 405.13
    Hydration Free Energy -6.47
    Log(D) at pH=7.4 3.22
    Log(P) 3.3
    Log S -3.16
    Log(Vapor Pressure) -7.23
    Melting Point 170.27
    pKa Acid 8.44
    pKa Basic 7.07