Conodiparine A






Names

    • IBOGAMINE-18-CARBOXYLIC ACID, 20-HYDROXY-12-((3.ALPHA.)-16-(HYDROXYMETHYL)-17-METHOXY-17-OXOVOBASAN-3-YL)-13-METHOXY-, METHYL ESTER, (20S)-
    • Conodiparine A
    • Methyl (1S,15R,17S,18S)-7-((1S,12S,14S,15E,18S)-15-ethylidene-18-(hydroxymethyl)-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo(12.3.1.0,.0,)octadeca-3(11),4,6,8-tetraen-12-yl)-17-((1S)-1-hydroxyethyl)-6-methoxy-3,13-diazapentacyclo(13.3.1.0,.0,.0,)nonadeca-2(10),4,6,8-tetraene-1-carboxylic acid
    • 213748-27-7
    • BR58MM3QEU
    • (-)-Conodiparine A
    • methyl (1S,15R,17S,18S)-7-[(1S,12R,14S,15E,18S)-15-ethylidene-18-(hydroxymethyl)-18-methoxycarbonyl-17-methyl-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraen-12-yl]-17-[(1S)-1-hydroxyethyl]-6-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene-1-carboxylate
    • Methyl (1S,15R,17S,18S)-7-[(1S,12S,14S,15E,18S)-15-ethylidene-18-(hydroxymethyl)-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0,.0,]octadeca-3(11),4,6,8-tetraen-12-yl]-17-[(1S)-1-hydroxyethyl]-6-methoxy-3,13-diazapentacyclo[13.3.1.0,.0,.0,]nonadeca-2(10),4,6,8-tetraene-1-carboxylic acid
    • methyl (1S,15R,17S,18S)-7-((1S,12R,14S,15E,18S)-15-ethylidene-18-(hydroxymethyl)-18-methoxycarbonyl-17-methyl-10,17-diazatetracyclo(12.3.1.03,11.04,9)octadeca-3(11),4,6,8-tetraen-12-yl)-17-((1S)-1-hydroxyethyl)-6-methoxy-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4,6,8-tetraene-1-carboxylate
    • Ibogamine-18-carboxylic acid, 20-hydroxy-12-((3alpha)-16-(hydroxymethyl)-17-methoxy-17-oxovobasan-3-yl)-13-methoxy-, methyl ester, (20S)-
    • UNII-BR58MM3QEU

Attributes

  • Canonical SMILES

    C/C=C\1/CN([C@H]2CC3=C([C@H](C[C@@H]1[C@]2(CO)C(=O)OC)C4=C(C=C5C(=C4)C6=C(N5)[C@@]7(C[C@H]8C[C@@H]([C@@H]7N(C8)CC6)[C@H](C)O)C(=O)OC)OC)NC9=CC=CC=C39)C

  • InChI

    InChI=1S/C44H54N4O7/c1-7-25-21-47(3)37-17-32-26-10-8-9-11-34(26)45-38(32)31(16-33(25)44(37,22-49)42(52)55-6)30-15-29-27-12-13-48-20-24-14-28(23(2)50)40(48)43(19-24,41(51)54-5)39(27)46-35(29)18-36(30)53-4/h7-11,15,18,23-24,28,31,33,37,40,45-46,49-50H,12-14,16-17,19-22H2,1-6H3/b25-7-/t23-,24+,28+,31+,33-,37-,40-,43+,44-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 140.35
  • #RotBonds: 6
  • MW: 750.9370000000004
  • HBD: 4
  • HBA: 9
  • logP: 4.822200000000004
  • Chemical Formula: C44H54N4O7


Species

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

External Databases


References

  • Conodiparines A-D, new bisindoles from Tabernaemontana. Reversal of vincristine-resistance with cultured cells. Bioorg Med Chem Lett, 1998 (PMID 9873417).
  • New bisindole alkaloids from Tabernaemontana corymbosa. J Nat Prod, 2003 (PMID 12542336).

Compound-Protein Relationships

  • No relationship found

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) -5.98
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 74.04
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 10463.92
    Distribution Blood-Brain Barrier (Central Nervous System) -3.74
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.03
    Plasma Protein Binding 86.28
    Steady State Volume of Distribution 4.16
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 8.28
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -247.09
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.32
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.45
    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 -18988398.82
    Rat (Acute) 2.9
    Rat (Chronic Oral) 2.29
    Fathead Minnow 23971.26
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 2131487.81
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.4
    Log(P) 3.58
    Log S -5.06
    Log(Vapor Pressure) -70113.27
    Melting Point 294.98
    pKa Acid -458.05
    pKa Basic 6.22