Conodurine






Names

    • AKOS040761523
    • 2665-57-8
    • Q15410924
    • CONODURINE B640243K102
    • DA-72329
    • B640928K229
    • Methyl 3-(13-methoxy-18-(methoxycarbonyl)ibogamin-14-yl)vobasan-17-oate
    • DTXSID50420416
    • Conodurine
    • methyl 17-ethyl-5-[(15Z)-15-ethylidene-18-methoxycarbonyl-17-methyl-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraen-12-yl]-6-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate
    • 13-Methoxy-14-[(3R)-17-methoxy-17-oxovobasan-3alpha-yl]ibogamine-18-carboxylic acid methyl ester
    • NSC289066
    • NSC628058

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=C4C=CC(=C5[C@H]6C[C@@H]\7[C@@H]([C@H](CC8=C6NC9=CC=CC=C89)N(C/C7=C/C)C)C(=O)OC)OC)C(=O)OC

  • InChI

    InChI=1S/C43H52N4O5/c1-7-24-17-23-20-43(42(49)52-6)39-28(15-16-47(21-23)40(24)43)27-13-14-34(50-4)36(38(27)45-39)31-18-29-25(8-2)22-46(3)33(35(29)41(48)51-5)19-30-26-11-9-10-12-32(26)44-37(30)31/h8-14,23-24,29,31,33,35,40,44-45H,7,15-22H2,1-6H3/b25-8-/t23-,24+,29+,31-,33+,35+,40+,43-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 99.89
  • #RotBonds: 5
  • MW: 704.9120000000001
  • HBD: 2
  • HBA: 7
  • logP: 6.488900000000006
  • Chemical Formula: C43H52N4O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. chippii Ivory Coast - Lg12291
    T. corymbosa Malaysia, China 1679252 GK604
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. holstii Kenya - -
    T. johnstonii Kenya - -
    T. laeta Brazil 761076 WAG
    T. van heurkii Moretti - 1455

External Databases


References

  • Antioxidant Activity of Methanol Extract of Tinospora crispa and Tabernaemontana corymbosa Sains Malaysiana, 2013 (DOI).
  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).
  • Taburnaemines A-I, Cytotoxic Vobasinyl-Iboga-Type Bisindole Alkaloids from Tabernaemontana corymbosa. J Nat Prod, 2018 (PMID 29319316).
  • New Iboga-Type Indole Alkaloids from Tabernaemontana divaricata. Nat Prod Bioprospect, 2019 (PMID 31724098).
  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • Vobasinyl-iboga bisindole alkaloids, potent acetylcholinesterase inhibitors from Tabernaemontana divaricata root. J Pharm Pharmacol, 2006 (PMID 16734986).
  • Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures. An Acad Bras Cienc, 2008 (PMID 18797794).
  • New vobasinyl-ibogan type bisindole alkaloids from Tabernaemontana corymbosa. Fitoterapia, 2015 (PMID 25449423).
  • A new natural auaternary indole alkaloid isolated from Tabernaemontana laeta Mart. (Apocynaceae) Journal of the Brazilian Chemical Society, 2001 (DOI).
  • Conodurine, conoduramine, and ervahanine derivatives from Tabernaemontana corymbosa. Phytochemistry, 2003 (PMID 12809725).
  • Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina. Planta Med, 2018 (PMID 29689587).
  • Plant anticancer agents III: Isolation of indole and bisindole alkaloids from Tabernaemontana holstii roots. J Pharm Sci, 1977 (PMID 561182).
  • Tabercarpamines A-J, apoptosis-inducing indole alkaloids from the leaves of Tabernaemontana corymbosa. J Nat Prod, 2014 (PMID 24773071).
  • Plant anticancer agents V: new bisindole alkaloids from Tabernaemontana johnstonii stem bark. J Pharm Sci, 1978 (PMID 621649).
  • Isolation of bis-indole alkaloids with antileishmanial and antibacterial activities from Peschiera van heurkii (syn. Tabernaemontana van heurkii). Planta Med, 1994 (PMID 7997477).
  • Cytotoxic Monoterpenoid Indole Alkaloids from Tabernaemontana corymbosa as Potent Autophagy Inhibitors by the Attenuation of Lysosomal Acidification. J Nat Prod, 2020 (PMID 32356659).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Reproducible
    • Antibacterial
    • Anticancer
    • Antiproliferative
    • Xanthine oxidase inhibitory
    • Cholinesterase
    • Antiinflammatory
    • Inhibitory
    • Antileukemic
    • Antileishmanial
    • Antioxidant
    • Antimicrobial
    • Acetylcholinesterase inhibitory
    • Acetylbutyrylcholinesterase inhibitory
    • Lysosomal acidification
    • Cytotoxicity
    • Growth inhibitory

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) -5.91
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 17.9
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 3099.53
    Distribution Blood-Brain Barrier (Central Nervous System) -3.24
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.32
    Plasma Protein Binding 86.84
    Steady State Volume of Distribution 5.02
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate 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 Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 10.96
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -75.34
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.21
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 7.23
    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 -5623551.07
    Rat (Acute) 2.87
    Rat (Chronic Oral) 2.42
    Fathead Minnow 7100.69
    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 628830.3
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 5.77
    Log(P) 5.97
    Log S -5.74
    Log(Vapor Pressure) -20645.22
    Melting Point 279.48
    pKa Acid -114.1
    pKa Basic 5.96