Pleiocarpamine






Names

    • Q15425259
    • 6393-66-4
    • NSC374523
    • NSC 374523
    • Methyl (13Z,14S,16S,18R)-13-ethylidene-1,11-diazapentacyclo(12.3.1.0,.0,.0,)octadeca-2,4,6,8(17)-tetraene-18-carboxylic acid
    • (+)-PLEIOCARPAMINE
    • methyl (13E,14S,16S,18S)-13-ethylidene-1,11-diazapentacyclo[12.3.1.02,7.08,17.011,16]octadeca-2,4,6,8(17)-tetraene-18-carboxylate
    • methyl (13E,14S,16S,18S)-13-ethylidene-1,11-diazapentacyclo(12.3.1.02,7.08,17.011,16)octadeca-2,4,6,8(17)-tetraene-18-carboxylate
    • CHEBI:141939
    • 4J3PV95ANL
    • PLEOCARPAMINE
    • NSC-374523
    • (16S,19E)-17-methoxy-17-oxo-19,20-didehydro-1,16-cyclocorynan
    • DTXCID10370463
    • CHEMBL3338254
    • 2H-2,12-METHANOINDOLO(2,3-A)QUINOLIZINE-13-CARBOXYLIC ACID, 3-ETHYLIDENE-1,3,4,6,7,12B-HEXAHYDRO-, METHYL ESTER, (2S,3E,12BS,13S)-
    • UNII-4J3PV95ANL
    • DTXSID80419616
    • 1,16-Cyclocorynan-17-oic acid, 19,20-didehydro-, methyl ester, (16S,19E)-
    • Pleiocarpamine
    • Methyl (13Z,14S,16S,18R)-13-ethylidene-1,11-diazapentacyclo[12.3.1.0,.0,.0,]octadeca-2,4,6,8(17)-tetraene-18-carboxylic acid

Attributes

  • Canonical SMILES

    C/C=C\1/CN2CCC3=C4[C@@H]2C[C@@H]1[C@H](N4C5=CC=CC=C35)C(=O)OC

  • InChI

    InChI=1S/C20H22N2O2/c1-3-12-11-21-9-8-14-13-6-4-5-7-16(13)22-18(14)17(21)10-15(12)19(22)20(23)24-2/h3-7,15,17,19H,8-11H2,1-2H3/b12-3-/t15-,17-,19-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 34.47
  • #RotBonds: 1
  • MW: 322.40800000000013
  • HBD: 0
  • HBA: 4
  • logP: 3.2344000000000017
  • Chemical Formula: C20H22N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. chippii Ivory Coast - Lg12291
    T. contorta Cameroon 761060 N43440/HNC

External Databases


References

  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).
  • Indoline alkaloids from Tabernaemontana contorta with cancer chemopreventive activity. Phytochemistry, 2017 (PMID 28950224).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antimicrobial
    • Inhibitory
    • Cancer chemopreventive

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 -4.67
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.26
    Distribution Blood-Brain Barrier (Central Nervous System) -2.4
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.18
    Plasma Protein Binding 62.05
    Steady State Volume of Distribution 5.41
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.26
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.99
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.2
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.91
    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 -1.11
    Rat (Acute) 2.82
    Rat (Chronic Oral) 1.8
    Fathead Minnow 4.58
    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 428.03
    Hydration Free Energy -4.33
    Log(D) at pH=7.4 2.27
    Log(P) 3.15
    Log S -2.68
    Log(Vapor Pressure) -7.64
    Melting Point 187.43
    pKa Acid 10.36
    pKa Basic 7.19