Heyneanine






Names

    • 19(R)-Heyneanine
    • BDBM50329106
    • methyl (1S,15S,17S,18S)-17-[(1R)-1-hydroxyethyl]-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate
    • CHEMBL512646
    • Heyneanine
    • 19-epi-voacristine
    • methyl (1S,15S,17S,18S)-17-((1R)-1-hydroxyethyl)-7-methoxy-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate

Attributes

  • Canonical SMILES

    C[C@@H]([C@@H]1C[C@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=CC=CC=C45)O

  • InChI

    InChI=1S/C19H24N2O/c1-11(22)15-8-12-9-16-18-14(6-7-21(10-12)19(15)16)13-4-2-3-5-17(13)20-18/h2-5,11-12,15-16,19-20,22H,6-10H2,1H3/t11-,12-,15-,16-,19-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 39.260000000000005
  • #RotBonds: 1
  • MW: 296.414
  • HBD: 2
  • HBA: 2
  • logP: 2.898800000000001
  • Chemical Formula: C19H24N2O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. albiflora France - -
    T. bufalina China 403123 Cai20170220
    T. calcarea Madagascar 761054 -
    T. catharinensis Brazil 403124 UEC117862
    T. corymbosa Malaysia, China 1679252 GK604
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. heyneana India 2563820 -
    T. laeta Brazil 761076 WAG
    T. officinalis China - Cai20120227
    T. penduliflora Cameroon, 37036/HNC, Nigeria 761088 40,411 HCN

External Databases


References

  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • A new alkaloid and other anti-implantation principles from Tabernaemontana heyneana. Planta Med, 2001 (PMID 11509989).
  • Biologically active ibogan and vallesamine derivatives from Tabernaemontana divaricata. Chem Biodivers, 2004 (PMID 17191876).
  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).
  • Cytotoxicity and genotoxicity of coronaridine from Tabernaemontana catharinensis A.DC in a human laryngeal epithelial carcinoma cell line (Hep-2). Genet Mol Biol, 2013 (PMID 23569415).
  • Cytotoxic Monoterpenoid Indole Alkaloids from Tabernaemontana corymbosa as Potent Autophagy Inhibitors by the Attenuation of Lysosomal Acidification. J Nat Prod, 2020 (PMID 32356659).
  • [Determination of structures by H NMR at 400 MHz: albifloranine, a new alkaloid from Tabernaemontana albiflora]. Planta Med, 1981 (PMID 17401820).
  • Isolation of 10-hydroxycoronaridine from Tabernaemontana penduliflora and its estrogen-like activity. Planta Med, 2000 (PMID 10763593).
  • New cytotoxic indole alkaloids from Tabernaemontana calcarea from the Madagascar rainforest. J Nat Prod, 2003 (PMID 12713407).
  • Tabercarpamines A-J, apoptosis-inducing indole alkaloids from the leaves of Tabernaemontana corymbosa. J Nat Prod, 2014 (PMID 24773071).
  • Three New Indole Alkaloids from Tabernaemontana divaricata. Nat Prod Bioprospect, 2018 (PMID 29754315).
  • 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).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Genotoxicity
    • Uterotrophic
    • Apoptotic
    • Xanthine oxidase inhibitory
    • Antitumor
    • Inhibitory
    • Growth inhibitory
    • Lysosomal acidification
    • Acetylbutyrylcholinesterase inhibitory
    • Cytotoxicity
    • Cidal
    • Estrogenic

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) -5.04
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.05
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.85
    Distribution Blood-Brain Barrier (Central Nervous System) -2.99
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.41
    Plasma Protein Binding 68.83
    Steady State Volume of Distribution 3.95
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 10.17
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.46
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.43
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.91
    Micronucleos Toxic
    NR-AhR Toxic
    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 -1.61
    Rat (Acute) 3.1
    Rat (Chronic Oral) 1.95
    Fathead Minnow 4.07
    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 388.17
    Hydration Free Energy -5.92
    Log(D) at pH=7.4 1.92
    Log(P) 1.88
    Log S -2.68
    Log(Vapor Pressure) -7.95
    Melting Point 213.9
    pKa Acid 11.51
    pKa Basic 7.9