Isovoacristine






Names

    • 5525-37-1
    • ISOVOACRISTINE
    • DTXSID901337312
    • Isovoacristine

Attributes

  • Canonical SMILES

    C[C@H]([C@H]1C[C@@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=C4C=CC(=C5)OC)C(=O)OC)O

  • InChI

    InChI=1S/C22H28N2O4/c1-12(25)17-8-13-10-22(21(26)28-3)19-16(6-7-24(11-13)20(17)22)15-5-4-14(27-2)9-18(15)23-19/h4-5,9,12-13,17,20,23,25H,6-8,10-11H2,1-3H3/t12-,13-,17-,20+,22-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 74.79
  • #RotBonds: 3
  • MW: 384.4760000000001
  • HBD: 2
  • HBA: 5
  • logP: 2.234600000000001
  • Chemical Formula: C22H28N2O4


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bovina China, Vietnam 3036760 Cai20150423
    T. calcarea Madagascar 761054 -
    T. corymbosa Malaysia, China 1679252 GK604
    T. cymosa Colombia 761066 JBC3243
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. laeta Brazil 761076 WAG
    T. officinalis China - Cai20120227

External Databases


References

  • Bis-indole alkaloids from Tabernaemontana bovina. Phytochemistry, 1998 (PMID 11711104).
  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • Cytotoxic indole alkaloids from Tabernaemontana divaricata. J Nat Prod, 2013 (PMID 23944995).
  • Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry, 2015 (PMID 25687604).
  • Five new iboga alkaloids from Tabernaemontana corymbosa. J Nat Prod, 2002 (PMID 12027738).
  • Molecular Human Targets of Bioactive Alkaloid-Type Compounds from Tabernaemontana cymose Jacq. Molecules, 2021 (PMID 34205626).
  • 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).
  • 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

    • Anticancer
    • Antiinflammatory
    • Antioxidant
    • Cytotoxicity
    • Acetylbutyrylcholinesterase inhibitory
    • 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) -4.87
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.05
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -0.99
    Distribution Blood-Brain Barrier (Central Nervous System) -3.04
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.66
    Plasma Protein Binding 52.02
    Steady State Volume of Distribution 6.32
    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 Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.07
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.65
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.05
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.03
    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 -19.92
    Rat (Acute) 2.91
    Rat (Chronic Oral) 2.12
    Fathead Minnow 4.08
    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 431.31
    Hydration Free Energy -5.8
    Log(D) at pH=7.4 2.42
    Log(P) 1.57
    Log S -3.12
    Log(Vapor Pressure) -8.76
    Melting Point 209.74
    pKa Acid 8.71
    pKa Basic 7.7