Pedunculine






Names

    • 8-hydroxy-salvigenin
    • Pedunculin
    • DTXSID70182261
    • LMPK12111448', "flavone, 5,8-dihydroxy-4',6,7-trimethoxy-"
    • 2798-22-3
    • CHEBI:192704
    • Pedunculine
    • 8-hydroxysalvigenin
    • 8-OH-salvigenin
    • 4H-1-Benzopyran-4-one, 5,8-dihydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)-

Attributes

  • Canonical SMILES

    OC1=C(C(OC)=C(C2=C1)NC3=C(C[C@@]4([C@@H]5[C@@]32CCN5[C@H]([C@H]6[C@@H]4O6)C7=CC=C8C([C@]9%10CCN(C[C@@H]%11[C@H]%12O%11)[C@H]9[C@]%12(CC)CCC%10N8C)=C7)CC)C(OC)=O)OC

  • InChI

    InChI=1S/C43H52N4O7/c1-7-40-12-11-28-42(13-15-46(38(40)42)20-27-35(40)53-27)23-17-21(9-10-25(23)45(28)3)30-33-36(54-33)41(8-2)19-22(37(49)52-6)34-43(14-16-47(30)39(41)43)24-18-26(48)31(50-4)32(51-5)29(24)44-34/h9-10,17-18,27-28,30,33,35-36,38-39,44,48H,7-8,11-16,19-20H2,1-6H3/t27-,28?,30+,33+,35-,36+,38+,39-,40-,41+,42+,43-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 111.8
  • #RotBonds: 6
  • MW: 736.9099999999999
  • HBD: 2
  • HBA: 11
  • logP: 4.998200000000005
  • Chemical Formula: C43H52N4O7


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Two new monoterpenoid indole alkaloids from Tabernaemontana divaricata. Nat Prod Res, 2019 (PMID 30445827).

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) -5.32
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 124.48
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 17013.06
    Distribution Blood-Brain Barrier (Central Nervous System) -3.05
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.88
    Plasma Protein Binding 52.21
    Steady State Volume of Distribution 2.64
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-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 Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.2
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -397.55
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.9
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 6.09
    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 Toxic
    T. Pyriformis -30879437.96
    Rat (Acute) 2.78
    Rat (Chronic Oral) 1.5
    Fathead Minnow 38980.31
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Toxic
    General Properties Boiling Point 3469918.41
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.97
    Log(P) 3.79
    Log S -4.73
    Log(Vapor Pressure) -114155.12
    Melting Point 239.74
    pKa Acid -787.9
    pKa Basic 8.4