Alasmontamine A






Names

    • Alasmontamine A

Attributes

  • Canonical SMILES

    OC1=CC=CC2=C1N3[C@]4(O)[C@@]25[C@]6([H])[C@]([C@@H]7CCN6CC5)(CCO7)CC4C[C@]8(CN(C=C9C(C%10)=[N+]%11C[C@]%12(C[C@@](C[C@@]%13%14[C@@]%15([H])[C@]%16(C%17=C%18C(O)=CC=C%17)CCN%15CC[C@@H]%13OCC%14)([H])[C@]%16(O)N%18C%12)[C@H]%19[C@@]%20(CCO%19)CC(C(OC)=O)=C([C@@]%21%10[C@]%20%11[H])NC%22=C%21C=CC=C%22)[C@@]([C@@]9(C(C=CC=C%23)=C%23N%24)C%24=C(C(OC)=O)C%25)([H])[C@]%26%25[C@H]8OCC%26)C3

  • InChI

    InChI=1S/C84H90N8O12/c1-99-65(95)47-37-77-23-31-104-72(77)74(34-46-36-76-22-30-102-60(76)18-26-88-28-20-81(69(76)88)52-12-8-16-58(94)62(52)92(44-74)84(46,81)98)42-90-56(39-79(67(77)90)49-9-3-5-13-54(49)85-63(47)79)53-40-89-41-73(71-78(24-32-103-71)38-48(66(96)100-2)64-82(53,70(78)89)50-10-4-6-14-55(50)86-64)33-45-35-75-21-29-101-59(75)17-25-87-27-19-80(68(75)87)51-11-7-15-57(93)61(51)91(43-73)83(45,80)97/h3-16,40,45-46,59-60,67-72,97-98H,17-39,41-44H2,1-2H3,(H3-,85,86,93,94,95,96)/p+1/t45?,46-,59+,60+,67+,68+,69+,70+,71+,72+,73+,74+,75-,76-,77+,78+,79+,80-,81-,82-,83-,84-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 213.70999999999998
  • #RotBonds: 3
  • MW: 1404.6959999999995
  • HBD: 6
  • HBA: 19
  • logP: 7.37770000000001
  • Chemical Formula: C84H91N8O12+


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. elegans Mozambique, South Africa, Indonesia 761068 23/SM

External Databases


References

  • Alasmontamine A, A first tetrakis monoterpene indole alkaloid from Tabernaemontana elegans. Org Lett, 2009 (PMID 19921789).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Cell 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) -6.04
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 6323457314456035000000
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 826401706281019300000000
    Distribution Blood-Brain Barrier (Central Nervous System) -1.43
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.96
    Plasma Protein Binding 83.39
    Steady State Volume of Distribution 4.77
    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 Inhibitor
    Excretion Clearance 4.74
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Safe
    Bioconcentration Factor -19220231481423840000000
    Biodegradation Toxic
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -7847848449402802.0
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.05
    Micronucleos Toxic
    NR-AhR Safe
    NR-AR Safe
    NR-AR-LBD Toxic
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Safe
    NR-PPAR-gamma Safe
    NR-TR Toxic
    T. Pyriformis -1499879249971800200000000000
    Rat (Acute) 1209590522576.63
    Rat (Chronic Oral) 3217110021820930600
    Fathead Minnow 1893277332082068000000000
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Toxic
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Toxic
    SR-p53 Toxic
    General Properties Boiling Point 168694852811803230000000000
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 -93777512053273580000
    Log(P) -10916807732217120
    Log S -7.23
    Log(Vapor Pressure) -5555036490783778000000000
    Melting Point -1687976286184314400
    pKa Acid -40477204725048130000000
    pKa Basic -325637849376528000000