Biscarpamontamine B






Names

    • Biscarpamontamine B', "Methyl (1R,1'r,7S,11R,12'r,13S,15S,16'r,18'r,22'r,24R,25S)-18',24-dihydroxy-19-methoxy-9-oxo-8,15'-dioxa-4,8',17,19'-tetraazaspiro(heptacyclo(11.10.1.1,.0,.0,.0,.0,)pentacosane-15,17'-hexacyclo(10.9.1.0,.0,.0,.0,)docosane)-2',4',6',9',18(23),19,21-heptaene-10'-carboxylic acid", "Methyl (1R,1'r,7S,11R,12'r,13S,15S,16'r,18'r,22'r,24R,25S)-18',24-dihydroxy-19-methoxy-9-oxo-8,15'-dioxa-4,8',17,19'-tetraazaspiro[heptacyclo[11.10.1.1,.0,.0,.0,.0,]pentacosane-15,17'-hexacyclo[10.9.1.0,.0,.0,.0,]docosane]-2',4',6',9',18(23),19,21-heptaene-10'-carboxylic acid", 'CHEMBL1079127
    • Biscarpamontamine B

Attributes

  • Canonical SMILES

    [H][C@]12[C@]34CC(C(OC)=O)=C5NC6=CC=CC=C6[C@@]51CCN2[C@H](O)[C@]7(C[C@@](C[C@@]([C@@H]8CCN9CC%10)(CC(O8)=O)[C@@]9([H])[C@@]%11%10C%12=C%13C(OC)=CC=C%12)([H])[C@]%11(O)N%13C7)[C@@H]3OCC4

  • InChI

    InChI=1S/C43H48N4O8/c1-52-28-9-5-7-26-31(28)47-22-40(19-23-18-39-21-30(48)55-29(39)10-14-45-15-12-42(26,35(39)45)43(23,47)51)36-38(13-17-54-36)20-24(33(49)53-2)32-41(11-16-46(34(38)41)37(40)50)25-6-3-4-8-27(25)44-32/h3-9,23,29,34-37,44,50-51H,10-22H2,1-2H3/t23-,29-,34-,35-,36+,37+,38-,39-,40-,41-,42+,43+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 133.27
  • #RotBonds: 2
  • MW: 748.8770000000001
  • HBD: 3
  • HBA: 12
  • logP: 3.0074000000000014
  • Chemical Formula: C43H48N4O8


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. sphaerocarpa Indonesia 761099 AP070902

External Databases


References

  • Biscarpamontamines A and B, an aspidosperma-iboga bisindole alkaloid and an aspidosperma-aspidosperma bisindole alkaloid, from Tabernaemontana sphaerocarpa. J Nat Prod, 2009 (PMID 19711971).

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) -5.92
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney 244.66
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 32732.23
    Distribution Blood-Brain Barrier (Central Nervous System) -2.88
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.85
    Plasma Protein Binding 76.78
    Steady State Volume of Distribution 3.77
    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 1.27
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Toxic
    Bee Toxic
    Bioconcentration Factor -764.26
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.15
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.86
    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 -59408073.68
    Rat (Acute) 3.31
    Rat (Chronic Oral) 2.56
    Fathead Minnow 74990.92
    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 6678204.64
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 4.12
    Log(P) 2.28
    Log S -4.28
    Log(Vapor Pressure) -219802.51
    Melting Point 352.98
    pKa Acid -1545.12
    pKa Basic 9.06