Strictosidine lactam






Names

    • (1S,18S,19R,20S)-19-ethenyl-18-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-17-oxa-3,13-diazapentacyclo(11.8.0.02,10.04,9.015,20)henicosa-2(10),4,6,8,15-pentaen-14-one
    • SCHEMBL7906980
    • CHEMBL4438424
    • DTXCID20389243
    • MS-29249
    • Strictosamide
    • Q27149725
    • CHEBI:80684
    • CS-0016490
    • HY-N1198
    • DTXSID60438421
    • XS163684
    • 3-epi-Vincosamide; Isovincoside lactam; Strictosidine lactam
    • E80799
    • Strictosidine lactam
    • 1,2,7,8,13,13BBETA,14,14AALPHA-OCTAHYDRO-1BETA-VINYL-2ALPHA-(BETA-D-GLUCOPYRANOSYLOXY)-5H-INDOLO[2,3-A]PYRANO[3,4-G]QUINOLIZINE-5-ONE
    • 5H-Indolo[2,3-a]pyrano[3,4-g]quinolizin-5-one, 1-ethenyl-2-(beta-D-glucopyranosyloxy)-1,2,7,8,13,13b,14,14a-octahydro-, (1R,2S,13bS,14aS)-
    • BDBM50531272
    • DA-78062
    • AKOS032948641
    • (1S,18S,19R,20S)-19-ethenyl-18-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15-pentaen-14-one
    • 23141-25-5

Attributes

  • Canonical SMILES

    C=CC1[C@H]2C[C@H]3C4=C(CCN3C(=O)C2=CO[C@H]1O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C6=CC=CC=C6N4

  • InChI

    InChI=1S/C26H30N2O8/c1-2-12-15-9-18-20-14(13-5-3-4-6-17(13)27-20)7-8-28(18)24(33)16(15)11-34-25(12)36-26-23(32)22(31)21(30)19(10-29)35-26/h2-6,11-12,15,18-19,21-23,25-27,29-32H,1,7-10H2/t12?,15-,18+,19-,21-,22+,23-,25+,26+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 144.71
  • #RotBonds: 4
  • MW: 498.53200000000015
  • HBD: 5
  • HBA: 8
  • logP: 0.47250000000000014
  • Chemical Formula: C26H30N2O8


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. contorta Cameroon 761060 N43440/HNC

External Databases


References

  • Indoline alkaloids from Tabernaemontana contorta with cancer chemopreventive activity. Phytochemistry, 2017 (PMID 28950224).

Compound-Protein Relationships


Compound Activities

    • Inhibitory
    • Cancer chemopreventive

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) -6.11
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.14
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 0.61
    Distribution Blood-Brain Barrier (Central Nervous System) -3.83
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.03
    Plasma Protein Binding 63.65
    Steady State Volume of Distribution 1.54
    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 7.57
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Safe
    Bioconcentration Factor -2.42
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.29
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 4.94
    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 -1368.51
    Rat (Acute) 3.89
    Rat (Chronic Oral) 3.11
    Fathead Minnow 4.29
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Toxic
    SR-p53 Safe
    General Properties Boiling Point 523.81
    Hydration Free Energy -2.93
    Log(D) at pH=7.4 1.86
    Log(P) 0.48
    Log S -2.9
    Log(Vapor Pressure) -12.94
    Melting Point 197.09
    pKa Acid 4.95
    pKa Basic 6.74