Aspidospermine






Names

    • (-)-Aspidospermine
    • ASPIDOSPERMINE
    • UNII-U1475W62Q5
    • HMS1536J13
    • BDBM50252054
    • 2H-3,7-Methanoazacycloundecino(5,4-b)indole-9-carboxylic acid, 7-ethyl-1,4,5,6,7,8,9,10-octahydro-10-methyl-, methyl ester, (7S-(7R*,9R*))-
    • ASPIDOSPERMINE [MI]
    • SCHEMBL918176
    • NCI60_005440
    • 1-(17-methoxyaspidospermidin-1-yl)ethanone
    • CHEBI:28463
    • 5-23-12-00210 (Beilstein Handbook Reference)
    • TimTec1_000915
    • 1-(17-Methoxyaspidospermidin-1-yl)-ethanone
    • U1475W62Q5
    • DTXSID70196883
    • NSC-61811
    • NSC 19508
    • CCG-36039
    • NCGC00174986-01
    • 1-[(1R,9R,12R,19R)-12-ethyl-6-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5-trien-8-yl]ethanone
    • 1935-07-5
    • NSC61811
    • ARQOGCYMPUOVHK-ZHHKINOHSA-N
    • 1-Acetyl-17-methoxyaspidospermidine
    • NSC19508
    • EINECS 207-376-7
    • ETHANONE, 1-(17-METHOXYASPIDOSPERMIDIN-1-YL)-
    • Aspidospermine
    • NS00031621
    • 1-Acetyl-17-methoxyaspidospermidine, 9CI
    • CCG-35302
    • 1-[ethyl(methoxy)[?]yl]ethanone
    • Q27103707
    • C09042
    • CHEMBL519457
    • BRD-K06579228-001-01-6
    • 1-[(1R,9R,12R,19R)-12-ethyl-6-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5-trien-8-yl]ethan-1-one
    • 466-49-9
    • Vincaminorein (Aspidospermine)
    • Vincaminorine
    • Aspidospermidine, 1-acetyl-17-methoxy-
    • NSC-19508
    • BRN 0048882
    • Aspidospermin
    • WLN: T C6 B5665 2AB S BX IN QN JH&&TTTJ GO1 IV1 M2
    • 1-((3aR,5aR,10bR,12bR)-3a-Ethyl-7-methoxy-2,3,3a,5,5a,11,12,12b-octahydro-1H,4H-6,12a-diaza-indeno[7,1-cd]fluoren-6-yl)-ethanone

Attributes

  • Canonical SMILES

    CC[C@]12CCCN3[C@H]1[C@@]4(CC3)[C@@H](CC2)N(C5=C4C=CC=C5OC)C(=O)C

  • InChI

    InChI=1S/C22H30N2O2/c1-4-21-10-6-13-23-14-12-22(20(21)23)16-7-5-8-17(26-3)19(16)24(15(2)25)18(22)9-11-21/h5,7-8,18,20H,4,6,9-14H2,1-3H3/t18-,20-,21-,22-/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 32.78
  • #RotBonds: 2
  • MW: 354.4940000000001
  • HBD: 0
  • HBA: 3
  • logP: 3.7264000000000026
  • Chemical Formula: C22H30N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. catharinensis Brazil 403124 UEC117862

External Databases


References

  • Chromatographic analysis and antioxidant capacity of Tabernaemontana catharinensis. Nat Prod Commun, 2014 (PMID 24660464).

Compound-Protein Relationships


Compound Activities

    • Antioxidant

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) -4.63
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.65
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.41
    Distribution Blood-Brain Barrier (Central Nervous System) -2.65
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.76
    Plasma Protein Binding 55.25
    Steady State Volume of Distribution 1.61
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 8.33
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.27
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.25
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.67
    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 -7.56
    Rat (Acute) 3.26
    Rat (Chronic Oral) 1.62
    Fathead Minnow 3.92
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 440.32
    Hydration Free Energy -4.81
    Log(D) at pH=7.4 2.5
    Log(P) 3.05
    Log S -2.78
    Log(Vapor Pressure) -7.38
    Melting Point 173.5
    pKa Acid 11.07
    pKa Basic 7.32