Deoxytubulosine






Names

    • Deoxytubulosine
    • Q27106381
    • CHEBI:4433
    • AC1Q56PD
    • Tubulosan, 10,11-dimethoxy-
    • 2632-30-6
    • 2H-Benzo[a]quinolizine, 3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2-[[(1R)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-, (2S,3R,11bS)-
    • C11817
    • AC1L4VWR
    • DTXSID10949173
    • 10,11-Dimethoxytubulosan
    • (2S,3R,11bS)-3-ethyl-9,10-dimethoxy-2-[[(1R)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine
    • CHEMBL4212545

Attributes

  • Canonical SMILES

    CC[C@H]1CN2CCC3=CC(=C(C=C3[C@@H]2C[C@@H]1C[C@@H]4C5=C(CCN4)C6=CC=CC=C6N5)OC)OC

  • InChI

    InChI=1S/C29H37N3O2/c1-4-18-17-32-12-10-19-15-27(33-2)28(34-3)16-23(19)26(32)14-20(18)13-25-29-22(9-11-30-25)21-7-5-6-8-24(21)31-29/h5-8,15-16,18,20,25-26,30-31H,4,9-14,17H2,1-3H3/t18-,20-,25+,26-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 49.519999999999996
  • #RotBonds: 5
  • MW: 459.6340000000002
  • HBD: 2
  • HBA: 4
  • logP: 5.407500000000005
  • Chemical Formula: C29H37N3O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671

External Databases


References

  • Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata. J Nat Prod, 2018 (PMID 30169038).
  • Iboga-type alkaloids with Indolizidino[8,7-b]Indole scaffold and bisindole alkaloids from Tabernaemontana bufalina Lour. Phytochemistry, 2022 (PMID 35074605).

Compound-Protein Relationships


Compound Activities

    • α-glucosidase inhibitory
    • Antiproliferative
    • Antimicrobial
    • Butyrylcholinesterase

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) -5.18
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -5.05
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.86
    Distribution Blood-Brain Barrier (Central Nervous System) -2.94
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.09
    Plasma Protein Binding 78.26
    Steady State Volume of Distribution 2.92
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 10.75
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.32
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.61
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.81
    Micronucleos Toxic
    NR-AhR Toxic
    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 -694.51
    Rat (Acute) 2.57
    Rat (Chronic Oral) 1.51
    Fathead Minnow 5.64
    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 480.12
    Hydration Free Energy -3.08
    Log(D) at pH=7.4 4.24
    Log(P) 4.71
    Log S -3.97
    Log(Vapor Pressure) -8.53
    Melting Point 160.01
    pKa Acid 13.49
    pKa Basic 9.04