Tubotaiwine






Names

    • 20(S)-tubotaiwine
    • 6711-69-9
    • AKOS040762459
    • Tubotaiwine
    • GLXC-18348
    • SCHEMBL6239856
    • FS-8690
    • Methyl (3aR,4S,5S,11bS)-4-ethyl-1,2,3a,4,5,7-hexahydro-3,5-ethanopyrrolo[2,3-d]carbazole-6-carboxylate
    • Q27138847
    • CS-0016403
    • Condyfolan-16-carboxylic acid, 2,16-didehydro-, methyl ester
    • CHEBI:70515
    • HY-N1115
    • methyl (1S,11S,17R,18S)-18-ethyl-8,14-diazapentacyclo[9.5.2.01,9.02,7.014,17]octadeca-2,4,6,9-tetraene-10-carboxylate

Attributes

  • Canonical SMILES

    CC[C@H]1[C@@H]2CCN3[C@H]1[C@]4(CC3)C5=CC=CC=C5NC4=C2C(=O)OC

  • InChI

    InChI=1S/C20H24N2O2/c1-3-12-13-8-10-22-11-9-20(18(12)22)14-6-4-5-7-15(14)21-17(20)16(13)19(23)24-2/h4-7,12-13,18,21H,3,8-11H2,1-2H3/t12-,13-,18+,20+/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 41.57000000000001
  • #RotBonds: 2
  • MW: 324.4240000000001
  • HBD: 1
  • HBA: 4
  • logP: 2.9110000000000005
  • Chemical Formula: C20H24N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. chippii Ivory Coast - Lg12291
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. elegans Mozambique, South Africa, Indonesia 761068 23/SM
    T. pachysiphon Nigeria, Netherlands 403125 HXJ20171220

External Databases


References

  • Accumulation of indole alkaloids in a suspension culture of Tabernaemontana divaricata. Planta Med, 1988 (PMID 17265301).
  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).
  • Antimicrobially active alkaloids from Tabernaemontana chippii. J Nat Prod, 1985 (PMID 4031898).
  • Biologically active ibogan and vallesamine derivatives from Tabernaemontana divaricata. Chem Biodivers, 2004 (PMID 17191876).
  • Characterization of a Suspension Culture of Tabernaemontana elegans on Growth, Nutrient Uptake, and Accumulation of Indole Alkaloids*. Planta Med, 1989 (PMID 17262332).
  • Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata. J Nat Prod, 2018 (PMID 30169038).
  • Isolation of opioid-active compounds from Tabernaemontana pachysiphon leaves. J Pharm Pharmacol, 1999 (PMID 10678501).

Compound-Protein Relationships

  • No relationship found

Compound Activities

    • Antiproliferative
    • Xanthine oxidase inhibitory
    • Analgesic
    • Inhibitory
    • Antimicrobial
    • 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) -4.8
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.84
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.74
    Distribution Blood-Brain Barrier (Central Nervous System) -2.32
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.91
    Plasma Protein Binding 54.49
    Steady State Volume of Distribution 3.83
    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 Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 7.41
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.19
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.75
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 5.19
    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 -2.06
    Rat (Acute) 3.5
    Rat (Chronic Oral) 2.04
    Fathead Minnow 3.97
    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 406.09
    Hydration Free Energy -4.33
    Log(D) at pH=7.4 3.06
    Log(P) 3.06
    Log S -3.05
    Log(Vapor Pressure) -7.01
    Melting Point 184.43
    pKa Acid 9.13
    pKa Basic 7.61