Tetrahydroalstonine






Names

    • methyl (19alpha,20alpha)-19-methyl-16,17-didehydro-18-oxayohimban-16-carboxylate
    • Alstonine, 3,4,5,6-tetrahydro
    • CHEMBL498734
    • CCG-208423
    • AKOS037515397
    • Oxayohimban-16-carboxylic acid, 16,17-didehydro-19-methyl-, methyl ester, (19-alpha,20-alpha)-
    • (3.ALPHA.)-3,4,5,6-TETRAHYDROALSTONINE
    • Tetrahydroalstonine
    • UNII-6U62R2Y5Y2
    • Methyl (19alpha,20alpha)-16,17-didehydro-19-methyloxayohimban-16-carboxylate
    • DTXSID201020629
    • Alstonine, 3,4,5,6-tetrahydro-, (3alpha)-
    • 6U62R2Y5Y2
    • (3alpha)-3,4,5,6-Tetrahydroalstonine
    • 815B4D52-2710-4B1D-B671-7CCBD7EC8A81
    • 16,17-Didehydro-19-methyloxayohimban-16-carboxylic acid, methyl ester
    • HY-N1163
    • PDSP2_001642
    • (-)-Tetrahydroalstonine
    • NCGC00163632-01
    • EINECS 229-331-0
    • Alstonine, 3,4,5,6-tetrahydro-, (3.alpha.)-
    • 4H-INDOLO(2,3-A)PYRANO(3,4-G)QUINOLIZINE-1-CARBOXYLIC ACID, 4A,5,7,8,13,13B,14,14A-OCTAHYDRO-4-METHYL-, METHYL ESTER, (4S,4AS,13BS,14AS)-
    • MS-25467
    • Oxayohimban-16-carboxylic acid, 16,17-didehydro-19-methyl-, methyl ester, (19.alpha.,20.alpha.)-
    • methyl (20alpha)-16,17-didehydro-19alpha-methyl-18-oxayohimban-16-carboxylate
    • NS00082054
    • NSC-72115
    • BRN 0097270
    • BDBM50407156
    • SCHEMBL564502
    • DA-58436
    • CS-0016454
    • Q27108406
    • Oxayohimban-16-carboxylic acid, 16,17-didehydro-19-methyl-, methyl ester, (19alpha,20alpha)-
    • Alstonine, 3,4,5,6-tetrahydro-
    • 4-27-00-07926 (Beilstein Handbook Reference)
    • NSC 72115
    • CHEBI:9479
    • 6474-90-4
    • Alstonine, tetrahydro-

Attributes

  • Canonical SMILES

    C[C@H]1[C@]2([H])CN3CCC4=C(NC5=CC=CC=C45)[C@]3([H])C[C@]2([H])C(C(OC)=O)=CO1

  • InChI

    InChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16-,19-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 54.56
  • #RotBonds: 1
  • MW: 352.43400000000014
  • HBD: 1
  • HBA: 4
  • logP: 3.1788000000000016
  • Chemical Formula: C21H24N2O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. psorocarpa Ghana, Ivory Coast 761091 8134

External Databases


References

  • Alkaloids from Tabernaemontana psorocarpa. Planta Med, 1983 (PMID 17405098).
  • Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry, 2019 (PMID 31302343).

Compound-Protein Relationships


Compound Activities

    • Inhibitory
    • Xanthine oxidase inhibitory

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

    Category Property Name Predicted Value
    Absorption Caco-2 (logPaap) -4.77
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.85
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -2.01
    Distribution Blood-Brain Barrier (Central Nervous System) -2.66
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.77
    Plasma Protein Binding 50.71
    Steady State Volume of Distribution 7.1
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 11.12
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.63
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.48
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.53
    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 Safe
    T. Pyriformis -10.3
    Rat (Acute) 2.85
    Rat (Chronic Oral) 1.84
    Fathead Minnow 4.02
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 413.3
    Hydration Free Energy -5.42
    Log(D) at pH=7.4 3.34
    Log(P) 3.17
    Log S -3.34
    Log(Vapor Pressure) -8.04
    Melting Point 205.17
    pKa Acid 9.98
    pKa Basic 7.59