Catharantine






Names

    • MFCD01753356
    • Q-100319
    • NSC-823867
    • HMS3712F15
    • UNII-WT0YJV846J
    • Catharantine
    • Methyl (2alpha,5beta,6alpha)-3,4-didehydroibogamine-18beta-carboxylate
    • AC-34053
    • BRD-K92377961-001-03-7', "(6R,6aR,9R,11R)-Methyl 7-ethyl-6,6a,9,10,12,13-hexahydro-5H-6,9-methanopyrido[1',2':1,2]azepino[4,5-b]indole-6-carboxylate", "(6R,6aR,9R,11R)-Methyl7-ethyl-6,6a,9,10,12,13-hexahydro-5H-6,9-methanopyrido[1',2':1,2]azepino[4,5-b]indole-6-carboxylate", 'Ibogamine-18-carboxylic acid, 3,4-didehydro-, methyl ester, (2-alpha,5-beta,6-alpha,18-beta)-
    • BRD-K92377961-001-02-9
    • CHEMBL2163793
    • Catharanthine Base
    • HMS3885K13
    • Ibogamine-18-carboxylic acid, 3,4-didehydro-, methyl ester, (2alpha,5beta,6alpha,18beta)-
    • CHEBI:3469
    • HMS3652A13
    • SW198653-2
    • CCG-220187
    • 2468-21-5
    • EINECS 219-586-6
    • (+)-Catharanthine
    • AKOS024463388
    • BDBM50396009
    • Catharanthine (free base)
    • s3202
    • HMS2095F15
    • (+)-3,4-Didehydrocoronaridine
    • NSC823867
    • Methyl (2-alpha,5-beta,6-alpha,18-beta)-3,4-didehydroibogamine-18-carboxylate
    • Catharanthine, (+)-
    • CATHARANTHINE [MI]
    • NS00018340
    • AB01566866_01
    • WT0YJV846J
    • DTXSID80947621
    • IBOGAMINE-18-CARBOXYLIC ACID, 3,4-DIDEHYDRO-, METHYL ESTER,(2.ALPHA.,5.BETA.,6.ALPHA.,18.BETA.)-
    • 1ST168797
    • Catharanthine, >=95% (HPLC)
    • methyl (1R,15R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate
    • Catharanthin
    • Catharanthine

Attributes

  • Canonical SMILES

    CCC1=C[C@H]2C[C@]3([C@@H]1N(C2)CCC4=C3NC5=CC=CC=C45)C(=O)OC

  • InChI

    InChI=1S/C21H24N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3/t13-,19+,21-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 45.33
  • #RotBonds: 2
  • MW: 336.43500000000006
  • HBD: 1
  • HBA: 3
  • logP: 3.175300000000002
  • Chemical Formula: C21H24N2O2


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. penduliflora Cameroon, 37036/HNC, Nigeria 761088 40,411 HCN

External Databases


References

  • Antiplasmodial activities of indole alkaloids from Tabernaemontana penduliflora K. Schum (Apocynaceae). Fitoterapia, 2021 (PMID 34029654).

Compound-Protein Relationships


Compound Activities

    • 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

    Property Model Name Predicted Value
    Absorption Caco-2 (logPaap) -4.85
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.95
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.96
    Distribution Blood-Brain Barrier (Central Nervous System) -2.15
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.94
    Plasma Protein Binding 59.4
    Steady State Volume of Distribution 5.95
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor 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 Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.66
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.85
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.97
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 6.23
    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 -3.68
    Rat (Acute) 2.8
    Rat (Chronic Oral) 1.91
    Fathead Minnow 4.12
    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 421.88
    Hydration Free Energy -5.81
    Log(D) at pH=7.4 3.3
    Log(P) 3.41
    Log S -3.7
    Log(Vapor Pressure) -8.33
    Melting Point 207.73
    pKa Acid 10.14
    pKa Basic 6.51