2,3-dihydroxybutanedioic acid methyl (1R,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

• ChemBase ID: 163857
• Molecular Formular: C25H30N2O8
• Molecular Mass: 486.5143
• Monoisotopic Mass: 486.20021593
• SMILES: C(C(O)C(=O)O)(O)C(=O)O.[C@]12([C@H]3C(=CC(C1)CN3CCc1c2[nH]c2c1cccc2)CC)C(=O)OC
• Canonical SMILES: OC(=O)C(C(C(=O)O)O)O.CCC1=CC2CN3[C@H]1[C@@](C2)(C(=O)OC)c1[nH]c2c(c1CC3)cccc2
• InChI: InChI=1S/C21H24N2O2.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/h4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10)/t13?,19-,21+;/m1./s1
• InChIKey: JYBKPXVXYJDIFX-SADKPMMYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dihydroxybutanedioic acid methyl (1R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.0^2,^1^0.0^4,^9.0^1^3,^1^8]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate
• IUPAC Traditional name: (.+-.)-tartaric acid methyl (1R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.0^2,^1^0.0^4,^9.0^1^3,^1^8]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate
• Synonyms: (2α,5β,6α,18β)-3,4-Didehydro-ibogamine-18-carboxylic Acid Methyl Ester Tartrate; (+)-3,4-Didehydrocoronaridine Tartrate; (+)-Catharanthine Tartrate; Catharanthin Tartrate; Catharanthine Tartrate

Database IDs

• CAS Number: 4168-17-6
• PubChem SID: 162257992
• PubChem CID: 46780196

CALCULATED PROPERTIES

• Acid pKa: 16.37115
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.2133898
• LogD (pH = 7.4): 2.8449984
• Log P: 3.191243
• Molar Refractivity: 98.7115 cm^3
• Polarizability: 39.27758 Å^3
• Polar Surface Area: 45.33 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Beige Solid
• Melting Point: 145-147°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C225400

Precursor of Vinblastine-type alkaloids.

REFERENCES

• Thomas, J., et al.: Plant TPhysiol., 109, 717 (1995)
• Contin, A., et al.: Plant Sci., 147, 177 (1995)
• Yalamanchili, R., et al.: J. Biol. Chem., 277, 28424 (1995)