methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate

• ChemBase ID: 130407
• Molecular Formular: C21H26N2O3
• Molecular Mass: 354.44274
• Monoisotopic Mass: 354.1943427
• SMILES: O=C(OC)[C@]1(O)n2c3c(c4ccccc24)CCN2CCC[C@](C1)(CC)[C@@H]32
• Canonical SMILES: COC(=O)[C@@]1(O)C[C@]2(CC)CCCN3[C@@H]2c2n1c1ccccc1c2CC3
• InChI: InChI=1S/C21H26N2O3/c1-3-20-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(17(15)18(20)22)21(25,13-20)19(24)26-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3/t18-,20+,21+/m1/s1
• InChIKey: RXPRRQLKFXBCSJ-GIVPXCGWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.0^2,^7.0^8,^1^8.0^1^5,^1^9]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
• IUPAC Traditional name: minorin; methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.0^2,^7.0^8,^1^8.0^1^5,^1^9]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
• Synonyms: Vincamine; Vincamine; Vincamarine; Minorine; Pervincamine; Vincafor; 长春胺

Database IDs

• CAS Number: 1617-90-9
• EC Number: 216-576-3
• MDL Number: MFCD00078054
• PubChem SID: 162224686; 24851332
• PubChem CID: 15376
• ATC CODE: C04AX07
• Chemspider ID: 14635
• IUPHAR ligand ID: 349
• KEGG ID: D08677
• Unique Ingredient Identifier: 996XVD0JHT
• Wikipedia Title: Vincamine

CALCULATED PROPERTIES

• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 10.52077
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.896797
• LogD (pH = 7.4): 3.249398
• Log P: 3.3907504
• Molar Refractivity: 99.5741 cm^3
• Polarizability: 40.111816 Å^3
• Polar Surface Area: 54.7 Å^2

PROPERTIES

Physical Property

• Melting Point: 232 °C (dec.)(lit.)
• Optical Rotation: [α]23/D +42.8°, c = 1 in pyridine

Safety Information

• RTECS: YY8575000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Mechanism of Action: Potent blockers of voltage-gated Na[+] channels

Product Information

• Purity: 98%
• Biological Source: Alkaloid from Tabernaemontana rigida (Apocynaceae)
• Application(s): Hypotensive; Vasodilator increasing blood flow to the brain
• Empirical Formula (Hill Notation): C21H26N2O3

DETAILS

Sigma Aldrich - 194719

Packaging
1 g in glass bottle
250 mg in glass bottle

REFERENCES

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