(10S)-10-amino-5-hydroxy-3,4-dimethoxy-14-(methylsulfanyl)tricyclo[9.5.0.02,7]hexadeca-1(16),2(7),3,5,11,14-hexaen-13-one

• ChemBase ID: 166050
• Molecular Formular: C19H21NO4S
• Molecular Mass: 359.43934
• Monoisotopic Mass: 359.11912916
• SMILES: c1(=O)cc2c(ccc1SC)c1c(CC[C@@H]2N)cc(c(c1OC)OC)O
• Canonical SMILES: COc1c2c(CC[C@@H](c3c2ccc(c(=O)c3)SC)N)cc(c1OC)O
• InChI: InChI=1S/C19H21NO4S/c1-23-18-15(22)8-10-4-6-13(20)12-9-14(21)16(25-3)7-5-11(12)17(10)19(18)24-2/h5,7-9,13,22H,4,6,20H2,1-3H3/t13-/m0/s1
• InChIKey: YSTRXCPUTQBTQG-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S)-10-amino-5-hydroxy-3,4-dimethoxy-14-(methylsulfanyl)tricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-13-one
• IUPAC Traditional name: (10S)-10-amino-5-hydroxy-3,4-dimethoxy-14-(methylsulfanyl)tricyclo[9.5.0.0^2,^7]hexadeca-1(16),2(7),3,5,11,14-hexaen-13-one
• Synonyms: (7S)-7-Amino-6,7-dihydro-3-hydroxy-1,2-dimethoxy-10-(methylthio)-benzo[a]heptalen-9(5H)-one; N-Desacetyl 3-Demethyl Thiocolchicine

Database IDs

• CAS Number: 97043-09-9
• PubChem SID: 162260183
• PubChem CID: 44368973

CALCULATED PROPERTIES

• Acid pKa: 9.335147
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.6942645
• LogD (pH = 7.4): 0.30792952
• Log P: 1.9299705
• Molar Refractivity: 103.4763 cm^3
• Polarizability: 38.721146 Å^3
• Polar Surface Area: 81.78 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - D288420

Thiocolchicine derivative.

REFERENCES

• Muzaffar, A., et al.: J. Med. Chem., 33, 567 (1990)
• Bartusik, D., et al.: Bioorg. Chem., 38, 1 (1990)