(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-trien-5-yl N,N-bis(2-chloroethyl)carbamate

• ChemBase ID: 127308
• Molecular Formular: C23H31Cl2NO3
• Molecular Mass: 440.40314
• Monoisotopic Mass: 439.16809922
• SMILES: ClCCN(C(=O)Oc1cc2c(cc1)[C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CCCl
• Canonical SMILES: ClCCN(C(=O)Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C)CCCl
• InChI: InChI=1S/C23H31Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-21,27H,2,4,6-13H2,1H3/t18-,19-,20+,21+,23+/m1/s1
• InChIKey: FRPJXPJMRWBBIH-RBRWEJTLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-trien-5-yl N,N-bis(2-chloroethyl)carbamate
• IUPAC Traditional name: estramustine
• Brand Name: Emcyt
• Synonyms: Estramustine

Database IDs

• CAS Number: 2998-57-4
• PubChem SID: 162221629
• PubChem CID: 259331
• CHEBI ID: 4868
• ATC CODE: L01XX11
• CHEMBL: 1575
• Chemspider ID: 227635
• DrugBank ID: DB01196
• KEGG ID: D04066
• Unique Ingredient Identifier: 35LT29625A
• Wikipedia Title: Estramustine
• Medline Plus: a608046

CALCULATED PROPERTIES

• LogD (pH = 5.5): 5.099114
• LogD (pH = 7.4): 5.099114
• Log P: 5.099114
• Molar Refractivity: 116.2129 cm^3
• Polarizability: 45.46336 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false
• Acid pKa: 19.377693
• H Acceptors: 2
• H Donor: 1

PROPERTIES

Pharmacology Properties

• Half Life: 20 hours
• Legal Status: Rx-only
• Pregnancy Category: X (US)