1-(2-{4-[(3S,4S)-7-methoxy-2,2-bis(2H3)methyl-3-phenyl-3,4-dihydro-2H-1-benzopyran-4-yl]phenoxy}ethyl)pyrrolidine

• ChemBase ID: 163971
• Molecular Formular: C30H35NO3
• Molecular Mass: 457.6038
• Monoisotopic Mass: 457.26169399
• SMILES: c1(ccc2c(c1)OC([C@@H]([C@H]2c1ccc(cc1)OCCN1CCCC1)c1ccccc1)(C)C)OC
• Canonical SMILES: COc1ccc2c(c1)OC([C@@H]([C@H]2c1ccc(cc1)OCCN1CCCC1)c1ccccc1)(C)C
• InChI: InChI=1S/C30H35NO3/c1-30(2)29(23-9-5-4-6-10-23)28(26-16-15-25(32-3)21-27(26)34-30)22-11-13-24(14-12-22)33-20-19-31-17-7-8-18-31/h4-6,9-16,21,28-29H,7-8,17-20H2,1-3H3/t28-,29+/m0/s1
• InChIKey: XZEUAXYWNKYKPL-URLMMPGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2-{4-[(3S,4S)-7-methoxy-2,2-bis(^2H₃)methyl-3-phenyl-3,4-dihydro-2H-1-benzopyran-4-yl]phenoxy}ethyl)pyrrolidine
• IUPAC Traditional name: 1-(2-{4-[(3S,4S)-7-methoxy-2,2-bis(^2H₃)methyl-3-phenyl-3,4-dihydro-1-benzopyran-4-yl]phenoxy}ethyl)pyrrolidine
• Synonyms: rel-1-[2-[4-[(3R,4R)-3,4-Dihydro-7-methoxy-2,2-(dimethyl-d6)-3-phenyl-2H-1-benzopyran-4-yl]phenoxy]ethyl]pyrrolidine; 1-[2-[p-(trans-7-Methoxy-2,2-(dimethyl-d6)-3-phenyl-4-chromanyl)phenoxy]ethyl]pyrrolidine; 3,4-trans-2,2-(Dimethyl-d6)-3-phenyl-4-[p-(β-pyrrolidinoethoxy)phenyl]-7-methoxychroman; 67/20; trans-Centchroman; Ormeloxifene; Centchroman-d6

Database IDs

• PubChem SID: 162258106
• PubChem CID: 71314638

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.8261492
• LogD (pH = 7.4): 4.420659
• Log P: 6.0258827
• Molar Refractivity: 137.1855 cm^3
• Polarizability: 53.586983 Å^3
• Polar Surface Area: 30.93 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C256602

Labelled Centchroman (C256600). Centchroman is an estrogen antagonist. Centchroman is a synthetic nonsteroidal postcoital antifertility agent.

REFERENCES

• Saeed, A., et al.: J. Med. Chem., 33, 3210 (1990)
• Richard, J., et al.: Drug Metab. Dispos., 28, 503 (1990)
• Delmas, P., et al.: Lancet, 359, 2018 (1990)
• Makker, A., et al.: Fertil Steril, 91, 2298 (1990)