(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(8S)-8-(2-propanamidoethyl)-1H,2H,6H,7H,8H-indeno[5,4-b]furan-4-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 171261
• Molecular Formular: C22H29NO9
• Molecular Mass: 451.46696
• Monoisotopic Mass: 451.18423151
• SMILES: [C@@H]1([C@@H](O[C@@H]([C@H]([C@H]1O)O)C(=O)O)Oc1c2c(c3c(c1)CC[C@H]3CCNC(=O)CC)CCO2)O
• Canonical SMILES: CCC(=O)NCC[C@@H]1CCc2c1c1CCOc1c(c2)O[C@@H]1O[C@H](C(=O)O)[C@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C22H29NO9/c1-2-14(24)23-7-5-10-3-4-11-9-13(19-12(15(10)11)6-8-30-19)31-22-18(27)16(25)17(26)20(32-22)21(28)29/h9-10,16-18,20,22,25-27H,2-8H2,1H3,(H,23,24)(H,28,29)/t10-,16-,17-,18+,20-,22+/m0/s1
• InChIKey: JZXYMHQWDSDNPN-JKQJZOLFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(8S)-8-(2-propanamidoethyl)-1H,2H,6H,7H,8H-indeno[5,4-b]furan-4-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(8S)-8-(2-propanamidoethyl)-1H,2H,6H,7H,8H-indeno[5,4-b]furan-4-yl]oxy}oxane-2-carboxylic acid
• Synonyms: 4-Hydroxy Ramelteon β-D-Glucuronide

Database IDs

• PubChem SID: 164227171
• PubChem CID: 71749323

CALCULATED PROPERTIES

• Acid pKa: 3.1652381
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -1.9907889
• LogD (pH = 7.4): -3.1321857
• Log P: 0.31919953
• Molar Refractivity: 109.5112 cm^3
• Polarizability: 43.283993 Å^3
• Polar Surface Area: 154.78 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H953290

A metabolite of Ramelteon (R110051)