{[(2S,5R)-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy}phosphonic acid

• ChemBase ID: 4227
• Molecular Formular: C10H13N2O7P
• Molecular Mass: 304.193181
• Monoisotopic Mass: 304.0460374
• SMILES: OP(=O)(O)OC[C@H]1O[C@H](C=C1)n1cc(C)c(=O)[nH]c1=O
• Canonical SMILES: O=c1[nH]c(=O)n(cc1C)[C@H]1C=C[C@H](O1)COP(=O)(O)O
• InChI: InChI=1S/C10H13N2O7P/c1-6-4-12(10(14)11-9(6)13)8-3-2-7(19-8)5-18-20(15,16)17/h2-4,7-8H,5H2,1H3,(H,11,13,14)(H2,15,16,17)/t7-,8+/m0/s1
• InChIKey: XLPGURCDSRIXFL-JGVFFNPUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,5R)-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: cTMP
• Synonyms: 2',3'-dehydro-2',3'-deoxy-thymidine 5'-monophosphate; 2',3'-dideoxy-2',3-didehydrothymidine 5'-monophosphate; Cyclic tmp; cTMP; d4TMP; 3',5'-Cyclic dtmp; D4T-MP; Cyclic 3',5'-thymidine monophosphate; cyclic 3',5'-thymidine monophosphate

Database IDs

• PubChem SID: 46508608; 160967659
• PubChem CID: 461278

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.2405522
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -2.7944655
• LogD (pH = 7.4): -3.872989
• Log P: -0.35537213
• Molar Refractivity: 66.1892 cm^3
• Polarizability: 25.591352 Å^3
• Polar Surface Area: 125.4 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.98
• LOG S: -1.82
• Solubility (Water): 4.64e+00 g/l

DETAILS

DrugBank - DB04672

Drug information: experimental