(2S)-5-[(5R,7S,8R,9R)-8,9-dihydroxy-2,4-dioxo-7-[(phosphonooxy)methyl]-6-oxa-1,3-diazaspiro[4.4]nonan-3-yl]-2-[N-hydroxy-N-(hydroxymethyl)amino]pentanoic acid

• ChemBase ID: 2392
• Molecular Formular: C13H22N3O13P
• Molecular Mass: 459.299841
• Monoisotopic Mass: 459.08902441
• SMILES: OCN(O)[C@@H](CCCN1C(=O)N[C@]2(O[C@@H](COP(=O)(O)O)[C@H](O)[C@H]2O)C1=O)C(=O)O
• Canonical SMILES: OCN([C@H](C(=O)O)CCCN1C(=O)N[C@@]2(C1=O)O[C@H]([C@@H]([C@H]2O)O)COP(=O)(O)O)O
• InChI: InChI=1S/C13H22N3O13P/c17-5-16(24)6(10(20)21)2-1-3-15-11(22)13(14-12(15)23)9(19)8(18)7(29-13)4-28-30(25,26)27/h6-9,17-19,24H,1-5H2,(H,14,23)(H,20,21)(H2,25,26,27)/t6-,7-,8-,9+,13+/m0/s1
• InChIKey: MAXSFYCTFIBEAR-MHHWUYOGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5-[(5R,7S,8R,9R)-8,9-dihydroxy-2,4-dioxo-7-[(phosphonooxy)methyl]-6-oxa-1,3-diazaspiro[4.4]nonan-3-yl]-2-[N-hydroxy-N-(hydroxymethyl)amino]pentanoic acid
• IUPAC Traditional name: (2S)-5-[(5R,7S,8R,9R)-8,9-dihydroxy-2,4-dioxo-7-[(phosphonooxy)methyl]-6-oxa-1,3-diazaspiro[4.4]nonan-3-yl]-2-[N-hydroxy-N-(hydroxymethyl)amino]pentanoic acid
• Brand Name: [8,9-DIHYDROXY-3-(4-CARBOXY-HYDROXY-HYDROXYMETHYL-AMINO-BUTYL)-2,4-DIOXO-6-OXA-1,3-DIAZA-SPIRO[4.4]NON-7-YLMETHYL] PHOSPHATE
• Synonyms: (C8-R)-Hydantocidin 5'-Phosphate; [8,9-DIHYDROXY-3-(4-CARBOXY-HYDROXY-HYDROXYMETHYL-AMINO-BUTYL)-2,4-DIOXO-6-OXA-1,3-DIAZA-SPIRO[4.4]NON-7-YLMETHYL] PHOSPHATE; (C8-S)-Hydantocidin 5'-Phosphate

Database IDs

• PubChem SID: 160965843; 46508804; 46506271
• PubChem CID: 46936448

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.2204844
• H Acceptors: 13
• H Donor: 8
• LogD (pH = 5.5): -8.436863
• LogD (pH = 7.4): -12.134033
• Log P: -3.6540425
• Molar Refractivity: 89.7038 cm^3
• Polarizability: 36.66173 Å^3
• Polar Surface Area: 246.86 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.24
• LOG S: -1.66
• Solubility (Water): 1.00e+01 g/l

DETAILS

DrugBank - DB02666

Drug information: experimental

DrugBank - DB04460

Drug information: experimental