(3S,4R,5S)-5-[(1R)-1-carboxy-1-(phosphonooxy)ethoxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid

• ChemBase ID: 2818
• Molecular Formular: C10H16O14P2
• Molecular Mass: 422.173162
• Monoisotopic Mass: 422.00152845
• SMILES: C[C@@](O[C@H]1CC(=C[C@H](OP(=O)(O)O)[C@@H]1O)C(=O)O)(OP(=O)(O)O)C(=O)O
• Canonical SMILES: O[C@H]1[C@H](C=C(C[C@@H]1O[C@@](C(=O)O)(OP(=O)(O)O)C)C(=O)O)OP(=O)(O)O
• InChI: InChI=1S/C10H16O14P2/c1-10(9(14)15,24-26(19,20)21)22-5-2-4(8(12)13)3-6(7(5)11)23-25(16,17)18/h3,5-7,11H,2H2,1H3,(H,12,13)(H,14,15)(H2,16,17,18)(H2,19,20,21)/t5-,6-,7+,10+/m0/s1
• InChIKey: QUQKBSPZUVNKIF-CLIVKXMMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R,5S)-5-[(1R)-1-carboxy-1-(phosphonooxy)ethoxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid
• IUPAC Traditional name: (3S,4R,5S)-5-[(1R)-1-carboxy-1-(phosphonooxy)ethoxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid
• Synonyms: 5-(1-Carboxy-1-Phosphonooxy-Ethoxyl)-Shikimate-3-Phosphate

Database IDs

• PubChem SID: 46505941; 160966266
• PubChem CID: 46936579

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.7216174
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -10.410415
• LogD (pH = 7.4): -15.222936
• Log P: -1.5778791
• Molar Refractivity: 77.7438 cm^3
• Polarizability: 31.424503 Å^3
• Polar Surface Area: 237.58 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.32
• LOG S: -1.73
• Solubility (Water): 7.87e+00 g/l

DETAILS

DrugBank - DB03116

Drug information: experimental