6-[(1R,2R,3S,5S)-2-[(2Z)-4-carboxy(,3,4-13C3)but-2-en-1-yl]-3,5-dihydroxycyclopentyl]-4-oxohexanoic acid

• ChemBase ID: 176427
• Molecular Formular: C16H24O7
• Molecular Mass: 331.33552451
• Monoisotopic Mass: 331.16226762
• SMILES: [C@@H]1(C/C=[13CH]\[13CH2][13C](=O)O)[C@@H](CCC(=O)CCC(=O)O)[C@H](C[C@@H]1O)O
• Canonical SMILES: O=C(CC[C@H]1[C@@H](O)C[C@@H]([C@@H]1C/C=[13CH]\[13CH2][13C](=O)O)O)CCC(=O)O
• InChI: InChI=1S/C16H24O7/c17-10(6-8-16(22)23)5-7-12-11(13(18)9-14(12)19)3-1-2-4-15(20)21/h1-2,11-14,18-19H,3-9H2,(H,20,21)(H,22,23)/b2-1-/t11-,12-,13+,14+/m1/s1/i2+1,4+1,15+1
• InChIKey: XSGSZQDCVYMZGQ-LKSZDKPASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-[(1R,2R,3S,5S)-2-[(2Z)-4-carboxy(,3,4-^1^3C₃)but-2-en-1-yl]-3,5-dihydroxycyclopentyl]-4-oxohexanoic acid
• IUPAC Traditional name: 6-[(1R,2R,3S,5S)-2-[(2Z)-4-carboxy(,3,4-^1^3C₃)but-2-en-1-yl]-3,5-dihydroxycyclopentyl]-4-oxohexanoic acid
• Synonyms: (1R,2R,3S,5S)-2-[(2Z)-4-Carboxy-2-buten-1-yl]-3,5-dihydroxy-γ-oxocyclopentanehexanoic Acid-13C3; (1R,2R,3S,5S)-2-[(2Z)-4-Carboxy-2-butenyl]-3,5-dihydroxy-γ-oxocyclopentanehexanoic Acid-13C3; PGD-M-13C3

Database IDs

• PubChem SID: 164232337
• PubChem CID: 71751557

CALCULATED PROPERTIES

• Acid pKa: 4.0737042
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.3594608
• LogD (pH = 7.4): -5.861975
• Log P: -0.07394701
• Molar Refractivity: 81.7414 cm^3
• Polarizability: 31.71864 Å^3
• Polar Surface Area: 132.13 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P294082

Labelled PGD-M (P294080). PGD-M is the major urinary metabolite of PGD2 in humans.

REFERENCES

• Morrow, J.D., et al.: Anal. Biochem., 193, 142 (1991)
• Awad, J.A., et al.: J. Biol. Chem., 268, 4161 (1991)