(2-{[(2R)-2,3-bis(docosa-4,7,10,13,16,19-hexaenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

• ChemBase ID: 154129
• Molecular Formular: C52H80NO8P
• Molecular Mass: 878.167261
• Monoisotopic Mass: 877.56215516
• SMILES: CC/C=C/C/C=C/C/C=C/C/C=C/C/C=C/C/C=C/CCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CC/C=C/C/C=C/C/C=C/C/C=C/C/C=C/C/C=C/CC
• Canonical SMILES: CC/C=C/C/C=C/C/C=C/C/C=C/C/C=C/C/C=C/CCC(=O)OC[C@@H](OC(=O)CC/C=C/C/C=C/C/C=C/C/C=C/C/C=C/C/C=C/CC)COP(=O)(OCC[N+](C)(C)C)[O-]
• InChI: InChI=1S/C52H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-51(54)58-48-50(49-60-62(56,57)59-47-46-53(3,4)5)61-52(55)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h8-11,14-17,20-23,26-29,32-35,38-41,50H,6-7,12-13,18-19,24-25,30-31,36-37,42-49H2,1-5H3/t50-/m1/s1
• InChIKey: XLKQWAMTMYIQMG-VCZQVZGSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[(2R)-2,3-bis(docosa-4,7,10,13,16,19-hexaenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
• IUPAC Traditional name: (2-{[(2R)-2,3-bis(docosa-4,7,10,13,16,19-hexaenoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
• Synonyms: (7R,13Z,16Z,19Z,22Z,25Z,28Z)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[[(4Z,7Z,10Z,13Z,16Z,19Z)-1-oxo-4,7,10,13,16,19-docosahexaenyl]oxy]-3,5,9-trioxa-4-phosphahentriaconta-13,16,19,22,25,28-hexaen-1-aminium 4-oxide, inner salt; 1,2-Di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine; DHAPC; PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)); PC(22:6/22:6); 1,2-Didocosahexaenoyl-sn-glycero-3-phosphocholine

Database IDs

• CAS Number: 99296-81-8
• MDL Number: MFCD00674317
• PubChem SID: 162248268
• PubChem CID: 23425881

CALCULATED PROPERTIES

• Acid pKa: 1.8550572
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 11.129065
• LogD (pH = 7.4): 11.129161
• Log P: 9.10556
• Molar Refractivity: 284.4763 cm^3
• Polarizability: 101.60532 Å^3
• Polar Surface Area: 111.19 Å^2
• Rotatable Bonds: 40
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥99.0% (TLC)
• Biological Source: from synthetic
• Empirical Formula (Hill Notation): C52H80NO8P

DETAILS

Sigma Aldrich - 78896

General description
Phosphatidylcholine species with highly unsaturated acyl groups in both positions are relatively uncommon, but the didocosahexaenoyl (C22:6) species is unusually abundant in bonito muscle. The action of bonito cytosolic lysophosphatidylcholine transacylase on endogenous lysophosphatidylcholine produces this species as the most abundand product.1