5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]-N'-[(13S)-13-hydroxyoctadeca-9,11-dienoyl]pentanehydrazide

• ChemBase ID: 155590
• Molecular Formular: C28H48N4O4S
• Molecular Mass: 536.77012
• Monoisotopic Mass: 536.33962704
• SMILES: CCCCC[C@@H](/C=C/C=C/CCCCCCCC(=O)NNC(=O)CCCC[C@H]1[C@@H]2[C@H](CS1)NC(=O)N2)O
• Canonical SMILES: CCCCC[C@@H](/C=C/C=C/CCCCCCCC(=O)NNC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2)O
• InChI: InChI=1S/C28H48N4O4S/c1-2-3-11-16-22(33)17-12-9-7-5-4-6-8-10-13-19-25(34)31-32-26(35)20-15-14-18-24-27-23(21-37-24)29-28(36)30-27/h7,9,12,17,22-24,27,33H,2-6,8,10-11,13-16,18-21H2,1H3,(H,31,34)(H,32,35)(H2,29,30,36)/t22-,23-,24-,27-/m0/s1
• InChIKey: VGSREJALHGALEV-TTZMFTMZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]-N'-[(13S)-13-hydroxyoctadeca-9,11-dienoyl]pentanehydrazide
• IUPAC Traditional name: 5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]-N'-[(13S)-13-hydroxyoctadeca-9,11-dienoyl]pentanehydrazide
• Synonyms: 13(S)-HODE-biotin; 13S-Hydroxy-9Z,11E-octadecadiene-(2-biotinyl)hydrazide

Database IDs

• MDL Number: MFCD02259354
• PubChem SID: 162249728
• PubChem CID: 35025234

CALCULATED PROPERTIES

• Acid pKa: 10.706621
• H Acceptors: 4
• H Donor: 5
• LogD (pH = 5.5): 4.3374405
• LogD (pH = 7.4): 4.337253
• Log P: 4.337443
• Molar Refractivity: 152.1296 cm^3
• Polarizability: 58.81236 Å^3
• Polar Surface Area: 119.56 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: ethanol solution

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1170
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-36/37/38
• Safety Statements: 7-16-26-36
• RID/ADR: UN 1170 3/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%
• Impurities: biotin, may contain traces
• Shipped in: wet ice
• abs.: εmax/234 nm 30,000
• Empirical Formula (Hill Notation): C28H28N4O4S

DETAILS

Sigma Aldrich - H6910

Application
May be used as a probe to detect binding proteins and/or receptors for 13(S)-HODE.
Biochem/physiol Actions
Modulates the platelet-activating factor, leukotriene B4, and formyl-Met-Leu-Phe-induced calcium influx in human polymorphonuclear leukocytes.
Other Notes
13(S)-HODE is the lipoxygenase metabolite of linoleic acid.