(9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid

• ChemBase ID: 4580
• Molecular Formular: C18H32O3
• Molecular Mass: 296.44488
• Monoisotopic Mass: 296.23514488
• SMILES: OC(=O)CCCCCCC/C=C\C=C\[C@@H](O)CCCCC
• Canonical SMILES: CCCCC[C@@H](/C=C/C=C\CCCCCCCC(=O)O)O
• InChI: InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+/t17-/m0/s1
• InChIKey: HNICUWMFWZBIFP-IRQZEAMPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid
• IUPAC Traditional name: 13-hode; 13-hydroxyoctadecadienoic acid
• Synonyms: (9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid; 13(S)-HODE; 13(S)-Hydroxyoctadeca-9Z,11E-dienoic acid

Database IDs

• CAS Number: 29623-28-7
• EC Number: 200-578-6
• MDL Number: MFCD00065833
• PubChem SID: 99443397; 24895844; 160968012
• PubChem CID: 6443013

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.9881673
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.5631323
• LogD (pH = 7.4): 2.809476
• Log P: 5.191066
• Molar Refractivity: 90.0343 cm^3
• Polarizability: 34.529655 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.88
• LOG S: -5.0
• Solubility (Water): 2.98e-03 g/l

PROPERTIES

Safety Information

• European Hazard Symbols: Flammable (F)
• UN Number: 1170
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11
• Safety Statements: 7-16
• GHS Pictograms: GHS02
• GHS Signal Word: Danger
• GHS Hazard statements: H225
• GHS Precautionary statements: P210
• RID/ADR: UN 1170 3/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%
• Concentration: 90-100 μg/mL in ethanol

DETAILS

DrugBank - DB06926

Drug information: experimental

Sigma Aldrich - H9146

Biochem/physiol Actions
PPARγ agonist
Expression of 15-lipoxygenase-1 (15-LOX-1) and its main product, 13(S)-HODE, are decreased in human colorectal and esophageal cancers. Certain non-steroidal anti-inflammatory drugs (NSAIDs) can induce apoptosis in human colon cancer cells by increased expression of 15-LOX-1, which down-regulates PPAR-delta through 13-HODE.
包装
Packaged under Argon.