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54397-83-0 molecular structure
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(12S)-12-hydroxyicosa-5,8,10,14-tetraenoic acid

ChemBase ID: 155431
Molecular Formular: C20H32O3
Molecular Mass: 320.46628
Monoisotopic Mass: 320.23514488
SMILES and InChIs

SMILES:
CCCCC/C=C/C[C@@H](/C=C/C=C/C/C=C/CCCC(=O)O)O
Canonical SMILES:
CCCCC/C=C/C[C@@H](/C=C/C=C/C/C=C/CCCC(=O)O)O
InChI:
InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/t19-/m0/s1
InChIKey:
ZNHVWPKMFKADKW-IBGZPJMESA-N

Cite this record

CBID:155431 http://www.chembase.cn/molecule-155431.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(12S)-12-hydroxyicosa-5,8,10,14-tetraenoic acid
IUPAC Traditional name
(12S)-12-hydroxyicosa-5,8,10,14-tetraenoic acid
Synonyms
(S)-12-HETE
12(S)-Hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoic acid
CAS Number
54397-83-0
MDL Number
MFCD00036916
Beilstein Number
2656104
PubChem SID
24895806
162249569
PubChem CID
6442490

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
H7768 external link Add to cart Please log in.
Data Source Data ID
PubChem 6442490 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 4.889631  H Acceptors
H Donor LogD (pH = 5.5) 4.6512523 
LogD (pH = 7.4) 2.8843422  Log P 5.35636 
Molar Refractivity 101.4695 cm3 Polarizability 37.740055 Å3
Polar Surface Area 57.53 Å2 Rotatable Bonds 14 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Flash Point
14 °C expand Show data source
57 °F expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Irritant Irritant (Xi) expand Show data source
UN Number
1170 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
1 expand Show data source
Hazard Class
3 expand Show data source
Packing Group
2 expand Show data source
Risk Statements
11-36/37/38 expand Show data source
Safety Statements
7-16-26-36 expand Show data source
RID/ADR
UN 1170 3/PG 2 expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
≥95% (HPLC) expand Show data source
Concentration
~100 μg/mL in ethanol expand Show data source
Shipped in
dry ice expand Show data source
Empirical Formula (Hill Notation)
C20H32O3 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - H7768 external link
Biochem/physiol Actions
Prometastatic metabolite of arachidonic acid via the 12-lipoxygenase pathway that is expressed in many tumor cell lines. It is produced in coronary microvasculature and is a potent inducer of relaxation and hyperpolarization of these microvessels. It activates large-conductance Ca2+-activated K+ currents in coronary microvascular smooth muscle.
12(S)-HETE is a bioactive lipid implicated in angiogenesis, growth, and metastasic action in tumor cell lines and in animal models. Arachidonate 12-lipoxygenase (12-LOX) converts arachidonic acid to 12(S)-(HETE). Alteration in 12-LOX expression or activity has been reported in various carcinomas including prostate carcinoma.
Packaging
Packaged under Argon.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H7768.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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