CAS 506-32-1|全顺式-5,8,11,14-二十碳四烯酸|Immunocytophyte|arachidonic acid|Arachidonic acid|(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid|二十碳-5Z,8Z,11Z,14Z-四烯酸|花生四烯酸|Arachidonic Acid, ...

General Information

Structure

Molecular Formula

C₂₀H₃₂O₂

Molecular Mass

304.46688

Exact Mass

304.24023026

Charge

0

InChI

InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-

InChIKey

YZXBAPSDXZZRGB-DOFZRALJSA-N

Canonic Smiles

CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O

Isomeric Smiles

CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O

Calculated Properties

JChem

LogD (pH = 7.4)

4.05

LogD (pH = 5.5)

5.83

Log P

6.59

Rotatable Bonds

14

H Donor

1

H Acceptors

2

Lipinski's Rule of Five

false

Acid pKa

4.82

Polar Surface Area

37.30

Polarizability

37.78

Molar Refractivity

99.95

LOG S

-8.05

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Synonyms

Immunocytophyte全顺式-5,8,11,14-二十碳四烯酸Arachidonic acid二十碳-5Z,8Z,11Z,14Z-四烯酸花生四烯酸Arachidonic Acid, >90% Technical Gradecis-5,8,11,14-Eicosatetraenoic Acid(all-Z)-5,8,11,14-Eicosatetraenoic AcidArachidonic Acid, 99% 5,8,11,14-all-cis-Eicosatetraenoicmmunocytophyteall-cis-5,8,11,14-Eicosatetraenoic Acid(5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic Acidarachidonic acidcis-5,8,11,14-Eicosatetraenoic acid(5Z,8Z,11Z,14Z)-5,8,11,14-icosatetraenoic acidAAcis-Delta(5,8,11,14)-eicosatetraenoic acidARAARACHIDONIC ACID(5Z,8Z,11Z,14Z)-Icosatetraenoic acidArachidonateall-cis-5,8,11,14-eicosatetraenoic acidArachidonsaeureArachidonic acidicosa-5,8,11,14-tetraenoic acids5,8,11,14-20:45,8,11,14-eicosatetraenoic acid5,8,11,14-icosatetraenoic acideicosa-5,8,11,14-tetraenoic acid5,8,11,14-icosatetraenoic acidsC20:4, n-6,9,12,15eicosa-5,8,11,14-tetraenoic acids5,8,11,14-eicosatetraenoic acidsicosa-5,8,11,14-tetraenoic acid

IUPAC Traditional name

arachidonic acid 5,8,11,14-icosatetraenoic acid

IUPAC name

(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid icosa-5,8,11,14-tetraenoic acid

Names and Identifiers

Registration numbers

PubChem SID

248907332489078424891487162227241814510914718149

Beilstein Number

MDL Number

EC Number

CAS Number

PubChem CID

SABIO-RK Database

158421745141779885103256601792915844775517471134077021493117403408240817421744

KNApSAcK Database

C00000388

Protein Data Bank

2lbv3krk1cvu5j5l6oii5ecf4qwt3v991diy1u671vyg6mcz6lx95csd6nbn3hs55fb76ofy1gnj1adl6md24de63tzi3olt4zga3fg44b0n

UniProt Database

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

Patent number

EP1410822EP1714564EP1905446WO2006036131EP1020179US2007202206US2008090803US2008153142US2006039962US2007184135WO2005095378US2003199581US2007184006EP1629850EP1731602US2008166781US2007237848EP1707198EP1785492US2007244192EP1604675US2004162437EP0947523US2007259051US2003143659US2006160891US2008076164WO2007130882US2003092762WO2008125616WO2006110804EP1911837EP1974728US2007202194US2008153899US2005075362EP0976748WO2007135518EP1726217US2005130881US2007248650EP1803451US2003065023US2004049062US2007270493EP0839806EP1656839EP1792977US2002102340EP1156050US2007185201EP1774973EP1679068US2007254954US2008293728EP1435353EP1666092EP1970438EP1642983US2001023259US2007281993WO2006092623EP0950661EP0950657EP1557427WO2007128344US2006099693EP1797869US2001025114US2004158087US2008269329EP1886660US2002045606US2007238695US2007249520US2007265341US2008139649WO2007124465EP1506996WO2007103368US2007190001US2007191274US2003118715US2004170658WO2007089745US2004131648US2007232579WO2008144399EP1277743EP1801226US2008194684WO2007103201EP1676488US2007197606US2004110844US2006025385EP1634599EP1985307US2008176956WO2007094000

BKMS React Database

99975516180195914895725789864732906194541542609

CHEBI ID

CHEBI:22608CHEBI:15843CHEBI:40501CHEBI:2799CHEBI:36306

HMDB Database

HMDB0001043

SureChEMBL Database

SCHEMBL16162SCHEMBL16163

PDBeChem Database

ACD

CHEMBL

CHEMBL15594

Gmelin ID

58972

EnzymePortal Database

Q84XU2Q84K11Q7YSW8

Wikipedia Title

Arachidonic_acid

BioModels Database

BIOMD0000000436BIOMD0000000490

PubMed Citation Links

151293021897399728200552558401218931599

BRENDA Ligand Database

99974541595724260957898551691481801952906196473

KEGG ID

C00219

IntAct Database

EBI-6662101EBI-6662204EBI-6662198EBI-6662089EBI-6662107EBI-6662212

BindingDB Database

22319

Golm Database

cb4ad1f3-1626-4d0e-8ab3-43c0fb8a70581cb66c44-2153-4160-821c-2ff7eb00644e858a89fe-1485-4982-914a-06059e6f901a80995bdc-fdf6-40a9-b7ad-6e53d0fd4948

CompTox Database

DTXSID4040420

LIPID MAPS Instance

LMFA01030001

ACToR Database

93444-49-6506-32-17771-44-0

Reaxys Registry

1913991

MetaCyc Database

ARACHIDONIC_ACID

DrugBank ID

DB04557

ArrayExpress (Gene Expression Altlas)

E-GEOD-3737

LINCS Database

LSM-6527

Registration numbers

Properties

Safety Information

German water hazard class

3

RTECS

CE6675000

Supplemental Hazard Statements

May form explosive peroxides.

Storage Temperature

-20°C

Risk Statements

19

Eyeshields, Faceshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

-86°C Freezer

Download link

Product Information

Suitability

suitable for cell culture

Purity

≥99% (GC)

≥85% (capillary GC)

Shipped in

dry ice

Biological Source

from porcine liver

Certificate of Analysis

Download link

Properties

Related Proteins

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Sigma Aldrich

A3555

包装
Sealed ampule.
Biochem/physiol Actions
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .
花生四烯酸 (AA) 是一种 ω6 不饱和脂肪酸，是细胞膜磷脂的组分。在炎症反应中，水解磷脂酶 A2 可将 AA 从膜磷脂中释放出来。然后，AA 可被至少两种环加氧酶 (COX) 亚型代谢为前列腺素和血栓烷，被脂氧合酶代谢为白三烯和脂氧素，以及通过细胞色素 p450 催化代谢为环氧-二十碳三烯酸。AA 及其代谢产物在多种生物过程中发挥着重要作用，包括信号转导、平滑肌收缩、趋化性、细胞增殖和分化，以及细胞凋亡。已证实 AA 可与 G 蛋白的亚基结合，抑制 Ras GTP 酶激活蛋白 (GAP) 的活性。AA 的细胞摄取需要消耗能量并涉及跨细胞质膜的蛋白质辅助运输。

A9673

包装
1 g in ampule
10, 50, 100, 500 mg in ampule
Sealed ampule
Biochem/physiol Actions
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .
花生四烯酸 (AA) 是一种 ω6 不饱和脂肪酸，是细胞膜磷脂的组分。在炎症反应中，水解磷脂酶 A2 可将 AA 从膜磷脂中释放出来。然后，AA 可被至少两种环加氧酶 (COX) 亚型代谢为前列腺素和血栓烷，被脂氧合酶代谢为白三烯和脂氧素，以及通过细胞色素 p450 催化代谢为环氧-二十碳三烯酸。AA 及其代谢产物在多种生物过程中发挥着重要作用，包括信号转导、平滑肌收缩、趋化性、细胞增殖和分化，以及细胞凋亡。已证实 AA 可与 G 蛋白的亚基结合，抑制 Ras GTP 酶激活蛋白 (GAP) 的活性。AA 的细胞摄取需要消耗能量并涉及跨细胞质膜的蛋白质辅助运输。

A3925

Biochem/physiol Actions
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .
花生四烯酸 (AA) 是一种 ω6 不饱和脂肪酸，是细胞膜磷脂的组分。在炎症反应中，水解磷脂酶 A2 可将 AA 从膜磷脂中释放出来。然后，AA 可被至少两种环加氧酶 (COX) 亚型代谢为前列腺素和血栓烷，被脂氧合酶代谢为白三烯和脂氧素，以及通过细胞色素 p450 催化代谢为环氧-二十碳三烯酸。AA 及其代谢产物在多种生物过程中发挥着重要作用，包括信号转导、平滑肌收缩、趋化性、细胞增殖和分化，以及细胞凋亡。已证实 AA 可与 G 蛋白的亚基结合，抑制 Ras GTP 酶激活蛋白 (GAP) 的活性。AA 的细胞摄取需要消耗能量并涉及跨细胞质膜的蛋白质辅助运输。

TRC

A765000

Arachidonic Acid is an essential fatty acid and a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. Arachidonic Acid occurs in liver, brain, glandular organs, and depot fats of animals, in small amounts in human depot fats,

A765001

Arachidonic Acid is an essential fatty acid and a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. Arachidonic Acid occurs in liver, brain, glandular organs, and depot fats of animals, in small amounts in human depot fats,

ChEBI

CHEBI:15843

A long-chain fatty acid that is a C20, polyunsaturated fatty acid having four (Z)-double bonds at positions 5, 8, 11 and 14.

CHEBI:36306

Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.

Molecule Details

References

PubChem Literature

From Data Sources

• Kurosawa, T., et al.: J. Cell. Physiol., 219, 606 (2009)

• Mazalli, M., et al.: J. Agric. Food Chem., 57, 5028 (2009)

• Kurosawa, T., et al.: J. Cell. Physiol., 219, 606 (2009)