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15 (R) -Lipoxin A4

CAT: 0931-T37265-01Size: 25 µgDry Ice: NoHazardous: No
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CAT#:0931-T37265-01Size:25 µg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
171030-11-8
Target
STAT, Others
Related Pathways
Stem Cells, Others, JAK/STAT signaling
Bioactivity
Lipid-derived lipoxins are produced at the site of vascular and mucosal inflammation where they down-regulate polymorphonuclear leukocyte recruitment and function. 15 (R) -Lipoxin A4 (15 (R) -LXA4) is derived from the aspirin-triggered formation of 15 (R) -HETE from arachidonic acid. [1] [2] 15 (R) -LXA4 inhibits LTB4-induced chemotaxis, adherence, and transmigration of neutrophils with twice the potency of LXA4 demonstrating activity in the nM range.[2] [3] The anti-inflammatory effects of aspirin may be ascribed in part to the ability of 15 (R) -LXA4 to regulate leukocyte function.[4] 15 (R) -LXA4 is reported to promote resolution of inflammation in LPS-treated stromal cells derived from intermediate-stage diseased supraspinatus tendons as evidenced by increased expression of the STAT-6 pathway target genes, ALOX15 and CD206.[5]
Smiles
[C@H]([C@H](CCCC(O)=O)O)(/C=C/C=C/C=C\C=C\[C@@H](CCCCC)O)O
Molecular Formula
C20H32O5
Molecular Weight
352.47
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

15-epi-Lipoxin A4

15-epi-lipoxin A4 is a C20 hydroxy polyunsaturated fatty acid having (5S)-, (6R)- and (15R)-hydroxy groups as well as (7E)- (9E)-, (11Z)- and (13E)-double bonds. It has a role as a metabolite. It is a hydroxy polyunsaturated fatty acid, a long-chain fatty acid and a lipoxin.

CAS Number171030-11-8
PubChem CID9841438
IUPAC Name(5S,6R,7E,9E,11Z,13E,15R)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid
Molecular FormulaC20H32O5
Molecular Weight352.5
XLogP3.1
Topological Polar Surface Area98
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count14
Heavy Atom Count25
Formal Charge0
Complexity451
SMILES
CCCCC[C@H](/C=C/C=C\C=C\C=C\[C@H]([C@H](CCCC(=O)O)O)O)O
InChI
InChI=1S/C20H32O5/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18(22)19(23)15-11-16-20(24)25/h4-7,9-10,13-14,17-19,21-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t17-,18-,19+/m1/s1
InChIKey
IXAQOQZEOGMIQS-JEWNPAEBSA-N
Chemical Structure
2D Structure
2D structure of 15-epi-Lipoxin A4
CAS: 171030-11-8
CID: 9841438
Formula: C20H32O5
MW: 352.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight352.5
XLogP33.1
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count14
Exact Mass352.22497412
Monoisotopic Mass352.22497412
Topological Polar Surface Area98 Ų
Heavy Atom Count25
Formal Charge0
Complexity451
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count4
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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