leukotriene A(4) (CHEBI:15651)

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CHEBI:15651 - leukotriene A₄

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ChEBI Name	leukotriene A₄

ChEBI ID	CHEBI:15651

ChEBI ASCII Name	leukotriene A4

Definition	A leukotriene that is the (5S,6S)-epoxy derivative of (7E,9E,11Z,14Z)-icosa-7,9,11,14-tetraenoic acid.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:6420, CHEBI:14503, CHEBI:25023, CHEBI:10937

Supplier Information	ZINC000004632133

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

DJ3 - Ideal conformer

Mrv1927 06102110363D

starting HoverWatcher_5

Time for openFile(DJ3 - Ideal conformer

Mrv1927 06102110363D

53 53 0 0 0 0 999 V2000

-7.9010 1.7040 -1.4950 O 0 0 0 0 0 0 0 0 0 0 0 0

-7.6380 2.3550 -0.5120 C 0 0 0 0 0 0 0 0 0 0 0 0

-8.3050 3.4920 -0.2620 O 0 0 0 0 0 0 0 0 0 0 0 0

-6.5660 1.8850 0.4380 C 0 0 1 0 0 0 0 0 0 0 0 0

-5.9730 0.5700 -0.0720 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.8850 0.0940 0.8910 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.2920 -1.2210 0.3820 C 0 0 2 0 0 0 0 0 0 0 0 0

-4.4120 -2.3740 1.2170 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.1020 -1.8090 1.1430 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.0600 -2.5550 0.3490 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.7950 -2.1330 0.3480 C 0 0 0 0 0 0 0 0 0 0 0 0

0.2170 -2.8580 -0.4230 C 0 0 0 0 0 0 0 0 0 0 0 0

1.4970 -2.4320 -0.4240 C 0 0 0 0 0 0 0 0 0 0 0 0

2.5100 -3.1560 -1.1950 C 0 0 0 0 0 0 0 0 0 0 0 0

3.7550 -2.6850 -1.2680 C 0 0 0 0 0 0 0 0 0 0 0 0

4.1600 -1.4940 -0.4390 C 0 0 1 0 0 0 0 0 0 0 0 0

5.3710 -1.8450 0.3870 C 0 0 0 0 0 0 0 0 0 0 0 0

6.4330 -1.0790 0.3500 C 0 0 0 0 0 0 0 0 0 0 0 0

6.3920 0.2310 -0.3920 C 0 0 1 0 0 0 0 0 0 0 0 0

6.8440 1.3590 0.5390 C 0 0 1 0 0 0 0 0 0 0 0 0

6.8010 2.6900 -0.2150 C 0 0 1 0 0 0 0 0 0 0 0 0

7.2530 3.8170 0.7160 C 0 0 1 0 0 0 0 0 0 0 0 0

7.2110 5.1480 -0.0370 C 0 0 0 0 0 0 0 0 0 0 0 0

-8.9870 3.7500 -0.8970 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.7810 2.6380 0.4990 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.9990 1.7300 1.4260 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.7590 -0.1830 -0.1340 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.5410 0.7260 -1.0610 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.0990 0.8470 0.9530 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.3170 -0.0620 1.8800 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.3280 -1.3690 -0.6980 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7340 -1.2630 2.0110 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.3380 -3.4300 -0.2190 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5170 -1.2580 0.9160 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0600 -3.7330 -0.9910 H 0 0 0 0 0 0 0 0 0 0 0 0

1.7750 -1.5560 0.1440 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2480 -4.0720 -1.7050 H 0 0 0 0 0 0 0 0 0 0 0 0

4.4730 -3.1580 -1.9220 H 0 0 0 0 0 0 0 0 0 0 0 0

4.3980 -0.6580 -1.0960 H 0 0 0 0 0 0 0 0 0 0 0 0

3.3390 -1.2150 0.2210 H 0 0 0 0 0 0 0 0 0 0 0 0

5.3630 -2.7280 1.0090 H 0 0 0 0 0 0 0 0 0 0 0 0

7.3390 -1.3880 0.8520 H 0 0 0 0 0 0 0 0 0 0 0 0

7.0580 0.1830 -1.2530 H 0 0 0 0 0 0 0 0 0 0 0 0

5.3740 0.4260 -0.7300 H 0 0 0 0 0 0 0 0 0 0 0 0

6.1780 1.4080 1.4000 H 0 0 0 0 0 0 0 0 0 0 0 0

7.8610 1.1650 0.8770 H 0 0 0 0 0 0 0 0 0 0 0 0

7.4680 2.6410 -1.0760 H 0 0 0 0 0 0 0 0 0 0 0 0

5.7840 2.8840 -0.5530 H 0 0 0 0 0 0 0 0 0 0 0 0

6.5880 3.8660 1.5770 H 0 0 0 0 0 0 0 0 0 0 0 0

8.2710 3.6230 1.0540 H 0 0 0 0 0 0 0 0 0 0 0 0

6.1940 5.3420 -0.3760 H 0 0 0 0 0 0 0 0 0 0 0 0

7.5330 5.9510 0.6260 H 0 0 0 0 0 0 0 0 0 0 0 0

7.8770 5.0990 -0.8990 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 2 0 0 0 0

2 3 1 0 0 0 0

2 4 1 0 0 0 0

4 5 1 0 0 0 0

5 6 1 0 0 0 0

6 7 1 0 0 0 0

14 15 2 0 0 0 0

14 13 1 0 0 0 0

12 13 2 0 0 0 0

12 11 1 0 0 0 0

10 11 2 0 0 0 0

10 9 1 0 0 0 0

7 9 1 0 0 0 0

7 8 1 0 0 0 0

15 16 1 0 0 0 0

9 8 1 0 0 0 0

16 17 1 0 0 0 0

17 18 2 0 0 0 0

19 18 1 0 0 0 0

19 20 1 0 0 0 0

21 20 1 0 0 0 0

21 22 1 0 0 0 0

22 23 1 0 0 0 0

3 24 1 0 0 0 0

4 25 1 0 0 0 0

4 26 1 0 0 0 0

5 27 1 0 0 0 0

5 28 1 0 0 0 0

6 29 1 0 0 0 0

6 30 1 0 0 0 0

7 31 1 6 0 0 0

9 32 1 1 0 0 0

10 33 1 0 0 0 0

11 34 1 0 0 0 0

12 35 1 0 0 0 0

13 36 1 0 0 0 0

14 37 1 0 0 0 0

15 38 1 0 0 0 0

16 39 1 0 0 0 0

16 40 1 0 0 0 0

17 41 1 0 0 0 0

18 42 1 0 0 0 0

19 43 1 0 0 0 0

19 44 1 0 0 0 0

20 45 1 0 0 0 0

20 46 1 0 0 0 0

21 47 1 0 0 0 0

21 48 1 0 0 0 0

22 49 1 0 0 0 0

22 50 1 0 0 0 0

23 51 1 0 0 0 0

23 52 1 0 0 0 0

23 53 1 0 0 0 0

M END): 18 ms

reading 53 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

53 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Leukotriene A4 (LTA4) is a leukotriene, and is the precursor for the productions of leukotriene B4 (LTB4) and leukotriene C4 (LTC4).
Read full article at Wikipedia

Formula

C20H30O3

Net Charge

Average Mass

318.457

Monoisotopic Mass

318.21949

InChI

InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1

InChIKey

UFPQIRYSPUYQHK-WAQVJNLQSA-N

SMILES

CCCCC\C=C/C\C=C/C=C/C=C/[C@@H]1O[C@H]1CCCC(O)=O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Phaseolus vulgaris (NCBI:txid3885)	See: DOI

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	leukotriene A₄ (CHEBI:15651) has functional parent icosa-7,9,11,14-tetraenoic acid (CHEBI:36038) leukotriene A₄ (CHEBI:15651) has role human metabolite (CHEBI:77746) leukotriene A₄ (CHEBI:15651) has role mouse metabolite (CHEBI:75771) leukotriene A₄ (CHEBI:15651) has role plant metabolite (CHEBI:76924) leukotriene A₄ (CHEBI:15651) is a epoxy fatty acid (CHEBI:61498) leukotriene A₄ (CHEBI:15651) is a leukotriene (CHEBI:25029) leukotriene A₄ (CHEBI:15651) is a long-chain fatty acid (CHEBI:15904) leukotriene A₄ (CHEBI:15651) is a oxylipin (CHEBI:61121) leukotriene A₄ (CHEBI:15651) is a polyunsaturated fatty acid (CHEBI:26208) leukotriene A₄ (CHEBI:15651) is conjugate acid of leukotriene A₄(1−) (CHEBI:57463)

Incoming	4,5-leukotriene A₄ (CHEBI:28367) has functional parent leukotriene A₄ (CHEBI:15651) leukotriene A₄(1−) (CHEBI:57463) is conjugate base of leukotriene A₄ (CHEBI:15651)

IUPAC Name

(5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoic acid

Synonyms	Sources
(7E,9E,11Z,14Z)-(5S,6S)-5,6-epoxyeicosa-7,9,11,14-tetraenoic acid	KEGG COMPOUND
5(S)-5,6-oxido-7,9-trans-11,14-cis-eicosatetraenoic acid	ChEBI
5S,6S-epoxy-7E,9E,11Z,14Z-eicosatetraenoic acid	LIPID MAPS
5S,6S-leukotriene A₄	ChEBI
Leukotriene A4	KEGG COMPOUND
LTA4	KEGG COMPOUND
Oxiranebutanoic acid, 3-(1,3,5,8-tetradecatetraenyl)-, (2S-(2alpha,3beta(1E,3Z,5Z,8Z)))-	ChemIDplus

Manual Xrefs	Databases
C00053424	KNApSAcK
C00909	KEGG COMPOUND
DJ3	PDBeChem
HMDB0001337	HMDB
Leukotriene_A4	Wikipedia
LMFA03020023	LIPID MAPS
View more database links

Registry Numbers	Types	Sources
5756170	Reaxys Registry Number	Reaxys
72059-45-1	CAS Registry Number	KEGG COMPOUND
72059-45-1	CAS Registry Number	ChemIDplus

Citations

Qin R, Wang H, Yan A (2021)
Classification and QSAR models of leukotriene A4 hydrolase (LTA4H) inhibitors by machine learning methods.
SAR and QSAR in environmental research 32, 411-431 [PubMed:33896285]
[show Abstract]

Stsiapanava A, Samuelsson B, Haeggström JZ (2017)
Capturing LTA₄ hydrolase in action: Insights to the chemistry and dynamics of chemotactic LTB₄ synthesis.
Proceedings of the National Academy of Sciences of the United States of America 114, 9689-9694 [PubMed:28827365]
[show Abstract]

Paz PB, Vega-Hissi EG, Estrada MR, Garro Martinez JC (2012)
In silico modeling of the molecular structure and binding of leukotriene A4 into leukotriene A4 hydrolase.
Chemical biology & drug design 80, 902-908 [PubMed:22913921]
[show Abstract]

Funk D, Sorg BL, Lindner SC, Schmeiser HH (2010)
32P-postlabeling analysis of DNA adducts formed by leukotriene A4 (LTA4).
Environmental and molecular mutagenesis 51, 338-343 [PubMed:20120015]
[show Abstract]

Jeong CH, Bode AM, Pugliese A, Cho YY, Kim HG, Shim JH, Jeon YJ, Li H, Jiang H, Dong Z (2009)
[6]-Gingerol suppresses colon cancer growth by targeting leukotriene A4 hydrolase.
Cancer research 69, 5584-5591 [PubMed:19531649]
[show Abstract]

Fitzpatrick FA, Lepley R, Orning L, Duffin K (1994)
Effects of leukotriene A4 on neutrophil activation.
Annals of the New York Academy of Sciences 714, 64-74 [PubMed:8017792]

Edenius C, Stenke L, Tornhamre S, Heidvall K, Forsberg I, Näsman-Glaser B, Lindgren JA (1991)
Metabolism of granulocyte-derived leukotriene A4 in human platelets and respiratory tissue: transcellular formation of lipoxins and leukotrienes.
Advances in experimental medicine and biology 314, 281-288 [PubMed:1667967]

Last Modified

10 June 2021

CHEBI:15651 - leukotriene A4

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CHEBI:15651 - leukotriene A₄