leukotriene C(4) (CHEBI:16978)

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CHEBI:16978 - leukotriene C₄

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ChEBI Name	leukotriene C₄

ChEBI ID	CHEBI:16978

ChEBI ASCII Name	leukotriene C4

Definition	A leukotriene that is (5S,7E,9E,11Z,14Z)-5-hydroxyicosa-7,9,11,14-tetraenoic acid in which a glutathionyl group is attached at position 6 via a sulfide linkage.

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

Secondary ChEBI IDs	CHEBI:6422, CHEBI:14504, CHEBI:25025

Supplier Information	ChemicalBook:CB8672212, eMolecules:494216, eMolecules:1937952, Selleckchem:creatinine, ZINC000000967189

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

LTX - Ideal conformer

Mrv1927 06062213473D

starting HoverWatcher_5

Time for openFile(LTX - Ideal conformer

Mrv1927 06062213473D

90 89 0 0 0 0 999 V2000

-4.3240 7.9290 -2.8620 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.6160 7.3820 -1.8610 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.4710 7.9850 -0.8240 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.0030 6.0160 -2.0300 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.2570 5.6290 -0.7520 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.6340 4.2420 -0.9240 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.8880 3.8560 0.3550 C 0 0 2 0 0 0 0 0 0 0 0 0

0.1860 4.7730 0.5750 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.3280 2.4400 0.2110 C 0 0 1 0 0 0 0 0 0 0 0 0

0.4220 2.0660 1.4630 C 0 0 0 0 0 0 0 0 0 0 0 0

1.7170 1.7570 1.3980 C 0 0 0 0 0 0 0 0 0 0 0 0

2.4460 1.3930 2.6150 C 0 0 0 0 0 0 0 0 0 0 0 0

3.7560 1.0810 2.5490 C 0 0 0 0 0 0 0 0 0 0 0 0

4.4850 0.7170 3.7660 C 0 0 0 0 0 0 0 0 0 0 0 0

5.7560 0.3230 3.6890 C 0 0 0 0 0 0 0 0 0 0 0 0

6.4850 0.3830 2.3720 C 0 0 1 0 0 0 0 0 0 0 0 0

7.7560 1.1770 2.5370 C 0 0 0 0 0 0 0 0 0 0 0 0

8.9020 0.6650 2.1630 C 0 0 0 0 0 0 0 0 0 0 0 0

8.9350 -0.6470 1.4220 C 0 0 1 0 0 0 0 0 0 0 0 0

9.7360 -0.4830 0.1290 C 0 0 1 0 0 0 0 0 0 0 0 0

9.7690 -1.8150 -0.6230 C 0 0 1 0 0 0 0 0 0 0 0 0

10.5700 -1.6510 -1.9160 C 0 0 1 0 0 0 0 0 0 0 0 0

10.6030 -2.9840 -2.6680 C 0 0 0 0 0 0 0 0 0 0 0 0

1.5260 -2.7460 -3.9400 O 0 0 0 0 0 0 0 0 0 0 0 0

1.4260 -3.8220 -3.4000 C 0 0 0 0 0 0 0 0 0 0 0 0

2.1760 -4.8550 -3.8190 O 0 0 0 0 0 0 0 0 0 0 0 0

0.4610 -4.0060 -2.2580 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.2310 -2.7420 -1.9950 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.1480 -2.6680 -1.0100 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.4000 -3.6480 -0.3410 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.8600 -1.3680 -0.7400 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.8360 -0.2920 -0.3730 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.6930 1.2730 -0.0480 S 0 0 0 0 0 0 0 0 0 0 0 0

-2.7990 -1.5460 0.3700 N 0 0 0 0 0 0 0 0 0 0 0 0

-4.0360 -2.0260 0.1360 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.3730 -2.3100 -0.9940 O 0 0 0 0 0 0 0 0 0 0 0 0

-5.0020 -2.2100 1.2780 C 0 0 1 0 0 0 0 0 0 0 0 0

-6.3250 -2.7630 0.7430 C 0 0 1 0 0 0 0 0 0 0 0 0

-7.3050 -2.9500 1.9030 C 0 0 2 0 0 0 0 0 0 0 0 0

-6.7930 -3.9810 2.8160 N 0 0 1 0 0 0 0 0 0 0 0 0

-8.6460 -3.3780 1.3630 C 0 0 0 0 0 0 0 0 0 0 0 0

-8.9670 -4.5420 1.3960 O 0 0 0 0 0 0 0 0 0 0 0 0

-9.4830 -2.4650 0.8460 O 0 0 0 0 0 0 0 0 0 0 0 0

-4.6970 8.8070 -2.7060 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.7890 5.2860 -2.2260 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.3060 6.0310 -2.8670 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.4700 6.3590 -0.5560 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9540 5.6140 0.0860 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4210 3.5130 -1.1190 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.9370 4.2580 -1.7610 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5740 3.8910 1.2010 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8370 4.7950 -0.1400 H 0 0 0 0 0 0 0 0 0 0 0 0

0.3490 2.4020 -0.6430 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0900 2.0480 2.4140 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2290 1.7740 0.4470 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9340 1.3760 3.5660 H 0 0 0 0 0 0 0 0 0 0 0 0

4.2680 1.0980 1.5980 H 0 0 0 0 0 0 0 0 0 0 0 0

3.9930 0.7690 4.7260 H 0 0 0 0 0 0 0 0 0 0 0 0

6.2630 -0.0400 4.5710 H 0 0 0 0 0 0 0 0 0 0 0 0

6.7290 -0.6280 2.0450 H 0 0 0 0 0 0 0 0 0 0 0 0

5.8510 0.8630 1.6270 H 0 0 0 0 0 0 0 0 0 0 0 0

7.7210 2.1680 2.9640 H 0 0 0 0 0 0 0 0 0 0 0 0

9.8230 1.1830 2.3850 H 0 0 0 0 0 0 0 0 0 0 0 0

9.4060 -1.4060 2.0470 H 0 0 0 0 0 0 0 0 0 0 0 0

7.9170 -0.9550 1.1820 H 0 0 0 0 0 0 0 0 0 0 0 0

9.2650 0.2750 -0.4960 H 0 0 0 0 0 0 0 0 0 0 0 0

10.7530 -0.1760 0.3690 H 0 0 0 0 0 0 0 0 0 0 0 0

10.2400 -2.5740 0.0020 H 0 0 0 0 0 0 0 0 0 0 0 0

8.7510 -2.1230 -0.8630 H 0 0 0 0 0 0 0 0 0 0 0 0

10.0990 -0.8930 -2.5410 H 0 0 0 0 0 0 0 0 0 0 0 0

11.5880 -1.3440 -1.6760 H 0 0 0 0 0 0 0 0 0 0 0 0

9.5850 -3.2910 -2.9080 H 0 0 0 0 0 0 0 0 0 0 0 0

11.1740 -2.8670 -3.5890 H 0 0 0 0 0 0 0 0 0 0 0 0

11.0740 -3.7420 -2.0420 H 0 0 0 0 0 0 0 0 0 0 0 0

2.7810 -4.6880 -4.5540 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.2690 -4.7730 -2.5190 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0070 -4.3140 -1.3660 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0300 -1.9590 -2.5300 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4060 -1.0600 -1.6320 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.2890 -0.5990 0.5180 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1370 -0.1590 -1.1990 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.5300 -1.3200 1.2740 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.5820 -2.9090 2.0000 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.1800 -1.2500 1.7620 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.7460 -2.0640 0.0210 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.1480 -3.7240 0.2590 H 0 0 0 0 0 0 0 0 0 0 0 0

-7.4140 -2.0090 2.4420 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.6840 -4.8640 2.3390 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.9260 -3.6890 3.2410 H 0 0 0 0 0 0 0 0 0 0 0 0

-10.3320 -2.7870 0.5120 H 0 0 0 0 0 0 0 0 0 0 0 0

24 25 2 0 0 0 0

23 22 1 0 0 0 0

22 21 1 0 0 0 0

25 26 1 0 0 0 0

25 27 1 0 0 0 0

27 28 1 0 0 0 0

21 20 1 0 0 0 0

20 19 1 0 0 0 0

14 15 2 0 0 0 0

14 13 1 0 0 0 0

3 2 2 0 0 0 0

8 7 1 0 0 0 0

28 29 1 0 0 0 0

15 16 1 0 0 0 0

12 13 2 0 0 0 0

12 11 1 0 0 0 0

19 18 1 0 0 0 0

30 29 2 0 0 0 0

10 11 2 0 0 0 0

10 9 1 0 0 0 0

29 31 1 0 0 0 0

2 4 1 0 0 0 0

2 1 1 0 0 0 0

7 6 1 0 0 0 0

7 9 1 0 0 0 0

5 6 1 0 0 0 0

5 4 1 0 0 0 0

16 17 1 0 0 0 0

18 17 2 0 0 0 0

33 9 1 0 0 0 0

33 32 1 0 0 0 0

31 32 1 0 0 0 0

31 34 1 0 0 0 0

34 35 1 0 0 0 0

35 37 1 0 0 0 0

35 36 2 0 0 0 0

42 41 2 0 0 0 0

37 38 1 0 0 0 0

40 39 1 0 0 0 0

41 43 1 0 0 0 0

41 39 1 0 0 0 0

38 39 1 0 0 0 0

1 44 1 0 0 0 0

4 45 1 0 0 0 0

4 46 1 0 0 0 0

5 47 1 0 0 0 0

5 48 1 0 0 0 0

6 49 1 0 0 0 0

6 50 1 0 0 0 0

7 51 1 1 0 0 0

8 52 1 0 0 0 0

9 53 1 6 0 0 0

10 54 1 0 0 0 0

11 55 1 0 0 0 0

12 56 1 0 0 0 0

13 57 1 0 0 0 0

14 58 1 0 0 0 0

15 59 1 0 0 0 0

16 60 1 0 0 0 0

16 61 1 0 0 0 0

17 62 1 0 0 0 0

18 63 1 0 0 0 0

19 64 1 0 0 0 0

19 65 1 0 0 0 0

20 66 1 0 0 0 0

20 67 1 0 0 0 0

21 68 1 0 0 0 0

21 69 1 0 0 0 0

22 70 1 0 0 0 0

22 71 1 0 0 0 0

23 72 1 0 0 0 0

23 73 1 0 0 0 0

23 74 1 0 0 0 0

26 75 1 0 0 0 0

27 76 1 0 0 0 0

27 77 1 0 0 0 0

28 78 1 0 0 0 0

31 79 1 6 0 0 0

32 80 1 0 0 0 0

32 81 1 0 0 0 0

34 82 1 0 0 0 0

37 83 1 0 0 0 0

37 84 1 0 0 0 0

38 85 1 0 0 0 0

38 86 1 0 0 0 0

39 87 1 1 0 0 0

40 88 1 0 0 0 0

40 89 1 0 0 0 0

43 90 1 0 0 0 0

M END): 25 ms

reading 90 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

90 atoms created

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

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Creatinine (; from Ancient Greek κρέας (kréas) 'flesh') is a breakdown product of creatine phosphate from muscle and protein metabolism. It is released at a constant rate by the body (depending on muscle mass).
Read full article at Wikipedia

Formula

C30H47N3O9S

Net Charge

Average Mass

625.780

Monoisotopic Mass

625.30330

InChI

InChI=1S/C30H47N3O9S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-25(24(34)15-14-17-27(36)37)43-21-23(29(40)32-20-28(38)39)33-26(35)19-18-22(31)30(41)42/h6-7,9-13,16,22-25,34H,2-5,8,14-15,17-21,31H2,1H3,(H,32,40)(H,33,35)(H,36,37)(H,38,39)(H,41,42)/b7-6-,10-9-,12-11+,16-13+/t22-,23-,24-,25+/m0/s1

InChIKey

GWNVDXQDILPJIG-NXOLIXFESA-N

SMILES

CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O)[C@@H](O)CCCC(O)=O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Found in bronchoalveolar lavage (BTO:0000155). From MetaboLights See: MetaboLights Study
Mus musculus (NCBI:txid10090)	From MetaboLights See: MetaboLights Study
Mus musculus (NCBI:txid10090)	From MetaboLights See: MetaboLights Study
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606)	Found in blood (UBERON:0000178). See: PubMed
Homo sapiens (NCBI:txid9606)	Found in cerebrospinal fluid (UBERON:0001359). See: PubMed

Roles Classification
Biological Role(s):	mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).

Application(s):	bronchoconstrictor agent A drug which causes a narrowing of the lumen of a bronchus or bronchiole.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	leukotriene C₄ (CHEBI:16978) has functional parent icosa-7,9,11,14-tetraenoic acid (CHEBI:36038) leukotriene C₄ (CHEBI:16978) has role bronchoconstrictor agent (CHEBI:50141) leukotriene C₄ (CHEBI:16978) has role human metabolite (CHEBI:77746) leukotriene C₄ (CHEBI:16978) has role mouse metabolite (CHEBI:75771) leukotriene C₄ (CHEBI:16978) is a leukotriene (CHEBI:25029) leukotriene C₄ (CHEBI:16978) is conjugate acid of leukotriene C₄(2−) (CHEBI:57973)

Incoming	11,12-dihydro-(12R)-hydroxyleukotriene C₄ (CHEBI:134519) has functional parent leukotriene C₄ (CHEBI:16978) 11,12-dihydro-12-oxoleukotriene C₄ (CHEBI:134518) has functional parent leukotriene C₄ (CHEBI:16978) leukotriene C₄ methyl ester (CHEBI:138115) has functional parent leukotriene C₄ (CHEBI:16978) leukotriene C₄(2−) (CHEBI:57973) is conjugate base of leukotriene C₄ (CHEBI:16978)

IUPAC Name

L-γ-glutamyl-S-[(1R,2E,4E,6Z,9Z)-1-[(1S)-4-carboxy-1-hydroxybutyl]pentadeca-2,4,6,9-tetraen-1-yl]-L-cysteinylglycine

Synonyms	Sources
(R-(R,S-(E,E,Z,Z)))-N-(S-(1-(4-Carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-N-L-gamma-glutamyl-L-cysteinyl)glycine	ChemIDplus
5S,6R-Ltc(sub 4)	ChemIDplus
5S-hydroxy,6R-(S-glutathionyl),7E,9E,11Z,14Z-eicosatetraenoic acid	LIPID MAPS
Leukotriene C4	KEGG COMPOUND
LTC (sub 4)	ChemIDplus
LTC4	LIPID MAPS
LTC4	KEGG COMPOUND
LTC₄	ChEBI

Manual Xrefs	Databases
C02166	KEGG COMPOUND
DB08855	DrugBank
FDB022484	FooDB
HMDB0001198	HMDB
LEUKOTRIENE-C4	MetaCyc
Leukotriene_C4	Wikipedia
LMFA03020003	LIPID MAPS
LTX	PDBeChem
View more database links

Registry Numbers	Types	Sources
4732117	Reaxys Registry Number	Reaxys
72025-60-6	CAS Registry Number	KEGG COMPOUND
72025-60-6	CAS Registry Number	ChemIDplus

Citations	Types	Sources
10064732	PubMed citation	Europe PMC
11156567	PubMed citation	Europe PMC
12895596	PubMed citation	Europe PMC
15243994	PubMed citation	Europe PMC
15537867	PubMed citation	Europe PMC
1652771	PubMed citation	Europe PMC
2007712	PubMed citation	Europe PMC
20671299	PubMed citation	Europe PMC
2411760	PubMed citation	Europe PMC
24244016	PubMed citation	Europe PMC
2509375	PubMed citation	Europe PMC
2512259	PubMed citation	Europe PMC
2558123	PubMed citation	Europe PMC
2633615	PubMed citation	Europe PMC
26656251	PubMed citation	Europe PMC
27124118	PubMed citation	Europe PMC
28238471	PubMed citation	Europe PMC
28667163	PubMed citation	Europe PMC
31268744	PubMed citation	Europe PMC
3153930	PubMed citation	Europe PMC
33753496	PubMed citation	Europe PMC
3418380	PubMed citation	Europe PMC
3421265	PubMed citation	Europe PMC
6440558	PubMed citation	Europe PMC
7714683	PubMed citation	Europe PMC
8415814	PubMed citation	Europe PMC
8434868	PubMed citation	Europe PMC
8608646	PubMed citation	Europe PMC
8938552	PubMed citation	Europe PMC
8939179	PubMed citation	Europe PMC
9042024	PubMed citation	Europe PMC
9051719	PubMed citation	Europe PMC
9384524	PubMed citation	Europe PMC
9642160	PubMed citation	Europe PMC

Last Modified

06 June 2022

CHEBI:16978 - leukotriene C4

ChEBI is part of the ELIXIR infrastructure

CHEBI:16978 - leukotriene C₄