oleoyl-CoA (CHEBI:15534)

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CHEBI:15534 - oleoyl-CoA

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ChEBI Name	oleoyl-CoA

ChEBI ID	CHEBI:15534

Definition	An octadecenoyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of oleic acid.

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

Secondary ChEBI IDs	CHEBI:7743, CHEBI:14685, CHEBI:25668

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

3VV - Ideal conformer

Mrv1927 06092110323D

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Time for openFile(3VV - Ideal conformer

Mrv1927 06092110323D

135137 0 0 0 0 999 V2000

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15.7060 -0.9100 -0.6060 C 0 0 1 0 0 0 0 0 0 0 0 0

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11.5820 -1.1740 -0.8270 H 0 0 0 0 0 0 0 0 0 0 0 0

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4.9000 -3.8040 0.1540 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4170 -5.2600 2.5300 H 0 0 0 0 0 0 0 0 0 0 0 0

0.9430 -3.5760 2.2000 H 0 0 0 0 0 0 0 0 0 0 0 0

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37 36 1 0 0 0 0

67 61 1 0 0 0 0

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33 32 2 0 0 0 0

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39 40 1 0 0 0 0

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10 46 1 1 0 0 0

43 10 1 0 0 0 0

9 43 1 6 0 0 0

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1 68 1 0 0 0 0

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M END): 22 ms

reading 135 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

135 atoms created

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

Script completed

Jmol script terminated

Molfile expand

Formula

C39H68N7O17P3S

Net Charge

Average Mass

1031.990

Monoisotopic Mass

1031.36053

InChI

InChI=1S/C39H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h11-12,26-28,32-34,38,49-50H,4-10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b12-11-/t28-,32-,33-,34+,38-/m1/s1

InChIKey

XDUHQPOXLUAVEE-BPMMELMSSA-N

SMILES

CCCCCCCC\C=C/CCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Chemical Role(s):	acyl donor Any donor that can transfer acyl groups between molecular entities. (via acyl-CoA )

Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	oleoyl-CoA (CHEBI:15534) has functional parent coenzyme A (CHEBI:15346) oleoyl-CoA (CHEBI:15534) has role Escherichia coli metabolite (CHEBI:76971) oleoyl-CoA (CHEBI:15534) has role mouse metabolite (CHEBI:75771) oleoyl-CoA (CHEBI:15534) is a octadecenoyl-CoA (CHEBI:139574) oleoyl-CoA (CHEBI:15534) is conjugate acid of oleoyl-CoA(4−) (CHEBI:57387)

Incoming	oleoyl-CoA(4−) (CHEBI:57387) is conjugate base of oleoyl-CoA (CHEBI:15534)

IUPAC Name

3'-phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(9Z)-octadec-9-enoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphate}

Synonyms	Sources
(9Z)-octadec-9-enoyl-CoA	ChEBI
(9Z)-octadec-9-enoyl-coenzyme A	ChEBI
(9Z)-octadecenoyl-CoA	KEGG COMPOUND
cis-9-octadecenoyl-CoA	ChEBI
cis-9-octadecenoyl-coenzyme A	ChEBI
cis-Δ⁹-octadecenoyl-CoA	ChEBI
cis-Δ⁹-octadecenoyl-coenzyme A	ChEBI
oleoyl-CoA	KEGG COMPOUND
oleoyl-coenzyme A	ChemIDplus
S-[(9Z)-octadec-9-enoyl]-CoA	ChEBI
S-[(9Z)-octadec-9-enoyl]-coenzyme A	ChEBI
S-oleoyl-CoA	ChEBI
S-oleoylcoenzyme A	ChemIDplus

Manual Xrefs	Databases
3VV	PDBeChem
4593689	ChemSpider
C00510	KEGG COMPOUND
FDB022554	FooDB
HMDB0001322	HMDB
LMFA07050356	LIPID MAPS
View more database links

Registry Numbers	Types	Sources
1716-06-9	CAS Registry Number	ChemIDplus
604341	Reaxys Registry Number	Reaxys

Citations

Long T, Sun Y, Hassan A, Qi X, Li X (2020)
Structure of nevanimibe-bound tetrameric human ACAT1.
Nature 581, 339-343 [PubMed:32433613]
[show Abstract]

Wang L, Qian H, Nian Y, Han Y, Ren Z, Zhang H, Hu L, Prasad BVV, Laganowsky A, Yan N, Zhou M (2020)
Structure and mechanism of human diacylglycerol O-acyltransferase 1.
Nature 581, 329-332 [PubMed:32433610]
[show Abstract]

Qian H, Zhao X, Yan R, Yao X, Gao S, Sun X, Du X, Yang H, Wong CCL, Yan N (2020)
Structural basis for catalysis and substrate specificity of human ACAT1.
Nature 581, 333-338 [PubMed:32433614]
[show Abstract]

Schmidt RR, Fulda M, Paul MV, Anders M, Plum F, Weits DA, Kosmacz M, Larson TR, Graham IA, Beemster GTS, Licausi F, Geigenberger P, Schippers JH, van Dongen JT (2018)
Low-oxygen response is triggered by an ATP-dependent shift in oleoyl-CoA in Arabidopsis.
Proceedings of the National Academy of Sciences of the United States of America 115, E12101-E12110 [PubMed:30509981]
[show Abstract]

Panigrahi R, Matsui T, Song AH, Caldo KMP, Young HS, Weselake RJ, Lemieux MJ (2018)
Intrinsic disorder in the regulatory N-terminal domain of diacylglycerol acyltransferase 1 from Brassica napus.
Scientific reports 8, 16665 [PubMed:30420764]
[show Abstract]

Shi W, Kovacikova G, Lin W, Taylor RK, Skorupski K, Kull FJ (2015)
The 40-residue insertion in Vibrio cholerae FadR facilitates binding of an additional fatty acyl-CoA ligand.
Nature communications 6, 6032 [PubMed:25607896]
[show Abstract]

Turapov O, Waddell SJ, Burke B, Glenn S, Sarybaeva AA, Tudo G, Labesse G, Young DI, Young M, Andrew PW, Butcher PD, Cohen-Gonsaud M, Mukamolova GV (2014)
Oleoyl coenzyme A regulates interaction of transcriptional regulator RaaS (Rv1219c) with DNA in mycobacteria.
The Journal of biological chemistry 289, 25241-25249 [PubMed:25012658]
[show Abstract]

Leung KC, Li HY, Mishra G, Chye ML (2004)
ACBP4 and ACBP5, novel Arabidopsis acyl-CoA-binding proteins with kelch motifs that bind oleoyl-CoA.
Plant molecular biology 55, 297-309 [PubMed:15604682]
[show Abstract]

Miyazaki M, Kim HJ, Man WC, Ntambi JM (2001)
Oleoyl-CoA is the major de novo product of stearoyl-CoA desaturase 1 gene isoform and substrate for the biosynthesis of the Harderian gland 1-alkyl-2,3-diacylglycerol.
The Journal of biological chemistry 276, 39455-39461 [PubMed:11500518]
[show Abstract]

Domergue F, Chevalier S, Santarelli X, Cassagne C, Lessire R (1999)
Evidence that oleoyl-CoA and ATP-dependent elongations coexist in rapeseed (Brassica napus L.).
European journal of biochemistry 263, 464-470 [PubMed:10406955]
[show Abstract]

Garbay B, Boiron-Sargueil F, Shy M, Chbihi T, Jiang H, Kamholz J, Cassagne C (1998)
Regulation of oleoyl-CoA synthesis in the peripheral nervous system: demonstration of a link with myelin synthesis.
Journal of neurochemistry 71, 1719-1726 [PubMed:9751207]
[show Abstract]

Gribble FM, Proks P, Corkey BE, Ashcroft FM (1998)
Mechanism of cloned ATP-sensitive potassium channel activation by oleoyl-CoA.
The Journal of biological chemistry 273, 26383-26387 [PubMed:9756869]
[show Abstract]

Krcmery M, Zakim D (1993)
Effects of oleoyl-CoA on the activity and functional state of UDP-glucuronosyltransferase.
Biochemical pharmacology 46, 897-904 [PubMed:8373441]
[show Abstract]

Alberghina M, Lupo G, Anfuso CD (1993)
Lipid peroxidation inhibits oleoyl-CoA: 1-acyl-sn-glycero-3-phosphocholine O-acyltransferase in rat CNS axolemma-enriched fractions.
Neurochemistry international 23, 229-237 [PubMed:8220169]
[show Abstract]

Hills MJ, Murphy DJ, Beevers H (1989)
Inhibition of Neutral Lipase from Castor Bean Lipid Bodies by Coenzyme A (CoA) and Oleoyl-CoA.
Plant physiology 89, 1006-1010 [PubMed:16666608]
[show Abstract]

Zatz M, Engelsen SJ, Markey SP (1982)
Biosynthesis of S-methyl-N-oleoylmercaptoethylamide from oleoyl coenzyme A and S-adenosylmethionine.
The Journal of biological chemistry 257, 13673-13678 [PubMed:7142172]
[show Abstract]

Strosznajder J, Tang W, Manning R, Lin AY, MacQuarrie R, Sun GY (1981)
Metabolism of oleoyl-CoA in rat brain synaptosomes: effects of calcium and post-decapitative ischemia.
Neurochemical research 6, 1231-1240 [PubMed:6123958]
[show Abstract]

Stymne S, Appelqvist LA (1978)
The biosynthesis of linoleate from oleoyl-CoA via oleoyl-phosphatidylcholine in microsomes of developing safflower seeds.
European journal of biochemistry 90, 223-229 [PubMed:710426]
[show Abstract]

Hsu KH, Powell GL (1975)
Inhibition of citrate synthase by oleoyl-CoA: a regulatory phenomenon.
Proceedings of the National Academy of Sciences of the United States of America 72, 4729-4733 [PubMed:1061066]
[show Abstract]

Last Modified

09 June 2021

CHEBI:15534 - oleoyl-CoA

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