Showing metabocard for Oleoyl-CoA (BMDB0001322)
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Version | 1.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2016-09-30 22:44:08 UTC | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2020-05-21 16:28:08 UTC | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
BMDB ID | BMDB0001322 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Metabolite Identification | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Common Name | Oleoyl-CoA | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Oleoyl-CoA belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Oleoyl-CoA is a strong basic compound (based on its pKa). Oleoyl-CoA exists in all living organisms, ranging from bacteria to humans. Within cattle, oleoyl-CoA participates in a number of enzymatic reactions. In particular, oleoyl-CoA and glycerol 3-phosphate can be converted into lpa(18:1(9Z)/0:0); which is mediated by the enzyme glycerol-3-phosphate acyltransferase. In addition, lpa(18:1(9Z)/0:0) and oleoyl-CoA can be converted into PA(18:1(9Z)/18:1(9Z)); which is catalyzed by the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase. In cattle, oleoyl-CoA is involved in the metabolic pathway called de novo triacylglycerol biosynthesis pathway. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms |
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Chemical Formula | C39H68N7O17P3S | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Average Molecular Weight | 1031.98 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Monoisotopic Molecular Weight | 1031.360524011 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name | {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9Z)-octadec-9-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional Name | [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9Z)-octadec-9-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS Registry Number | 1716-06-9 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES | CCCCCCCC\C=C/CCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Identifier | 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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key | XDUHQPOXLUAVEE-ZXQNDDKTSA-N | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic acids and derivatives | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Carboxylic acids and derivatives | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Amino acids, peptides, and analogues | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | L-alpha-amino acids | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic acyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Ontology | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Status | Expected but not Quantified | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Origin |
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Biofunction | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Application | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular locations |
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Physical Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State | Solid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties |
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Predicted Properties |
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Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra |
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Biological Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations |
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Biospecimen Locations |
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Pathways | Not Available
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Normal Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Abnormal Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
HMDB ID | HMDB0001322 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
DrugBank ID | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Phenol Explorer Compound ID | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
FooDB ID | FDB022554 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
KNApSAcK ID | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemspider ID | 4444057 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
KEGG Compound ID | C00510 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
BioCyc ID | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
BiGG ID | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Wikipedia Link | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
METLIN ID | 6159 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
PubChem Compound | 5280355 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
PDB ID | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
ChEBI ID | 15534 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synthesis Reference | noue, Satoshi; Oba, Yuichi; Oga, Hajime. Manufacture of fatty acyl-coenzyme A using luciferase. Jpn. Kokai Tokkyo Koho (2004), 15 pp. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
General References | Not Available |
Enzymes
- General function:
- Energy production and conversion
- Specific function:
- Stearyl-CoA desaturase that utilizes O(2) and electrons from reduced cytochrome b5 to introduce the first double bond into saturated fatty acyl-CoA substrates. Catalyzes the insertion of a cis double bond at the delta-9 position into fatty acyl-CoA substrates including palmitoyl-CoA and stearoyl-CoA (By similarity). Gives rise to a mixture of 16:1 and 18:1 unsaturated fatty acids. Plays an important role in lipid biosynthesis. Plays an important role in regulating the expression of genes that are involved in lipogenesis and in regulating mitochondrial fatty acid oxidation (By similarity). Plays an important role in body energy homeostasis (By similarity). Contributes to the biosynthesis of membrane phospholipids, cholesterol esters and triglycerides (By similarity).
- Gene Name:
- SCD
- Uniprot ID:
- Q9TT94
- Molecular weight:
- 41705.0
- General function:
- Energy production and conversion
- Specific function:
- Stearyl-CoA desaturase that utilizes O(2) and electrons from reduced cytochrome b5 to introduce the first double bond into saturated fatty acyl-CoA substrates. Catalyzes the insertion of a cis double bond at the delta-9 position into fatty acyl-CoA substrates including palmitoyl-CoA and stearoyl-CoA. Gives rise to a mixture of 16:1 and 18:1 unsaturated fatty acids.
- Gene Name:
- SCD5
- Uniprot ID:
- Q2KIA4
- Molecular weight:
- 38215.0
- General function:
- Not Available
- Specific function:
- Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders. In liver, plays a role in esterifying exogenous fatty acids to glycerol.
- Gene Name:
- DGAT1
- Uniprot ID:
- Q8MK44
- Molecular weight:
- 55602.0
Reactions
DG(14:0/14:0/0:0) + Oleoyl-CoA → TG(14:0/14:0/18:1(9Z)) + Coenzyme A | details |
DG(14:0/14:1(9Z)/0:0) + Oleoyl-CoA → TG(14:0/14:1(9Z)/18:1(9Z))[iso6] + Coenzyme A | details |
DG(14:0/15:0/0:0) + Oleoyl-CoA → TG(14:0/15:0/18:1(9Z)) + Coenzyme A | details |
DG(14:0/16:0/0:0) + Oleoyl-CoA → TG(14:0/16:0/18:1(9Z)) + Coenzyme A | details |
DG(14:0/18:0/0:0) + Oleoyl-CoA → TG(14:0/18:0/18:1(9Z))[iso6] + Coenzyme A | details |
DG(14:0/18:1(11Z)/0:0) + Oleoyl-CoA → TG(14:0/18:1(11Z)/18:1(9Z)) + Coenzyme A | details |
DG(14:0/18:1(9Z)/0:0) + Oleoyl-CoA → TG(14:0/18:1(9Z)/18:1(9Z))[iso3] + Coenzyme A | details |
DG(14:1(9Z)/14:1(9Z)/0:0) + Oleoyl-CoA → TG(14:1(9Z)/14:1(9Z)/18:1(9Z)) + Coenzyme A | details |
DG(14:1(9Z)/15:0/0:0) + Oleoyl-CoA → TG(14:1(9Z)/15:0/18:1(9Z)) + Coenzyme A | details |
DG(14:1(9Z)/16:0/0:0) + Oleoyl-CoA → TG(14:1(9Z)/16:0/18:1(9Z))[iso6] + Coenzyme A | details |
DG(14:1(9Z)/16:1(9Z)/0:0) + Oleoyl-CoA → TG(14:1(9Z)/16:1(9Z)/18:1(9Z))[iso6] + Coenzyme A | details |
DG(14:1(9Z)/18:0/0:0) + Oleoyl-CoA → TG(14:1(9Z)/18:0/18:1(9Z))[iso6] + Coenzyme A | details |
DG(14:1(9Z)/18:1(11Z)/0:0) + Oleoyl-CoA → TG(14:1(9Z)/18:1(11Z)/18:1(9Z)) + Coenzyme A | details |
DG(14:1(9Z)/18:1(9Z)/0:0) + Oleoyl-CoA → TG(14:1(9Z)/18:1(9Z)/18:1(9Z))[iso3] + Coenzyme A | details |
DG(15:0/15:0/0:0) + Oleoyl-CoA → TG(15:0/15:0/18:1(9Z)) + Coenzyme A | details |
DG(15:0/16:0/0:0) + Oleoyl-CoA → TG(15:0/16:0/18:1(9Z))[iso6] + Coenzyme A | details |
DG(15:0/16:1(9Z)/0:0) + Oleoyl-CoA → TG(15:0/16:1(9Z)/18:1(9Z))[iso6] + Coenzyme A | details |
DG(15:0/18:1(11Z)/0:0) + Oleoyl-CoA → TG(15:0/18:1(11Z)/18:1(9Z)) + Coenzyme A | details |
DG(15:0/18:1(9Z)/0:0) + Oleoyl-CoA → TG(15:0/18:1(9Z)/18:1(9Z)) + Coenzyme A | details |
DG(16:0/16:0/0:0) + Oleoyl-CoA → TG(16:0/16:0/18:1(9Z)) + Coenzyme A | details |
DG(16:0/16:1(9Z)/0:0) + Oleoyl-CoA → TG(16:0/16:1(9Z)/18:1(9Z)) + Coenzyme A | details |
DG(16:0/18:0/0:0) + Oleoyl-CoA → TG(16:0/18:0/18:1(9Z)) + Coenzyme A | details |
DG(16:0/18:1(11Z)/0:0) + Oleoyl-CoA → TG(16:0/18:1(11Z)/18:1(9Z)) + Coenzyme A | details |
DG(16:0/18:1(9Z)/0:0) + Oleoyl-CoA → TG(16:0/18:1(9Z)/18:1(9Z)) + Coenzyme A | details |
DG(16:1(9Z)/16:1(9Z)/0:0) + Oleoyl-CoA → TG(16:1(9Z)/16:1(9Z)/18:1(9Z)) + Coenzyme A | details |
DG(16:1(9Z)/18:0/0:0) + Oleoyl-CoA → TG(16:1(9Z)/18:0/18:1(9Z)) + Coenzyme A | details |
DG(16:1(9Z)/18:1(11Z)/0:0) + Oleoyl-CoA → TG(16:1(9Z)/18:1(11Z)/18:1(9Z)) + Coenzyme A | details |
DG(16:1(9Z)/18:1(9Z)/0:0) + Oleoyl-CoA → TG(16:1(9Z)/18:1(9Z)/18:1(9Z)) + Coenzyme A | details |
DG(18:0/18:0/0:0) + Oleoyl-CoA → TG(18:0/18:0/18:1(9Z)) + Coenzyme A | details |
DG(18:0/18:1(11Z)/0:0) + Oleoyl-CoA → TG(18:0/18:1(11Z)/18:1(9Z)) + Coenzyme A | details |
DG(18:0/18:1(9Z)/0:0) + Oleoyl-CoA → TG(18:0/18:1(9Z)/18:1(9Z)) + Coenzyme A | details |
DG(18:1(11Z)/18:1(11Z)/0:0) + Oleoyl-CoA → TG(18:1(11Z)/18:1(11Z)/18:1(9Z)) + Coenzyme A | details |
DG(18:1(11Z)/18:1(9Z)/0:0) + Oleoyl-CoA → TG(18:1(11Z)/18:1(9Z)/18:1(9Z)) + Coenzyme A | details |
DG(18:1(9Z)/18:1(9Z)/0:0) + Oleoyl-CoA → TG(18:1(9Z)/18:1(9Z)/18:1(9Z))[iso] + Coenzyme A | details |
- General function:
- Not Available
- Specific function:
- Converts 1-acyl-sn-glycerol-3-phosphate (lysophosphatidic acid or LPA) into 1,2-diacyl-sn-glycerol-3-phosphate (phosphatidic acid or PA) by incorporating an acyl moiety at the sn-2 position of the glycerol backbone.
- Gene Name:
- AGPAT1
- Uniprot ID:
- Q95JH2
- Molecular weight:
- 32005.0
Reactions
LPA(16:0/0:0) + Oleoyl-CoA → Coenzyme A + PA(16:0/18:1(9Z)) | details |
LPA(18:0/0:0) + Oleoyl-CoA → Coenzyme A + PA(18:0/18:1(9Z)) | details |
LysoPA(18:1(11Z)/0:0) + Oleoyl-CoA → Coenzyme A + PA(18:1(11Z)/18:1(9Z)) | details |
LysoPA(18:1(9Z)/0:0) + Oleoyl-CoA → Coenzyme A + PA(18:1(9Z)/18:1(9Z)) | details |
- General function:
- Not Available
- Specific function:
- Converts 1-acyl-sn-glycerol-3-phosphate (lysophosphatidic acid or LPA) into 1,2-diacyl-sn-glycerol-3-phosphate (phosphatidic acid or PA) by incorporating an acyl moiety at the sn-2 position of the glycerol backbone (By similarity). Exhibits high acyl-CoA specificity for polyunsaturated fatty acyl-CoA, especially docosahexaenoyl-CoA (22:6-CoA, DHA-CoA) (By similarity).
- Gene Name:
- AGPAT4
- Uniprot ID:
- Q5E9R2
- Molecular weight:
- 43907.0
Reactions
LPA(16:0/0:0) + Oleoyl-CoA → PA(16:0/18:1(9Z)) + Coenzyme A | details |
LPA(18:0/0:0) + Oleoyl-CoA → PA(18:0/18:1(9Z)) + Coenzyme A | details |
LysoPA(18:1(11Z)/0:0) + Oleoyl-CoA → PA(18:1(11Z)/18:1(9Z)) + Coenzyme A | details |
LysoPA(18:1(9Z)/0:0) + Oleoyl-CoA → PA(18:1(9Z)/18:1(9Z)) + Coenzyme A | details |