| Record Information |
| Version |
3.5 |
| Creation Date |
2006-05-22 08:17:47 -0600 |
| Update Date |
2013-02-08 17:11:43 -0700 |
| HMDB ID |
HMDB02307 |
| Secondary Accession Numbers |
|
| Metabolite Identification |
| Common Name |
Acrylyl-CoA |
| Description |
Acrylyl-CoA is involved in alternative pathways of propionate metabolism. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- Acryloyl coenzyme A
- Acryloyl-CoA
- Acryloyl-Coenzyme A
- Acrylyl coenzyme A
- Acrylyl-CoA
- Acrylyl-Coenzyme A
- CoA S-2-propenoate
- CoA S-2-propenoic acid
- CoA S-acrylate
- Coenzyme A S-2-propenoate
- Coenzyme A S-2-propenoic acid
- Coenzyme A S-acrylate
- Propenoyl-coa
- Thioacrylic acid S-ester with coenzyme A
|
| Chemical Formula |
C24H38N7O17P3S |
| Average Molecular Weight |
821.582 |
| Monoisotopic Molecular Weight |
821.125773051 |
| 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-(prop-2-enoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid |
| Traditional IUPAC Name |
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-(prop-2-enoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid |
| CAS Registry Number |
5776-58-9 |
| SMILES |
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)C(O)C(=O)NCCC(=O)NCCSC(=O)C=C |
| InChI Identifier |
InChI=1S/C24H38N7O17P3S/c1-4-15(33)52-8-7-26-14(32)5-6-27-22(36)19(35)24(2,3)10-45-51(42,43)48-50(40,41)44-9-13-18(47-49(37,38)39)17(34)23(46-13)31-12-30-16-20(25)28-11-29-21(16)31/h4,11-13,17-19,23,34-35H,1,5-10H2,2-3H3,(H,26,32)(H,27,36)(H,40,41)(H,42,43)(H2,25,28,29)(H2,37,38,39)/t13-,17-,18-,19?,23-/m1/s1 |
| InChI Key |
POODSGUMUCVRTR-UXYNFSPESA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Fatty Acid Esters |
| Sub Class |
Acyl CoAs |
| Other Descriptors |
- Aromatic Heteropolycyclic Compounds
|
| Substituents |
- 1 Phosphoribosyl Imidazole
- Aminopyrimidine
- Carboxamide Group
- Carboxylic Thioester
- Coenzyme A
- Enone
- Glycosyl Compound
- Imidazole
- Imidazopyrimidine
- Monosaccharide Phosphate
- N Glycosyl Compound
- Organic Hypophosphite
- Organic Phosphite
- Organic Pyrophosphate
- Oxolane
- Pentose Monosaccharide
- Phosphoric Acid Ester
- Purine
- Purine Ribonucleoside 3',5' Bisphosphate
- Pyrimidine
- Saccharide
- Secondary Alcohol
- Secondary Carboxylic Acid Amide
- Thiocarboxylic Acid Ester
|
| Direct Parent |
Acyl CoAs |
| Ontology |
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Lipid biosynthesis, Fatty acid transport
- Membrane integrity/stability
|
| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
|
| Cellular locations |
|
| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|
Not Available
|
| Biological Properties |
| Cellular Locations |
|
| Biofluid Locations |
Not Available
|
| Tissue Location |
Not Available
|
| Pathways |
|
| Normal Concentrations |
|
Not Available |
| Abnormal Concentrations |
|
Not Available |
| Associated Disorders and Diseases |
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB022958 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
388468  |
| KEGG Compound ID |
C00894  |
| BioCyc ID |
ACRYLYL-COA  |
| BiGG ID |
36320  |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB02307  |
| Metagene Link |
HMDB02307  |
| METLIN ID |
446  |
| PubChem Compound |
439340  |
| PDB ID |
Not Available |
| ChEBI ID |
15513  |
| References |
| Synthesis Reference |
Symes, Kenneth Charles; Collier, Simon Andrew; Armitage, Yvonne Christine; Mistry, Rajesh; Baranyai, Robert. Biocatalytic manufacturing of (meth)acrylic esters. PCT Int. Appl. (2007), 40pp. CODEN: PIXXD2 WO 2007039415 A1 20070412 CAN 146:400675 AN 2007:409912 |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
- OMMBID: http://genetics.accessmedicine.com/server-java/Arknoid/amed/mmbid/co_chapters/ch094/ch094_p03.html
|
| Enzymes |
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
| Name: |
Peroxisomal acyl-coenzyme A oxidase 2
|
| Reactions: |
- (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoA + H2O + acceptor = (24R,25R)-3alpha,7alpha,12alpha,24-tetrahydroxy-5beta-cholestan-26- oyl-CoA + reduced acceptor [RN:R07374]
|
| Gene Name: |
ACOX2 |
| Uniprot ID: |
Q99424  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
|
|
|
|
|
|
|
|
| Name: |
2-oxoisovalerate dehydrogenase subunit beta, mitochondrial
|
| Reactions: |
- 3-methyl-2-oxobutanoate + [dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] lipoyllysine = [dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(2-methylpropanoyl)dihydrolipoyllysine + CO2 [RN:R01701]
|
| Gene Name: |
BCKDHB |
| Uniprot ID: |
P21953  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial
|
| Reactions: |
- 3-methyl-2-oxobutanoate + [dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] lipoyllysine = [dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(2-methylpropanoyl)dihydrolipoyllysine + CO2 [RN:R01701]
|
| Gene Name: |
BCKDHA |
| Uniprot ID: |
P12694  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Acyl-CoA desaturase
|
| Reactions: |
- stearoyl-CoA + 2 ferrocytochrome b5 + O2 + 2 H+ = oleoyl-CoA + 2 ferricytochrome b5 + 2 H2O [RN:R02222]
|
| Gene Name: |
SCD |
| Uniprot ID: |
O00767  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
| Name: |
Bile acyl-CoA synthetase
|
| Reactions: |
- (1) ATP + cholate + CoA = AMP + diphosphate + choloyl-CoA [RN:R02794]
- (2) ATP + (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oate + CoA = AMP + diphosphate + (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoyl-CoA [RN:R04580]
|
| Gene Name: |
SLC27A5 |
| Uniprot ID: |
Q9Y2P5  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|