| Record Information |
| Version |
3.5 |
| Creation Date |
2006-08-13 09:25:23 -0600 |
| Update Date |
2013-02-08 17:13:08 -0700 |
| HMDB ID |
HMDB04257 |
| Secondary Accession Numbers |
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| Metabolite Identification |
| Common Name |
3Z-dodecenoyl-CoA |
| Description |
3Z-dodecenoyl-CoA is an intermediate in fatty acid metabolism. 3Z-dodecenoyl-CoA is converted from trans-Dodec-2-enoyl-CoA via acyl-CoA oxidase, acyl-CoA dehydrogenase, and long-chain-acyl-CoA dehydrogenase [EC:1.3.3.6, 1.3.99.3, 1.3.99.13]. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- (3Z)-dodec-3-enoyl-CoA
- (3Z)-dodec-3-enoyl-Coenzyme A
- S-[2-[3-[[(2R)-4-[[[(2R,3R,5R)-5-(6-Aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] (Z)-dodec-3-enethioate
- S-[2-[3-[[(2R)-4-[[[(2R,3R,5R)-5-(6-Aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] (Z)-dodec-3-enethioic acid
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| Chemical Formula |
C33H56N7O17P3S |
| Average Molecular Weight |
947.821 |
| Monoisotopic Molecular Weight |
947.266623627 |
| IUPAC Name |
{[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-{[2-({2-[(3Z)-dodec-3-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid |
| Traditional IUPAC Name |
[(2R,3R,5R)-5-(6-aminopurin-9-yl)-2-[({[(3R)-3-{[2-({2-[(3Z)-dodec-3-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxyphosphonic acid |
| CAS Registry Number |
2152-91-2 |
| SMILES |
CCCCCCCC\C=C/CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12 |
| InChI Identifier |
InChI=1S/C33H56N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-24(42)61-17-16-35-23(41)14-15-36-31(45)28(44)33(2,3)19-54-60(51,52)57-59(49,50)53-18-22-27(56-58(46,47)48)26(43)32(55-22)40-21-39-25-29(34)37-20-38-30(25)40/h11-12,20-22,26-28,32,43-44H,4-10,13-19H2,1-3H3,(H,35,41)(H,36,45)(H,49,50)(H,51,52)(H2,34,37,38)(H2,46,47,48)/b12-11-/t22-,26?,27+,28+,32-/m1/s1 |
| InChI Key |
XEMIVMKTVGRFTD-BFJLDWRUSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Fatty Acid Esters |
| Sub Class |
Acyl CoAs |
| Other Descriptors |
- Aromatic Heteropolycyclic Compounds
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| Substituents |
- 1 Phosphoribosyl Imidazole
- Aminopyrimidine
- Carboxamide Group
- Carboxylic Thioester
- Coenzyme A
- 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
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| Direct Parent |
Acyl CoAs |
| Ontology |
| Status |
Expected and Not Quantified |
| Origin |
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| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Lipid biosynthesis, Fatty acid transport
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
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| 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 |
-3.264 |
Not Available |
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| Predicted Properties |
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| Spectra |
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Not Available
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| Biological Properties |
| Cellular Locations |
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| Biofluid Locations |
Not Available
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| Tissue Location |
Not Available
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| Pathways |
Not Available
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| Normal Concentrations |
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Not Available |
| Abnormal Concentrations |
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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 |
FDB023353 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
17220833  |
| KEGG Compound ID |
C02944  |
| BioCyc ID |
CPD-7221  |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB04257  |
| Metagene Link |
HMDB04257  |
| METLIN ID |
Not Available |
| PubChem Compound |
16061154  |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
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| General References |
Not Available |
| Enzymes |
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| Name: |
Peroxisomal acyl-coenzyme A oxidase 2
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| 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]
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| Gene Name: |
ACOX2 |
| Uniprot ID: |
Q99424  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
2-oxoisovalerate dehydrogenase subunit beta, mitochondrial
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| Reactions: |
- 3-methyl-2-oxobutanoate + [dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] lipoyllysine = [dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(2-methylpropanoyl)dihydrolipoyllysine + CO2 [RN:R01701]
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| Gene Name: |
BCKDHB |
| Uniprot ID: |
P21953  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial
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| Reactions: |
- 3-methyl-2-oxobutanoate + [dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] lipoyllysine = [dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(2-methylpropanoyl)dihydrolipoyllysine + CO2 [RN:R01701]
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| Gene Name: |
BCKDHA |
| Uniprot ID: |
P12694  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Acyl-CoA desaturase
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| Reactions: |
- stearoyl-CoA + 2 ferrocytochrome b5 + O2 + 2 H+ = oleoyl-CoA + 2 ferricytochrome b5 + 2 H2O [RN:R02222]
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| Gene Name: |
SCD |
| Uniprot ID: |
O00767  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Bile acyl-CoA synthetase
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| 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]
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| Gene Name: |
SLC27A5 |
| Uniprot ID: |
Q9Y2P5  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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