Human Metabolome Database Version 3.5

Showing metabocard for Acrylyl-CoA (HMDB02307)

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
  • HMDB06507
Metabolite Identification
Common Name Acrylyl-CoA
Description Acrylyl-CoA is involved in alternative pathways of propionate metabolism.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Acryloyl coenzyme A
  2. Acryloyl-CoA
  3. Acryloyl-Coenzyme A
  4. Acrylyl coenzyme A
  5. Acrylyl-CoA
  6. Acrylyl-Coenzyme A
  7. CoA S-2-propenoate
  8. CoA S-2-propenoic acid
  9. CoA S-acrylate
  10. Coenzyme A S-2-propenoate
  11. Coenzyme A S-2-propenoic acid
  12. Coenzyme A S-acrylate
  13. Propenoyl-coa
  14. 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
  • Endogenous
  • Food
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
  • Extracellular
  • Membrane
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
Property Value Source
Water Solubility 4.22 g/L ALOGPS
LogP -0.49 ALOGPS
LogP -6 ChemAxon
LogS -2.29 ALOGPS
pKa (strongest acidic) 0.83 ChemAxon
pKa (strongest basic) 4.95 ChemAxon
Hydrogen Acceptor Count 17 ChemAxon
Hydrogen Donor Count 9 ChemAxon
Polar Surface Area 363.63 A2 ChemAxon
Rotatable Bond Count 21 ChemAxon
Refractivity 176.86 ChemAxon
Polarizability 71.4 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Propanoate Metabolism SMP00016 map00640 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite 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 Link_out
KEGG Compound ID C00894 Link_out
BioCyc ID ACRYLYL-COA Link_out
BiGG ID 36320 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB02307 Link_out
Metagene Link HMDB02307 Link_out
METLIN ID 446 Link_out
PubChem Compound 439340 Link_out
PDB ID Not Available
ChEBI ID 15513 Link_out
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
  1. OMMBID: http://genetics.accessmedicine.com/server-java/Arknoid/amed/mmbid/co_chapters/ch094/ch094_p03.html Link_out

Enzymes

Show all enzymes and transporters Important Only showing the first 50 enzymes. There are 113 enzymes in total.

Name: 3-ketoacyl-CoA thiolase, mitochondrial
Reactions: Not Available
Gene Name: ACAA2
Uniprot ID: P42765 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3-ketoacyl-CoA thiolase, peroxisomal
Reactions: Not Available
Gene Name: ACAA1
Uniprot ID: P09110 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Trifunctional enzyme subunit beta, mitochondrial
Reactions: Not Available
Gene Name: HADHB
Uniprot ID: P55084 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial
Reactions: Not Available
Gene Name: ALDH6A1
Uniprot ID: Q02252 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Long-chain specific acyl-CoA dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: ACADL
Uniprot ID: P28330 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Short-chain specific acyl-CoA dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: ACADS
Uniprot ID: P16219 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Medium-chain specific acyl-CoA dehydrogenase, mitochondrial
Reactions:
Propionyl-CoA + FAD unknown FADH + Acrylyl-CoA details
Electron-transferring flavoprotein + Propionyl-CoA unknown Reduced electron-transferring flavoprotein + Acrylyl-CoA details
Gene Name: ACADM
Uniprot ID: P11310 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisomal acyl-coenzyme A oxidase 1
Reactions: Not Available
Gene Name: ACOX1
Uniprot ID: Q15067 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisomal acyl-coenzyme A oxidase 2
Reactions: Not Available
Gene Name: ACOX2
Uniprot ID: Q99424 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Isovaleryl-CoA dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: IVD
Uniprot ID: P26440 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisomal acyl-coenzyme A oxidase 3
Reactions: Not Available
Gene Name: ACOX3
Uniprot ID: O15254 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glutaryl-CoA dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: GCDH
Uniprot ID: Q92947 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hepatic triacylglycerol lipase
Reactions: Not Available
Gene Name: LIPC
Uniprot ID: P11150 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol O-acyltransferase 1
Reactions: Not Available
Gene Name: DGAT1
Uniprot ID: O75907 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial
Reactions: Not Available
Gene Name: BCKDHB
Uniprot ID: P21953 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial
Reactions: Not Available
Gene Name: BCKDHA
Uniprot ID: P12694 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-CoA desaturase
Reactions: Not Available
Gene Name: SCD
Uniprot ID: O00767 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisomal bifunctional enzyme
Reactions:
3-Hydroxypropionyl-CoA unknown Acrylyl-CoA + Water details
Gene Name: EHHADH
Uniprot ID: Q08426 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Enoyl-CoA hydratase, mitochondrial
Reactions:
3-Hydroxypropionyl-CoA unknown Acrylyl-CoA + Water details
Gene Name: ECHS1
Uniprot ID: P30084 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Trifunctional enzyme subunit alpha, mitochondrial
Reactions:
3-Hydroxypropionyl-CoA unknown Acrylyl-CoA + Water details
Gene Name: HADHA
Uniprot ID: P40939 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sterol O-acyltransferase 2
Reactions: Not Available
Gene Name: SOAT2
Uniprot ID: O75908 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sterol O-acyltransferase 1
Reactions: Not Available
Gene Name: SOAT1
Uniprot ID: P35610 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bile acid-CoA:amino acid N-acyltransferase
Reactions: Not Available
Gene Name: BAAT
Uniprot ID: Q14032 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Long-chain-fatty-acid--CoA ligase 4
Reactions: Not Available
Gene Name: ACSL4
Uniprot ID: O60488 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Long-chain-fatty-acid--CoA ligase 1
Reactions: Not Available
Gene Name: ACSL1
Uniprot ID: P33121 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Long-chain-fatty-acid--CoA ligase 6
Reactions: Not Available
Gene Name: ACSL6
Uniprot ID: Q9UKU0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Long-chain-fatty-acid--CoA ligase 5
Reactions: Not Available
Gene Name: ACSL5
Uniprot ID: Q9ULC5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Long-chain-fatty-acid--CoA ligase 3
Reactions: Not Available
Gene Name: ACSL3
Uniprot ID: O95573 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycerol-3-phosphate acyltransferase 1, mitochondrial
Reactions: Not Available
Gene Name: GPAM
Uniprot ID: Q9HCL2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Trans-2-enoyl-CoA reductase, mitochondrial
Reactions: Not Available
Gene Name: MECR
Uniprot ID: Q9BV79 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisomal trans-2-enoyl-CoA reductase
Reactions: Not Available
Gene Name: PECR
Uniprot ID: Q9BY49 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic acyl coenzyme A thioester hydrolase
Reactions: Not Available
Gene Name: ACOT7
Uniprot ID: O00154 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-coenzyme A thioesterase 2, mitochondrial
Reactions: Not Available
Gene Name: ACOT2
Uniprot ID: P49753 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-coenzyme A thioesterase 4
Reactions: Not Available
Gene Name: ACOT4
Uniprot ID: Q8N9L9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-coenzyme A thioesterase 8
Reactions: Not Available
Gene Name: ACOT8
Uniprot ID: O14734 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dihydroxyacetone phosphate acyltransferase
Reactions: Not Available
Gene Name: GNPAT
Uniprot ID: O15228 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase gamma
Reactions: Not Available
Gene Name: AGPAT3
Uniprot ID: Q9NRZ7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase beta
Reactions: Not Available
Gene Name: AGPAT2
Uniprot ID: O15120 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase alpha
Reactions: Not Available
Gene Name: AGPAT1
Uniprot ID: Q99943 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Short/branched chain specific acyl-CoA dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: ACADSB
Uniprot ID: P45954 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Very long-chain acyl-CoA synthetase
Reactions: Not Available
Gene Name: SLC27A2
Uniprot ID: O14975 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisome proliferator-activated receptor gamma
Reactions: Not Available
Gene Name: PPARG
Uniprot ID: P37231 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisome proliferator-activated receptor alpha
Reactions: Not Available
Gene Name: PPARA
Uniprot ID: Q07869 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisome proliferator-activated receptor delta
Reactions: Not Available
Gene Name: PPARD
Uniprot ID: Q03181 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-CoA-binding protein
Reactions: Not Available
Gene Name: DBI
Uniprot ID: P07108 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fatty acid-binding protein, heart
Reactions: Not Available
Gene Name: FABP3
Uniprot ID: P05413 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase epsilon
Reactions: Not Available
Gene Name: AGPAT5
Uniprot ID: Q9NUQ2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bile acyl-CoA synthetase
Reactions: Not Available
Gene Name: SLC27A5
Uniprot ID: Q9Y2P5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrial
Reactions: Not Available
Gene Name: DBT
Uniprot ID: P11182 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-acylglycerol O-acyltransferase 2
Reactions: Not Available
Gene Name: MOGAT2
Uniprot ID: Q3SYC2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Name: Long-chain fatty acid transport protein 1
Reactions: Not Available
Gene Name: SLC27A1
Uniprot ID: Q6PCB7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA