Record Information
Version3.6
Creation Date2006-05-22 14:17:47 UTC
Update Date2013-02-09 00:11:43 UTC
HMDB IDHMDB02307
Secondary Accession Numbers
  • HMDB06507
Metabolite Identification
Common NameAcrylyl-CoA
DescriptionAcrylyl-CoA is involved in alternative pathways of propionate metabolism.
Structure
Thumb
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 FormulaC24H38N7O17P3S
Average Molecular Weight821.582
Monoisotopic Molecular Weight821.125773051
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 Number5776-58-9
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 KeyPOODSGUMUCVRTR-UXYNFSPESA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acid Esters
Sub ClassAcyl 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 ParentAcyl CoAs
Ontology
StatusExpected 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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility4.22 g/LALOGPS
logP-0.49ALOGPS
logP-6ChemAxon
logS-2.3ALOGPS
pKa (strongest acidic)0.83ChemAxon
pKa (strongest basic)4.95ChemAxon
physiological charge-4ChemAxon
hydrogen acceptor count17ChemAxon
hydrogen donor count9ChemAxon
polar surface area363.63ChemAxon
rotatable bond count21ChemAxon
refractivity176.86ChemAxon
polarizability71.4ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Propanoate MetabolismSMP00016map00640
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022958
KNApSAcK IDNot Available
Chemspider ID388468
KEGG Compound IDC00894
BioCyc IDACRYLYL-COA
BiGG ID36320
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02307
Metagene LinkHMDB02307
METLIN ID446
PubChem Compound439340
PDB IDNot Available
ChEBI ID15513
References
Synthesis ReferenceSymes, 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

Only showing the first 50 proteins. There are 114 proteins in total.

Enzymes

Gene Name:
ACAA1
Uniprot ID:
P09110
Gene Name:
ACADM
Uniprot ID:
P11310
Reactions
Propionyl-CoA + FAD unknown FADH + Acrylyl-CoAdetails
Electron-transferring flavoprotein + Propionyl-CoA unknown Reduced electron-transferring flavoprotein + Acrylyl-CoAdetails
Gene Name:
ACOX3
Uniprot ID:
O15254
Gene Name:
LIPC
Uniprot ID:
P11150
Gene Name:
DGAT1
Uniprot ID:
O75907
Gene Name:
SCD
Uniprot ID:
O00767
Gene Name:
EHHADH
Uniprot ID:
Q08426
Reactions
3-Hydroxypropionyl-CoA unknown Acrylyl-CoA + Waterdetails
Gene Name:
ECHS1
Uniprot ID:
P30084
Reactions
3-Hydroxypropionyl-CoA unknown Acrylyl-CoA + Waterdetails
Gene Name:
HADHA
Uniprot ID:
P40939
Reactions
3-Hydroxypropionyl-CoA unknown Acrylyl-CoA + Waterdetails
Gene Name:
SOAT2
Uniprot ID:
O75908
Gene Name:
SOAT1
Uniprot ID:
P35610
Gene Name:
ACSL4
Uniprot ID:
O60488
Gene Name:
ACSL1
Uniprot ID:
P33121
Gene Name:
ACSL6
Uniprot ID:
Q9UKU0
Gene Name:
ACSL5
Uniprot ID:
Q9ULC5
Gene Name:
ACSL3
Uniprot ID:
O95573
Gene Name:
ACOT4
Uniprot ID:
Q8N9L9
Gene Name:
ACOT8
Uniprot ID:
O14734
Gene Name:
SLC27A2
Uniprot ID:
O14975
Gene Name:
DBI
Uniprot ID:
P07108
Gene Name:
FABP3
Uniprot ID:
P05413
Gene Name:
SLC27A5
Uniprot ID:
Q9Y2P5
Gene Name:
MOGAT2
Uniprot ID:
Q3SYC2

Transporters

Only showing the first 50 proteins. There are 114 proteins in total.