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Human Metabolome Database Version 3.5

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Showing metabocard for 3-Hydroxypropionyl-CoA (HMDB06807)

Record Information
Version 3.5
Creation Date 2008-08-12 07:32:54 -0600
Update Date 2013-02-08 17:15:21 -0700
HMDB ID HMDB06807
Secondary Accession Numbers
  • HMDB02125
Metabolite Identification
Common Name 3-Hydroxypropionyl-CoA
Description 3-Hydroxypropionyl-CoA is an intermediate in b-Alanine (beta-alanine) metabolism. It can be produced from 3-hydroxypropanoic acid via the enzyme 3-hydroxyisobutyryl-Coenzyme A hydrolase (EC:3.1.2.4) or it can be generated from acrylyl CoA via the enzyme enoyl-CoA hydratase (EC:4.2.1.17). Acrylyl CoA is derived from propionyl CoA.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3-Hydroxypropanoyl coenzymeA
  2. 3-Hydroxypropanoyl-CoA
  3. 3-Hydroxypropanoyl-Coenzyme A
  4. 3-Hydroxypropionyl coenzyme A
Chemical Formula C24H40N7O18P3S
Average Molecular Weight 839.597
Monoisotopic Molecular Weight 839.136337737
IUPAC Name {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxypropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)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-3-{[2-({2-[(3-hydroxypropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number 157786-88-4
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)CCO
InChI Identifier InChI=1S/C24H40N7O18P3S/c1-24(2,19(36)22(37)27-5-3-14(33)26-6-8-53-15(34)4-7-32)10-46-52(43,44)49-51(41,42)45-9-13-18(48-50(38,39)40)17(35)23(47-13)31-12-30-16-20(25)28-11-29-21(16)31/h11-13,17-19,23,32,35-36H,3-10H2,1-2H3,(H,26,33)(H,27,37)(H,41,42)(H,43,44)(H2,25,28,29)(H2,38,39,40)/t13-,17-,18-,19?,23-/m1/s1
InChI Key BERBFZCUSMQABM-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
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Primary Alcohol
  • 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 121.5 °C 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 4.35 g/L ALOGPS
LogP -0.62 ALOGPS
LogP -7.6 ChemAxon
LogS -2.29 ALOGPS
pKa (strongest acidic) 0.83 ChemAxon
pKa (strongest basic) 4.95 ChemAxon
Hydrogen Acceptor Count 18 ChemAxon
Hydrogen Donor Count 10 ChemAxon
Polar Surface Area 383.86 A2 ChemAxon
Rotatable Bond Count 22 ChemAxon
Refractivity 178.61 ChemAxon
Polarizability 73.37 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
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB024093
KNApSAcK ID Not Available
Chemspider ID 389623 Link_out
KEGG Compound ID C05668 Link_out
BioCyc ID 3-HYDROXY-PROPIONYL-COA Link_out
BiGG ID 46236 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB06807 Link_out
Metagene Link HMDB06807 Link_out
METLIN ID 6497 Link_out
PubChem Compound 440753 Link_out
PDB ID Not Available
ChEBI ID 27762 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Brass EP, Tahiliani AG, Allen RH, Stabler SP: Coenzyme A metabolism in vitamin B-12-deficient rats. J Nutr. 1990 Mar;120(3):290-7. Pubmed: 2319347 Link_out
  2. DeBuysere MS, Olson MS: The analysis of acyl-coenzyme A derivatives by reverse-phase high-performance liquid chromatography. Anal Biochem. 1983 Sep;133(2):373-9. Pubmed: 6638498 Link_out
  3. Bucholtz ML, Light RJ: Acetylation of 13-sophorosyloxydocosanoic acid by an acetyltransferase purified from Candida bogoriensis. J Biol Chem. 1976 Jan 25;251(2):424-30. Pubmed: 1245481 Link_out
Enzymes
Name: Peroxisomal bifunctional enzyme
Reactions:
  • (3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA [RN:R04100]
Gene Name: EHHADH
Uniprot ID: Q08426 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Enoyl-CoA hydratase, mitochondrial
Reactions:
  • (3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H2O [RN:R02685 R07314]
Gene Name: ECHS1
Uniprot ID: P30084 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Trifunctional enzyme subunit alpha, mitochondrial
Reactions:
  • (3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H2O [RN:R02685 R07314]
Gene Name: HADHA
Uniprot ID: P40939 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3-hydroxyisobutyryl-CoA hydrolase, mitochondrial
Reactions:
  • 3-hydroxy-2-methylpropanoyl-CoA + H2O = CoA + 3-hydroxy-2-methylpropanoate [RN:R03352]
Gene Name: HIBCH
Uniprot ID: Q6NVY1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA