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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-08-12 13:32:54 UTC
Update Date2017-12-07 01:59:47 UTC
HMDB IDHMDB0006807
Secondary Accession Numbers
  • HMDB02125
  • HMDB06807
Metabolite Identification
Common Name3-Hydroxypropionyl-CoA
Description3-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
Synonyms
ValueSource
3-Hydroxypropanoyl coenzymeaHMDB
3-Hydroxypropanoyl-CoAHMDB
3-Hydroxypropanoyl-coenzyme AHMDB
3-Hydroxypropionyl coenzyme AHMDB
Chemical FormulaC24H40N7O18P3S
Average Molecular Weight839.597
Monoisotopic Molecular Weight839.136337737
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 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 Number157786-88-4
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 KeyBERBFZCUSMQABM-UXYNFSPESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentAcyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Ribonucleoside 3'-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Monosaccharide
  • N-acyl-amine
  • Pyrimidine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Primary aromatic amine
  • Fatty amide
  • Imidolactam
  • Phosphoric acid ester
  • Alkyl phosphate
  • Azole
  • Oxolane
  • Heteroaromatic compound
  • Imidazole
  • Carbothioic s-ester
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Amino acid or derivatives
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Alcohol
  • Amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organosulfur compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Primary alcohol
  • Primary amine
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Biochemical process:

    Chemical reaction:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point121.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.35 g/LALOGPS
logP-0.62ALOGPS
logP-7.6ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area383.86 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity178.61 m³·mol⁻¹ChemAxon
Polarizability73.37 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1912000130-f25e6d4a887b423a5c81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0913000000-956da8fcf218cdc33b3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1911000000-f6e89badbdc71bf4cdfbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05x9-8930141670-3060a4d27840ac527e8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-5910210010-20aff099f09bc9db95d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-5900100000-3a8912a3ad1f6fa68a85View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Malonic AciduriaPw000207Pw000207 greyscalePw000207 simpleNot Available
Malonyl-coa decarboxylase deficiencyPw000478Pw000478 greyscalePw000478 simpleNot Available
Methylmalonic Aciduria Due to Cobalamin-Related DisordersPw000208Pw000208 greyscalePw000208 simpleNot Available
Propanoate MetabolismPw000149Pw000149 greyscalePw000149 simpleMap00640
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 IDFDB024093
KNApSAcK IDNot Available
Chemspider ID389623
KEGG Compound IDC05668
BioCyc ID3-HYDROXY-PROPIONYL-COA
BiGG ID46236
Wikipedia LinkNot Available
METLIN ID6497
PubChem Compound440753
PDB IDNot Available
ChEBI ID27762
References
Synthesis ReferenceNot 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 ]
  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 ]
  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 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
EHHADH
Uniprot ID:
Q08426
Molecular weight:
69153.26
Reactions
3-Hydroxypropionyl-CoA → Acrylyl-CoA + Waterdetails
General function:
Involved in catalytic activity
Specific function:
Straight-chain enoyl-CoA thioesters from C4 up to at least C16 are processed, although with decreasing catalytic rate.
Gene Name:
ECHS1
Uniprot ID:
P30084
Molecular weight:
31387.085
Reactions
3-Hydroxypropionyl-CoA → Acrylyl-CoA + Waterdetails
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional subunit.
Gene Name:
HADHA
Uniprot ID:
P40939
Molecular weight:
82998.97
Reactions
3-Hydroxypropionyl-CoA → Acrylyl-CoA + Waterdetails
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes 3-hydroxyisobutyryl-CoA (HIBYL-CoA), a saline catabolite. Has high activity toward isobutyryl-CoA. Could be an isobutyryl-CoA dehydrogenase that functions in valine catabolism. Also hydrolyzes 3-hydroxypropanoyl-CoA.
Gene Name:
HIBCH
Uniprot ID:
Q6NVY1
Molecular weight:
43481.935
Reactions
3-Hydroxypropionyl-CoA + Phosphoric acid + ADP → Hydroxypropionic acid + Coenzyme A + Adenosine triphosphatedetails
Hydroxypropionic acid + Coenzyme A → 3-Hydroxypropionyl-CoA + Waterdetails