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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-12 13:32:54 UTC
Update Date2022-03-07 02:49:33 UTC
HMDB IDHMDB0006807
Secondary Accession Numbers
  • HMDB0002125
  • HMDB02125
  • HMDB06807
Metabolite Identification
Common Name3-Hydroxypropionyl-CoA
Description3-Hydroxypropionyl-CoA, also known as beta-hydroxypropionyl-CoA, belongs to the class of organic compounds known as acyl-CoAs. These are organic compounds containing a coenzyme A substructure linked to an acyl chain. Thus, 3-hydroxypropionyl-CoA is considered to be a fatty ester lipid molecule. 3-Hydroxypropionyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Hydroxypropionyl-CoA is an intermediate in 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
Data?1586455740
Synonyms
ValueSource
3-Hydroxypropanoyl coenzymeaChEBI
3-Hydroxypropionyl coenzyme AChEBI
3-Hydroxypropionyl-CoAChEBI
beta-Hydroxypropionyl-CoAChEBI
b-Hydroxypropionyl-CoAGenerator
Β-hydroxypropionyl-CoAGenerator
3-Hydroxypropanoyl coenzyme AHMDB
3-Hydroxypropanoyl-CoAHMDB
3-Hydroxypropanoyl-coenzyme AHMDB
3-Hydroxypropionyl-coenzyme AHMDB
beta-Hydroxypropionyl-coenzyme AHMDB
Chemical FormulaC24H40N7O18P3S
Average Molecular Weight839.6
Monoisotopic Molecular Weight839.136339644
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-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 Name3-hydroxypropionyl coenzyme A
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=C1N=CN=C2N)[C@@H](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-IEXPHMLFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentAcyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose-5-phosphate
  • Pentose phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Imidolactam
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Tetrahydrofuran
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Carbothioic s-ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Amino acid or derivatives
  • Thiocarboxylic acid or derivatives
  • Sulfenyl compound
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organosulfur compound
  • Organonitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point121.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.35 g/LALOGPS
logP-0.62ALOGPS
logP-6.5ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area383.86 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity178.61 m³·mol⁻¹ChemAxon
Polarizability75.37 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+242.90430932474
DeepCCS[M-H]-241.1830932474
DeepCCS[M-2H]-275.21630932474
DeepCCS[M+Na]+249.23330932474
AllCCS[M+H]+252.432859911
AllCCS[M+H-H2O]+252.832859911
AllCCS[M+NH4]+252.032859911
AllCCS[M+Na]+251.932859911
AllCCS[M-H]-251.932859911
AllCCS[M+Na-2H]-255.932859911
AllCCS[M+HCOO]-260.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxypropionyl-CoACC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCO5702.4Standard polar33892256
3-Hydroxypropionyl-CoACC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCO4277.0Standard non polar33892256
3-Hydroxypropionyl-CoACC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCO6602.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
MSMass Spectrum (Electron Ionization)Not Available2022-08-06Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropionyl-CoA 10V, Positive-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropionyl-CoA 20V, Positive-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropionyl-CoA 40V, Positive-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropionyl-CoA 10V, Negative-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropionyl-CoA 20V, Negative-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropionyl-CoA 40V, Negative-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropionyl-CoA 10V, Positive-QTOFsplash10-0006-0300000090-a82d2d516ca943d72c802021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropionyl-CoA 20V, Positive-QTOFsplash10-000i-1902000020-b39da26a998aa34c50d82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropionyl-CoA 40V, Positive-QTOFsplash10-001i-1209000000-fa0e10752c42179b290b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropionyl-CoA 10V, Negative-QTOFsplash10-000i-0000000190-d665b090f2618519db912021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropionyl-CoA 20V, Negative-QTOFsplash10-000w-9100002850-e526e5730e2eaa7d53722021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropionyl-CoA 40V, Negative-QTOFsplash10-002f-9002304800-0d1446692ec238dd61c42021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024093
KNApSAcK IDNot Available
Chemspider ID10140164
KEGG Compound IDC05668
BioCyc ID3-HYDROXY-PROPIONYL-COA
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11966171
PDB IDNot Available
ChEBI ID27762
Food Biomarker OntologyNot Available
VMH ID3HPCOA
MarkerDB IDNot Available
Good Scents IDNot Available
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 + Phosphate + ADP → Hydroxypropionic acid + Coenzyme A + Adenosine triphosphatedetails
Hydroxypropionic acid + Coenzyme A → 3-Hydroxypropionyl-CoA + Waterdetails