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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 14:59:12 UTC
HMDB IDHMDB0001373
Secondary Accession Numbers
  • HMDB01373
Metabolite Identification
Common NameDephospho-CoA
DescriptionDephospho-CoA, also known as 3'-dephospho-CoA, belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribonucleosides with a diphosphate group linked to the ribose moiety. Thus, dephospho-CoA is considered to be a fatty ester lipid molecule. Dephospho-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, dephospho-CoA has been detected, but not quantified in, several different foods, such as wild leeks, summer savouries, arctic blackberries, biscuits, and persimmons. This could make dephospho-CoA a potential biomarker for the consumption of these foods. Dephospho-CoA is an intermediate in pantothenate and CoA biosynthesis. It is a substrate for bifunctional coenzyme A synthase which contains the dephospho-CoA kinase (EC 2.7.1.24). This enzyme catalyzes the final step in CoA biosynthesis: the phosphorylation of the 3'-hydroxyl group of ribose using ATP as a phosphate donor. The reaction is ATP + 3'-dephospho-CoA = ADP + CoA.
Structure
Data?1588363134
Synonyms
ValueSource
Dephospho-CoAChEBI
Dephosphocoenzyme AChEBI
3'-Dephospho-CoAKegg
Dephospho CoAMeSH
DpCoAMeSH
2'-(5''-Triphosphoribosyl)-3'-dephospho-CoAMeSH
3'-Desphospho-coenzyme AMeSH
Desphospho-CoAMeSH
3'-Dephospho-coenzyme AHMDB
3'-Dephosphocoenzyme AHMDB
3'-O-Dephosphonocoenzyme AHMDB
3’-Dephospho-CoAHMDB
3’-Dephospho-coenzyme AHMDB
3’-Dephosphocoenzyme AHMDB
3’-O-Dephosphonocoenzyme AHMDB
Dephospho-coenzyme AHMDB
Chemical FormulaC21H35N7O13P2S
Average Molecular Weight687.554
Monoisotopic Molecular Weight687.148877955
IUPAC Name[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphinic acid
Traditional Name3'-dephospho-coa
CAS Registry Number3633-59-8
SMILES
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCS
InChI Identifier
InChI=1S/C21H35N7O13P2S/c1-21(2,16(32)19(33)24-4-3-12(29)23-5-6-44)8-39-43(36,37)41-42(34,35)38-7-11-14(30)15(31)20(40-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-32,44H,3-8H2,1-2H3,(H,23,29)(H,24,33)(H,34,35)(H,36,37)(H2,22,25,26)/t11-,14-,15-,16+,20-/m1/s1
InChI KeyKDTSHFARGAKYJN-IBOSZNHHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside diphosphates
Alternative Parents
Substituents
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Pentose monosaccharide
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Fatty amide
  • Imidolactam
  • Monosaccharide
  • Fatty acyl
  • Phosphoric acid ester
  • Alkyl phosphate
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Tetrahydrofuran
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Alkylthiol
  • Oxacycle
  • Azacycle
  • Organic oxide
  • Organooxygen compound
  • Organosulfur compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organonitrogen compound
  • Primary amine
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available232.511http://allccs.zhulab.cn/database/detail?ID=AllCCS00000121
[M+H]+Not Available239.53http://allccs.zhulab.cn/database/detail?ID=AllCCS00000121
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.56 g/LALOGPS
logP-0.98ALOGPS
logP-5.3ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area300.03 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity151.87 m³·mol⁻¹ChemAxon
Polarizability63.64 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]+221.82230932474
DeepCCS[M-H]-219.92730932474
DeepCCS[M-2H]-253.42130932474
DeepCCS[M+Na]+227.630932474
AllCCS[M+H]+233.932859911
AllCCS[M+H-H2O]+233.632859911
AllCCS[M+NH4]+234.232859911
AllCCS[M+Na]+234.332859911
AllCCS[M-H]-232.332859911
AllCCS[M+Na-2H]-235.232859911
AllCCS[M+HCOO]-238.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dephospho-CoACC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCS5124.6Standard polar33892256
Dephospho-CoACC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCS3583.0Standard non polar33892256
Dephospho-CoACC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCS5740.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_2_15) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dephospho-CoA GC-MS (TMS_2_16) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Dephospho-CoA 30V, Negative-QTOFsplash10-052r-3019602000-8f7d5837950327bad2692021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dephospho-CoA 30V, Positive-QTOFsplash10-000i-0010009000-a1396569e10326789a1c2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dephospho-CoA 10V, Positive-QTOFsplash10-000i-2930102000-19d2796dee5d14788e392015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dephospho-CoA 20V, Positive-QTOFsplash10-000i-3930000000-d4541feacee9a6c7a4e32015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dephospho-CoA 40V, Positive-QTOFsplash10-000i-4900000000-1307cbce80b215d981b92015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dephospho-CoA 10V, Negative-QTOFsplash10-0040-2910618000-58e100b1447a771ecd7c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dephospho-CoA 20V, Negative-QTOFsplash10-001i-1910200000-ba57f132dee9798389fa2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dephospho-CoA 40V, Negative-QTOFsplash10-0a7i-3900000000-d382c7ac6874be7ea1512015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dephospho-CoA 10V, Negative-QTOFsplash10-000i-0000009000-6bb1727ae8d28e18aad42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dephospho-CoA 20V, Negative-QTOFsplash10-001i-2900023000-137fd3830c40fcb18b8f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dephospho-CoA 40V, Negative-QTOFsplash10-05r0-4823906000-d707e02b69f32a1d64dd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dephospho-CoA 10V, Positive-QTOFsplash10-000i-0800009000-9da226b219deabf5a54d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dephospho-CoA 20V, Positive-QTOFsplash10-01p9-3960003000-62455c2483de897db0c62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dephospho-CoA 40V, Positive-QTOFsplash10-03di-1190000000-82c68976d04b3fab53ee2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Lysosome
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 IDDB03170
Phenol Explorer Compound IDNot Available
FooDB IDFDB022585
KNApSAcK IDC00007257
Chemspider ID392407
KEGG Compound IDC00882
BioCyc IDDEPHOSPHO-COA
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound444485
PDB IDNot Available
ChEBI ID15468
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Haugen HF, Skrede S: Nucleotide pyrophosphatase and phosphodiesterase I. Demonstration of activity in normal serum, and an increase in cholestatic liver disease. Scand J Gastroenterol. 1976;11(2):121-7. [PubMed:4880 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
Gene Name:
ENPP1
Uniprot ID:
P22413
Molecular weight:
104923.58
Reactions
Dephospho-CoA + Water → Pantetheine 4'-phosphate + Adenosine monophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Cleaves a variety of phosphodiester and phosphosulfate bonds including deoxynucleotides, nucleotide sugars, and NAD (By similarity).
Gene Name:
ENPP3
Uniprot ID:
O14638
Molecular weight:
100123.54
Reactions
Dephospho-CoA + Water → Pantetheine 4'-phosphate + Adenosine monophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Bifunctional enzyme that catalyzes the fourth and fifth sequential steps of CoA biosynthetic pathway. The fourth reaction is catalyzed by the phosphopantetheine adenylyltransferase, coded by the coaD domain; the fifth reaction is catalyzed by the dephospho-CoA kinase, coded by the coaE domain. May act as a point of CoA biosynthesis regulation.
Gene Name:
COASY
Uniprot ID:
Q13057
Molecular weight:
62328.245
Reactions
Adenosine triphosphate + Pantetheine 4'-phosphate → Pyrophosphate + Dephospho-CoAdetails
Adenosine triphosphate + Dephospho-CoA → ADP + Coenzyme Adetails