Showing metabocard for 3-Phosphoglyceric acid (BMDB0000807)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (11) Show 11 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:36:52 UTC
Update Date2020-05-21 16:29:05 UTC
BMDB IDBMDB0000807
Secondary Accession Numbers
  • BMDB00807
Metabolite Identification
Common Name3-Phosphoglyceric acid
Description3-Phosphoglyceric acid, also known as glycerate 3-phosphate or 3-PG, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. 3-Phosphoglyceric acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Phosphoglyceric acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-(Dihydrogen phosphate)glycerateChEBI
3-(Dihydrogen phosphate)glyceric acidChEBI
3-PhosphoglycerateChEBI
DL-Glycerate 3-phosphateChEBI
Glycerate 3-phosphateChEBI
Glycerate 3-phosphatesChEBI
Glyceric acid 3-phosphateChEBI
3-(Dihydrogen phosphoric acid)glyceric acidGenerator
DL-Glyceric acid 3-phosphoric acidGenerator
Glyceric acid 3-phosphoric acidGenerator
Glyceric acid 3-phosphatesGenerator
3-GlycerophosphorateHMDB
3-Glycerophosphoric acidHMDB
3-p-D-GlycerateHMDB
3-p-GlycerateHMDB
3-PGHMDB
3-PGAHMDB
3-Phospho-(R)-glycerateHMDB
3-Phospho-D-glycerateHMDB
3-Phospho-glycerateHMDB
3-Phospho-glyceric acidHMDB
D-(-)-3-Phosphoglyceric acidHMDB
D-Glycerate 3-phosphateHMDB
G3PHMDB
Glycerate-3-pHMDB
PhosphoglycerateHMDB
3-Phosphoglycerate, trisodium saltHMDB
3-Phosphoglycerate, (R)-isomerHMDB
3-Phosphoglycerate, monosodium saltHMDB
Chemical FormulaC3H7O7P
Average Molecular Weight186.0572
Monoisotopic Molecular Weight185.99293909
IUPAC Name2-hydroxy-3-(phosphonooxy)propanoic acid
Traditional Namephosphoglycerate
CAS Registry Number820-11-1
SMILES
OC(COP(O)(O)=O)C(O)=O
InChI Identifier
InChI=1S/C3H7O7P/c4-2(3(5)6)1-10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)
InChI KeyOSJPPGNTCRNQQC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Glyceric_acid
  • Monoalkyl phosphate
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.3ALOGPS
logP-1.6ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)1.3ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.26 m³·mol⁻¹ChemAxon
Polarizability13.29 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0974000000-41479250991be9cc1e07View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0974000000-41479250991be9cc1e07View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9200000000-2d6f0050126bbc72d771View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fu-9081000000-487a9a33cdad68046ff3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-002k-9300000000-4fafb3c93719c5a41327View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-004j-9000000000-c6bb9644e70a338c03beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-004i-9000000000-9d164579c98406ad7c88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4i-0900000000-cea59554251398a27835View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-0900000000-8a976aaa2f56f074d975View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a5c-9500000000-4bd264fcf029200c55c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9100000000-1a020681f04042ff6966View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-cea59554251398a27835View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0900000000-8a976aaa2f56f074d975View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a5c-9600000000-4bd264fcf029200c55c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9100000000-1a020681f04042ff6966View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0005-8900000000-bd4e0c8adef56968d87aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004i-9100000000-abd08e7a88ff6e65bc4bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-002b-9000000000-f8afa9e495e0f6c94717View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004i-9200000000-30ac9f237fd5b07a8ad8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004j-9000000000-623d31045a6d2723a66bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0005-9800000000-592cc43b2d6718b5e805View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-75f21a1b3e228e0af7f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-3900000000-9d9dc94243143123d53bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kv-8900000000-b21c05dfded763ce62a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-c460ca316484eef90129View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-5900000000-653e5055531f19df4952View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-15195031d70847a75881View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-59550676899d259aeab5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004j-9000000000-0b41dc890757740bbb51View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Liver
  • Milk
  • Placenta
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000807
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022255
KNApSAcK IDC00007286
Chemspider ID704
KEGG Compound IDC00597
BioCyc IDNot Available
BiGG ID34230
Wikipedia Link3-Phosphoglyceric_acid
METLIN ID150
PubChem Compound724
PDB IDNot Available
ChEBI ID17050
References
Synthesis ReferenceJakoby, Wm. B.; Brummond, Dewey O.; Ochoa, Severo. Formation of 3-phosphoglyceric acid by carbon dioxide fixation with spinach-leaf enzymes. Journal of Biological Chemistry (1956), 218 811-22.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  2. Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. [PubMed:26686724 ]

Enzymes

Enzyme Details
1. Phosphoglycerate mutase 2
General function:
Carbohydrate transport and metabolism
Specific function:
Interconversion of 3- and 2-phosphoglycerate with 2,3-bisphosphoglycerate as the primer of the reaction. Can also catalyze the reaction of EC 5.4.2.4 (synthase), but with a reduced activity.
Gene Name:
PGAM2
Uniprot ID:
Q32KV0
Molecular weight:
28685.0
Reactions
3-Phosphoglyceric acid → 2-Phospho-D-glyceric aciddetails
Enzyme Details
2. Bisphosphoglycerate mutase
General function:
Carbohydrate transport and metabolism
Specific function:
Plays a major role in regulating hemoglobin oxygen affinity by controlling the levels of its allosteric effector 2,3-bisphosphoglycerate (2,3-BPG). Also exhibits mutase (EC 5.4.2.11) activity.
Gene Name:
BPGM
Uniprot ID:
Q3T014
Molecular weight:
30061.0
Enzyme Details
3. Phosphoglycerate mutase 1
General function:
Carbohydrate transport and metabolism
Specific function:
Interconversion of 3- and 2-phosphoglycerate with 2,3-bisphosphoglycerate as the primer of the reaction. Can also catalyze the reaction of EC 5.4.2.4 (synthase), but with a reduced activity.
Gene Name:
PGAM1
Uniprot ID:
Q3SZ62
Molecular weight:
28852.0
Reactions
2,3-Diphosphoglyceric acid + Water → 3-Phosphoglyceric acid + Hydrogen phosphatedetails
Enzyme Details
4. D-3-phosphoglycerate dehydrogenase
General function:
Coenzyme transport and metabolism
Specific function:
Catalyzes the reversible oxidation of 3-phospho-D-glycerate to 3-phosphonooxypyruvate, the first step of the phosphorylated L-serine biosynthesis pathway. Also catalyzes the reversible oxidation of 2-hydroxyglutarate to 2-oxoglutarate and the reversible oxidation of (S)-malate to oxaloacetate.
Gene Name:
PHGDH
Uniprot ID:
Q5EAD2
Molecular weight:
56452.0
Reactions
3-Phosphoglyceric acid + NAD → Phosphohydroxypyruvic acid + NADHdetails
Enzyme Details
5. Glycerate kinase
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
GLYCTK
Uniprot ID:
Q2KJF7
Molecular weight:
54720.0
Reactions
3-Phosphoglyceric acid + Adenosine triphosphate → Glyceric acid + ADPdetails
Glyceric acid + Adenosine triphosphate → 3-Phosphoglyceric acid + ADPdetails
Enzyme Details
6. Phosphoglycerate kinase
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
PGK1
Uniprot ID:
Q58DJ6
Molecular weight:
23387.0
Enzyme Details
7. Phosphoglycerate kinase 1
General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes one of the two ATP producing reactions in the glycolytic pathway via the reversible conversion of 1,3-diphosphoglycerate to 3-phosphoglycerate. In addition to its role as a glycolytic enzyme, it seems that PGK-1 acts as a polymerase alpha cofactor protein (primer recognition protein). May play a role in sperm motility.
Gene Name:
PGK1
Uniprot ID:
Q3T0P6
Molecular weight:
44538.0
Reactions
Glyceric acid 1,3-biphosphate + ADP → 3-Phosphoglyceric acid + Adenosine triphosphatedetails
Enzyme Details
8. Phosphoglycerate kinase
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
PGK2
Uniprot ID:
Q32KN6
Molecular weight:
44758.0
Enzyme Details
9. Pantothenate kinase 3
General function:
Involved in ATP binding
Specific function:
Plays a role in the physiological regulation of coenzyme A (CoA) levels.
Gene Name:
PANK3
Uniprot ID:
Q08DA5
Molecular weight:
41117.0
Reactions
3-Phosphoglyceric acid + Adenosine triphosphate → Glyceric acid 1,3-biphosphate + ADPdetails
Enzyme Details
10. Phosphoglycerate kinase
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q862Q5
Molecular weight:
19072.0
Enzyme Details
11. PGM2L1 protein
General function:
Not Available
Specific function:
Not Available
Gene Name:
PGM2L1
Uniprot ID:
A5PKH8
Molecular weight:
70419.0
Reactions
Glucose 1-phosphate + Glyceric acid 1,3-biphosphate → Alpha-D-Glucose 1,6-bisphosphate + 3-Phosphoglyceric aciddetails