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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:00:08 UTC
HMDB IDHMDB0001270
Secondary Accession Numbers
  • HMDB0062758
  • HMDB01270
  • HMDB62758
Metabolite Identification
Common NameGlyceric acid 1,3-biphosphate
DescriptionGlyceric acid 1,3-biphosphate (CAS: 1981-49-3), also known as 1,3-bisphosphoglycerate (1,3BPG) or PGAP, is a 3-carbon organic molecule present in most, if not all living creatures. It primarily exists as a metabolic intermediate in glycolysis during respiration. 1,3BPG has been recognized as regulatory signal implicated in the control of metabolism, oxygen affinity of red cells, and other cellular functions. 1,3BPG concentration in erythrocytes changes in a number of pathological conditions, such as inherited phosphoglycerate kinase deficiency in erythrocytes (involved in the synthesis and breakdown of 1,3BPG) (PMID: 3555887 ). Glyceric acid 1,3-biphosphate is phosphorylated at the number 1 and 3 carbons. The result of this phosphorylation gives 1,3BPG important biological properties such as the ability to phosphorylate ADP to form the energy storage molecule ATP (Wikipedia ).
Structure
Data?1588008946
Synonyms
ValueSource
(R)-2-Hydroxy-3-(phosphonooxy)-1-monoanhydride with phosphoric propanoic acidChEBI
1,3-Bisphospho-D-glycerateChEBI
3-Phospho-D-glyceroyl phosphateChEBI
D-Glycerate 1,3-diphosphateKegg
(R)-2-Hydroxy-3-(phosphonooxy)-1-monoanhydride with phosphoric propanoateGenerator
1,3-Bisphospho-D-glyceric acidGenerator
3-Phospho-D-glyceroyl phosphoric acidGenerator
D-Glyceric acid 1,3-diphosphoric acidGenerator
Glycerate 1,3-biphosphateGenerator
Glyceric acid 1,3-biphosphoric acidGenerator
3-Phospho-D-glyceroyl dihydrogen phosphoric acidHMDB
1,3-BiphosphoglycerateHMDB
1,3-BisphosphoglycerateHMDB
1,3-Bisphosphoglyceric acidHMDB
1,3-DiphosphoglycerateHMDB
1,3-Diphosphoglyceric acidHMDB
3-Phospho-D-glyceroyl-phosphateHMDB
3-Phosphoglyceroyl phosphateHMDB
3-Phosphoglyceroyl-pHMDB
3-Phosphoglyceroyl-phosphateHMDB
3-Phosphonato-D-glyceroyl phosphateHMDB
3-Phosphonatoglyceroyl phosphateHMDB
3-p-Glyceroyl-pHMDB
D-Glycerate 1,3-biphosphateHMDB
D-Glycerate 1,3-bisphosphateHMDB
D-Glyceric acid 1,3-biphosphateHMDB
D-Glyceric acid 1,3-bisphosphateHMDB
D-Glyceric acid 1,3-diphosphateHMDB
DPGHMDB
Glycerate 1,3-bisphosphateHMDB
Glycerate 1,3-diphosphateHMDB
Glyceric acid 1,3-bisphosphateHMDB
Glyceric acid 1,3-diphosphateHMDB
Phosphoglyceroyl-pHMDB
p-Glyceroyl-pHMDB
Glyceric acid 1,3-biphosphateHMDB
Chemical FormulaC3H8O10P2
Average Molecular Weight266.0371
Monoisotopic Molecular Weight265.9592695
IUPAC Name{[(2R)-2-hydroxy-3-(phosphonooxy)propanoyl]oxy}phosphonic acid
Traditional Name1,3-bisphospho-D-glycerate
CAS Registry Number38168-82-0
SMILES
O[C@H](COP(O)(O)=O)C(=O)OP(O)(O)=O
InChI Identifier
InChI=1S/C3H8O10P2/c4-2(1-12-14(6,7)8)3(5)13-15(9,10)11/h2,4H,1H2,(H2,6,7,8)(H2,9,10,11)/t2-/m1/s1
InChI KeyLJQLQCAXBUHEAZ-UWTATZPHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyl monophosphates. These are organic compounds containing a monophosphate linked to an acyl group. They have the general structure R-CO-P(O)(O)OH, R=H or organyl.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentAcyl monophosphates
Alternative Parents
Substituents
  • Acyl monophosphate
  • Glyceric_acid
  • Monoalkyl phosphate
  • Monosaccharide
  • Alkyl phosphate
  • Carboxylic acid salt
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Naturally occurring 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 PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility9.64 g/LALOGPS
logP-1.1ALOGPS
logP-2.3ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.01ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.82 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.42 m³·mol⁻¹ChemAxon
Polarizability18.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+129.32930932474
DeepCCS[M-H]-126.93130932474
DeepCCS[M-2H]-160.21330932474
DeepCCS[M+Na]+135.28430932474
AllCCS[M+H]+154.232859911
AllCCS[M+H-H2O]+150.932859911
AllCCS[M+NH4]+157.232859911
AllCCS[M+Na]+158.132859911
AllCCS[M-H]-142.832859911
AllCCS[M+Na-2H]-143.632859911
AllCCS[M+HCOO]-144.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Glyceric acid 1,3-biphosphateO[C@H](COP(O)(O)=O)C(=O)OP(O)(O)=O2862.2Standard polar33892256
Glyceric acid 1,3-biphosphateO[C@H](COP(O)(O)=O)C(=O)OP(O)(O)=O1699.0Standard non polar33892256
Glyceric acid 1,3-biphosphateO[C@H](COP(O)(O)=O)C(=O)OP(O)(O)=O2259.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glyceric acid 1,3-biphosphate,1TMS,isomer #1C[Si](C)(C)O[C@H](COP(=O)(O)O)C(=O)OP(=O)(O)O2068.8Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,1TMS,isomer #2C[Si](C)(C)OP(=O)(O)OC[C@@H](O)C(=O)OP(=O)(O)O2124.3Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,1TMS,isomer #3C[Si](C)(C)OP(=O)(O)OC(=O)[C@H](O)COP(=O)(O)O2096.1Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,2TMS,isomer #1C[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C)C(=O)OP(=O)(O)O2092.4Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,2TMS,isomer #1C[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C)C(=O)OP(=O)(O)O2202.5Standard non polar33892256
Glyceric acid 1,3-biphosphate,2TMS,isomer #1C[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C)C(=O)OP(=O)(O)O3277.1Standard polar33892256
Glyceric acid 1,3-biphosphate,2TMS,isomer #2C[Si](C)(C)O[C@H](COP(=O)(O)O)C(=O)OP(=O)(O)O[Si](C)(C)C2091.6Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,2TMS,isomer #2C[Si](C)(C)O[C@H](COP(=O)(O)O)C(=O)OP(=O)(O)O[Si](C)(C)C2202.4Standard non polar33892256
Glyceric acid 1,3-biphosphate,2TMS,isomer #2C[Si](C)(C)O[C@H](COP(=O)(O)O)C(=O)OP(=O)(O)O[Si](C)(C)C3339.3Standard polar33892256
Glyceric acid 1,3-biphosphate,2TMS,isomer #3C[Si](C)(C)OP(=O)(OC[C@@H](O)C(=O)OP(=O)(O)O)O[Si](C)(C)C2088.7Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,2TMS,isomer #3C[Si](C)(C)OP(=O)(OC[C@@H](O)C(=O)OP(=O)(O)O)O[Si](C)(C)C2218.2Standard non polar33892256
Glyceric acid 1,3-biphosphate,2TMS,isomer #3C[Si](C)(C)OP(=O)(OC[C@@H](O)C(=O)OP(=O)(O)O)O[Si](C)(C)C3036.4Standard polar33892256
Glyceric acid 1,3-biphosphate,2TMS,isomer #4C[Si](C)(C)OP(=O)(O)OC[C@@H](O)C(=O)OP(=O)(O)O[Si](C)(C)C2144.1Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,2TMS,isomer #4C[Si](C)(C)OP(=O)(O)OC[C@@H](O)C(=O)OP(=O)(O)O[Si](C)(C)C2167.1Standard non polar33892256
Glyceric acid 1,3-biphosphate,2TMS,isomer #4C[Si](C)(C)OP(=O)(O)OC[C@@H](O)C(=O)OP(=O)(O)O[Si](C)(C)C3071.5Standard polar33892256
Glyceric acid 1,3-biphosphate,2TMS,isomer #5C[Si](C)(C)OP(=O)(OC(=O)[C@H](O)COP(=O)(O)O)O[Si](C)(C)C2091.4Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,2TMS,isomer #5C[Si](C)(C)OP(=O)(OC(=O)[C@H](O)COP(=O)(O)O)O[Si](C)(C)C2238.3Standard non polar33892256
Glyceric acid 1,3-biphosphate,2TMS,isomer #5C[Si](C)(C)OP(=O)(OC(=O)[C@H](O)COP(=O)(O)O)O[Si](C)(C)C3127.1Standard polar33892256
Glyceric acid 1,3-biphosphate,3TMS,isomer #1C[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OP(=O)(O)O2109.4Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,3TMS,isomer #1C[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OP(=O)(O)O2217.7Standard non polar33892256
Glyceric acid 1,3-biphosphate,3TMS,isomer #1C[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OP(=O)(O)O2891.0Standard polar33892256
Glyceric acid 1,3-biphosphate,3TMS,isomer #2C[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C)C(=O)OP(=O)(O)O[Si](C)(C)C2117.2Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,3TMS,isomer #2C[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C)C(=O)OP(=O)(O)O[Si](C)(C)C2185.1Standard non polar33892256
Glyceric acid 1,3-biphosphate,3TMS,isomer #2C[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C)C(=O)OP(=O)(O)O[Si](C)(C)C2943.0Standard polar33892256
Glyceric acid 1,3-biphosphate,3TMS,isomer #3C[Si](C)(C)O[C@H](COP(=O)(O)O)C(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2090.6Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,3TMS,isomer #3C[Si](C)(C)O[C@H](COP(=O)(O)O)C(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2247.1Standard non polar33892256
Glyceric acid 1,3-biphosphate,3TMS,isomer #3C[Si](C)(C)O[C@H](COP(=O)(O)O)C(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2969.3Standard polar33892256
Glyceric acid 1,3-biphosphate,3TMS,isomer #4C[Si](C)(C)OP(=O)(O)OC(=O)[C@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2151.8Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,3TMS,isomer #4C[Si](C)(C)OP(=O)(O)OC(=O)[C@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2204.0Standard non polar33892256
Glyceric acid 1,3-biphosphate,3TMS,isomer #4C[Si](C)(C)OP(=O)(O)OC(=O)[C@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2757.7Standard polar33892256
Glyceric acid 1,3-biphosphate,3TMS,isomer #5C[Si](C)(C)OP(=O)(O)OC[C@@H](O)C(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2130.5Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,3TMS,isomer #5C[Si](C)(C)OP(=O)(O)OC[C@@H](O)C(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2214.7Standard non polar33892256
Glyceric acid 1,3-biphosphate,3TMS,isomer #5C[Si](C)(C)OP(=O)(O)OC[C@@H](O)C(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2785.0Standard polar33892256
Glyceric acid 1,3-biphosphate,4TMS,isomer #1C[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OP(=O)(O)O[Si](C)(C)C2163.6Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,4TMS,isomer #1C[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OP(=O)(O)O[Si](C)(C)C2234.9Standard non polar33892256
Glyceric acid 1,3-biphosphate,4TMS,isomer #1C[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OP(=O)(O)O[Si](C)(C)C2668.5Standard polar33892256
Glyceric acid 1,3-biphosphate,4TMS,isomer #2C[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C)C(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2151.8Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,4TMS,isomer #2C[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C)C(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2250.3Standard non polar33892256
Glyceric acid 1,3-biphosphate,4TMS,isomer #2C[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C)C(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2701.3Standard polar33892256
Glyceric acid 1,3-biphosphate,4TMS,isomer #3C[Si](C)(C)OP(=O)(OC[C@@H](O)C(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2187.0Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,4TMS,isomer #3C[Si](C)(C)OP(=O)(OC[C@@H](O)C(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2254.5Standard non polar33892256
Glyceric acid 1,3-biphosphate,4TMS,isomer #3C[Si](C)(C)OP(=O)(OC[C@@H](O)C(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2556.7Standard polar33892256
Glyceric acid 1,3-biphosphate,5TMS,isomer #1C[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2200.1Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,5TMS,isomer #1C[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2270.9Standard non polar33892256
Glyceric acid 1,3-biphosphate,5TMS,isomer #1C[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2483.4Standard polar33892256
Glyceric acid 1,3-biphosphate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O)C(=O)OP(=O)(O)O2313.5Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@@H](O)C(=O)OP(=O)(O)O2357.5Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(O)OC(=O)[C@H](O)COP(=O)(O)O2342.9Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)OP(=O)(O)O2496.0Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)OP(=O)(O)O2619.7Standard non polar33892256
Glyceric acid 1,3-biphosphate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)OP(=O)(O)O3400.0Standard polar33892256
Glyceric acid 1,3-biphosphate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O)C(=O)OP(=O)(O)O[Si](C)(C)C(C)(C)C2467.9Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O)C(=O)OP(=O)(O)O[Si](C)(C)C(C)(C)C2613.1Standard non polar33892256
Glyceric acid 1,3-biphosphate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O)C(=O)OP(=O)(O)O[Si](C)(C)C(C)(C)C3458.3Standard polar33892256
Glyceric acid 1,3-biphosphate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OC[C@@H](O)C(=O)OP(=O)(O)O)O[Si](C)(C)C(C)(C)C2524.8Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OC[C@@H](O)C(=O)OP(=O)(O)O)O[Si](C)(C)C(C)(C)C2615.5Standard non polar33892256
Glyceric acid 1,3-biphosphate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OC[C@@H](O)C(=O)OP(=O)(O)O)O[Si](C)(C)C(C)(C)C3213.7Standard polar33892256
Glyceric acid 1,3-biphosphate,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@@H](O)C(=O)OP(=O)(O)O[Si](C)(C)C(C)(C)C2550.7Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@@H](O)C(=O)OP(=O)(O)O[Si](C)(C)C(C)(C)C2599.8Standard non polar33892256
Glyceric acid 1,3-biphosphate,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@@H](O)C(=O)OP(=O)(O)O[Si](C)(C)C(C)(C)C3220.8Standard polar33892256
Glyceric acid 1,3-biphosphate,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP(=O)(OC(=O)[C@H](O)COP(=O)(O)O)O[Si](C)(C)C(C)(C)C2496.7Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP(=O)(OC(=O)[C@H](O)COP(=O)(O)O)O[Si](C)(C)C(C)(C)C2629.8Standard non polar33892256
Glyceric acid 1,3-biphosphate,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP(=O)(OC(=O)[C@H](O)COP(=O)(O)O)O[Si](C)(C)C(C)(C)C3298.0Standard polar33892256
Glyceric acid 1,3-biphosphate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)OP(=O)(O)O2729.4Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)OP(=O)(O)O2752.1Standard non polar33892256
Glyceric acid 1,3-biphosphate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)OP(=O)(O)O3105.0Standard polar33892256
Glyceric acid 1,3-biphosphate,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)OP(=O)(O)O[Si](C)(C)C(C)(C)C2734.6Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)OP(=O)(O)O[Si](C)(C)C(C)(C)C2760.4Standard non polar33892256
Glyceric acid 1,3-biphosphate,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)OP(=O)(O)O[Si](C)(C)C(C)(C)C3132.4Standard polar33892256
Glyceric acid 1,3-biphosphate,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O)C(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2687.1Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O)C(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2782.3Standard non polar33892256
Glyceric acid 1,3-biphosphate,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O)C(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3177.7Standard polar33892256
Glyceric acid 1,3-biphosphate,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(O)OC(=O)[C@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2767.4Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(O)OC(=O)[C@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2736.1Standard non polar33892256
Glyceric acid 1,3-biphosphate,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(O)OC(=O)[C@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2987.0Standard polar33892256
Glyceric acid 1,3-biphosphate,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@@H](O)C(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2747.1Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@@H](O)C(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2757.2Standard non polar33892256
Glyceric acid 1,3-biphosphate,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@@H](O)C(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3009.2Standard polar33892256
Glyceric acid 1,3-biphosphate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)OP(=O)(O)O[Si](C)(C)C(C)(C)C2953.9Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)OP(=O)(O)O[Si](C)(C)C(C)(C)C2844.7Standard non polar33892256
Glyceric acid 1,3-biphosphate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)OP(=O)(O)O[Si](C)(C)C(C)(C)C2951.3Standard polar33892256
Glyceric acid 1,3-biphosphate,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2938.4Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2864.0Standard non polar33892256
Glyceric acid 1,3-biphosphate,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2979.8Standard polar33892256
Glyceric acid 1,3-biphosphate,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OC[C@@H](O)C(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2965.4Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OC[C@@H](O)C(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2833.2Standard non polar33892256
Glyceric acid 1,3-biphosphate,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OC[C@@H](O)C(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2877.8Standard polar33892256
Glyceric acid 1,3-biphosphate,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3154.4Semi standard non polar33892256
Glyceric acid 1,3-biphosphate,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2949.0Standard non polar33892256
Glyceric acid 1,3-biphosphate,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2896.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Glyceric acid 1,3-biphosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9500000000-cb3071f9249ee92b7d2c2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glyceric acid 1,3-biphosphate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceric acid 1,3-biphosphate 10V, Positive-QTOFsplash10-014i-1950000000-2cde7b5739871a8825422015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceric acid 1,3-biphosphate 20V, Positive-QTOFsplash10-014m-3910000000-72f2c46eab20369380562015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceric acid 1,3-biphosphate 40V, Positive-QTOFsplash10-000f-9500000000-c835034f0ac11618922d2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceric acid 1,3-biphosphate 10V, Negative-QTOFsplash10-03fr-6190000000-6f4870543fc6131d14a72015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceric acid 1,3-biphosphate 20V, Negative-QTOFsplash10-004i-9000000000-d9d9c6d217a255d791fd2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceric acid 1,3-biphosphate 40V, Negative-QTOFsplash10-004i-9000000000-1fef400a1ea8ca54c8022015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceric acid 1,3-biphosphate 10V, Negative-QTOFsplash10-03dj-0090000000-def40aa9bb3094302ce82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceric acid 1,3-biphosphate 20V, Negative-QTOFsplash10-01r2-9040000000-374a9ff8c866f10f2f3c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceric acid 1,3-biphosphate 40V, Negative-QTOFsplash10-004i-9000000000-4bf2b9a14f4e1c8fc62a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceric acid 1,3-biphosphate 10V, Positive-QTOFsplash10-00kb-1390000000-8fe62bbfc56bf59f28a62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceric acid 1,3-biphosphate 20V, Positive-QTOFsplash10-0002-9410000000-e17767e21640a6f815322021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceric acid 1,3-biphosphate 40V, Positive-QTOFsplash10-0002-9000000000-c41dab2684b9d54afd312021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cellular Cytoplasm
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Cellular CytoplasmDetected and Quantified0.4 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia
details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Xuan J, Pan G, Qiu Y, Yang L, Su M, Liu Y, Chen J, Feng G, Fang Y, Jia W, Xing Q, He L: Metabolomic profiling to identify potential serum biomarkers for schizophrenia and risperidone action. J Proteome Res. 2011 Dec 2;10(12):5433-43. doi: 10.1021/pr2006796. Epub 2011 Nov 8. [PubMed:22007635 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030188
KNApSAcK IDC00019552
Chemspider IDNot Available
KEGG Compound IDC00236
BioCyc IDDPG
BiGG IDNot Available
Wikipedia Link1,3-Bisphosphoglyceric acid
METLIN IDNot Available
PubChem Compound439191
PDB IDNot Available
ChEBI ID16001
Food Biomarker OntologyNot Available
VMH ID13DPG
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. [PubMed:15882454 ]
  2. Fujii H: [Red cell glycolytic intermediates]. Nihon Rinsho. 1995 Mar;53 Su Pt 2:234-8. [PubMed:8753225 ]
  3. Sayed A, Matsuyama S, Inoue K, Alsina J, Cai F, Chen J, Inouye M: ATPase and GTPase activities copurifying with GTP-binding proteins in E. coli. J Mol Microbiol Biotechnol. 2000 Jul;2(3):261-3. [PubMed:10937433 ]
  4. Inoue H, Moriyasu M, Hamasaki N: Metabolism of 3-phosphoglyceroyl phosphate in phosphoenolpyruvate-enriched human erythrocytes. J Biol Chem. 1987 Jun 5;262(16):7635-8. [PubMed:3584133 ]
  5. Fabry ME, Nagel RL: Heterogeneity of red cells in the sickler: a characteristic with practical clinical and pathophysiological implications. Blood Cells. 1982;8(1):9-15. [PubMed:7115982 ]
  6. Flachner B, Varga A, Szabo J, Barna L, Hajdu I, Gyimesi G, Zavodszky P, Vas M: Substrate-assisted movement of the catalytic Lys 215 during domain closure: site-directed mutagenesis studies of human 3-phosphoglycerate kinase. Biochemistry. 2005 Dec 27;44(51):16853-65. [PubMed:16363799 ]
  7. Carreras J, Bartrons R, Climent F, Cusso R: Bisphosphorylated metabolites of glycerate, glucose, and fructose: functions, metabolism and molecular pathology. Clin Biochem. 1986 Dec;19(6):348-58. [PubMed:3555887 ]
  8. Fokina KV, Dainyak MB, Nagradova NK, Muronetz VI: A study on the complexes between human erythrocyte enzymes participating in the conversions of 1,3-diphosphoglycerate. Arch Biochem Biophys. 1997 Sep 15;345(2):185-92. [PubMed:9308888 ]
  9. Jovanovic S, Du Q, Crawford RM, Budas GR, Stagljar I, Jovanovic A: Glyceraldehyde 3-phosphate dehydrogenase serves as an accessory protein of the cardiac sarcolemmal K(ATP) channel. EMBO Rep. 2005 Sep;6(9):848-52. [PubMed:16082386 ]
  10. Oimomi M, Yoshimura Y, Kubota S, Tanke G, Takagi K, Baba S: Effect of hydrocortisone on the synthesis of 2,3-diphosphoglycerate in human erythrocytes. Transfusion. 1982 Jul-Aug;22(4):266-8. [PubMed:7101418 ]
  11. Joao HC, Williams RJ: The anatomy of a kinase and the control of phosphate transfer. Eur J Biochem. 1993 Aug 15;216(1):1-18. [PubMed:8365395 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Enzymes

General function:
Involved in catalytic activity
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 5.4.2.1) and phosphatase (EC 3.1.3.13) activities.
Gene Name:
BPGM
Uniprot ID:
P07738
Molecular weight:
30004.98
Reactions
Glyceric acid 1,3-biphosphate → 2,3-Diphosphoglyceric aciddetails
General function:
Involved in catalytic activity
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) and EC 3.1.3.13 (phosphatase), but with a reduced activity.
Gene Name:
PGAM2
Uniprot ID:
P15259
Molecular weight:
28765.96
Reactions
Glyceric acid 1,3-biphosphate → 2,3-Diphosphoglyceric aciddetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PGAM4
Uniprot ID:
Q8N0Y7
Molecular weight:
28776.605
Reactions
Glyceric acid 1,3-biphosphate → 2,3-Diphosphoglyceric aciddetails
General function:
Involved in catalytic activity
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) and EC 3.1.3.13 (phosphatase), but with a reduced activity.
Gene Name:
PGAM1
Uniprot ID:
P18669
Molecular weight:
28803.675
Reactions
Glyceric acid 1,3-biphosphate → 2,3-Diphosphoglyceric aciddetails
General function:
Involved in acylphosphatase activity
Specific function:
Its physiological role is not yet clear.
Gene Name:
ACYP2
Uniprot ID:
P14621
Molecular weight:
11139.52
Reactions
Glyceric acid 1,3-biphosphate + Water → 3-Phosphoglyceric acid + Phosphatedetails
General function:
Involved in acylphosphatase activity
Specific function:
Its physiological role is not yet clear.
Gene Name:
ACYP1
Uniprot ID:
P07311
Molecular weight:
11260.84
Reactions
Glyceric acid 1,3-biphosphate + Water → 3-Phosphoglyceric acid + Phosphatedetails
General function:
Involved in glyceraldehyde-3-phosphate dehydrogenase activity
Specific function:
May play an important role in regulating the switch between different pathways for energy production during spermiogenesis and in the spermatozoon. Required for sperm motility and male fertility (By similarity).
Gene Name:
GAPDHS
Uniprot ID:
O14556
Molecular weight:
44500.835
Reactions
Glyceraldehyde 3-phosphate + Phosphate + NAD → Glyceric acid 1,3-biphosphate + NADHdetails
Glyceraldehyde 3-phosphate + Phosphate + NAD → Glyceric acid 1,3-biphosphate + NADH + Hydrogen Iondetails
General function:
Involved in glyceraldehyde-3-phosphate dehydrogenase activity
Specific function:
Has both glyceraldehyde-3-phosphate dehydrogenase and nitrosylase activities, thereby playing a role in glycolysis and nuclear functions, respectively. Participates in nuclear events including transcription, RNA transport, DNA replication and apoptosis. Nuclear functions are probably due to the nitrosylase activity that mediates cysteine S-nitrosylation of nuclear target proteins such as SIRT1, HDAC2 and PRKDC. Modulates the organization and assembly of the cytoskeleton. Facilitates the CHP1-dependent microtubule and membrane associations through its ability to stimulate the binding of CHP1 to microtubules (By similarity). Glyceraldehyde-3-phosphate dehydrogenase is a key enzyme in glycolysis that catalyzes the first step of the pathway by converting D-glyceraldehyde 3-phosphate (G3P) into 3-phospho-D-glyceroyl phosphate. Component of the GAIT (gamma interferon-activated inhibitor of translation) complex which mediates interferon-gamma-induced transcript-selective translation inhibition in inflammation processes. Upon interferon-gamma treatment assembles into the GAIT complex which binds to stem loop-containing GAIT elements in the 3'-UTR of diverse inflammatory mRNAs (such as ceruplasmin) and suppresses their translation.
Gene Name:
GAPDH
Uniprot ID:
P04406
Molecular weight:
31547.76
Reactions
Glyceraldehyde 3-phosphate + Phosphate + NAD → Glyceric acid 1,3-biphosphate + NADHdetails
Glyceraldehyde 3-phosphate + Phosphate + NAD → Glyceric acid 1,3-biphosphate + NADH + Hydrogen Iondetails
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
PGK2
Uniprot ID:
P07205
Molecular weight:
44795.79
Reactions
Adenosine triphosphate + 3-Phosphoglyceric acid → ADP + Glyceric acid 1,3-biphosphatedetails
General function:
Involved in phosphoglycerate kinase activity
Specific function:
In addition to its role as a glycolytic enzyme, it seems that PGK-1 acts as a polymerase alpha cofactor protein (primer recognition protein).
Gene Name:
PGK1
Uniprot ID:
P00558
Molecular weight:
44614.36
Reactions
Adenosine triphosphate + 3-Phosphoglyceric acid → ADP + Glyceric acid 1,3-biphosphatedetails

Only showing the first 10 proteins. There are 11 proteins in total.