Show more...
Record Information
Version1.0
Creation Date2016-09-30 22:41:13 UTC
Update Date2020-05-21 16:27:10 UTC
BMDB IDBMDB0001112
Secondary Accession Numbers
  • BMDB01112
Metabolite Identification
Common NameD-Glyceraldehyde 3-phosphate
DescriptionGlyceraldehyde 3-phosphate, also known as 3-phosphoglyceraldehyde or GAP, belongs to the class of organic compounds known as glyceraldehyde-3-phosphates. Glyceraldehyde-3-phosphates are compounds containing a glyceraldehyde substituted at position O3 by a phosphate group. Glyceraldehyde 3-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Glyceraldehyde 3-phosphate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
Chemical FormulaC3H7O6P
Average Molecular Weight170.0578
Monoisotopic Molecular Weight169.998024468
IUPAC Name(2-hydroxy-3-oxopropoxy)phosphonic acid
Traditional Nameglyceraldehyde 3 phosphate
CAS Registry Number142-10-9
SMILES
OC(COP(O)(O)=O)C=O
InChI Identifier
InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)
InChI KeyLXJXRIRHZLFYRP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glyceraldehyde-3-phosphates. Glyceraldehyde-3-phosphates are compounds containing a glyceraldehyde substituted at position O3 by a phosphate group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlyceraldehyde-3-phosphates
Alternative Parents
Substituents
  • Glyceraldehyde-3-phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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-1.7ALOGPS
logP-1.8ChemAxon
logS-0.92ALOGPS
pKa (Strongest Acidic)1.4ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.33 m³·mol⁻¹ChemAxon
Polarizability12.61 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-MS (Non-derivatized)splash10-0m5s-3952000000-862ad552658a2dad7631View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03dj-2943000000-879f36e9ffb61cdb7e7eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0m5s-3952000000-862ad552658a2dad7631View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03dj-2943000000-879f36e9ffb61cdb7e7eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9300000000-7c325d284fb0e3770da5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00xs-9720000000-2a59591392eaadc8cb67View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002b-9000000000-6e7cef3b048204ad747cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-00di-1900000000-f7a7b256e1a0b030f168View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-00di-2900000000-eacc8d6b246e46b2340fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-00dj-4900000000-a66af0aa75aba70cb82aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-006t-7900000000-8b419c2e8472f9f74a49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-006t-9600000000-6504648a31d96ef44d49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0002-9400000000-5a167503e18109d4af5bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0002-9200000000-76cd396626689c9235beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0002-9100000000-9b592d8b0cba5a7af4c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0002-9100000000-7a7901afb70f6d8627c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0002-9000000000-bcb4ecbf7bc0e3ce3164View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0002-9000000000-13cecd1b3662f69b69d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0002-9000000000-ad2b828477c8005d6ec0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0002-9000000000-c4278124075952af95f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0002-9000000000-4387fd6f7164cef7bd72View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-0002-9000000000-4c200ed3c50ff96956b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-0002-9000000000-c9b13016720f097cecbcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, positivesplash10-0002-9000000000-f2389881e7483c78942fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-0005-9700000000-3e08f8453aeb088eee03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-4900000000-416f405681faaf774486View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9300000000-e5728592219561b9203cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-eeb354dbde88d3794c6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-6900000000-50b19733dd05329d82c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-22bcce954e030ff911edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5dbce0b156c269157c00View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Fibroblasts
  • Kidney
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001112
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001619
KNApSAcK IDC00007285
Chemspider ID709
KEGG Compound IDC00661
BioCyc IDCPD0-2032
BiGG ID35637
Wikipedia Link3-phosphoglyceraldehyde
METLIN ID3294
PubChem Compound729
PDB IDNot Available
ChEBI ID17138
References
Synthesis ReferenceBallou, Clinton E.; Fischer, Hermann O. L. The synthesis of D-glyceraldehyde 3-phosphate. Journal of the American Chemical Society (1955), 77 3329-31.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Nucleotide transport and metabolism
Specific function:
Catalyzes a reversible aldol reaction between acetaldehyde and D-glyceraldehyde 3-phosphate to generate 2-deoxy-D-ribose 5-phosphate. Participates in stress granule (SG) assembly. May allow ATP production from extracellular deoxyinosine in conditions of energy deprivation.
Gene Name:
DERA
Uniprot ID:
Q3T0V9
Molecular weight:
35246.0
Reactions
D-Glyceraldehyde 3-phosphate + Acetaldehyde → Deoxyribose 5-phosphatedetails
General function:
Carbohydrate transport and metabolism
Specific function:
Has both glyceraldehyde-3-phosphate dehydrogenase and nitrosylase activities, thereby playing a role in glycolysis and nuclear functions, respectively. 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. 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. Also 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. 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 (By similarity).
Gene Name:
GAPDH
Uniprot ID:
P10096
Molecular weight:
35868.0
Reactions
D-Glyceraldehyde 3-phosphate + NAD + Hydrogen phosphate → Glyceric acid 1,3-biphosphate + NADHdetails
D-Glyceraldehyde 3-phosphate + NAD → Glyceric acid 1,3-biphosphate + Hydrogen phosphate + NADHdetails
General function:
Carbohydrate transport and metabolism
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:
Q2KJE5
Molecular weight:
43288.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
ALDOA
Uniprot ID:
A6QLL8
Molecular weight:
39436.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
ALDOC
Uniprot ID:
Q3ZBY4
Molecular weight:
39382.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
ALDOB
Uniprot ID:
A5PK73
Molecular weight:
39527.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
ALDOB
Uniprot ID:
Q3T0S5
Molecular weight:
39543.0
General function:
Energy production and conversion
Specific function:
Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate.
Gene Name:
TKT
Uniprot ID:
Q6B855
Molecular weight:
67906.0
Reactions
D-Erythrose 4-phosphate + Xylulose 5-phosphate → Fructose 6-phosphate + D-Glyceraldehyde 3-phosphatedetails
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
GAPDL17
Uniprot ID:
Q9XSN4
Molecular weight:
11514.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q862K5
Molecular weight:
15626.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
GAPDH
Uniprot ID:
Q0QES8
Molecular weight:
24259.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
gapdh
Uniprot ID:
Q4H0Z3
Molecular weight:
10913.0
General function:
Carbohydrate transport and metabolism
Specific function:
Triosephosphate isomerase is an extremely efficient metabolic enzyme that catalyzes the interconversion between dihydroxyacetone phosphate (DHAP) and D-glyceraldehyde-3-phosphate (G3P) in glycolysis and gluconeogenesis.
Gene Name:
TPI1
Uniprot ID:
Q5E956
Molecular weight:
26690.0
Reactions
Dihydroxyacetone phosphate → D-Glyceraldehyde 3-phosphatedetails
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
GAPDH
Uniprot ID:
Q712W6
Molecular weight:
28755.0