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Human Metabolome Database Version 3.5

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Showing metabocard for D-Glyceraldehyde 3-phosphate (HMDB01112)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:54 -0700
HMDB ID HMDB01112
Secondary Accession Numbers None
Metabolite Identification
Common Name D-Glyceraldehyde 3-phosphate
Description Glyceraldehyde 3-phosphate (G3P) or triose phosphate is an aldotriose, an important metabolic intermediate in both glycolysis and gluconeogenesis, and in tryptophan biosynthesis. G3P is formed from Fructose-1,6-bisphosphate, Dihydroxyacetone phosphate (DHAP),and 1,3-bisphosphoglycerate, (1,3BPG), and this is how glycerol (as DHAP) enters the glycolytic and gluconeogenesis pathways.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-Hydroxy-3-(phosphonooxy)-Propanal
  2. 3-Phosphoglyceraldehyde
  3. D-Glyceraldehyde 3-phosphate
  4. D-Glyceraldehyde-3-P
  5. DL-Glyceraldehyde 3-phosphate
  6. GAP
  7. Glyceraldehyde-3-P
  8. Glyceraldehyde-3-phosphate
  9. Glyceraldehyde-P
  10. Glyceraldehyde-phosphate
Chemical Formula C3H7O6P
Average Molecular Weight 170.0578
Monoisotopic Molecular Weight 169.998024468
IUPAC Name (2-hydroxy-3-oxopropoxy)phosphonic acid
Traditional IUPAC Name 2-hydroxy-3-oxopropoxyphosphonic acid
CAS Registry Number 142-10-9
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 Key LXJXRIRHZLFYRP-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organophosphorus Compounds
Class Organic Phosphoric Acids and Derivatives
Sub Class Organophosphate Esters
Other Descriptors
  • Aliphatic Acyclic Compounds
  • glyceraldehyde 3-phosphate(ChEBI)
Substituents
  • Aldehyde
  • Organic Hypophosphite
  • Organic Phosphite
  • Secondary Alcohol
Direct Parent Organophosphate Esters
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Fructose and mannose metabolism
  • Component of Inositol metabolism
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 20.5 g/L ALOGPS
LogP -1.69 ALOGPS
LogP -1.8 ChemAxon
LogS -0.92 ALOGPS
pKa (strongest acidic) 1.4 ChemAxon
pKa (strongest basic) -3.8 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 104.06 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 30.33 ChemAxon
Polarizability 12.61 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
Tissue Location
  • Muscle
  • Fibroblasts
  • Kidney
Pathways
Name SMPDB Link KEGG Link
Fructose and Mannose Degradation SMP00064 map00051 Link_out
Pentose Phosphate Pathway SMP00031 map00030 Link_out
Glycerol Phosphate Shuttle SMP00124 Not Available
Mitochondrial Electron Transport Chain SMP00355 map00190 Link_out
Glycolysis SMP00040 map00010 Link_out
Gluconeogenesis SMP00128 map00010 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
4.8 +/- 1.6 uM Adult (>18 years old) Both Normal Not Available
Cellular Cytoplasm Detected and Quantified
Article_icon
6.70 (5.70-7.70) uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB02263 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB001619
KNApSAcK ID C00007564 Link_out
Chemspider ID 709 Link_out
KEGG Compound ID C00661 Link_out
BioCyc ID GAP Link_out
BiGG ID 35637 Link_out
Wikipedia Link GAP Link_out
NuGOwiki Link HMDB01112 Link_out
Metagene Link HMDB01112 Link_out
METLIN ID 3294 Link_out
PubChem Compound 729 Link_out
PDB ID 1DC4 Link_out
ChEBI ID 17138 Link_out
References
Synthesis Reference Ballou, 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 References
  1. Modun B, Morrissey J, Williams P: The staphylococcal transferrin receptor: a glycolytic enzyme with novel functions. Trends Microbiol. 2000 May;8(5):231-7. Pubmed: 10785640 Link_out
  2. Zhang J, Jung K, Lein M, Kristiansen G, Rudolph B, Hauptmann S, Schnorr D, Loening SA, Lichtinghagen R: Differential expression of matrix metalloproteinases and their tissue inhibitors in human primary cultured prostatic cells and malignant prostate cell lines. Prostate. 2002 Jan 1;50(1):38-45. Pubmed: 11757034 Link_out
  3. Kogler H, Schott P, Toischer K, Milting H, Van PN, Kohlhaas M, Grebe C, Kassner A, Domeier E, Teucher N, Seidler T, Knoll R, Maier LS, El-Banayosy A, Korfer R, Hasenfuss G: Relevance of brain natriuretic peptide in preload-dependent regulation of cardiac sarcoplasmic reticulum Ca2+ ATPase expression. Circulation. 2006 Jun 13;113(23):2724-32. Epub 2006 Jun 5. Pubmed: 16754798 Link_out
  4. Yang Y, Hou Y, Wang CL, Ji SJ: Renal expression of epidermal growth factor and transforming growth factor-beta1 in children with congenital hydronephrosis. Urology. 2006 Apr;67(4):817-21; discussion 821-2. Pubmed: 16618565 Link_out
  5. Yamamoto T, Moriwaki Y, Takahashi S, Ohata H, Nakano T, Yamakita J, Higashino K: Effect of glucagon on the xylitol-induced increase in the plasma concentration and urinary excretion of purine bases. Metabolism. 1996 Nov;45(11):1354-9. Pubmed: 8931639 Link_out
  6. 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(1):18. Pubmed: 15882454 Link_out
  7. Choei H, Sasaki N, Takeuchi M, Yoshida T, Ukai W, Yamagishi S, Kikuchi S, Saito T: Glyceraldehyde-derived advanced glycation end products in Alzheimer's disease. Acta Neuropathol (Berl). 2004 Sep;108(3):189-93. Epub 2004 Jun 17. Pubmed: 15221334 Link_out
  8. Harper LV, Hilton AC, Jones AF: RT-PCR for the pseudogene-free amplification of the glyceraldehyde-3-phosphate dehydrogenase gene (gapd). Mol Cell Probes. 2003 Oct;17(5):261-5. Pubmed: 14580401 Link_out
Enzymes
Name: Glyceraldehyde-3-phosphate dehydrogenase, testis-specific
Reactions:
  • D-glyceraldehyde 3-phosphate + phosphate + NAD+ = 3-phospho-D-glyceroyl phosphate + NADH + H+ [RN:R01061]
Gene Name: GAPDHS
Uniprot ID: O14556 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glyceraldehyde-3-phosphate dehydrogenase
Reactions:
  • D-glyceraldehyde 3-phosphate + phosphate + NAD+ = 3-phospho-D-glyceroyl phosphate + NADH + H+ [RN:R01061]
Gene Name: GAPDH
Uniprot ID: P04406 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Transaldolase
Reactions:
  • sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-erythrose 4-phosphate + D-fructose 6-phosphate [RN:R08575]
Gene Name: TALDO1
Uniprot ID: P37837 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Transketolase
Reactions:
  • sedoheptulose 7-phosphate + D-glyceraldehyde 3-phosphate = D-ribose 5-phosphate + D-xylulose 5-phosphate [RN:R01641]
Gene Name: TKT
Uniprot ID: P29401 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative deoxyribose-phosphate aldolase
Reactions:
  • 2-deoxy-D-ribose 5-phosphate = D-glyceraldehyde 3-phosphate + acetaldehyde [RN:R01066]
Gene Name: DERA
Uniprot ID: Q9Y315 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-bisphosphate aldolase A
Reactions:
  • D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate [RN:R01068]
Gene Name: ALDOA
Uniprot ID: P04075 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-bisphosphate aldolase C
Reactions:
  • D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate [RN:R01068]
Gene Name: ALDOC
Uniprot ID: P09972 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-bisphosphate aldolase B
Reactions:
  • D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate [RN:R01068]
Gene Name: ALDOB
Uniprot ID: P05062 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Triosephosphate isomerase
Reactions:
  • D-glyceraldehyde 3-phosphate = glycerone phosphate [RN:R01015]
Gene Name: TPI1
Uniprot ID: P60174 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Triosephosphate isomerase
Reactions:
  • D-glyceraldehyde 3-phosphate = glycerone phosphate [RN:R01015]
Gene Name: Not Available
Uniprot ID: Q2QD09 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glyceraldehyde-3-phosphate dehydrogenase
Reactions:
  • D-glyceraldehyde 3-phosphate + phosphate + NAD+ = 3-phospho-D-glyceroyl phosphate + NADH + H+ [RN:R01061]
Gene Name: Not Available
Uniprot ID: Q2TSD0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Name: Solute carrier organic anion transporter family member 2A1
Reactions:
  • Bicarbonate[c] + Prostaglandin E1[e] <==> Bicarbonate[e] + Prostaglandin E1[c]
Gene Name: SLCO2A1
Uniprot ID: Q92959 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA