D-glyceraldehyde 3-phosphate (PAMDB110577)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110577
Identification
Name: D-glyceraldehyde 3-phosphate
Description:Dianion of D-glyceraldehyde 3-phosphate arising from deprotonation of both OH groups of the phosphate.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 3-phosphoglyceraldehyde
  • D-glyceraldehyde-3-P
  • glyceraldehyde 3-phosphate
  • GAP
  • glyceraldehyde-phosphate
  • glyceraldehyde-P
  • glyceraldehyde-3-P
  • (2R)-2-hydroxy-3-(phosphonooxy)-propanal
  • triose phosphate
Chemical Formula: C3H5O6P
Average Molecular Weight: 168.04
Monoisotopic Molecular Weight: 169.9980244673
InChI Key: LXJXRIRHZLFYRP-VKHMYHEASA-L
InChI: InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)/p-2/t3-/m0/s1
CAS number: 142-10-9
IUPAC Name:(2R)-2-hydroxy-3-oxopropyl phosphate
Traditional IUPAC Name: glyceraldehyde 3 phosphate
SMILES:[CH](=O)C(O)COP(=O)([O-])[O-]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as glyceraldehyde-3-phosphates. These are compounds containing a glyceraldehyde substituted at position O3 by a phosphate group.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic oxygen compounds
Sub ClassOrganooxygen compounds
Direct Parent Glyceraldehyde-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 Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility20.5 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.33 m3·mol-1ChemAxon
Polarizability12.61 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
D-glyceraldehyde 3-phosphate + phosphate + NAD-P-OR-NOP → 1,3-bisphospho-D-glycerate + NADH-P-OR-NOP + Hydrogen ion
D-glyceraldehyde 3-phosphate + NADP+ + Water → Hydrogen ion + 3-phospho-D-glycerate + NADPH
D-glyceraldehyde 3-phosphate + phosphate + NADP+ → 1,3-bisphospho-D-glycerate + NADPH + Hydrogen ion
D-glyceraldehyde 3-phosphate + Water → 3-phospho-D-glycerate + Hydrogen ion
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-0m5s-3952000000-862ad552658a2dad7631View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-03dj-2943000000-879f36e9ffb61cdb7e7eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
References:
  • 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. [15882454 ]
  • 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. [8931639 ]
  • 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. [15221334 ]
  • Modun B, Morrissey J, Williams P: The staphylococcal transferrin receptor: a glycolytic enzyme with novel functions. Trends Microbiol. 2000 May;8(5):231-7. [10785640 ]
  • 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. [11757034 ]
  • 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. [16754798 ]
  • 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. [16618565 ]
  • 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. [14580401 ]
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
External Links:
ResourceLink
CAS591-57-1
ChEBI59776
HMDBHMDB01112
IAF126035637
KEGGC00118
PubChem24794350