Identification

Name
Glyceraldehyde-3-Phosphate
Accession Number
DB02263  (EXPT01530)
Type
Small Molecule
Groups
Experimental
Description

An aldotriose which is an important intermediate in glycolysis and in tryptophan biosynthesis. [PubChem]

Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
142-10-9
Weight
Average: 170.0578
Monoisotopic: 169.998024468
Chemical Formula
C3H7O6P
InChI Key
LXJXRIRHZLFYRP-VKHMYHEASA-N
InChI
InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)/t3-/m0/s1
IUPAC Name
[(2R)-2-hydroxy-3-oxopropoxy]phosphonic acid
SMILES
O[[email protected]](COP(O)(O)=O)C=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlyceraldehyde-3-phosphate dehydrogenase ANot AvailableEscherichia coli (strain K12)
UGlyceraldehyde-3-phosphate dehydrogenaseNot AvailableGeobacillus stearothermophilus
UNADP-dependent glyceraldehyde-3-phosphate dehydrogenaseNot AvailableStreptococcus mutans serotype c (strain ATCC 700610 / UA159)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke DiseaseDisease
Phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1)Disease
Triosephosphate isomeraseDisease
Fructose intolerance, hereditaryDisease
Pentose Phosphate PathwayMetabolic
Transaldolase deficiencyDisease
Fructose-1,6-diphosphatase deficiencyDisease
Fanconi-bickel syndromeDisease
GlycolysisMetabolic
Glucose-6-phosphate dehydrogenase deficiencyDisease
Ribose-5-phosphate isomerase deficiencyDisease
Glycogenosis, Type IA. Von gierke diseaseDisease
Glycerol Phosphate ShuttleMetabolic
Mitochondrial Electron Transport ChainMetabolic
FructosuriaDisease
Warburg EffectMetabolic
Fructose and Mannose DegradationMetabolic
GluconeogenesisMetabolic
Glycogenosis, Type VII. Tarui diseaseDisease
Glycogenosis, Type IBDisease
Glycogenosis, Type ICDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Young-Hoon Park, So-Yeon Rah, Seong-Jun Kim, Mun-Su Rhee, "Microorganism of Escherichia Sp, or Corynebacterium Sp, comprising foreign NADP dependent glyceraldehyde-3-phosphate dehydrogenase gene and method for producing L-lysine using the same." U.S. Patent US07566553, issued July 28, 2009.

US07566553
General References
Not Available
External Links
KEGG Compound
C00118
PubChem Compound
439168
PubChem Substance
46508786
ChemSpider
388314
BindingDB
50420199
ChEBI
29052
ChEMBL
CHEMBL1232918
HET
G3H
PDB Entries
1c7z / 1glc / 1gld / 1gle / 1m7p / 1nqa / 1nqo / 1qi1 / 1uod / 1uxu
show 17 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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
Polarizability12.54 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6115
Blood Brain Barrier+0.95
Caco-2 permeable-0.7473
P-glycoprotein substrateNon-substrate0.7469
P-glycoprotein inhibitor INon-inhibitor0.8258
P-glycoprotein inhibitor IINon-inhibitor0.8755
Renal organic cation transporterNon-inhibitor0.942
CYP450 2C9 substrateNon-substrate0.8621
CYP450 2D6 substrateNon-substrate0.8556
CYP450 3A4 substrateNon-substrate0.6634
CYP450 1A2 substrateNon-inhibitor0.94
CYP450 2C9 inhibitorNon-inhibitor0.9253
CYP450 2D6 inhibitorNon-inhibitor0.9322
CYP450 2C19 inhibitorNon-inhibitor0.9096
CYP450 3A4 inhibitorNon-inhibitor0.9694
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9806
Ames testNon AMES toxic0.7789
CarcinogenicityNon-carcinogens0.6037
BiodegradationReady biodegradable0.6262
Rat acute toxicity2.1206 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9683
hERG inhibition (predictor II)Non-inhibitor0.9257
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)GC-MSsplash10-03gs-2974000000-49a55c276e0ad196e48b
GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)GC-MSsplash10-03dj-1954000000-b38d318554d6563bd853
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-4900000000-c2523768fc807c3c2be4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9300000000-f776376958b2b72f623a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-e259d091dff097ba4725
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-016r-6900000000-c0ca9a77a4d78aab0dfe
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-0bed37562fdba4181b72
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-1a41399517f85b66b213

Taxonomy

Description
This compound belongs to the class of organic compounds known as glyceraldehyde-3-phosphates. These are compounds containing a glyceraldehyde substituted at position O3 by a phosphate group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Glyceraldehyde-3-phosphates
Alternative Parents
Monoalkyl phosphates / Alpha-hydroxyaldehydes / Secondary alcohols / Organic oxides / Hydrocarbon derivatives
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
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
glyceraldehyde 3-phosphate (CHEBI:29052)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Nadp binding
Specific Function
Catalyzes the oxidative phosphorylation of glyceraldehyde 3-phosphate (G3P) to 1,3-bisphosphoglycerate (BPG) using the cofactor NAD. The first reaction step involves the formation of a hemiacetal i...
Gene Name
gapA
Uniprot ID
P0A9B2
Uniprot Name
Glyceraldehyde-3-phosphate dehydrogenase A
Molecular Weight
35532.24 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Geobacillus stearothermophilus
Pharmacological action
Unknown
General Function
Nadp binding
Specific Function
Catalyzes the oxidative phosphorylation of glyceraldehyde 3-phosphate (G3P) to 1,3-bisphosphoglycerate (BPG) using the cofactor NAD. The first reaction step involves the formation of a hemiacetal i...
Gene Name
gap
Uniprot ID
P00362
Uniprot Name
Glyceraldehyde-3-phosphate dehydrogenase
Molecular Weight
36074.99 Da
Kind
Protein
Organism
Streptococcus mutans serotype c (strain ATCC 700610 / UA159)
Pharmacological action
Unknown
General Function
Glyceraldehyde-3-phosphate dehydrogenase (nadp+) (phosphorylating) activity
Specific Function
Not Available
Gene Name
gapN
Uniprot ID
Q59931
Uniprot Name
NADP-dependent glyceraldehyde-3-phosphate dehydrogenase
Molecular Weight
51193.14 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, a...
Gene Name
SLCO2A1
Uniprot ID
Q92959
Uniprot Name
Solute carrier organic anion transporter family member 2A1
Molecular Weight
70043.33 Da
References
  1. Chan BS, Endo S, Kanai N, Schuster VL: Identification of lactate as a driving force for prostanoid transport by prostaglandin transporter PGT. Am J Physiol Renal Physiol. 2002 Jun;282(6):F1097-102. [PubMed:11997326]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:55