2-phospho-D-glyceric acid

Identification

Name
2-phospho-D-glyceric acid
Accession Number
DB01709  (EXPT00143, EXPT02490, DB03465)
Type
Small Molecule
Groups
Experimental
Description

A 2-phosphoglyceric acid in which the glyceric acid moiety has D (R) configuration.

Structure
Thumb
Synonyms
  • 2-phospho-D-glycerate
  • D-glycerate 2-phosphate
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 186.0572
Monoisotopic: 185.99293909
Chemical Formula
C3H7O7P
InChI Key
GXIURPTVHJPJLF-UWTATZPHSA-N
InChI
InChI=1S/C3H7O7P/c4-1-2(3(5)6)10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)/t2-/m1/s1
IUPAC Name
(2R)-3-hydroxy-2-(phosphonooxy)propanoic acid
SMILES
OC[[email protected]@H](OP(O)(O)=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U2-dehydro-3-deoxyphosphooctonate aldolaseNot AvailableAquifex aeolicus (strain VF5)
U2,3-bisphosphoglycerate-independent phosphoglycerate mutaseNot AvailableGeobacillus stearothermophilus
UTriosephosphate isomeraseNot AvailablePlasmodium falciparum
UBeta-enolaseNot AvailableHuman
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
Warburg EffectMetabolic
Fructose-1,6-diphosphatase deficiencyDisease
Fanconi-bickel syndromeDisease
GlycolysisMetabolic
Glycogenosis, Type IA. Von gierke diseaseDisease
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke DiseaseDisease
Phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1)Disease
Triosephosphate isomeraseDisease
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

General References
Not Available
External Links
Human Metabolome Database
HMDB03391
KEGG Compound
C00631
PubChem Compound
439278
PubChem Substance
46506872
ChemSpider
388411
ChEBI
17835
HET
2PG
PDB Entries
1eqj / 1o5x / 1o98 / 1o99 / 1one / 1p43 / 1pe1 / 1zji / 2al1 / 2al2
show 20 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 Solubility20.3 mg/mLALOGPS
logP-2.2ALOGPS
logP-1.6ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)0.81ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.26 m3·mol-1ChemAxon
Polarizability13.36 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9403
Blood Brain Barrier+0.9382
Caco-2 permeable-0.7554
P-glycoprotein substrateNon-substrate0.7893
P-glycoprotein inhibitor INon-inhibitor0.9051
P-glycoprotein inhibitor IINon-inhibitor0.9223
Renal organic cation transporterNon-inhibitor0.933
CYP450 2C9 substrateNon-substrate0.8132
CYP450 2D6 substrateNon-substrate0.8497
CYP450 3A4 substrateNon-substrate0.6523
CYP450 1A2 substrateNon-inhibitor0.9177
CYP450 2C9 inhibitorNon-inhibitor0.8961
CYP450 2D6 inhibitorNon-inhibitor0.9223
CYP450 2C19 inhibitorNon-inhibitor0.8942
CYP450 3A4 inhibitorNon-inhibitor0.9474
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9754
Ames testNon AMES toxic0.8232
CarcinogenicityNon-carcinogens0.704
BiodegradationReady biodegradable0.8083
Rat acute toxicity2.0931 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9726
hERG inhibition (predictor II)Non-inhibitor0.9122
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 (4 TMS)GC-MSsplash10-014j-1986100000-67b36247ae0c01d6630f
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-014j-1986100000-67b36247ae0c01d6630f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000j-9300000000-24ac9683b32428f58197
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9600000000-b12281d6d89eef904e6b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0007-9000000000-a07c4a51c820b32ec8bd
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-4900000000-516a86a1a17689399892
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9500000000-b33f3e08e2e8b3d5aed5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-07016cc3ecca7d5e323b
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-0900000000-80caf2498862e856c8fc
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9100000000-1518e606c03a8697d1b9
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9000000000-66ec419add3cb3e1fd32
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9000000000-b7f464912df9166dc597
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9000000000-d09faea5291df7a04b70
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udr-0900000000-09027263f64d0e1059c6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-1900000000-8eeb1d2a8432d1e44448
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0f6t-8900000000-3b714e664b948f61ac7e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0023-9000000000-ed83591fbfd15323cd6d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001m-9000000000-39cdf9729f381069e45f

Taxonomy

Description
This compound belongs to the class of organic compounds known as sugar acids and derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Sugar acids and derivatives
Alternative Parents
Monoalkyl phosphates / Beta hydroxy acids and derivatives / Monosaccharides / Monocarboxylic acids and derivatives / Carboxylic acids / Primary alcohols / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Beta-hydroxy acid / Glyceric_acid / Monoalkyl phosphate / Hydroxy acid / Monosaccharide / Organic phosphoric acid derivative / Phosphoric acid ester / Alkyl phosphate / Monocarboxylic acid or derivatives / Carboxylic acid
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
2-phosphoglyceric acid (CHEBI:17835)

Targets

Kind
Protein
Organism
Aquifex aeolicus (strain VF5)
Pharmacological action
Unknown
General Function
3-deoxy-8-phosphooctulonate synthase activity
Specific Function
Not Available
Gene Name
kdsA
Uniprot ID
O66496
Uniprot Name
2-dehydro-3-deoxyphosphooctonate aldolase
Molecular Weight
29734.17 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
Manganese ion binding
Specific Function
Essential for rapid growth and for sporulation. Catalyzes the interconversion of 2-phosphoglycerate (2-PGA) and 3-phosphoglycerate (3-PGA).
Gene Name
gpmI
Uniprot ID
Q9X519
Uniprot Name
2,3-bisphosphoglycerate-independent phosphoglycerate mutase
Molecular Weight
57002.48 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
Plasmodium falciparum
Pharmacological action
Unknown
General Function
Triose-phosphate isomerase activity
Specific Function
Not Available
Gene Name
TPI
Uniprot ID
Q07412
Uniprot Name
Triosephosphate isomerase
Molecular Weight
27934.505 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
Human
Pharmacological action
Unknown
General Function
Phosphopyruvate hydratase activity
Specific Function
Appears to have a function in striated muscle development and regeneration.
Gene Name
ENO3
Uniprot ID
P13929
Uniprot Name
Beta-enolase
Molecular Weight
46986.485 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:03