Record Information
Version1.0
Creation date2011-04-11 15:40:04 UTC
Update date2018-05-28 18:29:22 UTC
Primary IDFDB021800
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlycerol 1-monophosphate
DescriptionGlycerol 3-phosphate is a chemical intermediate in the glycolysis metabolic pathway. It is commonly confused with the similarly named glycerate 3-phosphate or glyceraldehyde 3-phosphate. Glycerol 3-phosphate is produced from glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phospate may then be converted by dehydrogenation to dihydroxyacetone phosphate (DHAP) by the enzyme glycerol-3-phosphate dehydrogenase. DHAP can then be rearranged into glyceraldehyde 3-phosphate (GA3P) by triose phosphate isomerase (TIM), and feed into glycolysis. The glycerol 3-phosphate shuttle is used to rapidly regenerate NAD+ in brain and skeletal muscle cells of mammals (wikipedia). [HMDB]
CAS Number57-03-4
Structure
Thumb
Synonyms
SynonymSource
1,2,3-Propanetriol, 1-(dihydrogen phosphate)ChEBI
1-GlycerophosphateChEBI
1-Glycerophosphoric acidChEBI
1-PhosphoglycerolChEBI
2,3-Dihydroxypropyl dihydrogen phosphateChEBI
2,3-Hydroxy-1-propyl dihydrogen phosphateChEBI
3-GlycerophosphateChEBI
alpha-Glycerophosphoric acidChEBI
alpha-PhosphoglycerolChEBI
D,L-alpha-Glycerol-phosphateChEBI
DL-Glycerol 1-phosphateChEBI
DL-Glycerol 3-phosphateChEBI
DL-Glyceryl 1-phosphateChEBI
Glycerol alpha-phosphateChEBI
PGChEBI
rac-Glycerol 1-phosphateChEBI
1,2,3-Propanetriol, 1-(dihydrogen phosphoric acid)Generator
Glycerol-3-phosphoric acidGenerator
2,3-Dihydroxypropyl dihydrogen phosphoric acidGenerator
2,3-Hydroxy-1-propyl dihydrogen phosphoric acidGenerator
3-Glycerophosphoric acidGenerator
a-GlycerophosphateGenerator
a-Glycerophosphoric acidGenerator
alpha-GlycerophosphateGenerator
α-glycerophosphateGenerator
α-glycerophosphoric acidGenerator
a-PhosphoglycerolGenerator
α-phosphoglycerolGenerator
D,L-a-Glycerol-phosphateGenerator
D,L-a-Glycerol-phosphoric acidGenerator
D,L-alpha-Glycerol-phosphoric acidGenerator
D,L-α-glycerol-phosphateGenerator
D,L-α-glycerol-phosphoric acidGenerator
DL-Glycerol 1-phosphoric acidGenerator
DL-Glycerol 3-phosphoric acidGenerator
DL-Glyceryl 1-phosphoric acidGenerator
Glycerol a-phosphateGenerator
Glycerol a-phosphoric acidGenerator
Glycerol alpha-phosphoric acidGenerator
Glycerol α-phosphateGenerator
Glycerol α-phosphoric acidGenerator
rac-Glycerol 1-phosphoric acidGenerator
alpha-Glycerophosphoric acid, 1,2,3-propanetriol-1-(18)O,3-(dihydrogen phosphate)-labeledMeSH
alpha-Glycerophosphoric acid, fe(+3) salt (3:2)MeSH
alpha-Glycerophosphoric acid, disodium saltMeSH
Disodium glycerophosphateMeSH
Glycerol 1-phosphateMeSH
Glycerol 3-phosphateMeSH
alpha-Glycerophosphoric acid, fe saltMeSH
alpha-Glycerophosphoric acid, monocalcium salt (S)-isomerMeSH
alpha-Glycerophosphoric acid, monomagnesium saltMeSH
alpha-Glycerophosphoric acid, sodium saltMeSH
alpha-Glycerophosphoric acid, (R)-isomerMeSH
alpha-Glycerophosphoric acid, (S)-isomerMeSH
alpha-Glycerophosphoric acid, disodium salt hexahydrate(+-)-isomerMeSH
alpha-Glycerophosphoric acid, monocalcium saltMeSH
Sodium glycerophosphateMeSH
alpha-Glycerophosphoric acid, (DL)-isomerMeSH
alpha-Glycerophosphoric acid, 1,2,3-propanetriol-2-(18)O,3-(dihydrogen phosphate)-labeledMeSH
alpha-Glycerophosphoric acid, calcium saltMeSH
alpha-Glycerophosphoric acid, disodium salt (+-)-isomerMeSH
(R)-Glycerol 1-ateChEBI
(R)-Glycerol 1-ic acidGenerator
1-(Dihydrogen ate) glycerolHMDB
1-glyceroateHMDB
1-GlyceroOrateHMDB
1-glycerooric acidHMDB
1,2,3-Propanetriol 1-(dihydrogen phosphate), 9CIdb_source
3-glyceroateHMDB
a-glyceroateHMDB
a-GlyceroOrateHMDB
a-glycerooric acidHMDB
a-OglycerolHMDB
alpha-glyceroateHMDB
alpha-GlyceroOrateHMDB
alpha-glycerooric acidHMDB
alpha-OglycerolHMDB
D-(Glycerol 1-ate)ChEBI
D-(Glycerol 1-ic acid)Generator
D-Glycerol 1-ateChEBI
D-Glycerol 1-ic acidGenerator
Dihydrogen a-glyceroateHMDB
DL-a-glyceroateHMDB
DL-a-Glycerol ateHMDB
DL-a-GlyceroOrateHMDB
DL-a-glycerooric acidHMDB
DL-a-Glyceryl ateHMDB
DL-alpha-glyceroateHMDB
DL-alpha-Glycerol ateHMDB
DL-alpha-GlyceroOrateHMDB
DL-alpha-glycerooric acidHMDB
DL-alpha-Glyceryl ateHMDB
DL-Glycerol 1-ateHMDB
DL-Glycerol 3-ateHMDB
glyceroateGenerator
glyceroic acidGenerator
Glycerol 1-ateHMDB
Glycerol a-ateHMDB
Glycerol monoateHMDB
Glycerol-3-ateChEBI
Glycerol-3-ic acidGenerator
GlyceroOrateHMDB
glycerooric acidChEBI
glycerooric acid IHMDB
Glyceryl ateHMDB
L-(Glycerol 3-ate)ChEBI
L-(Glycerol 3-ic acid)Generator
Orate mono-((R)-2,3-dihydroxy-propyl) esterGenerator
oric acid Mono-((R)-2,3-dihydroxy-propyl) esterChEBI
Orsaeure-mono-((R)-2,3-dihydroxy-propylester)ChEBI
sn-Glycerol 3-ateChEBI
sn-Glycerol 3-ic acidGenerator
sn-GLYCEROL-3-ATEChEBI
sn-GLYCEROL-3-ic acidGenerator
sn-Gro-1-PChEBI
Predicted Properties
PropertyValueSource
Water Solubility30.6 g/LALOGPS
logP-1.8ALOGPS
logP-2ChemAxon
logS-0.75ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.39 m³·mol⁻¹ChemAxon
Polarizability13.45 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC3H9O6P
IUPAC name(2,3-dihydroxypropoxy)phosphonic acid
InChI IdentifierInChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)
InChI KeyAWUCVROLDVIAJX-UHFFFAOYSA-N
Isomeric SMILESOCC(O)COP(O)(O)=O
Average Molecular Weight172.0737
Monoisotopic Molecular Weight172.013674532
Classification
DescriptionThis compound belongs to the class of chemical entities known as glycerophosphates. These are compounds containing a glycerol linked to a phosphate group.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassGlycerophospholipids
Direct ParentGlycerophosphates
Alternative Parents
Substituents
  • Sn-glycerol-3-phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • 1,2-diol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0zgj-1976000000-019de1fa6314b95ef7feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-5900000000-64043ee94d742cc4c8a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9400000000-f030544d156b4b0111a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-7d3c25cddbefbb1f8b87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-6900000000-0018771a83ca8722e148View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-cd376066ff1f1f928911View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a6ed4a0320c8229c8621View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID388308
ChEMBL IDCHEMBL1232920
KEGG Compound IDC00093
Pubchem Compound ID439162
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB02515
HMDB IDHMDB00126
CRC / DFC (Dictionary of Food Compounds) IDCVS33-I:CVS33-I
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID137383
KNApSAcK IDNot Available
HET IDG3P
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glycerol-3-phosphate acyltransferase 3AGPAT9Q53EU6
Glycerol kinase 2GK2Q14410
Glycerol kinaseGKP32189
Putative glycerol kinase 3GK3PQ14409
Putative glycerol kinase 5GK5Q6ZS86
Glycerol-3-phosphate acyltransferase 1, mitochondrialGPAMQ9HCL2
Glycerol-3-phosphate acyltransferase 4AGPAT6Q86UL3
Putative uncharacterized protein DKFZp451B1115DKFZp451B1115Q86T70
Glycerol-3-phosphate acyltransferase 2, mitochondrialGPAT2Q6NUI2
N-acetyltransferase ESCO1ESCO1Q5FWF5
Pathways
NameSMPDB LinkKEGG Link
Glycerol Phosphate ShuttleSMP00124 Not Available
Glycerolipid MetabolismSMP00039 map00561
Mitochondrial Electron Transport ChainSMP00355 map00190
Phospholipid BiosynthesisSMP00025 map00564
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference