sn-glycerol 3-phosphate (PAMDB110409)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110409
Identification
Name: sn-glycerol 3-phosphate
Description:An organophosphate oxoanion that is the dianion of sn-glycerol 3-phosphate arising from deprotonation of both phosphate OH groups.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • L-α-glycerophosphate
  • L-G3P
  • L-glycerol 3-phosphate
  • α-glycerophosphoric acid
  • α-glycerophosphate
  • D-glycerol 1-phosphate
  • glycerol 3-phosphate
Chemical Formula: C3H7O6P
Average Molecular Weight: 170.06
Monoisotopic Molecular Weight: 172.0136745315
InChI Key: AWUCVROLDVIAJX-GSVOUGTGSA-L
InChI: InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/p-2/t3-/m1/s1
CAS number: 57-03-4
IUPAC Name:(2R)-2,3-dihydroxypropyl phosphate
Traditional IUPAC Name: 3-phosphoglycerol
SMILES:C(OP([O-])(=O)[O-])C(O)CO
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as glycerophosphates. These are compounds containing a glycerol linked to a phosphate group.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Lipids and lipid-like molecules
Sub ClassGlycerophospholipids
Direct Parent Glycerophosphates
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 Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: 102 - 104 °C
Experimental Properties:
PropertyValueReference
Melting Point102 - 104 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000.0 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility30.6 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.39 m3·mol-1ChemAxon
Polarizability13.58 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
sn-glycerol 3-phosphate + oleoyl-CoA → 1-oleyl-2-lyso-phosphatidate + coenzyme A
Glycerophosphoglycerol + Water → Glycerol + sn-glycerol 3-phosphate + Hydrogen ion
glycerone phosphate + Hydrogen ion → sn-glycerol 3-phosphate
ETR-Quinones + sn-glycerol 3-phosphate → ETR-Quinols + glycerone phosphate
sn-glycero-3-phosphoethanolamine + Water → sn-glycerol 3-phosphate + ethanolamine + Hydrogen ion
hexadecanedioyl-CoA + sn-glycerol 3-phosphate → coenzyme A + 1-C16:0-α,ω-dicaboxyl-2-lysophosphatidate
glycerophosphoserine + Water → sn-glycerol 3-phosphate + L-Serine + Hydrogen ion
sn-glycerol 3-phosphate + NAD+ → glycerone phosphate + NADH + Hydrogen ion
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-9200000000-bf06c1d1e56cb8853243View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-9200000000-ffce45222cab00a0c302View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001j-9000000000-7689cca8f9c9a12d9e75View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0902000000-00e3a7e1ee10fbd8b03eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-1a40c90fd2eb656ddf5cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-9000000000-f9bc5f552db38767c437View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0920000000-72f8b96355726dd3a5b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0901000000-2c3a8ed438d7ca0fa049View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-a3549fb5ec2675fbf615View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-9000000000-096e2ba9a6ef6fd20d88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0930000000-171708905bad289d6031View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0925110000-c1ced10d34f533b3fa1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-4ee8a36492a451beda75View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-9000000000-de2aacfb81476c7755e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-dd342482ade09e9ce749View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0fkc-0917520000-d61e6034525ac5f7588dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-9000000000-d537d3f23f3d9a789c20View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-2f1ca45b50402f6e62dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0009000000-5606781224d6ab5caed3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0pi0-1900000000-75b6ed57a4c9cd6378b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0a59-6900000000-1c46fbda1468f6fd803cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a5c-9400000000-305e9a2554d8c3274f32View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-007o-9000000000-d11ad04a048c3dca25deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00mo-9000000000-7b779b4be184b5b26b6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
  • Slomiany BL, Piotrowski J, Mojtahed H, Slomiany A: Ebrotidine effect on the proteolytic and lipolytic activities of Helicobacter pylori. Gen Pharmacol. 1992 Mar;23(2):203-6. [1639232 ]
  • Guminski T: Some glycolytic enzymes in normal cerebrospinal fluid, brain tissue and blood plasma of infants. Clin Chim Acta. 1976 Aug 16;71(1):61-6. [134854 ]
Synthesis Reference: Rios-Mercadillo, Victor M.; Whitesides, George M. Enzymic synthesis of sn-glycerol 3-phosphate. Journal of the American Chemical Society (1979), 101(19), 5828-9.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CAS57-03-4
ChEBI57597
ChemSpider2939444
HMDBHMDB00126
IAF1260137383
KEGGC00093
MetaboLightsMTBLC57597
PubChem7048686