1.0 2011-04-11 15:40:04 UTC 2025-11-19 02:39:42 UTC FDB021800 Glycerol 1-monophosphate Glycerol 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] (R)-Glycerol 1-ate (R)-Glycerol 1-ic acid 1-(Dihydrogen ate) glycerol 1-glyceroate 1-GlyceroOrate 1-glycerooric acid 1,2,3-Propanetriol 1-(dihydrogen phosphate), 9CI 3-glyceroate a-glyceroate a-GlyceroOrate a-glycerooric acid a-Glycerophosphoric acid a-Oglycerol alpha-glyceroate alpha-GlyceroOrate alpha-glycerooric acid alpha-Oglycerol D-(Glycerol 1-ate) D-(Glycerol 1-ic acid) D-Glycerol 1-ate D-Glycerol 1-ic acid Dihydrogen a-glyceroate DL-a-glyceroate DL-a-Glycerol ate DL-a-GlyceroOrate DL-a-glycerooric acid DL-a-Glyceryl ate DL-alpha-glyceroate DL-alpha-Glycerol ate DL-alpha-GlyceroOrate DL-alpha-glycerooric acid DL-alpha-Glyceryl ate DL-Glycerol 1-ate DL-Glycerol 3-ate glyceroate glyceroic acid Glycerol 1-ate Glycerol 1-phosphate Glycerol a-ate Glycerol monoate Glycerol-3-ate Glycerol-3-ic acid GlyceroOrate glycerooric acid glycerooric acid I Glyceryl ate L-(Glycerol 3-ate) L-(Glycerol 3-ic acid) Orate mono-((R)-2,3-dihydroxy-propyl) ester oric acid Mono-((R)-2,3-dihydroxy-propyl) ester Orsaeure-mono-((R)-2,3-dihydroxy-propylester) sn-Glycerol 3-ate sn-Glycerol 3-ic acid sn-GLYCEROL-3-ATE sn-GLYCEROL-3-ic acid sn-Gro-1-P C3H9O6P 172.0737 172.013674532 (2,3-dihydroxypropoxy)phosphonic acid α-glycerophosphate 57-03-4 OCC(O)COP(O)(O)=O InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8) AWUCVROLDVIAJX-UHFFFAOYSA-N belongs to the class of organic compounds known as glycerophosphates. Glycerophosphates are compounds containing a glycerol linked to a phosphate group. Glycerophosphates Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphates Aliphatic acyclic compounds 1,2-diols Hydrocarbon derivatives Monoalkyl phosphates Organic oxides Primary alcohols Secondary alcohols 1,2-diol Alcohol Aliphatic acyclic compound Alkyl phosphate Hydrocarbon derivative Monoalkyl phosphate Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organooxygen compound Phosphoric acid ester Primary alcohol Secondary alcohol Sn-glycerol-3-phosphate glycerol monophosphate Solid logp -1.84 ALOGPS logs -0.75 ALOGPS solubility 3.06e+01 g/l ALOGPS logp -2 ChemAxon pka_strongest_acidic 1.51 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2,3-dihydroxypropoxy)phosphonic acid ChemAxon average_mass 172.0737 ChemAxon mono_mass 172.013674532 ChemAxon smiles OCC(O)COP(O)(O)=O ChemAxon formula C3H9O6P ChemAxon inchi InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8) ChemAxon inchikey AWUCVROLDVIAJX-UHFFFAOYSA-N ChemAxon polar_surface_area 107.22 ChemAxon refractivity 31.39 ChemAxon polarizability 13.45 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycerol Phosphate Shuttle SMP00124 Glycerolipid Metabolism SMP00039 map00561 Mitochondrial Electron Transport Chain SMP00355 map00190 Phospholipid Biosynthesis SMP00025 map00564 Specdb::MsMs 27011 Specdb::MsMs 27012 Specdb::MsMs 27013 Specdb::MsMs 33569 Specdb::MsMs 33570 Specdb::MsMs 33571 Specdb::MsMs 3436981 Specdb::MsMs 3436982 Specdb::MsMs 3436983 Specdb::MsMs 3436984 Specdb::MsMs 3436985 Specdb::MsMs 3436986 Specdb::NmrOneD 5003 Specdb::NmrOneD 5004 Specdb::NmrOneD 189621 Specdb::NmrOneD 189622 Specdb::NmrOneD 189623 Specdb::NmrOneD 189624 Specdb::NmrOneD 189625 Specdb::NmrOneD 189626 Specdb::NmrOneD 189627 Specdb::NmrOneD 189628 Specdb::NmrOneD 189629 Specdb::NmrOneD 189630 Specdb::NmrOneD 189631 Specdb::NmrOneD 189632 Specdb::NmrOneD 189633 Specdb::NmrOneD 189634 Specdb::NmrOneD 189635 Specdb::NmrOneD 189636 Specdb::NmrOneD 189637 Specdb::NmrOneD 189638 Specdb::NmrOneD 189639 Specdb::NmrOneD 189640 Specdb::CMs 1426 Specdb::CMs 105043 Specdb::CMs 117084 Specdb::CMs 128828 Specdb::CMs 903275 Specdb::CMs 903276 Specdb::CMs 903277 Specdb::CMs 903278 Specdb::CMs 903279 Specdb::CMs 903280 Specdb::CMs 903281 Specdb::CMs 903282 Specdb::CMs 903283 Specdb::CMs 903284 Specdb::CMs 903285 HMDB00126 G3P #<Reference:0x000055ce30cbd7d0> #<Reference:0x000055ce30cbd488> #<Reference:0x000055ce30cbd2d0> Glycerol kinase P32189 GK Glycerol kinase 2 Q14410 GK2 Glycerol-3-phosphate acyltransferase 1, mitochondrial Q9HCL2 GPAM Glycerol-3-phosphate acyltransferase 2, mitochondrial Q6NUI2 GPAT2 Glycerol-3-phosphate acyltransferase 3 Q53EU6 AGPAT9 Glycerol-3-phosphate acyltransferase 4 Q86UL3 AGPAT6 N-acetyltransferase ESCO1 Q5FWF5 ESCO1 Putative glycerol kinase 3 Q14409 GK3P Putative glycerol kinase 5 Q6ZS86 GK5 Putative uncharacterized protein DKFZp451B1115 Q86T70 DKFZp451B1115