You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:23 UTC
Secondary Accession Numbers
  • HMDB60148
Metabolite Identification
Common NamePhosphoglycolic acid
DescriptionPhosphoglycolic acid is a substrate for triose-phosphate isomerase. This compound belongs to the family of Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group.
(Phosphonooxy)-acetic acidHMDB
(Phosphonooxy)acetic acidHMDB
2-Phosphoglycolic acidHMDB
Glycolic acid di-H phosphateHMDB
Glycolic acid dihydrogen phosphateHMDB
Glycolic acid phosphateHMDB
Glycophosphoric acidHMDB
Chemical FormulaC2H5O6P
Average Molecular Weight156.0313
Monoisotopic Molecular Weight155.982374404
IUPAC Name2-(phosphonooxy)acetic acid
Traditional Namephosphoglycolate
CAS Registry Number13147-57-4
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
KingdomOrganic compounds
Super ClassOrganophosphorus compounds
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentMonoalkyl phosphates
Alternative Parents
  • Monoalkyl phosphate
  • Organic phosphate
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
StatusExpected but not Quantified
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility18.4 mg/mLALOGPS
pKa (Strongest Acidic)1.14ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity25.22 m3·mol-1ChemAxon
Polarizability10.67 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0bwa-1954000000-58b32347feea7c57657dView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-72a0567ec4387e0d910fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0900000000-a18204a3ef12341ad757View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-9700000000-b6a20a78eceb3021333fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ufr-3900000000-e1fa686e95d11683b169View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-e7d5d6506767e5e94a14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-36a54b95f105df968214View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Bladder
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Myelin
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Stratum Corneum
  • Testes
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022263
KNApSAcK IDNot Available
Chemspider ID514
KEGG Compound IDC00988
BioCyc IDCPD-67
BiGG ID36550
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00816
Metagene LinkHMDB00816
PubChem Compound529
ChEBI ID17150
Synthesis ReferenceCourtois, Jean. Action of periodic acid on hexosediphosphoric acid. Compt. rend. (1941), 212 1172-4. CAN 38:22678 AN 1944:22678
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Morris ID, Higgins C, Matlin SA: Inhibition of testicular LDH-X from laboratory animals and man by gossypol and its isomers. J Reprod Fertil. 1986 Jul;77(2):607-12. [3735252 ]
  2. Hoffmann GF, Seppel CK, Holmes B, Mitchell L, Christen HJ, Hanefeld F, Rating D, Nyhan WL: Quantitative organic acid analysis in cerebrospinal fluid and plasma: reference values in a pediatric population. J Chromatogr. 1993 Jul 23;617(1):1-10. [8376520 ]
  3. Houghton LA, Atkinson W, Whitaker RP, Whorwell PJ, Rimmer MJ: Increased platelet depleted plasma 5-hydroxytryptamine concentration following meal ingestion in symptomatic female subjects with diarrhoea predominant irritable bowel syndrome. Gut. 2003 May;52(5):663-70. [12692050 ]
  4. Haag D, Tschahargane C, Ehemann V: Isolation of single cell nuclei from human epidermis for cytophotometric DNA--measurements. Arch Dermatol Res. 1975 Oct 29;253(3):301-10. [1200706 ]
  5. Shalom-Barak T, Knaus UG: A p21-activated kinase-controlled metabolic switch up-regulates phagocyte NADPH oxidase. J Biol Chem. 2002 Oct 25;277(43):40659-65. Epub 2002 Aug 19. [12189148 ]
  6. Novarino G, Fabrizi C, Tonini R, Denti MA, Malchiodi-Albedi F, Lauro GM, Sacchetti B, Paradisi S, Ferroni A, Curmi PM, Breit SN, Mazzanti M: Involvement of the intracellular ion channel CLIC1 in microglia-mediated beta-amyloid-induced neurotoxicity. J Neurosci. 2004 Jun 9;24(23):5322-30. [15190104 ]
  7. Anderson K, Simmons-Menchaca M, Lawson KA, Atkinson J, Sanders BG, Kline K: Differential response of human ovarian cancer cells to induction of apoptosis by vitamin E Succinate and vitamin E analogue, alpha-TEA. Cancer Res. 2004 Jun 15;64(12):4263-9. [15205340 ]
  8. Winters TA, Henner WD, Russell PS, McCullough A, Jorgensen TJ: Removal of 3'-phosphoglycolate from DNA strand-break damage in an oligonucleotide substrate by recombinant human apurinic/apyrimidinic endonuclease 1. Nucleic Acids Res. 1994 May 25;22(10):1866-73. [7516064 ]
  9. Nielsen JB, Frokiaer J, Rehling M, Jorgensen TM, Djurhuus JC: A 14-year follow-up of conservative treatment for vesico-ureteric reflux. BJU Int. 2000 Sep;86(4):502-7. [10971281 ]
  10. Goswami KK, Morris RJ, Rastogi SC, Lange LS, Russell WC: A neutralising monoclonal antibody against a paramyxovirus reacts with a brain antigen. J Neuroimmunol. 1985 Jul;9(1-2):99-108. [3891785 ]
  11. Yoshida H, Onda M, Tajiri T, Akimaru K, Uchida E, Arima Y, Mamada Y, Taniai N, Yamamoto K, Kaneko M, Kumazaki T: New techniques: splenic artery embolization followed by intraarterial infusion chemotherapy for the treatment of pancreatic cancer. Hepatogastroenterology. 1999 May-Jun;46(27):2024-7. [10430390 ]
  12. Yang N, Kays JS, Skillman TR, Burris L, Seng TW, Hammond C: C75 [4-methylene-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid] activates carnitine palmitoyltransferase-1 in isolated mitochondria and intact cells without displacement of bound malonyl CoA. J Pharmacol Exp Ther. 2005 Jan;312(1):127-33. Epub 2004 Sep 8. [15356215 ]
  13. Asahara T, Shimizu K, Nomoto K, Hamabata T, Ozawa A, Takeda Y: Probiotic bifidobacteria protect mice from lethal infection with Shiga toxin-producing Escherichia coli O157:H7. Infect Immun. 2004 Apr;72(4):2240-7. [15039348 ]
  14. Resmi KR, Krishnan LK: Protease action and generation of beta-thromboglobulin-like protein followed by platelet activation. Thromb Res. 2002 May 15;106(4-5):229-36. [12297130 ]
  15. Hou LT, Liu CM, Lei JY, Wong MY, Chen JK: Biological effects of cementum and bone extracts on human periodontal fibroblasts. J Periodontol. 2000 Jul;71(7):1100-9. [10960016 ]
  16. Hume WJ, Moore JK: Sheet preparations of the stratum granulosum from mammalian skin and oral epithelium. J Anat. 1985 Jun;140 ( Pt 4):669-78. [3908423 ]
  17. Guy J, Mancuso A, Beck R, Moster ML, Sedwick LA, Quisling RG, Rhoton AL Jr, Protzko EE, Schiffman J: Radiation-induced optic neuropathy: a magnetic resonance imaging study. J Neurosurg. 1991 Mar;74(3):426-32. [1993908 ]
  18. Fourtanier A, Berrebi C: Miniature pig as an animal model to study photoaging. Photochem Photobiol. 1989 Dec;50(6):771-84. [2626491 ]
  19. Liu Q, Cai H, Xu Y, Li Y, Li R, Wang P: Olfactory cell-based biosensor: A first step towards a neurochip of bioelectronic nose. Biosens Bioelectron. 2006 Aug 15;22(2):318-322. Epub 2006 Mar 29. [16567087 ]
  20. Adachi E, Takeda Y, Nakazato K, Muraoka M, Iwata M, Sasaki T, Imamura Y, Hopkinson I, Hayashi T: Isolated collagen IV retains the potential to form an 18-nm sided polygonal meshwork of the lamina densa. J Electron Microsc (Tokyo). 1997;46(3):233-41. [9279016 ]
  21. Ching LM, Joseph WR, Crosier KE, Baguley BC: Induction of tumor necrosis factor-alpha messenger RNA in human and murine cells by the flavone acetic acid analogue 5,6-dimethylxanthenone-4-acetic acid (NSC 640488). Cancer Res. 1994 Feb 15;54(4):870-2. [8313372 ]
  22. Nakamura M, Oda M, Inoue J, Ito T, Akiba Y, Kitajima M, Tsuchiya M, Ishii H: Effect of basic fibroblast growth factor on reinnervation of gastric microvessels. Possible relevance to ulcer recurrence. Dig Dis Sci. 1995 Jul;40(7):1451-8. [7628267 ]
  23. Ulusan S, Kizilkilic O, Yildirim T, Tercan F, Bolat F, Yildirim S: Primary hepatic carcinoid tumor: dynamic CT findings. Abdom Imaging. 2005 May-Jun;30(3):281-5. [15785908 ]
  24. Folkes LK, Greco O, Dachs GU, Stratford MR, Wardman P: 5-Fluoroindole-3-acetic acid: a prodrug activated by a peroxidase with potential for use in targeted cancer therapy. Biochem Pharmacol. 2002 Jan 15;63(2):265-72. [11841802 ]
  25. Maenhout A, Ham H, Ismaili K, Hall M, Dierckx RA, Piepsz A: Supranormal renal function in unilateral hydronephrosis: does it represent true hyperfunction? Pediatr Nephrol. 2005 Dec;20(12):1762-5. Epub 2005 Oct 20. [16237565 ]
  26. Faucet-Marquis V, Pont F, Stormer FC, Rizk T, Castegnaro M, Pfohl-Leszkowicz A: Evidence of a new dechlorinated ochratoxin A derivative formed in opossum kidney cell cultures after pretreatment by modulators of glutathione pathways: correlation with DNA-adduct formation. Mol Nutr Food Res. 2006 May;50(6):530-42. [16671059 ]
  27. Rugtveit J, Haraldsen G, Hogasen AK, Bakka A, Brandtzaeg P, Scott H: Respiratory burst of intestinal macrophages in inflammatory bowel disease is mainly caused by CD14+L1+ monocyte derived cells. Gut. 1995 Sep;37(3):367-73. [7590432 ]
  28. Yarat A, Ozcelik F, Emekli N: A method for preparing collagen graft materials. J Marmara Univ Dent Fac. 1996 Sep;2(2-3):527-9. [9569810 ]
  29. Dutt MK: Preparation of Schiff-type dye-SO2 reagents with phosphoric acid and their cytochemical properties. Microsc Acta. 1981 Mar;84(2):143-6. [6164904 ]
  30. Katofiasc MA, Nissen J, Audia JE, Thor KB: Comparison of the effects of serotonin selective, norepinephrine selective, and dual serotonin and norepinephrine reuptake inhibitors on lower urinary tract function in cats. Life Sci. 2002 Aug 2;71(11):1227-36. [12106588 ]
  31. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 Mar 3. doi: 10.1038/nbt.2488. [23455439 ]


General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
Phosphoglycolic acid + Water → Glycolic acid + Phosphoric aciddetails
General function:
Involved in catalytic activity
Specific function:
D-glyceraldehyde 3-phosphate = glycerone phosphate
Gene Name:
Not Available
Uniprot ID:
Molecular weight: