Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 00:20:44 UTC |
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Update Date | 2016-11-09 01:18:39 UTC |
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Accession Number | CHEM028278 |
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Identification |
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Common Name | Withaperuvin B |
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Class | Small Molecule |
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Description | A 2-hydroxy monocarboxylic acid that is acetic acid where the methyl group has been hydroxylated. |
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Contaminant Sources | |
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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2-Hydroxyacetic acid | ChEBI | 2-Hydroxyethanoic acid | ChEBI | alpha-Hydroxyacetic acid | ChEBI | Glycollic acid | ChEBI | HOCH2COOH | ChEBI | Hydroxyacetic acid | ChEBI | Hydroxyethanoic acid | ChEBI | 2-Hydroxyacetate | Generator | 2-Hydroxyethanoate | Generator | a-Hydroxyacetate | Generator | a-Hydroxyacetic acid | Generator | alpha-Hydroxyacetate | Generator | Α-hydroxyacetate | Generator | Α-hydroxyacetic acid | Generator | Glycollate | Generator | Hydroxyacetate | Generator | Hydroxyethanoate | Generator | Glycolate | Generator | Glycocide | HMDB | GlyPure | HMDB | GlyPure 70 | HMDB | Sodium glycolate | HMDB | Glycolic acid, 2-(14)C-labeled | HMDB | Glycolic acid, 1-(14)C-labeled | HMDB | Glycolic acid, potassium salt | HMDB | Glycolic acid, monopotassium salt | HMDB | Glycolic acid, calcium salt | HMDB | Glycolic acid, monoammonium salt | HMDB | Glycolic acid, monolithium salt | HMDB | Glycolic acid, monosodium salt | HMDB | Potassium glycolate | HMDB |
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Chemical Formula | C28H40O9 |
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Average Molecular Mass | 520.612 g/mol |
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Monoisotopic Mass | 520.267 g/mol |
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CAS Registry Number | 81644-35-1 |
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IUPAC Name | 6-(1-hydroxy-1-{6,7,8,11,14-pentahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}ethyl)-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one |
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Traditional Name | 6-(1-hydroxy-1-{6,7,8,11,14-pentahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}ethyl)-3,4-dimethyl-5,6-dihydropyran-2-one |
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SMILES | CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC(O)C4(O)C(O)C=CC(=O)C4(C)C3CCC12C |
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InChI Identifier | InChI=1S/C28H40O9/c1-14-12-21(37-22(32)15(14)2)25(5,33)27(35)11-10-26(34)17-13-20(31)28(36)19(30)7-6-18(29)24(28,4)16(17)8-9-23(26,27)3/h6-7,16-17,19-21,30-31,33-36H,8-13H2,1-5H3 |
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InChI Key | XLUKITCTLVOOAW-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Hydroxy acids and derivatives |
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Sub Class | Alpha hydroxy acids and derivatives |
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Direct Parent | Alpha hydroxy acids and derivatives |
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Alternative Parents | |
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Substituents | - Alpha-hydroxy acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udr-0489740000-3e53806f47d33a03eeb0 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-001a-3341269000-eb405f656e4d60540d77 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-016r-0103590000-b13bde068d144f6591bb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0gc0-1906220000-abdbc48f76a634c478b9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-9304000000-1608f0e187d3d78a514c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0uk9-0003490000-0a25379c004e3e6d9aa7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ue9-7114930000-fcadccfe4fc5a33f4ef5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uxr-3039000000-98bff6858130e8d7d45e | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB03085 |
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HMDB ID | HMDB0000115 |
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FooDB ID | FDB003298 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | C00007461 |
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BiGG ID | 34090 |
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BioCyc ID | GLYCOLLATE |
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METLIN ID | 3219 |
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PDB ID | Not Available |
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Wikipedia Link | Glycolic_acid |
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Chemspider ID | 737 |
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ChEBI ID | 17497 |
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PubChem Compound ID | 757 |
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Kegg Compound ID | C03547 |
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YMDB ID | YMDB00807 |
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ECMDB ID | ECMDB03035 |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14585457 | 2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15662707 | 3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15716481 | 4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15716482 | 5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18498500 | 6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19025792 | 7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21950544 | 8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22044748 | 9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22128110 | 10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22360337 | 11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22421647 | 12. Witzemann, Edgar J. Preparation of glycollic acid. Journal of the American Chemical Society (1917), 39 109-12. | 13. Witzemann, Edgar J. Preparation of glycollic acid. Journal of the American Chemical Society (1917), 39 109-12. | 14. Horikoshi T, Matsumoto M, Usuki A, Igarashi S, Hikima R, Uchiwa H, Hayashi S, Brysk MM, Ichihashi M, Funasaka Y: Effects of glycolic acid on desquamation-regulating proteinases in human stratum corneum. Exp Dermatol. 2005 Jan;14(1):34-40. | 15. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. | 16. DiNardo JC, Grove GL, Moy LS: Clinical and histological effects of glycolic acid at different concentrations and pH levels. Dermatol Surg. 1996 May;22(5):421-4. | 17. Marangella M, Petrarulo M, Bianco O, Vitale C, Finocchiaro P, Linari F: Glycolate determination detects type I primary hyperoxaluria in dialysis patients. Kidney Int. 1991 Jan;39(1):149-54. | 18. Tsiafoulis CG, Prodromidis MI, Karayannis MI: Development of amperometric biosensors for the determination of glycolic acid in real samples. Anal Chem. 2002 Jan 1;74(1):132-9. | 19. Porter WH, Rutter PW, Yao HH: Simultaneous determination of ethylene glycol and glycolic acid in serum by gas chromatography-mass spectrometry. J Anal Toxicol. 1999 Nov-Dec;23(7):591-7. | 20. Jacobsen D, Hewlett TP, Webb R, Brown ST, Ordinario AT, McMartin KE: Ethylene glycol intoxication: evaluation of kinetics and crystalluria. Am J Med. 1988 Jan;84(1):145-52. | 21. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. | 22. Bernstein EF, Lee J, Brown DB, Yu R, Van Scott E: Glycolic acid treatment increases type I collagen mRNA and hyaluronic acid content of human skin. Dermatol Surg. 2001 May;27(5):429-33. | 23. Leumann EP, Dietl A, Matasovic A: Urinary oxalate and glycolate excretion in healthy infants and children. Pediatr Nephrol. 1990 Sep;4(5):493-7. | 24. Booth ED, Dofferhoff O, Boogaard PJ, Watson WP: Comparison of the metabolism of ethylene glycol and glycolic acid in vitro by precision-cut tissue slices from female rat, rabbit and human liver. Xenobiotica. 2004 Jan;34(1):31-48. | 25. Mahul P, Molliex S, Auboyer C, Levigne F, Jospe R, Dumont A, Gilloz A: [Neurotoxic role of glycocolle and derivatives in transurethral resection of the prostate]. Ann Fr Anesth Reanim. 1993;12(5):512-4. | 26. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. | 27. Marangella M, Petrarulo M, Vitale C, Cosseddu D, Linari F: Plasma and urine glycolate assays for differentiating the hyperoxaluria syndromes. J Urol. 1992 Sep;148(3 Pt 2):986-9. | 28. Effendy I, Kwangsukstith C, Lee JY, Maibach HI: Functional changes in human stratum corneum induced by topical glycolic acid: comparison with all-trans retinoic acid. Acta Derm Venereol. 1995 Nov;75(6):455-8. | 29. Pien K, van Vlem B, van Coster R, Dacremont G, Piette M: An inherited metabolic disorder presenting as ethylene glycol intoxication in a young adult. Am J Forensic Med Pathol. 2002 Mar;23(1):96-100. | 30. Dietzen DJ, Wilhite TR, Kenagy DN, Milliner DS, Smith CH, Landt M: Extraction of glyceric and glycolic acids from urine with tetrahydrofuran: utility in detection of primary hyperoxaluria. Clin Chem. 1997 Aug;43(8 Pt 1):1315-20. | 31. Newman N, Newman A, Moy LS, Babapour R, Harris AG, Moy RL: Clinical improvement of photoaged skin with 50% glycolic acid. A double-blind vehicle-controlled study. Dermatol Surg. 1996 May;22(5):455-60. | 32. Roe FJ: Perspectives in carbohydrate toxicology with special reference to carcinogenicity. Swed Dent J. 1984;8(3):99-111. | 33. Porter WH, Rutter PW, Bush BA, Pappas AA, Dunnington JE: Ethylene glycol toxicity: the role of serum glycolic acid in hemodialysis. J Toxicol Clin Toxicol. 2001;39(6):607-15. | 34. Kataoka M, Sasaki M, Hidalgo AR, Nakano M, Shimizu S: Glycolic acid production using ethylene glycol-oxidizing microorganisms. Biosci Biotechnol Biochem. 2001 Oct;65(10):2265-70. doi: 10.1271/bbb.65.2265. | 35. Becker J, Lange A, Fabarius J, Wittmann C: Top value platform chemicals: bio-based production of organic acids. Curr Opin Biotechnol. 2015 Dec;36:168-75. doi: 10.1016/j.copbio.2015.08.022. Epub 2015 Sep 8. | 36. MARTIN SM, STEEL R: Effect of phosphate on production of organic acids by Aspergillus niger. Can J Microbiol. 1955 Jun;1(6):470-2. |
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