Withaperuvin B (CHEM028278)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:20:44 UTC
Update Date2016-11-09 01:18:39 UTC
Accession NumberCHEM028278
Identification
Common NameWithaperuvin B
ClassSmall Molecule
DescriptionA 2-hydroxy monocarboxylic acid that is acetic acid where the methyl group has been hydroxylated.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Hydroxyacetic acidChEBI
2-Hydroxyethanoic acidChEBI
alpha-Hydroxyacetic acidChEBI
Glycollic acidChEBI
HOCH2COOHChEBI
Hydroxyacetic acidChEBI
Hydroxyethanoic acidChEBI
2-HydroxyacetateGenerator
2-HydroxyethanoateGenerator
a-HydroxyacetateGenerator
a-Hydroxyacetic acidGenerator
alpha-HydroxyacetateGenerator
Α-hydroxyacetateGenerator
Α-hydroxyacetic acidGenerator
GlycollateGenerator
HydroxyacetateGenerator
HydroxyethanoateGenerator
GlycolateGenerator
GlycocideHMDB
GlyPureHMDB
GlyPure 70HMDB
Sodium glycolateHMDB
Glycolic acid, 2-(14)C-labeledHMDB
Glycolic acid, 1-(14)C-labeledHMDB
Glycolic acid, potassium saltHMDB
Glycolic acid, monopotassium saltHMDB
Glycolic acid, calcium saltHMDB
Glycolic acid, monoammonium saltHMDB
Glycolic acid, monolithium saltHMDB
Glycolic acid, monosodium saltHMDB
Potassium glycolateHMDB
Chemical FormulaC28H40O9
Average Molecular Mass520.612 g/mol
Monoisotopic Mass520.267 g/mol
CAS Registry Number81644-35-1
IUPAC Name6-(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
Traditional Name6-(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
SMILESCC1=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
InChI IdentifierInChI=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
InChI KeyXLUKITCTLVOOAW-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassAlpha hydroxy acids and derivatives
Direct ParentAlpha hydroxy acids and derivatives
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.04 g/LALOGPS
logP0.64ALOGPS
logP0.61ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)12.17ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area164.75 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity133.13 m³·mol⁻¹ChemAxon
Polarizability55.2 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-0489740000-3e53806f47d33a03eeb0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001a-3341269000-eb405f656e4d60540d77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0003490000-0a25379c004e3e6d9aa7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-7114930000-fcadccfe4fc5a33f4ef5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-3039000000-98bff6858130e8d7d45eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-0103590000-b13bde068d144f6591bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gc0-1906220000-abdbc48f76a634c478b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9304000000-1608f0e187d3d78a514cSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB03085
HMDB IDHMDB0000115
FooDB IDFDB003298
Phenol Explorer IDNot Available
KNApSAcK IDC00007461
BiGG ID34090
BioCyc IDGLYCOLLATE
METLIN ID3219
PDB IDNot Available
Wikipedia LinkGlycolic_acid
Chemspider ID737
ChEBI ID17497
PubChem Compound ID757
Kegg Compound IDC03547
YMDB IDYMDB00807
ECMDB IDECMDB03035
References
Synthesis ReferenceNot Available
MSDSNot Available
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.