Keratan (CHEM035098)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:29:18 UTC
Update Date2016-11-09 01:21:15 UTC
Accession NumberCHEM035098
Identification
Common NameKeratan
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Keratan 6'-sulfateHMDB
Keratan 6'-sulphateHMDB
Keratan sulfateHMDB
Keratan sulphateHMDB
Kerato 6'-sulfateHMDB
Kerato 6'-sulphateHMDB
Kerato sulfateHMDB
Kerato sulphateHMDB
N-[(2S,3R,4S,6S)-2-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-[(sulfooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-6-[(sulfooxy)methyl]oxan-4-yl]oxy}-4-hydroxy-6-[(sulfooxy)methyl]oxan-3-yl]ethanimidateHMDB
N-[(2S,3R,4S,6S)-2-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-[(sulphooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulphooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-6-[(sulphooxy)methyl]oxan-4-yl]oxy}-4-hydroxy-6-[(sulphooxy)methyl]oxan-3-yl]ethanimidateHMDB
N-[(2S,3R,4S,6S)-2-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-[(sulphooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulphooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-6-[(sulphooxy)methyl]oxan-4-yl]oxy}-4-hydroxy-6-[(sulphooxy)methyl]oxan-3-yl]ethanimidic acidHMDB
KeratosulfateHMDB
Sulfate, keratanHMDB
Chemical FormulaC28H48N2O32S4
Average Molecular Mass1052.935 g/mol
Monoisotopic Mass1052.107 g/mol
CAS Registry Number69992-87-6
IUPAC Name{[(2S,4S,5R,6S)-5-acetamido-6-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-[(sulfooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}-4-hydroxyoxan-2-yl]methoxy}sulfonic acid
Traditional Name[(2S,4S,5R,6S)-5-acetamido-6-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-[(sulfooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}-4-hydroxyoxan-2-yl]methoxysulfonic acid
SMILESCC(=O)N[C@@H]1[C@@H](O)C[C@@H](COS(O)(=O)=O)O[C@H]1O[C@H]1[C@@H](O)[C@@H](COS(O)(=O)=O)O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(C)=O)[C@H](O[C@@H]3[C@@H](O)[C@H](O)O[C@H](COS(O)(=O)=O)[C@@H]3O)O[C@@H]2COS(O)(=O)=O)[C@@H]1O
InChI IdentifierInChI=1S/C28H48N2O32S4/c1-8(31)29-15-11(33)3-10(4-52-63(40,41)42)56-26(15)62-24-18(35)13(6-54-65(46,47)48)58-28(21(24)38)60-22-14(7-55-66(49,50)51)59-27(16(19(22)36)30-9(2)32)61-23-17(34)12(5-53-64(43,44)45)57-25(39)20(23)37/h10-28,33-39H,3-7H2,1-2H3,(H,29,31)(H,30,32)(H,40,41,42)(H,43,44,45)(H,46,47,48)(H,49,50,51)/t10-,11-,12+,13+,14+,15+,16+,17-,18-,19+,20+,21+,22+,23-,24-,25+,26-,27-,28-/m0/s1
InChI KeyKXCLCNHUUKTANI-RBIYJLQWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as oligosaccharide sulfates. These are carbohydrates containing between 3 and 9 sugar units, one of which bear one or more sulfate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharide sulfates
Alternative Parents
Substituents
  • Oligosaccharide sulfate
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Sulfuric acid monoester
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Organic sulfuric acid or derivatives
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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 Solubility24.9 g/LALOGPS
logP-2.5ALOGPS
logP-15ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)-2.6ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count28ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area518.82 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity194.24 m³·mol⁻¹ChemAxon
Polarizability92.22 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-9010060104-bd5beed3fb36ee571573Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02bo-3150491228-122cd61bbffb584c1ac0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-2150790013-12506dbbd36791439626Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ziu-9542136212-13f8482db4e33a98a64bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-007o-7164060369-735c66971e575bbf22f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-4459062000-0d3d89401963ff1ea5dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-9000000102-47c8c6f51cd1bac1222eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0adi-2100203289-7780a86c7f9241ab8dbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-4910003000-91dddc0febefc20b0779Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-9010000000-68550e6696781bcc899aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ow-8590030400-aed895d213a3d63b4712Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9010000000-8ef963b454130a6b7e68Spectrum
MSMass Spectrum (Electron Ionization)Not AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
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 IDNot Available
HMDB IDHMDB0001165
FooDB IDFDB022459
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID394000
ChEBI IDNot Available
PubChem Compound ID446715
Kegg Compound IDC00573
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Isnard N, Fodil-Bourahla I, Robert AM, Robert L: Pharmacology of skin aging. Stimulation of glycosaminoglycan biosynthesis by L-fucose and fucose-rich polysaccharides, effect of in vitro aging of fibroblasts. Biomed Pharmacother. 2004 Apr;58(3):202-4.
2. Block JA, Schnitzer TJ, Andersson GB, Lenz ME, Jeffery R, McNeill TW, Thonar EJ: The effect of chemonucleolysis on serum keratan sulfate levels in humans. Arthritis Rheum. 1989 Jan;32(1):100-4.
3. Thonar EJ, Lenz ME, Klintworth GK, Caterson B, Pachman LM, Glickman P, Katz R, Huff J, Kuettner KE: Quantification of keratan sulfate in blood as a marker of cartilage catabolism. Arthritis Rheum. 1985 Dec;28(12):1367-76.
4. Sorrell JM, Caterson B: Detection of age-related changes in the distributions of keratan sulfates and chondroitin sulfates in developing chick limbs: an immunocytochemical study. Development. 1989 Aug;106(4):657-63.
5. Thonar EJ, Schnitzer TJ, Kuettner KE: Quantification of keratan sulfate in blood as a marker of cartilage catabolism. J Rheumatol. 1987 May;14 Spec No:23-4.
6. al-Hakim A, Linhardt RJ: Electrophoresis and detection of nanogram quantities of exogenous and endogenous glycosaminoglycans in biological fluids. Appl Theor Electrophor. 1991;1(6):305-12.
7. Kliner DJ, Gorski JP, Thonar EJ: Keratan sulfate levels in sera of patients bearing cartilage tumors. Cancer. 1987 Jun 1;59(11):1931-5.
8. Bautch JC, Malone DG, Vailas AC: Effects of exercise on knee joints with osteoarthritis: a pilot study of biologic markers. Arthritis Care Res. 1997 Feb;10(1):48-55.
9. Morocutti M, Marchini M, Colombo B, Ruggeri A: Heterogeneity of proteoglycan particles in thin sections and replicas of human articular cartilage. Acta Biol Hung. 1984;35(2-4):233-43.
10. Cameron M, Buchgraber A, Passler H, Vogt M, Thonar E, Fu F, Evans CH: The natural history of the anterior cruciate ligament-deficient knee. Changes in synovial fluid cytokine and keratan sulfate concentrations. Am J Sports Med. 1997 Nov-Dec;25(6):751-4.
11. Klintworth GK, Meyer R, Dennis R, Hewitt AT, Stock EL, Lenz ME, Hassell JR, Stark WJ Jr, Kuettner KE, Thonar EJ: Macular corneal dystrophy. Lack of keratan sulfate in serum and cornea. Ophthalmic Paediatr Genet. 1986 Dec;7(3):139-43.
12. Israel HA, Diamond BE, Saed-Nejad F, Ratcliffe A: Correlation between arthroscopic diagnosis of osteoarthritis and synovitis of the human temporomandibular joint and keratan sulfate levels in the synovial fluid. J Oral Maxillofac Surg. 1997 Mar;55(3):210-7; discussion 217-8.
13. Plaas AH, West LA, Thonar EJ, Karcioglu ZA, Smith CJ, Klintworth GK, Hascall VC: Altered fine structures of corneal and skeletal keratan sulfate and chondroitin/dermatan sulfate in macular corneal dystrophy. J Biol Chem. 2001 Oct 26;276(43):39788-96. Epub 2001 Aug 20.
14. Thonar EJ, Glant T: Serum keratan sulfate--a marker of predisposition to polyarticular osteoarthritis. Clin Biochem. 1992 Jun;25(3):175-80.
15. Willen MD, Sorrell JM, Lekan CC, Davis BR, Caplan AI: Patterns of glycosaminoglycan/proteoglycan immunostaining in human skin during aging. J Invest Dermatol. 1991 Jun;96(6):968-74.
16. Thonar EJ: Serum keratan sulfate concentration as a measure of the catabolism of cartilage proteoglycans. Ryumachi. 1990 Dec;30(6):461-8.
17. Brunnee T, Reddigari SR, Shibayama Y, Kaplan AP, Silverberg M: Mast cell derived heparin activates the contact system: a link to kinin generation in allergic reactions. Clin Exp Allergy. 1997 Jun;27(6):653-63.
18. Holland JW, Meehan KL, Redmond SL, Dawkins HJ: Purification of the keratan sulfate proteoglycan expressed in prostatic secretory cells and its identification as lumican. Prostate. 2004 May 15;59(3):252-9.
19. Israel HA, Saed-Nejad F, Ratcliffe A: Early diagnosis of osteoarthrosis of the temporomandibular joint: correlation between arthroscopic diagnosis and keratan sulfate levels in the synovial fluid. J Oral Maxillofac Surg. 1991 Jul;49(7):708-11; discussion 712.