Human Metabolome Database Version 3.5

Showing metabocard for Keratan (HMDB01165)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-07-24 11:51:44 -0600
HMDB ID HMDB01165
Secondary Accession Numbers None
Metabolite Identification
Common Name Keratan
Description Keratan is a sulfated mucopolysaccharide initially isolated from bovine cornea. At least two types are known. Type I, found mostly in the cornea, contains D-galactose and D-glucosamine-6-O-sulfate as the repeating unit; type II, found in skeletal tissues, contains D-galactose and D-galactosamine-6-O-sulfate as the repeating unit.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Keratan 6'-sulfate
  2. Keratan 6'-sulphate
  3. Keratan sulfate
  4. Keratan sulphate
  5. Kerato 6'-sulfate
  6. Kerato 6'-sulphate
  7. Kerato sulfate
  8. Kerato sulphate
Chemical Formula C28H48N2O32S4
Average Molecular Weight 1052.935
Monoisotopic Molecular Weight 1052.10730021
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 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-hydro
CAS Registry Number 69992-87-6
SMILES CC(=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 Identifier InChI=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 Key KXCLCNHUUKTANI-RBIYJLQWSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Tetrasaccharides
Sub Class Tetrahexoses
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • Acetal
  • Carboxamide Group
  • Glucosamine
  • Glycosyl Compound
  • Hemiacetal
  • Mannosamine
  • O Glycosyl Compound
  • Organic Sulfuric Acid Monoester
  • Oxane
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Sulfate Ester
Direct Parent Tetrahexoses
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 24.9 g/L ALOGPS
LogP -2.46 ALOGPS
LogP -15 ChemAxon
LogS -1.63 ALOGPS
pKa (strongest acidic) -2.6 ChemAxon
pKa (strongest basic) -4 ChemAxon
Hydrogen Acceptor Count 28 ChemAxon
Hydrogen Donor Count 13 ChemAxon
Polar Surface Area 518.82 A2 ChemAxon
Rotatable Bond Count 20 ChemAxon
Refractivity 194.24 ChemAxon
Polarizability 92.22 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
Tissue Location
  • Fibroblasts
  • Intestine
  • Epidermis
  • Prostate
  • Cartilage
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.14 (0.01-0.30) uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.75 (0.10-1.44) uM Adult (>18 years old) Both Mucopolysaccharidosis IVA
Associated Disorders and Diseases
Disease References
Mucopolysaccharidosis IVA
  • Tomatsu S, Okamura K, Taketani T, Orii KO, Nishioka T, Gutierrez MA, Velez-Castrillon S, Fachel AA, Grubb JH, Cooper A, Thornley M, Wraith E, Barrera LA, Giugliani R, Schwartz IV, Frenking GS, Beck M, Kircher SG, Paschke E, Yamaguchi S, Ullrich K, Isogai K, Suzuki Y, Orii T, Kondo N, Creer M, Noguchi A: Development and testing of new screening method for keratan sulfate in mucopolysaccharidosis IVA. Pediatr Res. 2004 Apr;55(4):592-7. Epub 2004 Jan 7. Pubmed: 14711889 Link_out
      Associated OMIM IDs
      • 253000 Link_out (Mucopolysaccharidosis IVA )
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB022459
      KNApSAcK ID Not Available
      Chemspider ID 394000 Link_out
      KEGG Compound ID C00573 Link_out
      BioCyc ID KERATAN Link_out
      BiGG ID Not Available
      Wikipedia Link keratan sulfate Link_out
      NuGOwiki Link HMDB01165 Link_out
      Metagene Link HMDB01165 Link_out
      METLIN ID Not Available
      PubChem Compound 446715 Link_out
      PDB ID Not Available
      ChEBI ID Not Available
      References
      Synthesis Reference Not Available
      Material Safety Data Sheet (MSDS) Not 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. Pubmed: 15082343 Link_out
      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. Pubmed: 2521451 Link_out
      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. Pubmed: 2935158 Link_out
      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. Pubmed: 2562661 Link_out
      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. Pubmed: 2957502 Link_out
      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. Pubmed: 1718441 Link_out
      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. Pubmed: 2952259 Link_out
      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. Pubmed: 9313390 Link_out
      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. Pubmed: 6242453 Link_out
      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. Pubmed: 9397261 Link_out
      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. Pubmed: 2951638 Link_out
      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. Pubmed: 9054908 Link_out
      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. Pubmed: 11514545 Link_out
      14. Thonar EJ, Glant T: Serum keratan sulfate--a marker of predisposition to polyarticular osteoarthritis. Clin Biochem. 1992 Jun;25(3):175-80. Pubmed: 1633632 Link_out
      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. Pubmed: 1710640 Link_out
      16. Thonar EJ: Serum keratan sulfate concentration as a measure of the catabolism of cartilage proteoglycans. Ryumachi. 1990 Dec;30(6):461-8. Pubmed: 2100374 Link_out
      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. Pubmed: 9208186 Link_out
      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. Pubmed: 15042600 Link_out
      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. Pubmed: 2056369 Link_out

      Enzymes
      Name: Carbohydrate sulfotransferase 3
      Reactions: Not Available
      Gene Name: CHST3
      Uniprot ID: Q7LGC8 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Carbohydrate sulfotransferase 1
      Reactions:
      Phosphoadenosine phosphosulfate + Keratan unknown Adenosine 3',5'-diphosphate + Keratan details
      Gene Name: CHST1
      Uniprot ID: O43916 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Carbohydrate sulfotransferase 7
      Reactions: Not Available
      Gene Name: CHST7
      Uniprot ID: Q9NS84 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Beta-glucuronidase
      Reactions: Not Available
      Gene Name: GUSB
      Uniprot ID: P08236 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: N-acetylglucosamine-6-sulfatase
      Reactions: Not Available
      Gene Name: GNS
      Uniprot ID: P15586 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: N-acetylgalactosamine-6-sulfatase
      Reactions: Not Available
      Gene Name: GALNS
      Uniprot ID: P34059 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Keratocan
      Reactions: Not Available
      Gene Name: KERA
      Uniprot ID: O60938 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Fibromodulin
      Reactions: Not Available
      Gene Name: FMOD
      Uniprot ID: Q06828 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Carbohydrate sulfotransferase 6
      Reactions: Not Available
      Gene Name: CHST6
      Uniprot ID: Q9GZX3 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UDP-GlcNAc:betaGal beta-1,3-N-acetylglucosaminyltransferase 7
      Reactions: Not Available
      Gene Name: B3GNT7
      Uniprot ID: Q8NFL0 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Osteomodulin
      Reactions: Not Available
      Gene Name: OMD
      Uniprot ID: Q99983 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Neuroendocrine secretory protein 55
      Reactions: Not Available
      Gene Name: GNAS
      Uniprot ID: O95467 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA