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Human Metabolome Database Version 3.5

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Showing metabocard for Dermatan (HMDB00632)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-01-28 19:27:10 -0700
HMDB ID HMDB00632
Secondary Accession Numbers
  • HMDB06265
Metabolite Identification
Common Name Dermatan
Description Dermatan is a naturally occurring glycosaminoglycan found mostly in the skin and in connective tissue. It differs from chondroitin sulfate A (see chondroitin sulfateS) by containing Iduronic acid in place of glucuronic acid, its epimer, at carbon atom 5. (from Merck, 12th ed). Dermatan sulfate consists of sulfated N-acetylgalactosamine alternating with uronic acid residues. The latter are predominantly L-Iduronic acid, some of which are sulfated; there are also occasional glucuronic acid residues. Degradation proceeds stepwise from the nonreducing end by the sequential action of three exo-glycosidases (alpha-L-iduronidase, beta-glucuronidase, and beta-hexosaminidase) and two sulfatases (iduronate 2-sulfatase and N-acetylgalactosamine 4-sulfatase). An endoglycosidase, hyaluronidase, may also participate to a limited extent in the degradation process by cleaving next to the occasional glucuronic acid residues. -- OMMBID 136-2.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. b-Heparin
  2. beta-Heparin
  3. Chondroitin sulfate B
  4. Chondroitin sulfate type B
  5. Chondroitinsulfuric acid B
  6. Chondroitinsulfuric acid type B
  7. Dermatan 4-sulfate
  8. Dermatan hydrogen sulfate
  9. Dermatan sulfate
  10. Dermatan sulphate
  11. Desmin 370
  12. DS 435
  13. MF 701
Chemical Formula Not Available
Average Molecular Weight Not Available
Monoisotopic Molecular Weight Not Available
IUPAC Name Not Available
Traditional IUPAC Name Not Available
CAS Registry Number 24967-94-0
SMILES Not Available
InChI Identifier InChI=1S/C18H31NO14S/c1-4-8-12(22)13(23)10(31-14(8)17(24)25)6-30-16-11(19-7(2)21)18(29-3)32-9(5-20)15(16)33-34(26,27)28/h8-16,18,20,22-23H,4-6H2,1-3H3,(H,19,21)(H,24,25)(H,26,27,28)/p-1/t8-,9+,10+,11+,12-,13-,14+,15-,16+,18+/m0/s1
InChI Key DYTJJIPHSVVNGF-IPUVJUKZSA-M
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Disaccharides
Sub Class Dihexoses
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Acetal
  • Carboxamide Group
  • Carboxylic Acid
  • Dialkyl Ether
  • Glucosamine
  • Glycosyl Compound
  • Mannosamine
  • O Glycosyl Compound
  • Organic Sulfuric Acid Monoester
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Sulfate Ester
Direct Parent Dihexoses
Ontology
Status Expected and Not 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
Formal Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location
  • Fibroblasts
  • Intestine
  • Neuron
  • Pancreas
  • Placenta
  • Testes
  • Kidney
  • Liver
  • Myelin
  • Skin
  • Platelet
  • Spleen
  • Cartilage
  • Connective Tissue
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022153
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID C00426 Link_out
BioCyc ID CPD-7276 Link_out
BiGG ID Not Available
Wikipedia Link Dermatan Link_out
NuGOwiki Link HMDB00632 Link_out
Metagene Link HMDB00632 Link_out
METLIN ID 5605 Link_out
PubChem Compound 53477708 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Nagasawa, Kinzo; Inoue, Yuko. Desulfation of glycosaminoglycuronan sulfates. Methods in Carbohydrate Chemistry (1980), 8 287-9.
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Akimoto S, Hayashi H, Ishikawa H: Disaccharide analysis of the skin glycosaminoglycans in systemic sclerosis. Br J Dermatol. 1992 Jan;126(1):29-34. Pubmed: 1536759 Link_out
  2. Habuchi H, Tsuji M, Nakanishi Y, Suzuki S: Separation and properties of five glycosaminoglycan sulfatases from rat skin. J Biol Chem. 1979 Aug 25;254(16):7570-8. Pubmed: 468769 Link_out
  3. Ungefroren H, Ergun S, Krull NB, Holstein AF: Expression of the small proteoglycans biglycan and decorin in the adult human testis. Biol Reprod. 1995 May;52(5):1095-105. Pubmed: 7626709 Link_out
  4. Sobel RA, Ahmed AS: White matter extracellular matrix chondroitin sulfate/dermatan sulfate proteoglycans in multiple sclerosis. J Neuropathol Exp Neurol. 2001 Dec;60(12):1198-207. Pubmed: 11764092 Link_out
  5. Poulsen JH, Cramers MK: Dermatan sulphate in urine reflects the extent of skin affection in psoriasis. Clin Chim Acta. 1982 Dec 9;126(2):119-26. Pubmed: 6817946 Link_out
  6. Minami R, Abo K, Tsugawa S, Oyanagi K, Nakao T: Acidic glycosaminoglycans in liver from five patients with mucopolysaccharidosis and mucolipidosis. Tohoku J Exp Med. 1981 Jun;134(2):215-20. Pubmed: 6797102 Link_out
  7. Zimmermann DR, Dours-Zimmermann MT, Schubert M, Bruckner-Tuderman L, Heitz PU: [Expression of the extracellular matrix proteoglycan, versican, in human skin] Verh Dtsch Ges Pathol. 1994;78:481-4. Pubmed: 7534020 Link_out
  8. Ji SL, Du HY, Chi YQ, Cui HF, Cao JC, Geng MY, Guan HS: Effects of dermatan sulfate derivatives on platelet surface P-selectin expression and protein C activity in blood of inflammatory bowel disease patients. World J Gastroenterol. 2004 Dec 1;10(23):3485-9. Pubmed: 15526370 Link_out
  9. Orii T, Sukegawa K, Minami R, Matsuura Y, Tsugawa S: Atypical Hurler syndrome without alpha-L-iduronidase deficiency. Tohoku J Exp Med. 1976 Oct;120(2):113-23. Pubmed: 136068 Link_out
  10. Grigoriu BD, Depontieu F, Scherpereel A, Gourcerol D, Devos P, Ouatas T, Lafitte JJ, Copin MC, Tonnel AB, Lassalle P: Endocan expression and relationship with survival in human non-small cell lung cancer. Clin Cancer Res. 2006 Aug 1;12(15):4575-82. Pubmed: 16899604 Link_out
  11. Nagashima K, Endo H, Sakakibara K, Konishi Y, Miyachi K, Wey JJ, Suzuki Y, Onisawa J: Morphological and biochemical studies of a case of mucopolysaccharidosis II (Hunter's syndrome). Acta Pathol Jpn. 1976 Jan;26(1):115-32. Pubmed: 132078 Link_out
  12. Wasserman L, Abramovici A, Shlesinger H, Goldman JA, Allalouf D: Histochemical localization of acidic glycosaminoglycans in normal human placentae. Placenta. 1983 Jan-Apr;4(1):101-8. Pubmed: 6406996 Link_out
  13. Longas MO, Wisch P, Lebwohl MG, Fleischmajer R: Glycosaminoglycans of skin and urine in pseudoxanthoma elasticum: evidence for chondroitin 6-sulfate alteration. Clin Chim Acta. 1986 Mar 28;155(3):227-36. Pubmed: 3085984 Link_out
  14. Laitio M, Terho T: Polysaccharides of metaplastic mucosa and carcinoma of the gallbladder. Lab Invest. 1975 Feb;32(2):183-9. Pubmed: 46329 Link_out
  15. Desnoyers L, Arnott D, Pennica D: WISP-1 binds to decorin and biglycan. J Biol Chem. 2001 Dec 14;276(50):47599-607. Epub 2001 Oct 11. Pubmed: 11598131 Link_out
  16. Celie JW, Keuning ED, Beelen RH, Drager AM, Zweegman S, Kessler FL, Soininen R, van den Born J: Identification of L-selectin binding heparan sulfates attached to collagen type XVIII. J Biol Chem. 2005 Jul 22;280(29):26965-73. Epub 2005 May 24. Pubmed: 15917223 Link_out
  17. Scott JE: Proteoglycan-collagen interactions. Ciba Found Symp. 1986;124:104-24. Pubmed: 3816415 Link_out
  18. Burkhardt D, Michel BA, Baici A, Kissling R, Theiler R: Comparison of chondroitin sulphate composition of femoral head articular cartilage from patients with femoral neck fractures and osteoarthritis and controls. Rheumatol Int. 1995;14(6):235-41. Pubmed: 7597379 Link_out
  19. Wasserman L, Shlesinger H, Goldman JA, Allalouf D: Pattern of glycosaminoglycan distribution in tissue and blood vessels of human placenta. Gynecol Obstet Invest. 1983;15(4):242-50. Pubmed: 6220947 Link_out
  20. Melching LI, Roughley PJ: The synthesis of dermatan sulphate proteoglycans by fetal and adult human articular cartilage. Biochem J. 1989 Jul 15;261(2):501-8. Pubmed: 2775229 Link_out
Enzymes
Name: Carbohydrate sulfotransferase 11
Reactions:
  • 3'-phosphoadenylyl sulfate + chondroitin = adenosine 3',5'-bisphosphate + chondroitin 4'-sulfate [RN:R02180]
Gene Name: CHST11
Uniprot ID: Q9NPF2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Carbohydrate sulfotransferase 12
Reactions:
  • 3'-phosphoadenylyl sulfate + chondroitin = adenosine 3',5'-bisphosphate + chondroitin 4'-sulfate [RN:R02180]
Gene Name: CHST12
Uniprot ID: Q9NRB3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Arylsulfatase B
Reactions:
  • Hydrolysis of the 4-sulfate groups of the N-acetyl-D-galactosamine 4-sulfate units of chondroitin sulfate and dermatan sulfate [RN:R07823] ALL_REAC R07823(G)
Gene Name: ARSB
Uniprot ID: P15848 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-glucuronidase
Reactions:
  • a beta-D-glucuronoside + H2O = D-glucuronate + an alcohol [RN:R01478]
Gene Name: GUSB
Uniprot ID: P08236 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-L-iduronidase
Reactions:
  • Hydrolysis of unsulfated alpha-L-iduronosidic linkages in dermatan sulfate ALL_REAC (other) R07813(G) R07822(G) REFERENCE 1 [PMID:4993544] AUTHORS Matalon R, Cifonelli JA, Dorfman A. TITLE L-iduronidase in cultured human fibroblasts and liver. JOURNAL Biochem. Biophys. Res. Commun. 42 (1971) 340-5. ORGANISM Homo sapiens [GN:hsa] REFERENCE 2 [PMID:30407] AUTHORS Rome LH, Garvin AJ, Neufeld EF. TITLE Human kidney alpha-L-iduronidase: purification and characterization. JOURNAL Arch. Biochem. Biophys. 189 (1978) 344-53. ORGANISM Homo sapiens [GN:hsa] REFERENCE 3 AUTHORS Srivastava, R.M., Hudson, N., Seymour, F.R. and Weissman, B. TITLE Preparation of (aryl alpha-L-idopyranosid)uronic acids. JOURNAL Carbohydr. Res. 60 (1978) 315-326.
Gene Name: IDUA
Uniprot ID: P35475 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Iduronate 2-sulfatase
Reactions:
  • Hydrolysis of the 2-sulfate groups of the L-iduronate 2-sulfate units of dermatan sulfate, heparan sulfate and heparin [RN:R07812 R07821] ALL_REAC R07812(G) R07821(G) REFERENCE 1 [PMID:6816283] AUTHORS Archer IM, Harper PS, Wusteman FS. TITLE Multiple forms of iduronate 2-sulphate sulphatase in human tissues and body fluids. JOURNAL Biochim. Biophys. Acta. 708 (1982) 134-40. ORGANISM Homo sapiens [GN:hsa] REFERENCE 2 [PMID:4269173] AUTHORS Bach G, Eisenberg F Jr, Cantz M, Neufeld EF. TITLE The defect in the Hunter syndrome: deficiency of sulfoiduronate sulfatase. JOURNAL Proc. Natl. Acad. Sci. U. S. A. 70 (1973) 2134-8. ORGANISM Homo sapiens [GN:hsa] REFERENCE 3 [PMID:6945876] AUTHORS Di Natale P, Ronsisvalle L. TITLE Identification and partial characterization of two enzyme forms of iduronate sulfatase from human placenta. JOURNAL Biochim. Biophys. Acta. 661 (1981) 106-11. ORGANISM Homo sapiens [GN:hsa] REFERENCE 4 [PMID:6950934] AUTHORS Yutaka T, Fluharty AL, Stevens RL, Kihara H. TITLE Purification and some properties of human liver iduronate sulfatase. JOURNAL J. Biochem. (Tokyo). 91 (1982) 433-41. ORGANISM Homo sapiens [GN:hsa]
Gene Name: IDS
Uniprot ID: P22304 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Carbohydrate sulfotransferase 14
Reactions:
    Gene Name: CHST14
    Uniprot ID: Q8NCH0 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Xylosyltransferase 1
    Reactions:
    • Transfers a beta-D-xylosyl residue from UDP-D-xylose to the serine hydroxy group of an acceptor protein substrate [RN:R05925] ALL_REAC R05925(G)
    Gene Name: XYLT1
    Uniprot ID: Q86Y38 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Xylosyltransferase 2
    Reactions:
    • Transfers a beta-D-xylosyl residue from UDP-D-xylose to the serine hydroxy group of an acceptor protein substrate [RN:R05925] ALL_REAC R05925(G)
    Gene Name: XYLT2
    Uniprot ID: Q9H1B5 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Uronyl 2-sulfotransferase
    Reactions:
      Gene Name: UST
      Uniprot ID: Q9Y2C2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Carbohydrate sulfotransferase 15
      Reactions:
      • (1) 3'-phosphoadenylyl sulfate + dermatan = adenosine 3',5'-bisphosphate + dermatan 6'-sulfate [RN:R07288]
      • (2) 3'-phosphoadenylyl sulfate + chondroitin = adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate [RN:R02181]
      Gene Name: CHST15
      Uniprot ID: Q7LFX5 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Matrix metalloproteinase-24
      Reactions:
        Gene Name: MMP24
        Uniprot ID: Q9Y5R2 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Dermatan-sulfate epimerase
        Reactions:
        • chondroitin D-glucuronate = dermatan L-iduronate [RN:R04104]
        Gene Name: DSE
        Uniprot ID: Q9UL01 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Kallikrein-6
        Reactions:
          Gene Name: KLK6
          Uniprot ID: Q92876 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA