Dermatan (CHEM034924)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:20:12 UTC
Update Date2016-11-09 01:21:13 UTC
Accession NumberCHEM034924
Identification
Common NameDermatan
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
b-HeparinHMDB
beta-HeparinHMDB
Chondroitin sulfate bHMDB
Chondroitin sulfate type bHMDB
Chondroitin sulphate bHMDB
Chondroitin sulphate type bHMDB
Chondroitinsulfuric acid bHMDB
Chondroitinsulfuric acid type bHMDB
Dermatan 4-sulfateHMDB
Dermatan 4-sulphateHMDB
Dermatan hydrogen sulfateHMDB
Dermatan hydrogen sulphateHMDB
Dermatan sulfateHMDB
Dermatan sulphateHMDB
Desmin 370HMDB
DS 435HMDB
MF 701HMDB
3-Ethyl-4,5-dihydroxy-6-[({3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-2-methoxy-5-(sulfooxy)oxan-4-yl}oxy)methyl]oxane-2-carboxylateHMDB
3-Ethyl-4,5-dihydroxy-6-[({3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-2-methoxy-5-(sulphooxy)oxan-4-yl}oxy)methyl]oxane-2-carboxylateHMDB
3-Ethyl-4,5-dihydroxy-6-[({3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-2-methoxy-5-(sulphooxy)oxan-4-yl}oxy)methyl]oxane-2-carboxylic acidHMDB
Chemical Formula(C16H24NO14S)nC2H6
Average Molecular MassNot Available
Monoisotopic MassNot Available
CAS Registry Number24967-94-0
IUPAC Name6-({[3-acetamido-6-(hydroxymethyl)-2-methoxy-5-(sulfooxy)oxan-4-yl]oxy}methyl)-3-ethyl-4,5-dihydroxyoxane-2-carboxylic acid
Traditional Name6-({[3-acetamido-6-(hydroxymethyl)-2-methoxy-5-(sulfooxy)oxan-4-yl]oxy}methyl)-3-ethyl-4,5-dihydroxyoxane-2-carboxylic acid
SMILESNot Available
InChI IdentifierInChI=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 KeyDYTJJIPHSVVNGF-IPUVJUKZSA-M
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acyl-alpha-hexosamines
Alternative Parents
Substituents
  • N-acyl-alpha-hexosamine
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Monosaccharide sulfate
  • Monosaccharide
  • Oxane
  • Pyran
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Sulfuric acid monoester
  • Organic sulfuric acid or derivatives
  • Secondary alcohol
  • Acetal
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organonitrogen compound
  • Primary alcohol
  • Organopnictogen compound
  • 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 Solubility23 g/LALOGPS
logP-1.3ALOGPS
logP-4.3ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)-2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area227.61 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity106.9 m³·mol⁻¹ChemAxon
Polarizability48.55 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-1200690000-86c93cd9a906d1d39896Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zn9-1011920000-13d3c57b32ed928f350dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9210000000-111e8c5a8d3ad36c843eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-1202940000-559e7875e0ef9863af9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06r2-9547600000-3823d48df58b52c887ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-3dd9cd300bcc06b8fee8Spectrum
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 IDHMDB0000632
FooDB IDFDB022153
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5605
PDB IDNot Available
Wikipedia LinkDermatan sulfate
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID72682693
Kegg Compound IDC00426
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Nagasawa, Kinzo; Inoue, Yuko. Desulfation of glycosaminoglycuronan sulfates. Methods in Carbohydrate Chemistry (1980), 8 287-9.
2. Akimoto S, Hayashi H, Ishikawa H: Disaccharide analysis of the skin glycosaminoglycans in systemic sclerosis. Br J Dermatol. 1992 Jan;126(1):29-34.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.
13. 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.
14. 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.
15. Laitio M, Terho T: Polysaccharides of metaplastic mucosa and carcinoma of the gallbladder. Lab Invest. 1975 Feb;32(2):183-9.
16. 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.
17. 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.
18. Scott JE: Proteoglycan-collagen interactions. Ciba Found Symp. 1986;124:104-24.
19. 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.
20. 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.
21. 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.