Record Information
Version1.0
Creation date2011-09-21 00:09:15 UTC
Update date2015-07-21 06:57:01 UTC
Primary IDFDB022153
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDermatan
DescriptionA 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 [HMDB]
CAS Number24967-94-0
Structure
Thumb
Synonyms
SynonymSource
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
Chondroitin sulfate Bhmdb
Chondroitin sulfate type Bhmdb
Chondroitinsulfuric acid Bhmdb
Chondroitinsulfuric acid type Bhmdb
Predicted Properties
PropertyValueSource
Water Solubility20.1 g/LALOGPS
logP-1ALOGPS
logP-3.2ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)-1.8ChemAxon
pKa (Strongest Basic)1.11ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area233.93 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity117.97 m³·mol⁻¹ChemAxon
Polarizability47.08 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical Formula(C16H24NO14S)nC2H6
IUPAC nameN-[(2R,3R,4R,5R,6R)-4-{[(2R,3R,4S,5S,6R)-6-carboxy-5-ethyl-3,4-dihydroxyoxan-2-yl]methoxy}-6-(hydroxymethyl)-2-methoxy-5-(sulfooxy)oxan-3-yl]ethanecarboximidate
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
Isomeric SMILESCC[C@H]1[C@H](O)[C@@H](O)[C@@H](CO[C@@H]2[C@@H](NC(C)=O)[C@H](OC)O[C@H](CO)[C@@H]2OS([O-])(=O)=O)O[C@H]1C(O)=O
Average Molecular Weight
Monoisotopic Molecular Weight
Classification
DescriptionThis compound 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 monoester
  • Sulfate-ester
  • Alkyl sulfate
  • Sulfuric acid ester
  • Acetamide
  • Organic sulfuric acid or derivatives
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Acetal
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Alcohol
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID30780115
ChEMBL IDNot Available
KEGG Compound IDC00426
Pubchem Compound ID53477708
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00632
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDermatan
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Beta-glucuronidaseGUSBP08236
Alpha-L-iduronidaseIDUAP35475
Carbohydrate sulfotransferase 11CHST11Q9NPF2
Carbohydrate sulfotransferase 12CHST12Q9NRB3
Carbohydrate sulfotransferase 14CHST14Q8NCH0
Carbohydrate sulfotransferase 15CHST15Q7LFX5
Dermatan-sulfate epimeraseDSEQ9UL01
Xylosyltransferase 1XYLT1Q86Y38
Xylosyltransferase 2XYLT2Q9H1B5
Uronyl 2-sulfotransferaseUSTQ9Y2C2
Kallikrein-6KLK6Q92876
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference