Bovine Metabolome Database: Showing metabocard for Dermatan (BMDB0000632)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:33:59 UTC

Update Date

2020-05-11 20:56:44 UTC

BMDB ID

BMDB0000632

Secondary Accession Numbers

BMDB00632

Metabolite Identification

Common Name

Dermatan

Description

3-ethyl-4,5-dihydroxy-6-[({3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-2-methoxy-5-(sulfooxy)oxan-4-yl}oxy)methyl]oxane-2-carboxylic acid 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. Based on a literature review very few articles have been published on 3-ethyl-4,5-dihydroxy-6-[({3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-2-methoxy-5-(sulfooxy)oxan-4-yl}oxy)methyl]oxane-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Ethyl-4,5-dihydroxy-6-[({3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-2-methoxy-5-(sulfooxy)oxan-4-yl}oxy)methyl]oxane-2-carboxylate	Generator
3-Ethyl-4,5-dihydroxy-6-[({3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-2-methoxy-5-(sulphooxy)oxan-4-yl}oxy)methyl]oxane-2-carboxylate	Generator
3-Ethyl-4,5-dihydroxy-6-[({3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-2-methoxy-5-(sulphooxy)oxan-4-yl}oxy)methyl]oxane-2-carboxylic acid	Generator
b-Heparin	HMDB
beta-Heparin	HMDB
Chondroitin sulfate b	HMDB
Chondroitin sulfate type b	HMDB
Chondroitin sulphate b	HMDB
Chondroitin sulphate type b	HMDB
Chondroitinsulfuric acid b	HMDB
Chondroitinsulfuric acid type b	HMDB
Dermatan 4-sulfate	HMDB
Dermatan 4-sulphate	HMDB
Dermatan hydrogen sulfate	HMDB
Dermatan hydrogen sulphate	HMDB
Dermatan sulfate	HMDB
Dermatan sulphate	HMDB
Desmin 370	HMDB
DS 435	HMDB
MF 701	HMDB

Chemical Formula

C₁₈H₃₁NO₁₄S

Average Molecular Weight

517.5

Monoisotopic Molecular Weight

517.146525856

IUPAC Name

6-({[3-acetamido-6-(hydroxymethyl)-2-methoxy-5-(sulfooxy)oxan-4-yl]oxy}methyl)-3-ethyl-4,5-dihydroxyoxane-2-carboxylic acid

Traditional Name

6-({[3-acetamido-6-(hydroxymethyl)-2-methoxy-5-(sulfooxy)oxan-4-yl]oxy}methyl)-3-ethyl-4,5-dihydroxyoxane-2-carboxylic acid

CAS Registry Number

24967-94-0

SMILES

CCC1C(O)C(O)C(COC2C(NC(C)=O)C(OC)OC(CO)C2OS(O)(=O)=O)OC1C(O)=O

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)

InChI Key

DYTJJIPHSVVNGF-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Status

Expected but not Quantified

Origin

Not Available

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
logP	-1.3	ALOGPS
logP	-4.3	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	-2	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	227.61 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	106.9 m³·mol⁻¹	ChemAxon
Polarizability	48.55 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Cartilage
Epidermis
Fibroblasts
Intestine
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Spleen
Testis

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cartilage	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Pancreas	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Spleen	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72682693

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

Not Available

Enzymes

Enzyme Details

1. Dermatan-sulfate epimerase

General function:: Involved in chondroitin-glucuronate 5-epimerase activity
Specific function:: Converts D-glucuronic acid to L-iduronic acid (IdoUA) residues.
Gene Name:: DSE
Uniprot ID:: P0C2H4
Molecular weight:: 109725.0

Enzyme Details

2. Vitrin

General function:: Not Available
Specific function:: Promotes matrix assembly and cell adhesiveness. Plays a role in spinal cord formation by regulating the proliferation and differentiation of neural stem cells.
Gene Name:: VIT
Uniprot ID:: Q95LI2
Molecular weight:: 70873.0

Enzyme Details

3. Cysteine-rich secretory protein LCCL domain-containing 2

General function:: Not Available
Specific function:: Promotes matrix assembly.
Gene Name:: CRISPLD2
Uniprot ID:: A6QLZ7
Molecular weight:: 55581.0

Showing metabocard for Dermatan (BMDB0000632)

Structure for BMDB0000632 (Dermatan)

Enzymes