Showing metabocard for Keratan (BMDB0001165)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:41:53 UTC
Update Date2020-05-11 20:48:26 UTC
BMDB IDBMDB0001165
Secondary Accession Numbers
  • BMDB01165
Metabolite Identification
Common NameKeratan
DescriptionKeratan, also known as kerato sulfate or sulfate, keratan, belongs to the class of organic compounds known as oligosaccharide sulfates. These are carbohydrates containing between 3 and 9 sugar units, one of which bear one or more sulfate groups. Keratan is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Keratan 6'-sulfateHMDB
Keratan 6'-sulphateHMDB
Keratan sulfateHMDB
Keratan sulphateHMDB
Kerato 6'-sulfateHMDB
Kerato 6'-sulphateHMDB
Kerato sulfateHMDB
Kerato sulphateHMDB
N-[(2S,3R,4S,6S)-2-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-[(sulfooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-6-[(sulfooxy)methyl]oxan-4-yl]oxy}-4-hydroxy-6-[(sulfooxy)methyl]oxan-3-yl]ethanimidateHMDB
N-[(2S,3R,4S,6S)-2-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-[(sulphooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulphooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-6-[(sulphooxy)methyl]oxan-4-yl]oxy}-4-hydroxy-6-[(sulphooxy)methyl]oxan-3-yl]ethanimidateHMDB
N-[(2S,3R,4S,6S)-2-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-[(sulphooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulphooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-6-[(sulphooxy)methyl]oxan-4-yl]oxy}-4-hydroxy-6-[(sulphooxy)methyl]oxan-3-yl]ethanimidic acidHMDB
KeratosulfateHMDB
Sulfate, keratanHMDB
Chemical FormulaC28H48N2O32S4
Average Molecular Weight1052.935
Monoisotopic Molecular Weight1052.10730021
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 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]methoxysulfonic acid
CAS Registry Number69992-87-6
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 KeyKXCLCNHUUKTANI-RBIYJLQWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as oligosaccharide sulfates. These are carbohydrates containing between 3 and 9 sugar units, one of which bear one or more sulfate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharide sulfates
Alternative Parents
Substituents
  • Oligosaccharide sulfate
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Sulfuric acid monoester
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Organic sulfuric acid or derivatives
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.5ALOGPS
logP-15ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)-2.6ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count28ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area518.82 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity194.24 m³·mol⁻¹ChemAxon
Polarizability92.22 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-9010060104-bd5beed3fb36ee571573View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02bo-3150491228-122cd61bbffb584c1ac0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-2150790013-12506dbbd36791439626View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ziu-9542136212-13f8482db4e33a98a64bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-007o-7164060369-735c66971e575bbf22f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-4459062000-0d3d89401963ff1ea5dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-9000000102-47c8c6f51cd1bac1222eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0adi-2100203289-7780a86c7f9241ab8dbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-4910003000-91dddc0febefc20b0779View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-9010000000-68550e6696781bcc899aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ow-8590030400-aed895d213a3d63b4712View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9010000000-8ef963b454130a6b7e68View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Cartilage
  • Epidermis
  • Fibroblasts
  • Intestine
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
CartilageExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001165
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022459
KNApSAcK IDNot Available
Chemspider ID394000
KEGG Compound IDC00573
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound446715
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Fibromodulin
General function:
Involved in protein binding
Specific function:
Affects the rate of fibrils formation. May have a primary role in collagen fibrillogenesis (By similarity).
Gene Name:
FMOD
Uniprot ID:
P13605
Molecular weight:
43038.0
Enzyme Details
2. Keratocan
General function:
Involved in protein binding
Specific function:
May be important in developing and maintaining corneal transparency and for the structure of the stromal matrix.
Gene Name:
KERA
Uniprot ID:
O62702
Molecular weight:
40406.0
Enzyme Details
3. Neuroendocrine secretory protein 55
General function:
Posttranslational modification, protein turnover, chaperones
Specific function:
Not Available
Gene Name:
GNAS
Uniprot ID:
O18979
Molecular weight:
27494.0