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Showing Compound Keratan (FDB022459)

Record Information
Version1.0
Creation date2011-09-21 00:14:21 UTC
Update date2015-07-21 06:57:13 UTC
Primary IDFDB022459
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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).
CAS Number69992-87-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
keratan 6'-sulfatehmdb
keratan sulfatehmdb
kerato 6'-sulfatehmdb
Predicted Properties
PropertyValueSource
Water Solubility24.9 g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC28H48N2O32S4
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
InChI IdentifierInChI=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
Isomeric SMILESCC(=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
Average Molecular Weight1052.935
Monoisotopic Molecular Weight1052.10730021
Classification
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
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physico-Chemical Properties
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)Not Available2022-08-06View Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-9010060104-bd5beed3fb36ee5715732017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02bo-3150491228-122cd61bbffb584c1ac02017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-2150790013-12506dbbd367914396262017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ziu-9542136212-13f8482db4e33a98a64b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-007o-7164060369-735c66971e575bbf22f92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-4459062000-0d3d89401963ff1ea5db2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-9000000102-47c8c6f51cd1bac1222e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0adi-2100203289-7780a86c7f9241ab8dbe2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-4910003000-91dddc0febefc20b07792021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-9010000000-68550e6696781bcc899a2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ow-8590030400-aed895d213a3d63b47122021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9010000000-8ef963b454130a6b7e682021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
ChemSpider ID394000
ChEMBL IDNot Available
KEGG Compound IDC00573
Pubchem Compound ID446715
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01165
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 IDkeratan sulfate
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
Carbohydrate sulfotransferase 3CHST3Q7LGC8
Carbohydrate sulfotransferase 1CHST1O43916
Carbohydrate sulfotransferase 7CHST7Q9NS84
UDP-GlcNAc:betaGal beta-1,3-N-acetylglucosaminyltransferase 7B3GNT7Q8NFL0
KeratocanKERAO60938
FibromodulinFMODQ06828
Carbohydrate sulfotransferase 6CHST6Q9GZX3
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference