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Showing Compound 3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid (FDB022038)

Record Information
Version1.0
Creation date2011-09-21 00:07:24 UTC
Update date2015-07-21 06:56:56 UTC
Primary IDFDB022038
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid
Description3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) is a sialic acid (Sia) that is ubiquitously expressed in vertebrates during normal development and tumorigenesis. Its expression is thought to be regulated by multiple biosynthetic steps catalyzed by several enzymes, including CMP-Sia synthetase. (PMID 11479279) Sialic acids are frequently the terminal sugars on secreted and cell surface glycoproteins and glycolipids, and their presence can have considerable influence on the biological properties of a cell. For example, the temporal appearance and disappearance of polysialic polymers has been intimately linked with the proper development of neural tissues during embryogenesis. In pathogenic diseases, including meningitis and gastric inflammation, particular microbes recognize cell surface sialic acids when invading host cells. Sialic acid residues can also mask recognition sites such as galactose residues on glycoproteins to prevent their in vivo removal by asialoglycoprotein receptors. In certain cancers, changes in sialic acid amounts, types, and linkages have been associated with tumorogenesis and cancer metastasis. (PMID 10749855) [HMDB]
CAS Number22594-61-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility55.2 g/LALOGPS
logP-2.7ALOGPS
logP-3.7ChemAxon
logS-0.69ALOGPS
pKa (Strongest Acidic)2.84ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area175.75 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity54.2 m³·mol⁻¹ChemAxon
Polarizability23.7 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H16O9
IUPAC name(4S,5R,6R,7R,8S)-4,5,6,7,8,9-hexahydroxy-2-oxononanoic acid
InChI IdentifierInChI=1S/C9H16O9/c10-2-5(13)7(15)8(16)6(14)3(11)1-4(12)9(17)18/h3,5-8,10-11,13-16H,1-2H2,(H,17,18)/t3-,5-,6+,7+,8+/m0/s1
InChI KeyFQHUAUMYHAJTDH-IMSDGWMTSA-N
Isomeric SMILESOC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)CC(=O)C(O)=O
Average Molecular Weight268.2179
Monoisotopic Molecular Weight268.07943211
Classification
Description Belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Nonose monosaccharide
  • Medium-chain keto acid
  • Sugar acid
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Monosaccharide
  • Keto acid
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Carbonyl group
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0r00-9740000000-c930432b896f25d4d1aeSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-3234029000-d1022a9541c88b2f1a32Spectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TBDMS_4_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TBDMS_4_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TBDMS_5_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TBDMS_5_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TBDMS_5_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TBDMS_5_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TBDMS_5_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TBDMS_5_16, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TBDMS_5_24, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TBDMS_5_36, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, "3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid,4TBDMS,#7" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0v4i-2390000000-e93669a48299b1218c952017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ir0-9410000000-0a259af5426f14d78fe52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-074l-9100000000-2b12c65b43609f80c27e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052k-9740000000-c5b31710f8ea5790c5992017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-9600000000-a7365904eac0c55dc0592017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btl-9300000000-4c90c187ac68bf1ec40a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016s-2960000000-c973ce8f4b6eb9a09b832021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zj0-6900000000-ec6b6fdadbc150dbc1652021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-9c3207c739457b16a7792021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-1970000000-a4f86ecfad5d0922bdf82021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w30-5900000000-0142aa21eb8b357d7d772021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03mi-9100000000-172be348fc5231e8e7f12021-09-25View Spectrum
NMRNot Available
ChemSpider ID17215951
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID22833524
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00425
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 IDKDN
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference