Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000918
Identification
Name: 3-Deoxy-D-manno-octulosonate
Description:3-deoxy-D-manno-octulosonate is a member of the chemical class known as Octoses. These are monosaccahride compounds in which the sugar moiety is an octose (8 carbon atoms). 3-Deoxy-D-manno-octulosonic acid (KDO) is an eight-carbon sugar ubiquitous in Gram-negative bacterial lipopolysaccharides (LPS). (PMID 20801884) The enzyme 3-deoxy-D-manno-octulosonic acid (KDO) transferase is encoded by the kdtA gene of Pseudomonas aeruginosa and plays a key role in lipopolysaccharide biosynthesis.(PMID 1577828) KDO is an essential component of the lipopolysaccharide envelope in Gram-negative bacteria. (PMID 19726684) KDO8P is the phosphorylated precursor of 3-deoxy-D-manno-octulosonate, an essential sugar of the lipopolysaccharide of Gram-negative bacteria. (PMID 10734095)
Structure
Thumb
Synonyms:
  • 2-Dehydro-3-deoxy-D-octonate
  • 2-Dehydro-3-deoxy-D-octonic acid
  • 2-Keto-3-deoxy-D-manno-octonate
  • 2-Keto-3-deoxy-D-manno-octonic acid
  • 2-Keto-3-deoxyoctonate
  • 2-Keto-3-deoxyoctonic acid
  • 2-Keto-3-deoxyoctulosonate
  • 2-Keto-3-deoxyoctulosonic acid
  • 3-Deoxy-2-Octulosonate
  • 3-Deoxy-2-Octulosonic acid
  • 3-Deoxy-a-D-manno-2-octulosonate
  • 3-Deoxy-a-D-manno-2-octulosonic acid
  • 3-Deoxy-alpha-D-manno-2-octulosonate
  • 3-Deoxy-alpha-D-manno-2-octulosonic acid
  • 3-Deoxy-D-manno-2-octulosonate
  • 3-Deoxy-D-manno-2-octulosonic acid
  • 3-deoxy-D-manno-octulosonate
  • 3-Deoxy-D-manno-octulosonic acid
  • 3-Deoxy-D-mannoctulosonate
  • 3-Deoxy-D-mannoctulosonic acid
  • 3-Deoxy-D-mannooctulosonate
  • 3-Deoxy-D-mannooctulosonic acid
  • 3-Deoxy-α-D-manno-2-octulosonate
  • 3-Deoxy-α-D-manno-2-octulosonic acid
  • 3-Deoxyoctulosonate
  • 3-Deoxyoctulosonic acid
  • 3-KDO
  • Deoxy-manno-octulosonate
  • Deoxy-manno-octulosonic acid
  • DManOA
  • KDO
  • Ketodeoxyoctonate
  • Ketodeoxyoctonic acid
Chemical Formula: C8H13O8
Average Molecular Weight: 237.185
Monoisotopic Molecular Weight: 237.061590959
InChI Key: KYQCXUMVJGMDNG-UHFFFAOYSA-M
InChI:InChI=1S/C8H14O8/c9-2-5(12)7(14)6(13)3(10)1-4(11)8(15)16/h3,5-7,9-10,12-14H,1-2H2,(H,15,16)/p-1
CAS number: 1069-03-0
IUPAC Name:(4R,5R,6R,7R)-4,5,6,7,8-pentahydroxy-2-oxooctanoic acid
Traditional IUPAC Name: 3-deoxy-D-manno-octulosonate
SMILES:OCC(O)C(O)C(O)C(O)CC(=O)C([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acids and conjugates
Direct Parent Hydroxy fatty acids
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • Medium-chain keto acid
  • Keto acid
  • Beta-hydroxy ketone
  • Beta-ketoaldehyde
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Polyol
  • Ketone
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility64.9 mg/mLALOGPS
logP-2.5ALOGPS
logP-3ChemAxon
logS-0.57ALOGPS
pKa (Strongest Acidic)2.9ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area155.52 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity48.24 m3·mol-1ChemAxon
Polarizability20.91 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-2590000000-c8365537f240bd17c092View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-9420000000-7c62b05f704b94da4ed3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-074m-9200000000-1f9f181dd8666e848b35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002s-7920000000-37d0c8b357cc7b9ec55bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9400000000-35aeded87e6a52f7d9d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rf-9300000000-6953cb4ddc486610ea71View in MoNA
References
References:
  • Belunis, C. J., Raetz, C. R. (1992). "Biosynthesis of endotoxins. Purification and catalytic properties of 3-deoxy-D-manno-octulosonic acid transferase from Escherichia coli." J Biol Chem 267:9988-9997. Pubmed: 1577828
  • Biswas, T., Yi, L., Aggarwal, P., Wu, J., Rubin, J. R., Stuckey, J. A., Woodard, R. W., Tsodikov, O. V. (2009). "The tail of KdsC: conformational changes control the activity of a haloacid dehalogenase superfamily phosphatase." J Biol Chem 284:30594-30603. Pubmed: 19726684
  • Chalabaev, S., Kim, T. H., Ross, R., Derian, A., Kasper, D. L. (2010). "3-Deoxy-D-manno-octulosonic acid (Kdo) hydrolase identified in Francisella tularensis, Helicobacter pylori, and Legionella pneumophila." J Biol Chem 285:34330-34336. Pubmed: 20801884
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Radaev, S., Dastidar, P., Patel, M., Woodard, R. W., Gatti, D. L. (2000). "Structure and mechanism of 3-deoxy-D-manno-octulosonate 8-phosphate synthase." J Biol Chem 275:9476-9484. Pubmed: 10734095
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID32817
HMDB IDNot Available
Pubchem Compound ID817
Kegg IDC01187
ChemSpider ID794
Wikipedia IDNot Available
BioCyc IDKDO
EcoCyc IDKDO