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Record Information
Version	2.0
Creation Date	2012-05-31 14:25:48 -0600
Update Date	2015-09-18 15:17:19 -0600
Secondary Accession Numbers	ECMDB20068
Identification
Name:	3-Deoxy-D-manno-octulosonate 8-phosphate
Description	3-deoxy-D-manno-octulosonate 8-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. KDO 8P is involved in the KDO biosynthetic pathway. 3-Deoxy-D-manno-octulosonate 8-phosphate (KDO 8-P) phosphatase, which catalyzes the hydrolysis of KDO 8-P to KDO and inorganic phosphate, is the last enzyme in the KDO biosynthetic pathway for which the gene has not been identified. (PMID 12639950)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaa8a80a4> Close
Synonyms:	2-Dehydro-3-deoxy-D-octonate 8-P 2-Dehydro-3-deoxy-D-octonate 8-phosphate 2-Dehydro-3-deoxy-D-octonic acid 8-P 2-Dehydro-3-deoxy-D-octonic acid 8-phosphate 2-dehydro-3-Deoxy-D-octonic acid 8-phosphoric acid 3-deoxy-D-manno-octulosonate 8-P 3-Deoxy-D-manno-octulosonate 8-P 3-Deoxy-D-manno-octulosonic acid 8-P 3-Deoxy-D-manno-octulosonic acid 8-phosphate 3-Deoxy-D-manno-octulosonic acid 8-phosphoric acid DManOP KDO-8P
Chemical Formula:	C8H12O11P
Weight:	Average: 315.148 Monoisotopic: 315.013368944
InChI Key:	RTNBXJBOAIDPME-UHFFFAOYSA-K
InChI:	InChI=1S/C8H15O11P/c9-3(1-4(10)8(14)15)6(12)7(13)5(11)2-19-20(16,17)18/h3,5-7,9,11-13H,1-2H2,(H,14,15)(H2,16,17,18)/p-3
CAS number:	Not Available
IUPAC Name:	(4R,5R,6R)-2,4,5-trihydroxy-6-[(1R)-1-hydroxy-2-(phosphonooxy)ethyl]oxane-2-carboxylic acid
Traditional IUPAC Name:	(4R,5R,6R)-2,4,5-trihydroxy-6-[(1R)-1-hydroxy-2-(phosphonooxy)ethyl]oxane-2-carboxylic acid
SMILES:	OC(COP([O-])([O-])=O)C(O)C(O)C(O)CC(=O)C([O-])=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as c-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through a C-glycosidic bond.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	C-glucuronides
Alternative Parents	C-glycosyl compounds Monoalkyl phosphates Pyrans Oxanes Monosaccharides Alpha hydroxy acids and derivatives Secondary alcohols Hemiacetals Polyols Oxacyclic compounds Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	C-glucuronide Glycosyl compound C-glycosyl compound Monoalkyl phosphate Alkyl phosphate Pyran Phosphoric acid ester Oxane Organic phosphoric acid derivative Monosaccharide Hydroxy acid Alpha-hydroxy acid Secondary alcohol Hemiacetal Oxacycle Organoheterocyclic compound Polyol Monocarboxylic acid or derivatives Carboxylic acid Carboxylic acid derivative Organic oxide Hydrocarbon derivative Carbonyl group Alcohol Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 27.8 g/L ALOGPS logP -2.5 ALOGPS logP -2.8 ChemAxon logS -1.1 ALOGPS pKa (Strongest Acidic) 1.47 ChemAxon pKa (Strongest Basic) -3.3 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 10 ChemAxon Hydrogen Donor Count 7 ChemAxon Polar Surface Area 194.21 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 57.59 m³·mol⁻¹ ChemAxon Polarizability 25.22 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	D-Arabinose 5-phosphate + Water + Phosphoenolpyruvic acid <> 3-Deoxy-D-manno-octulosonate 8-phosphate + Phosphate Water + 3-Deoxy-D-manno-octulosonate 8-phosphate <> 3-Deoxy-D-manno-octulosonate + Phosphate 3-Deoxy-D-manno-octulosonate 8-phosphate + Phosphate <> Phosphoenolpyruvic acid + D-Arabinose 5-phosphate + Water 3-Deoxy-D-manno-octulosonate 8-phosphate + Water > 3-Deoxy-D-manno-octulosonate + Phosphate D-Arabinose 5-phosphate + Water + Phosphoenolpyruvic acid > 3-Deoxy-D-manno-octulosonate 8-phosphate + Phosphate Phosphoenolpyruvic acid + D-Arabinose 5-phosphate + Water > 3-Deoxy-D-manno-octulosonate 8-phosphate + Inorganic phosphate 3-Deoxy-D-manno-octulosonate 8-phosphate + Water > 3-Deoxy-D-manno-octulosonate + Inorganic phosphate D-Arabinose 5-phosphate + Phosphoenolpyruvic acid + Water > Phosphate + 3-deoxy-D-manno-octulosonate 8-phosphate + 3-Deoxy-D-manno-octulosonate 8-phosphate 3-deoxy-D-manno-octulosonate 8-phosphate + Water + 3-Deoxy-D-manno-octulosonate 8-phosphate > Phosphate + 3-deoxy-D-manno-octulosonate + 3-Deoxy-D-manno-octulosonate D-Arabinose 5-phosphate + Water + Phosphoenolpyruvic acid <>3 3-Deoxy-D-manno-octulosonate 8-phosphate + Phosphate D-Arabinose 5-phosphate + Water + Phosphoenolpyruvic acid <>3 3-Deoxy-D-manno-octulosonate 8-phosphate + Phosphate
SMPDB Pathways:	Lipopolysaccharide biosynthesis PW000831 lipopolysaccharide biosynthesis II PW001905 lipopolysaccharide biosynthesis III PW002059
KEGG Pathways:	Lipopolysaccharide biosynthesis ec00540 Metabolic pathways eco01100
EcoCyc Pathways:	CMP-KDO biosynthesis I PWY-1269
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0uxr-1269000000-df8a4e5373abd52e41dc View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0udj-5793000000-874f76d92b1ffe948003 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0zfv-9620000000-e70fcfce57b800bc3052 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004j-5943000000-93bb7c83aa07800f779a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004r-9100000000-a5ff9a8019eede681d96 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-150c701ad4345220a8f5 View in MoNA
References
References:	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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 18069 HMDB ID Not Available Pubchem Compound ID 5280685 Kegg ID C04478 ChemSpider ID 4444275 Wikipedia ID Not Available BioCyc ID KDO-8P EcoCyc ID KDO-8P

Enzymes