P. aeruginosa Metabolome Database: 3-Deoxy-D-manno-octulosonate 8-phosphate (PAMDB000917)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000917

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

🔍MOL SDF PDB SMILES InChI View Structure

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

Average Molecular Weight:

315.148

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound 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

Organooxygen compounds

Class

Carbohydrates and carbohydrate conjugates

Sub Class

Sugar acids and derivatives

Direct Parent

C-glucuronides

Alternative Parents

Substituents

C-glucuronide
Glycosyl compound
C-glycosyl compound
Pyran carboxylic acid
Pyran carboxylic acid or derivatives
Monoalkyl phosphate
Alkyl phosphate
Pyran
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
Organic phosphate
Monosaccharide
Hydroxy acid
Alpha-hydroxy acid
Secondary alcohol
Polyol
Hemiacetal
1,2-diol
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
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 mg/mL	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 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	57.59 m³·mol^-1	ChemAxon
Polarizability	25.22 Å³	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:

Pathways:

Lipopolysaccharide biosynthesis pae00540
Metabolic pathways pae01100

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

3-Deoxy-D-manno-octulosonate 8-phosphate (PAMDB000917)

Structure for 3-Deoxy-D-manno-octulosonate 8-phosphate (PAMDB000917)