P. aeruginosa Metabolome Database: 2-Dehydro-3-deoxy-L-rhamnonate (PAMDB002038)

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

PAMDB002038

Identification

Name:

2-Dehydro-3-deoxy-L-rhamnonate

Description:

2-dehydro-3-deoxy-l-rhamnonate belongs to the class of Keto Fatty Acids. These are fatty acids containing a ketone group attached to the acyl chain.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

2-Dehydro-3,6-dideoxy-L-mannonate
2-Dehydro-3,6-dideoxy-L-mannonic acid
2-Dehydro-3-deoxy-L-rhamnonate
2-Dehydro-3-deoxy-L-rhamnonic acid
3,6-Dideoxy-L-arabino-hex-2-ulosonate
3,6-Dideoxy-L-arabino-hex-2-ulosonic acid

Chemical Formula:

C₆H₁₀O₅

Average Molecular Weight:

162.1406

Monoisotopic Molecular Weight:

162.05282343

InChI Key:

FRIWJYNKZPJVRL-IUYQGCFVSA-N

InChI:

InChI=1S/C6H10O5/c1-3(7)4(8)2-5(9)6(10)11/h3-4,7-8H,2H2,1H3,(H,10,11)/t3-,4+/m0/s1

CAS number:

Not Available

IUPAC Name:

(4R,5S)-4,5-dihydroxy-2-oxohexanoic acid

Traditional IUPAC Name:

(4R,5S)-4,5-dihydroxy-2-oxohexanoic acid

SMILES:

[H][C@@](C)(O)[C@]([H])(O)CC(=O)C(O)=O

Chemical Taxonomy

Taxonomy Description

This 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 Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty 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
Ketone
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ketoaldonic acid (CHEBI:18078 )
hexonic acid (CHEBI:18078 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	119.0 mg/mL	ALOGPS
logP	-1.3	ALOGPS
logP	-0.73	ChemAxon
logS	-0.14	ALOGPS
pKa (Strongest Acidic)	3.06	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	34.77 m³·mol^-1	ChemAxon
Polarizability	14.59 Å³	ChemAxon
Number of Rings	0	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:

2-Dehydro-3-deoxy-L-rhamnonate <> Lactaldehyde + Pyruvic acid + (S)-Lactaldehyde
L-Rhamnonate + L-Rhamnonate <> 2-Dehydro-3-deoxy-L-rhamnonate + Water
2-Dehydro-3-deoxy-L-rhamnonate > Pyruvic acid + D-Lactaldehyde
L-Rhamnonate > 2-Dehydro-3-deoxy-L-rhamnonate + Water

Pathways:

Fructose and mannose metabolism pae00051
Microbial metabolism in diverse environments pae01120

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ot-2900000000-527c02e76a89144a4ebe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002k-9700000000-058bac2bc8bc9e2a411e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dj-9100000000-58ffe2f9b9affc7bb4e4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-3900000000-d3497eb4995bd5913e87	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dr-9300000000-2f7eaa4710b6f7eb62aa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-9100000000-13f3f80adf78936c1b31	View in MoNA

References

References:

Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	18078
HMDB ID	Not Available
Pubchem Compound ID	49852300
Kegg ID	C03979
ChemSpider ID	26331139
Wikipedia ID	Not Available
BioCyc ID	Not Available

2-Dehydro-3-deoxy-L-rhamnonate (PAMDB002038)

Structure for 2-Dehydro-3-deoxy-L-rhamnonate (PAMDB002038)