ECMDB: L-Rhamnulose 1-phosphate (ECMDB20166) (M2MDB001013)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (123)

Record Information

Version

2.0

Creation Date

2012-05-31 14:31:00 -0600

Update Date

2015-09-17 15:42:01 -0600

Secondary Accession Numbers

ECMDB20166

Identification

Name:

L-Rhamnulose 1-phosphate

Description

L-rhamnulose 1-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms:

6-Deoxy-1-O-phosphono-L-sorbose
6-Deoxy-L-sorbose 1-(dihydrogen phosphate)
6-Deoxy-L-sorbose 1-(dihydrogen phosphoric acid)
6-Deoxy-L-sorbose 1-phosphate
6-Deoxy-L-sorbose 1-phosphoric acid
L-Rhamnulose 1-phosphoric acid
L-Rhamnulose-1P
Rhamnulose 1-phosphate
Rhamnulose 1-phosphoric acid
Rhamnulose-1-P
Rhamnulose-1-phosphate
Rhamnulose-1-phosphoric acid

Chemical Formula:

C₉H₁₉O₅P

Weight:

Average: 238.22
Monoisotopic: 238.09701071

InChI Key:

QRXAIBTYLQNPRQ-UHFFFAOYSA-N

InChI:

InChI=1S/C9H19O5P/c1-6(5-14-15(3,4)13)8(11)9(12)7(2)10/h7-13H,1,3,5H2,2,4H3

CAS number:

444-09-7

IUPAC Name:

{[(3S,4R,5S)-3,4,5-trihydroxy-2-oxohexyl]oxy}phosphonic acid

Traditional IUPAC Name:

L-rhamnulose 1-phosphate

SMILES:

CC(O)C(O)C(O)C(=C)COP(C)(O)=C

Chemical Taxonomy

Description

belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharide phosphates

Alternative Parents

Substituents

Octose monosaccharide
Monosaccharide phosphate
Glycerone phosphate
Monoalkyl phosphate
Sugar acid
Acyloin
Beta-hydroxy ketone
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Polyol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	24.9 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-2.3	ChemAxon
logS	-0.99	ALOGPS
pKa (Strongest Acidic)	1.18	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	46.89 m³·mol⁻¹	ChemAxon
Polarizability	20.08 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:

SMPDB Pathways:

fucose and rhamnose degradation

PW000826

KEGG Pathways:

Fructose and mannose metabolism ec00051
Microbial metabolism in diverse environments ec01120
Pentose and glucuronate interconversions ec00040

EcoCyc Pathways:

L-rhamnose degradation I RHAMCAT-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-4690000000-17d50e11374f92e3400b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0570-4920000000-9ae486510db3f7669f8d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052b-9400000000-f5b1483aaa2a22aee511	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fvi-9820000000-96d11cb52700915d345f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-748c93e00b37e4e87981	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-17db9f9872cd5d9166e0	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
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

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17892
HMDB ID	Not Available
Pubchem Compound ID	439413
Kegg ID	C01131
ChemSpider ID	388527
Wikipedia ID	Not Available
BioCyc ID	RHAMNULOSE-1P
EcoCyc ID	RHAMNULOSE-1P

Enzymes

Protein Details

1. Rhamnulose-1-phosphate aldolase

General function:: Involved in metal ion binding
Specific function:: Catalyzes the reversible cleavage of L-rhamnulose-1- phosphate to dihydroxyacetone phosphate (DHAP) and L-lactaldehyde
Gene Name:: rhaD
Uniprot ID:: P32169
Molecular weight:: 30145

Reactions

L-rhamnulose 1-phosphate = glycerone phosphate + (S)-lactaldehyde.

Protein Details

2. Rhamnulokinase

General function:: Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:: ATP + L-rhamnulose = ADP + L-rhamnulose 1- phosphate
Gene Name:: rhaB
Uniprot ID:: P32171
Molecular weight:: 54069

Reactions

ATP + L-rhamnulose = ADP + L-rhamnulose 1-phosphate.

L-Rhamnulose 1-phosphate (ECMDB20166) (M2MDB001013)

Structure for #<Compound:0xb0321c24>

Enzymes

Reactions

Reactions