L-Ascorbate 6-phosphate (ECMDB20164) (M2MDB001011)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (7)Transporters (1)XML
Proteins (334)
Record Information
Version2.0
Creation Date2012-05-31 14:30:53 -0600
Update Date2015-09-17 15:41:58 -0600
Secondary Accession Numbers
  • ECMDB20164
Identification
Name:L-Ascorbate 6-phosphate
DescriptionL-ascorbate 6-phosphate is a member of the chemical class known as Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • L-Ascorbic acid 6-phosphate
  • L-Ascorbic acid 6-phosphoric acid
Chemical Formula:C6H6O9P
Weight:Average: 253.08
Monoisotopic: 252.976589511
InChI Key:KIENGQUGHPTFGC-JLAZNSOCSA-K
InChI:InChI=1S/C6H9O9P/c7-2(1-14-16(11,12)13)5-3(8)4(9)6(10)15-5/h2,5,7-9H,1H2,(H2,11,12,13)/p-3/t2-,5+/m0/s1
CAS number:Not Available
IUPAC Name:[(2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethoxy]phosphonic acid
Traditional IUPAC Name:L-ascorbyl phosphate
SMILES:[H][C@@]1(OC(=O)C(O)=C1[O-])[C@@H](O)COP([O-])([O-])=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentMonoalkyl phosphates
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • 2-furanone
  • Dihydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Vinylogous acid
  • Carboxylic acid ester
  • Enediol
  • Lactone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility15.9 g/LALOGPS
logP-1.5ALOGPS
logP-2ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.48ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.75 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity47.9 m³·mol⁻¹ChemAxon
Polarizability19.59 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Phosphoenolpyruvic acid + Ascorbic acid > L-Ascorbate 6-phosphate + Pyruvic acid
L-Ascorbate 6-phosphate + Water > 3-Dehydro-L-gulonate 6-phosphate + Hydrogen ion
Protein N(pi)-phospho-L-histidine + Ascorbic acid <> Protein histidine + L-Ascorbate 6-phosphate
L-Ascorbate 6-phosphate + Water <> 3-Dehydro-L-gulonate 6-phosphate
Phosphoenolpyruvic acid + Ascorbic acid > L-Ascorbate 6-phosphate + Pyruvic acid
L-Ascorbate 6-phosphate + Water > 3-Dehydro-L-gulonate 6-phosphate
L-ascorbate 6-phosphate + Water + L-Ascorbate 6-phosphate > 3-keto-L-gulonate 6-phosphate + 3-Keto-L-gulonate 6-phosphate
Ascorbic acid + HPr - phosphorylated + Ascorbic acid > L-ascorbate 6-phosphate + HPr + L-Ascorbate 6-phosphate
SMPDB Pathways:
Ascorbate metabolismPW000793 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Ascorbate and aldarate metabolism ec00053
  • Phosphotransferase system (PTS) ec02060
EcoCyc Pathways:
  • L-ascorbate degradation I (bacterial, anaerobic) PWY0-301
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a5i-0970000000-8a74329cfba02724e23cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-4930000000-181f1b2bd22316c9e811View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f76-8900000000-90ded7e626ea2fbf6982View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0wpr-5930000000-5be155b163642c1fe463View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-663a0b95a5a8c1401860View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-61679dfcad4367bde4feView 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
External Links:
ResourceLink
CHEBI ID61701
HMDB IDNot Available
Pubchem Compound ID23724654
Kegg IDC16186
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDL-ASCORBATE-6-PHOSPHATE
EcoCyc IDL-ASCORBATE-6-PHOSPHATE

Enzymes

Protein Details
1. Phosphoenolpyruvate-protein phosphotransferase
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. Enzyme I transfers the phosphoryl group from phosphoenolpyruvate (PEP) to the phosphoryl carrier protein (HPr)
Gene Name:
ptsI
Uniprot ID:
P08839
Molecular weight:
63561
Reactions
Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine.
Protein Details
2. Putative phosphotransferase enzyme IIA component yadI
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane
Gene Name:
yadI
Uniprot ID:
P36881
Molecular weight:
16540
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein Details
3. Ascorbate-specific phosphotransferase enzyme IIA component
General function:
Involved in transporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in ascorbate transport
Gene Name:
ulaC
Uniprot ID:
P69820
Molecular weight:
17237
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein Details
4. Ascorbate-specific phosphotransferase enzyme IIB component
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in ascorbate transport
Gene Name:
ulaB
Uniprot ID:
P69822
Molecular weight:
10896
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
Protein Details
5. Ascorbate-specific permease IIC component ulaA
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active- transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in ascorbate transport
Gene Name:
ulaA
Uniprot ID:
P39301
Molecular weight:
50737
Protein Details
6. Probable L-ascorbate-6-phosphate lactonase ulaG
General function:
Involved in hydrolase activity
Specific function:
Probably catalyzes the hydrolysis of L-ascorbate-6-P into 3-keto-L-gulonate-6-P. Is essential for L-ascorbate utilization under anaerobic conditions. Also shows phosphodiesterase activity, hydrolyzing phosphodiester bond in the artificial chromogenic substrate bis-p-nitrophenyl phosphate (bis- pNPP)
Gene Name:
ulaG
Uniprot ID:
P39300
Molecular weight:
40060
Reactions
L-ascorbate 6-phosphate + H(2)O = 3-dehydro-L-gulonate 6-phosphate.
Protein Details
7. Phosphocarrier protein HPr
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. The phosphoryl group from phosphoenolpyruvate (PEP) is transferred to the phosphoryl carrier protein HPr by enzyme I. Phospho-HPr then transfers it to the permease (enzymes II/III)
Gene Name:
ptsH
Uniprot ID:
P0AA04
Molecular weight:
9119
Reactions
Protein HPr N(pi)-phospho-L-histidine + protein EIIA = protein HPr + protein EIIA N(tau)-phospho-L-histidine.

Transporters

Protein Details
1. Ascorbate-specific permease IIC component ulaA
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active- transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in ascorbate transport
Gene Name:
ulaA
Uniprot ID:
P39301
Molecular weight:
50737