D-Arabinose 5-phosphate (PAMDB000821)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000821
Identification
Name: D-Arabinose 5-phosphate
Description:D-Arabinose 5-phosphate is an intermediate in biosynthesis of lipopolysaccharide.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • Ara5P
  • Arabinose 5-phosphate
  • Arabinose 5-phosphoric acid
  • Arabinose-5-P
  • Arabinose-5P
  • D-A-5-P
  • D-Arabinose 5-phosphate
  • D-Arabinose 5-phosphoric acid
  • D-Arabinose-5-P
Chemical Formula: C5H11O8P
Average Molecular Weight: 230.1098
Monoisotopic Molecular Weight: 230.01915384
InChI Key: PPQRONHOSHZGFQ-WDCZJNDASA-N
InChI:InChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h1,3-5,7-9H,2H2,(H2,10,11,12)/t3-,4-,5+/m1/s1
CAS number: 13137-52-5
IUPAC Name:{[(2R,3R,4S)-2,3,4-trihydroxy-5-oxopentyl]oxy}phosphonic acid
Traditional IUPAC Name: arabinose 5-phosphate
SMILES:O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)C=O
Chemical Taxonomy
Taxonomy DescriptionThis compound 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 ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct Parent Monosaccharide phosphates
Alternative Parents
Substituents
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Beta-hydroxy aldehyde
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Hydrocarbon derivative
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility19.3 mg/mLALOGPS
logP-1.6ALOGPS
logP-3.1ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.26 m3·mol-1ChemAxon
Polarizability17.99 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
D-Ribulose 5-phosphate <> D-Arabinose 5-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
D-Arabinose 5-phosphate + Phosphoenolpyruvic acid + Water > Phosphate + 3-deoxy-D-manno-octulosonate 8-phosphate + 3-Deoxy-D-manno-octulosonate 8-phosphate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-3690000000-06b766b00394897d8276View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btd-9710000000-6f93a4202efb7ba3d3fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-a324e9f10ad080e0ea34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-9520000000-e3a1ec95af6dcad460c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-82ac7295f5c79a94ec38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-352da97e65dd9cc16df9View in MoNA
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • 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
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • 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) Download (PDF)
External Links:
ResourceLink
CHEBI ID16241
HMDB IDHMDB11734
Pubchem Compound ID230
Kegg IDC01112
ChemSpider ID163687
Wikipedia IDNot Available
BioCyc IDARABINOSE-5P
EcoCyc IDARABINOSE-5P