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Record Information
Version	2.0
Creation Date	2012-05-31 14:20:39 -0600
Update Date	2015-09-13 12:56:14 -0600
Secondary Accession Numbers	ECMDB11734
Identification
Name:	D-Arabinose 5-phosphate
Description	D-Arabinose 5-phosphate is an intermediate in biosynthesis of lipopolysaccharide.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xafff7b5c> Close
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
Weight:	Average: 230.1098 Monoisotopic: 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
Description	belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Pentose phosphates
Alternative Parents	Monosaccharide phosphates Monoalkyl phosphates Beta-hydroxy aldehydes Alpha-hydroxyaldehydes Secondary alcohols Polyols Organic oxides Hydrocarbon derivatives
Substituents	Pentose phosphate Monosaccharide phosphate Monoalkyl phosphate Beta-hydroxy aldehyde Organic phosphoric acid derivative Phosphoric acid ester Alkyl phosphate Alpha-hydroxyaldehyde Secondary alcohol Polyol Hydrocarbon derivative Aldehyde Organic oxide Carbonyl group Alcohol Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	D-arabinose 5-phosphate (CHEBI:16241 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 19.3 g/L ALOGPS logP -1.6 ALOGPS logP -3.1 ChemAxon logS -1.1 ALOGPS pKa (Strongest Acidic) 1.49 ChemAxon pKa (Strongest Basic) -3.5 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 144.52 Ų ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 42.26 m³·mol⁻¹ ChemAxon Polarizability 18 ų 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:	D-Ribulose 5-phosphate <> D-Arabinose 5-phosphate D-Arabinose 5-phosphate + Water + Phosphoenolpyruvic acid <> 3-Deoxy-D-manno-octulosonate 8-phosphate + Phosphate 3-Deoxy-D-manno-octulosonate 8-phosphate + Phosphate <> Phosphoenolpyruvic acid + D-Arabinose 5-phosphate + Water D-Arabinose 5-phosphate <> D-Ribulose 5-phosphate D-Arabinose 5-phosphate + Water + Phosphoenolpyruvic acid > 3-Deoxy-D-manno-octulosonate 8-phosphate + Phosphate D-Arabinose 5-phosphate > D-Ribulose 5-phosphate Phosphoenolpyruvic acid + D-Arabinose 5-phosphate + Water > 3-Deoxy-D-manno-octulosonate 8-phosphate + Inorganic phosphate D-Ribulose 5-phosphate > D-Arabinose 5-phosphate D-Arabinose 5-phosphate + Phosphoenolpyruvic acid + Water > Phosphate + 3-deoxy-D-manno-octulosonate 8-phosphate + 3-Deoxy-D-manno-octulosonate 8-phosphate D-Arabinose 5-phosphate + Water + Phosphoenolpyruvic acid <>3 3-Deoxy-D-manno-octulosonate 8-phosphate + Phosphate D-Arabinose 5-phosphate <> D-Ribulose 5-phosphate D-Arabinose 5-phosphate + Water + Phosphoenolpyruvic acid <>3 3-Deoxy-D-manno-octulosonate 8-phosphate + Phosphate D-Arabinose 5-phosphate <> D-Ribulose 5-phosphate
SMPDB Pathways:	Lipopolysaccharide biosynthesis PW000831 lipopolysaccharide biosynthesis II PW001905 lipopolysaccharide biosynthesis III PW002059
KEGG Pathways:	Lipopolysaccharide biosynthesis ec00540 Metabolic pathways eco01100
EcoCyc Pathways:	CMP-KDO biosynthesis I PWY-1269
Concentrations
	Concentration Strain Media Growth Status Growth System Temperature Details 1020± 0 uM K12 NCM3722 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 686± 0 uM K12 NCM3722 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 1320± 0 uM K12 NCM3722 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 Find out more about how we convert literature concentrations.
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-014j-0954000000-13c360ef6d50c290ff75 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-014j-1954000000-66deca60c06849233c1e View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-014j-0954000000-13c360ef6d50c290ff75 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-014j-1954000000-66deca60c06849233c1e View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0002-9100000000-b771da2f9bcb85359615 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive splash10-01c0-2934100000-c0832bdf2f33a1c2e0ae View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-004i-1090000000-31e1af2994eda21a1bc4 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0002-9100000000-2045507193c154fa6155 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-002b-9000000000-ea919a44fa730a6b30ac View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-004i-9000000000-585f803ae9cdd8a87b5b View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-004i-9000000000-39ddb0bbc9b7b081c7fd View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , negative splash10-002b-9000000000-f3fe9e7cc40f16c3578e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-01q9-3690000000-06b766b00394897d8276 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0btd-9710000000-6f93a4202efb7ba3d3fd View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4i-9200000000-a324e9f10ad080e0ea34 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-002r-9520000000-e3a1ec95af6dcad460c7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9100000000-82ac7295f5c79a94ec38 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-352da97e65dd9cc16df9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004j-9040000000-0b86189542286f55e20f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004j-9000000000-98c2dab693f3635a82c4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-a5e502a2627af2048a1f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-001j-9540000000-adbdd8414bace2c44f56 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0002-9200000000-b929bd8d4139b2fa147a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0007-9000000000-cbffc4c85bf45fc4aeef View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
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)
Links
External Links:	Resource Link CHEBI ID 16241 HMDB ID HMDB11734 Pubchem Compound ID 230 Kegg ID C01112 ChemSpider ID 163687 Wikipedia ID Not Available BioCyc ID ARABINOSE-5P EcoCyc ID ARABINOSE-5P

Enzymes