Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110597
Identification
Name: D-ribulose 5-phosphate
Description:An organophosphate oxoanion that is the dianion resulting from the removal of two protons from the phosphate group of D-ribulose 5-phosphate.
Structure
Thumb
Synonyms:
  • ribulose-5P
  • D-ribulose-5-P
  • ribulose-5-P
Chemical Formula: C5H9O8P
Average Molecular Weight: 228.1
Monoisotopic Molecular Weight: 230.0191538399
InChI Key: FNZLKVNUWIIPSJ-UHNVWZDZSA-L
InChI: InChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h4-6,8-9H,1-2H2,(H2,10,11,12)/p-2/t4-,5+/m1/s1
CAS number: 4151-19-3
IUPAC Name:5-O-phosphonato-D-ribulose
Traditional IUPAC Name: Ara
SMILES:C(C(C(C(CO)=O)O)O)OP([O-])([O-])=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 ketone
  • Beta-ketoaldehyde
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Polyol
  • Ketone
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility33.6 mg/mLALOGPS
logP-1.8ALOGPS
logP-2.8ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)1.48ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.47 m3·mol-1ChemAxon
Polarizability17.86 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)splash10-0a4i-2936000000-adde71232cd79c7c92aaView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)splash10-0a4i-2947000000-ae4da5853e1b24392d1dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-3790000000-6f5913e9948fa7667e41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btd-9710000000-3724bb9f611bbdc1fe11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-8bc9cecb2dddad8ca5e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-9520000000-c36fdbcc1d3b19b2fafdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-b67b8ea484aa4ddb40e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-82b17cf4f5a8c927fe64View in MoNA
References
References:
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  • Verhoeven NM, Huck JH, Roos B, Struys EA, Salomons GS, Douwes AC, van der Knaap MS, Jakobs C: Transaldolase deficiency: liver cirrhosis associated with a new inborn error in the pentose phosphate pathway. Am J Hum Genet. 2001 May;68(5):1086-92. Epub 2001 Mar 27. [11283793 ]
  • 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. [19212411 ]
  • Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. [15882454 ]
  • Lachant NA, Zerez CR, Tanaka KR: Pyrimidine nucleotides impair phosphoribosylpyrophosphate (PRPP) synthetase subunit aggregation by sequestering magnesium. A mechanism for the decreased PRPP synthetase activity in hereditary erythrocyte pyrimidine 5'-nucleotidase deficiency. Biochim Biophys Acta. 1989 Jan 19;994(1):81-8. [2535789 ]
  • Huck JH, Struys EA, Verhoeven NM, Jakobs C, van der Knaap MS: Profiling of pentose phosphate pathway intermediates in blood spots by tandem mass spectrometry: application to transaldolase deficiency. Clin Chem. 2003 Aug;49(8):1375-80. [12881455 ]
  • Boss GR: Decreased phosphoribosylpyrophosphate as the basis for decreased purine synthesis during amino acid starvation of human lymphoblasts. J Biol Chem. 1984 Mar 10;259(5):2936-41. [6199353 ]
  • Schenk G, Duggleby RG, Nixon PF: Heterologous expression of human transketolase. Int J Biochem Cell Biol. 1998 Mar;30(3):369-78. [9611778 ]
  • Cornwell MM, Tsuruo T, Gottesman MM, Pastan I: ATP-binding properties of P glycoprotein from multidrug-resistant KB cells. FASEB J. 1987 Jul;1(1):51-4. [2886389 ]
  • Boer P, Sperling O: Role of cellular ribose-5-phosphate content in the regulation of 5-phosphoribosyl-1-pyrophosphate and de novo purine synthesis in a human hepatoma cell line. Metabolism. 1995 Nov;44(11):1469-74. [7476336 ]
  • Delplanque J, Delpierre G, Opperdoes FR, Van Schaftingen E: Tissue distribution and evolution of fructosamine 3-kinase and fructosamine 3-kinase-related protein. J Biol Chem. 2004 Nov 5;279(45):46606-13. Epub 2004 Aug 25. [15331600 ]
  • Berthon HA, Kuchel PW, Nixon PF: High control coefficient of transketolase in the nonoxidative pentose phosphate pathway of human erythrocytes: NMR, antibody, and computer simulation studies. Biochemistry. 1992 Dec 29;31(51):12792-8. [1463749 ]
  • Gatsura VV: [Pentosephosphate cycle metabolites as energy-supplying anti-ischemic agents] Farmakol Toksikol. 1991 Jul-Aug;54(4):4-8. [1786823 ]
  • Parry RJ, Burns MR, Skae PN, Hoyt JC, Pal B: Carbocyclic analogues of D-ribose-5-phosphate: synthesis and behavior with 5-phosphoribosyl alpha-1-pyrophosphate synthetases. Bioorg Med Chem. 1996 Jul;4(7):1077-88. [8831979 ]
  • Song EK, Park HJ, Kim JS, Lee HH, Kim UH, Han MK: A novel fluorometric assay for ADP-ribose pyrophosphatase activity. J Biochem Biophys Methods. 2005 Jun 30;63(3):161-9. [15967507 ]
  • Chalmers AH: Fresh substrate essential for transketolase assay. Clin Chem. 1993 Jun;39(6):1347-8. [7980725 ]
  • Buttery JE, Chamberlain BR: Fresh vs frozen substrate for transketolase assay. Clin Chem. 1994 Sep;40(9):1786-7. [8070095 ]
  • Takeuchi T, Nishino K, Itokawa Y: Improved determination of transketolase activity in erythrocytes. Clin Chem. 1984 May;30(5):658-61. [6713626 ]
  • Kakuta Y, Tahara M, Maetani S, Yao M, Tanaka I, Kimura M: Crystal structure of the regulatory subunit of archaeal initiation factor 2B (aIF2B) from hyperthermophilic archaeon Pyrococcus horikoshii OT3: a proposed structure of the regulatory subcomplex of eukaryotic IF2B. Biochem Biophys Res Commun. 2004 Jul 2;319(3):725-32. [15184043 ]
  • Mocali A, Paoletti F: Transketolase from human leukocytes. Isolation, properties and induction of polyclonal antibodies. Eur J Biochem. 1989 Mar 1;180(1):213-9. [2495942 ]
  • Nordenberg J, Aviram R, Beery E, Stenzel KH, Novogrodsky A: Inhibition of 6-phosphogluconate dehydrogenase by glucose 1,6-diphosphate in human normal and malignant colon extracts. Cancer Lett. 1984 Jun;23(2):193-9. [6234985 ]
  • Pilz RB, Willis RC, Boss GR: The influence of ribose 5-phosphate availability on purine synthesis of cultured human lymphoblasts and mitogen-stimulated lymphocytes. J Biol Chem. 1984 Mar 10;259(5):2927-35. [6699001 ]
Synthesis Reference: Wong, Chi-Huey; McCurry, Stephen D.; Whitesides, George M. Practical enzymic syntheses of ribulose 1,5 bisphosphate and ribose 5-phosphate. Journal of the American Chemical Society (1980), 102(27), 7938-9.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CAS4151-19-3
ChEBI58121
ChemSpider20015724
HMDBHMDB00618
IAF126034237
KEGGC00199
MetaboLightsMTBLC58121
PubChem21144996