Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001122
Identification
Name: L-Ribose
Description:Ribose is an organic compound that occurs widely in nature. It is an aldopentose, a monosaccharide containing five carbon atoms that in its acyclic form has an aldehyde functional group at one end. Typically, ribose exists in the cyclic form. It comprises the backbone of RNA, a biopolymer that is the basis of genetic transcription. It is related to deoxyribose, as found in DNA, by the removal of one hydroxy group. Once phosphorylated, ribose can become a subunit of ATP, NADH, and several other compounds that are critical to metabolism. Ribose exists in two enantiomeric forms, primarily as D-ribose. L-ribose is the synthetic mirror image of D-ribose. (Wikipedia) In Pseudomonas aeruginosa, L-ribose can act as an competitive inhibitor of glucose dehydrogenase. (EcoCyc)
Structure
Thumb
Synonyms:
  • (2S,3S,4S)-2,3,4,5-tetrahydroxypentanal
  • Aldehydo-L-ribo-pentose
  • Aldehydo-L-ribose
  • Arabinose
Chemical Formula: C5H10O5
Average Molecular Weight: 150.1299
Monoisotopic Molecular Weight: 150.05282343
InChI Key: PYMYPHUHKUWMLA-MROZADKFSA-N
InChI:InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4+,5-/m1/s1
CAS number: 24259-59-4
IUPAC Name:(2S,3S,4S)-2,3,4,5-tetrahydroxypentanal
Traditional IUPAC Name: L-ribose
SMILES:[H][C@](O)(CO)[C@]([H])(O)[C@]([H])(O)C=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as monosaccharides. These are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct Parent Monosaccharides
Alternative Parents
Substituents
  • Monosaccharide
  • Beta-hydroxy aldehyde
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Primary alcohol
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 99 ?C, 372 K, 210 ?F
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility380.0 mg/mLALOGPS
logP-2.3ALOGPS
logP-2.9ChemAxon
logS0.4ALOGPS
pKa (Strongest Acidic)11.87ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.38 m3·mol-1ChemAxon
Polarizability13.38 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-d4b4d16fe2bdea6dccd0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-be87d057e4e6e95de7e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fv-9000000000-9a3060e3aacc77a20ccaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-9400000000-dbd7597b23c261cf03b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06ri-9200000000-bf3ea96e46d76c202a29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-6b0fd940d309cdea3a46View in MoNA
References
References:
  • 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 ID46997
HMDB IDNot Available
Pubchem Compound ID90428
Kegg IDNot Available
ChemSpider ID81643
Wikipedia IDRibose
BioCyc IDCPD-6001
EcoCyc IDCPD-6001

Enzymes

General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for ribose. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
rbsC
Locus Tag:
PA1948
Molecular weight:
34 kDa

Transporters

General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for ribose. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
rbsC
Locus Tag:
PA1948
Molecular weight:
34 kDa