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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-03-03 10:37:18 UTC
Update Date2020-02-26 21:35:45 UTC
HMDB IDHMDB0011734
Secondary Accession Numbers
  • HMDB11734
Metabolite Identification
Common NameD-Arabinose 5-phosphate
DescriptionD-Arabinose 5-phosphate, also known as arabinose-5-p or 5-O-phosphono-D-arabinose, 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. D-Arabinose 5-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Arabinose 5-phosphate exists in all living organisms, ranging from bacteria to humans. Outside of the human body, D-Arabinose 5-phosphate has been detected, but not quantified in, several different foods, such as other cereal products, hedge mustards, american pokeweeds, endives, and pepper (c. frutescens). This could make D-arabinose 5-phosphate a potential biomarker for the consumption of these foods.
Structure
Data?1582752945
Synonyms
ValueSource
5-O-Phosphono-D-arabinoseChEBI
D-a-5-pChEBI
D-Arabinose 5-phosphoric acidGenerator
Arabinose-5-pHMDB
Arabinose-5PHMDB
Arabinose 5-phosphate, di-li saltHMDB
Arabinose 5-phosphateHMDB
Arabinose 5-phosphate, (beta-D)-isomerHMDB
Chemical FormulaC5H11O8P
Average Molecular Weight230.1098
Monoisotopic Molecular Weight230.01915384
IUPAC Name{[(2R,3R,4S)-2,3,4-trihydroxy-5-oxopentyl]oxy}phosphonic acid
Traditional Namearabinose 5-phosphate
CAS Registry Number13137-52-5
SMILES
O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)C=O
InChI Identifier
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
InChI KeyPPQRONHOSHZGFQ-WDCZJNDASA-N
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility19.3 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.26 m³·mol⁻¹ChemAxon
Polarizability17.99 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014j-0954000000-13c360ef6d50c290ff75Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014j-1954000000-66deca60c06849233c1eSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014j-0954000000-13c360ef6d50c290ff75Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014j-1954000000-66deca60c06849233c1eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9100000000-b771da2f9bcb85359615Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01c0-2934100000-c0832bdf2f33a1c2e0aeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-1090000000-31e1af2994eda21a1bc4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9100000000-2045507193c154fa6155Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-002b-9000000000-ea919a44fa730a6b30acSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-585f803ae9cdd8a87b5bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-39ddb0bbc9b7b081c7fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002b-9000000000-f3fe9e7cc40f16c3578eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-3690000000-06b766b00394897d8276Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btd-9710000000-6f93a4202efb7ba3d3fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-a324e9f10ad080e0ea34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-9520000000-e3a1ec95af6dcad460c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-82ac7295f5c79a94ec38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-352da97e65dd9cc16df9Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028414
KNApSAcK IDNot Available
Chemspider ID163687
KEGG Compound IDC01112
BioCyc IDARABINOSE-5P
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound188324
PDB IDNot Available
ChEBI ID16241
Food Biomarker OntologyNot Available
VMH IDARA5P
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. doi: 10.1038/nature07762. [PubMed:19212411 ]