Record Information
Version1.0
Creation date2010-04-08 22:04:57 UTC
Update date2019-11-26 02:56:26 UTC
Primary IDFDB001398
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameShikimic acid 3-phosphate
DescriptionShikimic acid 3-phosphate is a member of the class of compounds known as monoalkyl phosphates. Monoalkyl phosphates are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Shikimic acid 3-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Shikimic acid 3-phosphate can be found in a number of food items such as date, hard wheat, common sage, and peppermint, which makes shikimic acid 3-phosphate a potential biomarker for the consumption of these food products. Shikimic acid 3-phosphate exists in E.coli (prokaryote) and yeast (eukaryote).
CAS Number63959-45-5
Structure
Thumb
Synonyms
SynonymSource
Shikimate 3-phosphateChEBI
Shikimate 5-phosphateChEBI
Shikimic acid 3-phosphoric acidGenerator
Shikimic acid 5-phosphoric acidGenerator
Shikimic acid-3-phosphoric acidGenerator
3-PhosphoshikimateGenerator
Shikimic acid-3-phosphateMeSH
3-phosphoshikimic Acidbiospider
S3Pbiospider
Shikimate-3-phosphatebiospider
Predicted Properties
PropertyValueSource
Water Solubility21 g/LALOGPS
logP-2.1ALOGPS
logP-1.8ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.83 m³·mol⁻¹ChemAxon
Polarizability20.46 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC7H11O8P
IUPAC name(3R,4S,5R)-4,5-dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid
InChI IdentifierInChI=1S/C7H11O8P/c8-4-1-3(7(10)11)2-5(6(4)9)15-16(12,13)14/h2,4-6,8-9H,1H2,(H,10,11)(H2,12,13,14)/t4-,5-,6+/m1/s1
InChI KeyQYOJSKGCWNAKGW-PBXRRBTRSA-N
Isomeric SMILESO[C@@H]1CC(=C[C@@H](OP(O)(O)=O)[C@H]1O)C(O)=O
Average Molecular Weight254.1312
Monoisotopic Molecular Weight254.01915384
Classification
Description belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentMonoalkyl phosphates
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Cyclitol or derivatives
  • Secondary alcohol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9420000000-24bff48841e0db52f23dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-2290000000-396028b52ce4cedbe2bbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-0490000000-529105b5a87b738ed617JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-6900000000-1e7071aa820eeb1c46baJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3190000000-efb4ce7028884fa42743JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9320000000-de7c749cb1ef8f00a7c2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5ea8917f66ef1d382869JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC03175
Pubchem Compound ID121947
Pubchem Substance IDNot Available
ChEBI ID17052
Phenol-Explorer IDNot Available
DrugBank IDDB04328
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00000002
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.