Showing Compound Shikimic acid 3-phosphate (FDB001398)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:57 UTC

Update date

2025-11-18 22:31:03 UTC

Primary ID

FDB001398

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Shikimic acid 3-phosphate

Description

Shikimic 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 Number

63959-45-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Shikimate 3-phosphate	ChEBI
Shikimate 5-phosphate	ChEBI
Shikimic acid 3-phosphoric acid	Generator
Shikimic acid 5-phosphoric acid	Generator
Shikimic acid-3-phosphoric acid	Generator
3-Phosphoshikimate	Generator
Shikimic acid-3-phosphate	MeSH
3-phosphoshikimic Acid	biospider
S3P	biospider
Shikimate-3-phosphate	biospider

Predicted Properties

Property	Value	Source
Water Solubility	21 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-1.8	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.32	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.83 m³·mol⁻¹	ChemAxon
Polarizability	20.46 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C7H11O8P

IUPAC name

(3R,4S,5R)-4,5-dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid

InChI Identifier

InChI=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 Key

QYOJSKGCWNAKGW-PBXRRBTRSA-N

Isomeric SMILES

O[C@@H]1CC(=C[C@@H](OP(O)(O)=O)[C@H]1O)C(O)=O

Average Molecular Weight

254.1312

Monoisotopic Molecular Weight

254.01915384

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Monoalkyl 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 Framework

Aliphatic homomonocyclic compounds

External Descriptors

phosphoshikimic acid (CHEBI:17052 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Shikimic acid 3-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9420000000-24bff48841e0db52f23d	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-2290000000-396028b52ce4cedbe2bb	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05n0-0490000000-529105b5a87b738ed617	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-6900000000-1e7071aa820eeb1c46ba	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3190000000-efb4ce7028884fa42743	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9320000000-de7c749cb1ef8f00a7c2	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-5ea8917f66ef1d382869	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004j-9010000000-3906ab4aee0305db4d4b	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9010000000-6a75ffa6c3d07241a675	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-9bbc041a48805948beff	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0490000000-6f7f3bbe06a56485d8f7	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-1950000000-f9d939de49ab972591e9	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aps-9000000000-a548a26753cac7a078d4	2021-10-21	View Spectrum