precursor

Showing entry for Shikimate

Identification

PhytoHub ID
PHUB002330
Name
Shikimate
Systematic Name
(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
Synonyms
  • (-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
  • (-)-Shikimic acid
  • (3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
  • 3,4,5-Trihydroxy-1-cyclohexenecarboxylate
  • 3a,4a,5b-Trihydroxy-1-cyclohexene-1-carboxylate
  • 3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylate
CAS Number
138-59-0
Average Mass
174.152
Monoisotopic Mass
174.052823422
Chemical Formula
C7H10O5
IUPAC Name
(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
InChI Key
JXOHGGNKMLTUBP-HSUXUTPPSA-N
InChI Identifier
InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1
SMILES
O[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(O)=O
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
2.06e+02 g/l
LogS (ALOGPS)
0.07
LogP (ALOGPS)
-1.70
Hydrogen Acceptors
5
Hydrogen Donors
4
Rotatable Bond Count
1
Polar Surface Area
97.99000000000001
Refractivity
38.9603
Polarizability
16.005040408136242
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-3.224778959977734
pKa (strongest acidic)
3.911274828419261
Number of Rings
1
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
No
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Food Phytochemical

Family
Miscellaneous phytochemicals
Class
Miscellaneous phytochemicals
Sub-class
Not Available

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Organooxygen compounds
Super-class
Organic oxygen compounds
Sub-class
Alcohols and polyols
Direct Parent Name
Shikimic acids and derivatves
Alternative Parent Names
["Carbonyl compounds", "Carboxylic acids", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides", "Polyols", "Secondary alcohols"]
External Descriptor Annotations
["alpha,beta-unsaturated monocarboxylic acid", "cyclohexenecarboxylic acid", "hydroxy monocarboxylic acid"]
Substituent Names
["Aliphatic homomonocyclic compound", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Hydrocarbon derivative", "Monocarboxylic acid or derivatives", "Organic oxide", "Polyol", "Secondary alcohol", "Shikimic acid or derivatives"]

Spectra from Online Resources

No spectra information available

Spectra from Phytohub

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-e6ca4ce5acb44dc23a742012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004r-9700000000-18afe769b0ef5ba3fbdb2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9100000000-7d0218e803b828de53b22012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-01b9-1900000000-fd80f5e7f51d927e8e152012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9300000000-cf8a3148fd132540bf972012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-ed28bc20ae43473043c92012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-65249fc24f2de4acf2c72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-26dfc876ae35c2cdb8452012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-006x-9600000000-3a5ab91754d9d837d8b42012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01b9-1900000000-6cba5b9b7c48915220452017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9300000000-12d15a049b141a37f34e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-ed28bc20ae43473043c92017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-9864f7359ffed65d6ef02017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-26dfc876ae35c2cdb8452017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-006x-9600000000-3a5ab91754d9d837d8b42017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00ks-4900000000-3c7c11a5c27e1018d3282021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-e7907b79b8fbcac9aa362021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-7900000000-d77a830354efe8731a422021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-9d3f05c288a1c32bd52b2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-2a02691107b26b47bfe72016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-d0e0c1c61a8cc849c4bc2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03kc-9500000000-1be2290fb516bd446a612016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-563539f2a2fed5cb4f8a2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-2900000000-229ad430d980f20f597b2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00b9-9300000000-db4467dbe0ef7549a6e72016-09-12View Spectrum

Food Sources

NameGroup
KiwiFruit, Tropical fruits PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

No metabolism information available

Inter-Individual Variations in Metabolism

No data on inter-individual variations available

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