Livestock Metabolome Database: Showing metabocard for Shikimic acid (LMDB00413)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:49:17 UTC

Update Date

2016-07-20 21:00:42 UTC

Lmdb

LMDB00413

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Shikimic acid

Description

Shikimic acid, more commonly known as its anionic form shikimate, is an important biochemical intermediate in plants and microorganisms. Its name comes from the Japanese flower shikimi (シキミ, Illicium anisatum), from which it was first isolated. Shikimic acid is a precursor for: the aromatic amino acids phenylalanine and tyrosine; indole, indole derivatives and tryptophan; many alkaloids and other aromatic metabolites; tannins; and lignin. In pharmaceutical industry, shikimic acid from chinese star anise is used as a base material for production of Tamiflu (oseltamivir). Although shikimic acid is present in most autotrophic organisms, it is a biosynthetic intermediate and generally found in very low concentrations (Wikipedia).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid	ChEBI
3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylic acid	ChEBI
[3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid	ChEBI
L-Shikimic acid	ChEBI
Shikimate	ChEBI
3,4,5-Trihydroxy-1-cyclohexenecarboxylate	Generator
3a,4a,5b-Trihydroxy-1-cyclohexene-1-carboxylate	Generator
3a,4a,5b-Trihydroxy-1-cyclohexene-1-carboxylic acid	Generator
3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylate	Generator
3Α,4α,5β-trihydroxy-1-cyclohexene-1-carboxylate	Generator
3Α,4α,5β-trihydroxy-1-cyclohexene-1-carboxylic acid	Generator
[3R-(3a,4a,5b)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylate	Generator
[3R-(3a,4a,5b)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid	Generator
[3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylate	Generator
[3R-(3Α,4α,5β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate	Generator
[3R-(3Α,4α,5β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid	Generator
L-Shikimate	Generator
Acid, shikimic	MeSH
(-)-Shikimate	HMDB
(-)-Shikimic acid	HMDB
Skikimate	HMDB
Skikimic acid	HMDB
(3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid	PhytoBank
(-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid	PhytoBank
Shikimic acid	PhytoBank

Chemical Formula

C₇H₁₀O₅

Average Molecular Weight

174.1513

Monoisotopic Molecular Weight

174.05282343

IUPAC Name

(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid

Traditional Name

(-)-shikimate

CAS Registry Number

138-59-0

SMILES

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

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

InChI Key

JXOHGGNKMLTUBP-HSUXUTPPSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as shikimic acids and derivatves. These are cyclitols containing a cyclohexanecarboxylic acid substituted with three hydroxyl groups at positions 3, 4, and 5.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Shikimic acids and derivatves

Alternative Parents

Substituents

Shikimic acid or derivatives
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

alpha,beta-unsaturated monocarboxylic acid (CHEBI:16119 )
cyclohexenecarboxylic acid (CHEBI:16119 )
hydroxy monocarboxylic acid (CHEBI:16119 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.7	ALOGPS
logP	-1.6	ChemAxon
logS	0.07	ALOGPS
pKa (Strongest Acidic)	4.1	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	38.96 m³·mol⁻¹	ChemAxon
Polarizability	15.75 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-0udj-0970000000-42465cd3f3e138b0bc12	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0udi-0790000000-1100443abb8605953f58	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-00di-9450000000-e6ca954dc1a9c1cc4285	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0udi-0491000000-49993b9b18e12b9461fc	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-0391000000-ddb2c574233062a911fa	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udj-0970000000-42465cd3f3e138b0bc12	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0790000000-1100443abb8605953f58	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9450000000-e6ca954dc1a9c1cc4285	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-0491000000-49993b9b18e12b9461fc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4900000000-817f1ed3feb4c763285f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0092-7119400000-67b0989b5019a72e1016	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0900000000-e6ca4ce5acb44dc23a74	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004r-9700000000-18afe769b0ef5ba3fbdb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9100000000-7d0218e803b828de53b2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-01b9-1900000000-fd80f5e7f51d927e8e15	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-9300000000-cf8a3148fd132540bf97	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9000000000-ed28bc20ae43473043c9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9000000000-65249fc24f2de4acf2c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-26dfc876ae35c2cdb845	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-006x-9600000000-3a5ab91754d9d837d8b4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-01b9-1900000000-6cba5b9b7c4891522045	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9300000000-12d15a049b141a37f34e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-ed28bc20ae43473043c9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-9864f7359ffed65d6ef0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-26dfc876ae35c2cdb845	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-006x-9600000000-3a5ab91754d9d837d8b4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00ks-4900000000-3c7c11a5c27e1018d328	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-e7907b79b8fbcac9aa36	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-7900000000-d77a830354efe8731a42	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-9d3f05c288a1c32bd52b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-2a02691107b26b47bfe7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-d0e0c1c61a8cc849c4bc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03kc-9500000000-1be2290fb516bd446a61	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-563539f2a2fed5cb4f8a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00b9-2900000000-229ad430d980f20f597b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00b9-9300000000-db4467dbe0ef7549a6e7	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Feces
Plasma

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Feces	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details