P. aeruginosa Metabolome Database: shikimate (PAMDB110055)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB110055

Identification

Name:

shikimate

Description:

A cyclohexenecarboxylate that is the conjugate base of shikimic acid.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

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

Chemical Formula:

C₇H₉O₅

Average Molecular Weight:

173.14

Monoisotopic Molecular Weight:

174.0528234315

InChI Key:

JXOHGGNKMLTUBP-HSUXUTPPSA-M

InChI:

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)/p-1/t4-,5-,6-/m1/s1

CAS number:

138-59-0

IUPAC Name:

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

Traditional IUPAC Name:

(-)-shikimate

SMILES:

C1(=C(CC(C(O)C(O)1)O)C(=O)[O-])

Chemical Taxonomy

Taxonomy Description

This compound 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
Organic anion
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

a small molecule (SHIKIMATE)

Physical Properties

State:

Solid

Charge:

-1

Melting point:

186 °C

Experimental Properties:

Property	Value	Reference
Melting Point	186 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	150 mg/mL at 21 °C	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	206.0 mg/mL	ALOGPS
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Not Available

Reactions:

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-0udj-0970000000-42465cd3f3e138b0bc12	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-0udi-0790000000-1100443abb8605953f58	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-00di-9450000000-e6ca954dc1a9c1cc4285	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0udi-0491000000-49993b9b18e12b9461fc	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0900000000-e6ca4ce5acb44dc23a74	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004r-9700000000-18afe769b0ef5ba3fbdb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9100000000-7d0218e803b828de53b2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-01b9-1900000000-fd80f5e7f51d927e8e15	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-9300000000-cf8a3148fd132540bf97	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9000000000-ed28bc20ae43473043c9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9000000000-65249fc24f2de4acf2c7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-26dfc876ae35c2cdb845	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-006x-9600000000-3a5ab91754d9d837d8b4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Liu Y, Xie MX, Jiang M, Wang YD: Spectroscopic investigation of the interaction between human serum albumin and three organic acids. Spectrochim Acta A Mol Biomol Spectrosc. 2005 Jul;61(9):2245-51. [15911418 ]
Rose GA: Studies on the chemical nature of urinary chemiluminescence. Br J Urol. 1976 Feb;48(1):61-71. [5168 ]

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CAS	138-59-0
ChEBI	36208
ChemSpider	5414360
HMDB	HMDB03070
IAF1260	35144
KEGG	C00493
PubChem	7057976

shikimate (PAMDB110055)

Structure for shikimate (PAMDB110055)