MiMeDB: Showing metabocard for 3-Phosphoshikimic acid (MMDBc0032963)

Plant

Animal

Pharmaceutical

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:29:06 UTC

Update Date

2024-10-13 07:19:28 UTC

Metabolite ID

MMDBc0032963

Metabolite Identification

Common Name

3-Phosphoshikimic acid

Description

3-Phosphoshikimic acid is an intermediate in the chorismate biosynthesis pathway also called shikimate pathway. This pathway occurs in plants and microorganisms. Chorismate is an important intermediate that leads to the biosynthesis of several essential metabolites, including the aromatic amino acids L-phenylalanine, L-tyrosine and L-tryptophan, vitamins E and K, ubiquinone and certain siderophore. [Biocyc ARO-PWY]

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241221422D          

 16 16  0  0  1  0            999 V2000
    0.4125    3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032963

> <DATABASE_NAME>
MIME

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

> <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

> <FORMULA>
C7H11O8P

> <MOLECULAR_WEIGHT>
254.1312

> <EXACT_MASS>
254.01915384

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
20.455959192130013

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.07

> <JCHEM_LOGP>
-1.7636401083333335

> <ALOGPS_LOGS>
-1.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.1018283495734575

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3157644234401227

> <JCHEM_PKA_STRONGEST_BASIC>
-3.225778459939349

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
49.833200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.10e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-phosphoshikimic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       0.770   5.954   0.000  0.00  0.00           O+0
HETATM    2  P   UNK     0       0.000   4.620   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.770   3.286   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0301781
HETATM    1  O1  UNL     1      -4.062   0.970   0.002  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.900   1.412   0.037  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.701   2.766   0.213  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.758   0.500  -0.108  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.517   0.911  -0.078  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.675   0.058  -0.216  1.00  0.00           C  
HETATM    7  O3  UNL     1       1.543   0.393   0.837  1.00  0.00           O  
HETATM    8  P1  UNL     1       2.984   1.043   0.303  1.00  0.00           P  
HETATM    9  O4  UNL     1       4.119   0.438   1.129  1.00  0.00           O  
HETATM   10  O5  UNL     1       2.975   2.715   0.564  1.00  0.00           O  
HETATM   11  O6  UNL     1       3.260   0.733  -1.339  1.00  0.00           O  
HETATM   12  C5  UNL     1       0.385  -1.400  -0.131  1.00  0.00           C  
HETATM   13  O7  UNL     1       1.370  -2.036   0.620  1.00  0.00           O  
HETATM   14  C6  UNL     1      -0.964  -1.680   0.534  1.00  0.00           C  
HETATM   15  O8  UNL     1      -1.195  -3.054   0.488  1.00  0.00           O  
HETATM   16  C7  UNL     1      -2.001  -0.954  -0.296  1.00  0.00           C  
HETATM   17  H1  UNL     1      -3.199   3.392  -0.408  1.00  0.00           H  
HETATM   18  H2  UNL     1      -0.345   1.981   0.060  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.142   0.302  -1.195  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.107   3.078   0.238  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.166   0.343  -1.469  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.331  -1.889  -1.143  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.468  -2.982   0.355  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.960  -1.296   1.572  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.106  -3.322  -0.470  1.00  0.00           H  
HETATM   26  H10 UNL     1      -3.035  -1.242  -0.031  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.781  -1.183  -1.366  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5    5   16
CONECT    5    6   18
CONECT    6    7   12   19
CONECT    7    8
CONECT    8    9    9   10   11
CONECT   10   20
CONECT   11   21
CONECT   12   13   14   22
CONECT   13   23
CONECT   14   15   16   24
CONECT   15   25
CONECT   16   26   27
END

Synonyms

Value	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

Molecular Formula

C₇H₁₁O₈P

Average Mass

254.1312

Monoisotopic Mass

254.01915384

IUPAC Name

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

Traditional Name

3-phosphoshikimic acid

CAS Registry Number

63959-45-5

SMILES

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

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

Chemical Taxonomy

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9420000000-24bff48841e0db52f23d	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-2290000000-396028b52ce4cedbe2bb	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05n0-0490000000-529105b5a87b738ed617	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-6900000000-1e7071aa820eeb1c46ba	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3190000000-efb4ce7028884fa42743	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9320000000-de7c749cb1ef8f00a7c2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-5ea8917f66ef1d382869	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004j-9010000000-3906ab4aee0305db4d4b	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9010000000-6a75ffa6c3d07241a675	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-9bbc041a48805948beff	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0490000000-6f7f3bbe06a56485d8f7	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-1950000000-f9d939de49ab972591e9	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aps-9000000000-a548a26753cac7a078d4	2021-10-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	538.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	410.4
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	46.1
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	243.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	301.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	299.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	525.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	811.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	874.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	169.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	426.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	178.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	34.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	531.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	774.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	71.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	285.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	704.2
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	597.0

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	3-Phosphoshikimic acid_TMS_1	C[Si](C)(C)O[C@@H]1CC(C(=O)O)=C[C@@H](OP(=O)(O)O)[C@H]1O	standard non polar	2025-10-24	1484.61
Gas Chromatography	3-Phosphoshikimic acid_TMS_2	C[Si](C)(C)O[C@H]1[C@H](O)CC(C(=O)O)=C[C@H]1OP(=O)(O)O	standard non polar	2025-10-24	1471.22
Gas Chromatography	3-Phosphoshikimic acid_TMS_3	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O)O)[C@@H](O)[C@H](O)C1	standard non polar	2025-10-24	1846.32
Gas Chromatography	3-Phosphoshikimic acid_TMS_4	C[Si](C)(C)OP(=O)(O)O[C@@H]1C=C(C(=O)O)C[C@@H](O)[C@@H]1O	standard non polar	2025-10-24	2049.65
Gas Chromatography	3-Phosphoshikimic acid_TMS_5	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O)O)[C@@H](O)[C@H](O[Si](C)(C)C)C1	standard non polar	2025-10-24	2299.93
Gas Chromatography	3-Phosphoshikimic acid_TMS_6	C[Si](C)(C)O[C@@H]1[C@H](OP(=O)(O)O)C=C(C(=O)O)C[C@H]1O[Si](C)(C)C	standard non polar	2025-10-24	1949.65
Gas Chromatography	3-Phosphoshikimic acid_TMS_7	C[Si](C)(C)O[C@@H]1CC(C(=O)O)=C[C@@H](OP(=O)(O)O[Si](C)(C)C)[C@H]1O	standard non polar	2025-10-24	1746.19
Gas Chromatography	3-Phosphoshikimic acid_TMS_8	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H](O)C1	standard non polar	2025-10-24	2136.39
Gas Chromatography	3-Phosphoshikimic acid_TMS_9	C[Si](C)(C)O[C@H]1[C@H](O)CC(C(=O)O)=C[C@H]1OP(=O)(O)O[Si](C)(C)C	standard non polar	2025-10-24	1920.14
Gas Chromatography	3-Phosphoshikimic acid_TMS_10	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H](O)C1	standard non polar	2025-10-24	2167.24
Gas Chromatography	3-Phosphoshikimic acid_TMS_11	C[Si](C)(C)OP(=O)(O[C@@H]1C=C(C(=O)O)C[C@@H](O)[C@@H]1O)O[Si](C)(C)C	standard non polar	2025-10-24	1673.42
Gas Chromatography	3-Phosphoshikimic acid_TMS_12	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	standard non polar	2025-10-24	2452.14
Gas Chromatography	3-Phosphoshikimic acid_TMS_13	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)C1	standard non polar	2025-10-24	1828.52
Gas Chromatography	3-Phosphoshikimic acid_TMS_14	C[Si](C)(C)O[C@@H]1[C@H](OP(=O)(O)O[Si](C)(C)C)C=C(C(=O)O)C[C@H]1O[Si](C)(C)C	standard non polar	2025-10-24	2043.58
Gas Chromatography	3-Phosphoshikimic acid_TMS_15	C[Si](C)(C)O[C@@H]1CC(C(=O)O)=C[C@@H](OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@H]1O	standard non polar	2025-10-24	1207.94
Gas Chromatography	3-Phosphoshikimic acid_TMS_16	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)C1	standard non polar	2025-10-24	2350.53
Gas Chromatography	3-Phosphoshikimic acid_TMS_17	C[Si](C)(C)O[C@H]1[C@H](O)CC(C(=O)O)=C[C@H]1OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1043.17
Gas Chromatography	3-Phosphoshikimic acid_TMS_18	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H](O)C1	standard non polar	2025-10-24	1601.79
Gas Chromatography	3-Phosphoshikimic acid_TMS_19	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	standard non polar	2025-10-24	2026.97
Gas Chromatography	3-Phosphoshikimic acid_TMS_20	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)C1	standard non polar	2025-10-24	597.385
Gas Chromatography	3-Phosphoshikimic acid_TMS_21	C[Si](C)(C)O[C@@H]1[C@H](OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C=C(C(=O)O)C[C@H]1O[Si](C)(C)C	standard non polar	2025-10-24	1533.21
Gas Chromatography	3-Phosphoshikimic acid_TMS_22	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)C1	standard non polar	2025-10-24	2660.96
Gas Chromatography	3-Phosphoshikimic acid_TMS_23	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	standard non polar	2025-10-24	2177.44
Gas Chromatography	3-Phosphoshikimic acid_TMS_1	C[Si](C)(C)O[C@@H]1CC(C(=O)O)=C[C@@H](OP(=O)(O)O)[C@H]1O	standard polar	2025-10-24	2287.9
Gas Chromatography	3-Phosphoshikimic acid_TMS_2	C[Si](C)(C)O[C@H]1[C@H](O)CC(C(=O)O)=C[C@H]1OP(=O)(O)O	standard polar	2025-10-24	2163.08
Gas Chromatography	3-Phosphoshikimic acid_TMS_3	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O)O)[C@@H](O)[C@H](O)C1	standard polar	2025-10-24	2487.01
Gas Chromatography	3-Phosphoshikimic acid_TMS_4	C[Si](C)(C)OP(=O)(O)O[C@@H]1C=C(C(=O)O)C[C@@H](O)[C@@H]1O	standard polar	2025-10-24	2490.33
Gas Chromatography	3-Phosphoshikimic acid_TMS_5	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O)O)[C@@H](O)[C@H](O[Si](C)(C)C)C1	standard polar	2025-10-24	1833.45
Gas Chromatography	3-Phosphoshikimic acid_TMS_6	C[Si](C)(C)O[C@@H]1[C@H](OP(=O)(O)O)C=C(C(=O)O)C[C@H]1O[Si](C)(C)C	standard polar	2025-10-24	2461.4
Gas Chromatography	3-Phosphoshikimic acid_TMS_7	C[Si](C)(C)O[C@@H]1CC(C(=O)O)=C[C@@H](OP(=O)(O)O[Si](C)(C)C)[C@H]1O	standard polar	2025-10-24	2313.7
Gas Chromatography	3-Phosphoshikimic acid_TMS_8	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H](O)C1	standard polar	2025-10-24	2314.09
Gas Chromatography	3-Phosphoshikimic acid_TMS_9	C[Si](C)(C)O[C@H]1[C@H](O)CC(C(=O)O)=C[C@H]1OP(=O)(O)O[Si](C)(C)C	standard polar	2025-10-24	2576.02
Gas Chromatography	3-Phosphoshikimic acid_TMS_10	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H](O)C1	standard polar	2025-10-24	2757.02
Gas Chromatography	3-Phosphoshikimic acid_TMS_11	C[Si](C)(C)OP(=O)(O[C@@H]1C=C(C(=O)O)C[C@@H](O)[C@@H]1O)O[Si](C)(C)C	standard polar	2025-10-24	1615.6
Gas Chromatography	3-Phosphoshikimic acid_TMS_12	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	standard polar	2025-10-24	3076.26
Gas Chromatography	3-Phosphoshikimic acid_TMS_13	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)C1	standard polar	2025-10-24	2414.09
Gas Chromatography	3-Phosphoshikimic acid_TMS_14	C[Si](C)(C)O[C@@H]1[C@H](OP(=O)(O)O[Si](C)(C)C)C=C(C(=O)O)C[C@H]1O[Si](C)(C)C	standard polar	2025-10-24	731.214
Gas Chromatography	3-Phosphoshikimic acid_TMS_15	C[Si](C)(C)O[C@@H]1CC(C(=O)O)=C[C@@H](OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@H]1O	standard polar	2025-10-24	1895.23
Gas Chromatography	3-Phosphoshikimic acid_TMS_16	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)C1	standard polar	2025-10-24	2247.48
Gas Chromatography	3-Phosphoshikimic acid_TMS_17	C[Si](C)(C)O[C@H]1[C@H](O)CC(C(=O)O)=C[C@H]1OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	1392.7
Gas Chromatography	3-Phosphoshikimic acid_TMS_18	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H](O)C1	standard polar	2025-10-24	1344.64
Gas Chromatography	3-Phosphoshikimic acid_TMS_19	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	standard polar	2025-10-24	1310.58
Gas Chromatography	3-Phosphoshikimic acid_TMS_20	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)C1	standard polar	2025-10-24	1894.54
Gas Chromatography	3-Phosphoshikimic acid_TMS_21	C[Si](C)(C)O[C@@H]1[C@H](OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C=C(C(=O)O)C[C@H]1O[Si](C)(C)C	standard polar	2025-10-24	1961.09
Gas Chromatography	3-Phosphoshikimic acid_TMS_22	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)C1	standard polar	2025-10-24	1998.06
Gas Chromatography	3-Phosphoshikimic acid_TMS_23	C[Si](C)(C)OC(=O)C1=C[C@@H](OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	standard polar	2025-10-24	1730.6

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0301781

DrugBank ID

DB04328

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001398

KNApSAcK ID

Not Available

Chemspider ID

108789

KEGG Compound ID

C03175

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

17052

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Larimer FW, Morse CC, Beck AK, Cole KW, Gaertner FH: Isolation of the ARO1 cluster gene of Saccharomyces cerevisiae. Mol Cell Biol. 1983 Sep;3(9):1609-14. doi: 10.1128/mcb.3.9.1609-1614.1983. [PubMed:6355828 ]
Herrgard MJ, Swainston N, Dobson P, Dunn WB, Arga KY, Arvas M, Bluthgen N, Borger S, Costenoble R, Heinemann M, Hucka M, Le Novere N, Li P, Liebermeister W, Mo ML, Oliveira AP, Petranovic D, Pettifer S, Simeonidis E, Smallbone K, Spasic I, Weichart D, Brent R, Broomhead DS, Westerhoff HV, Kirdar B, Penttila M, Klipp E, Palsson BO, Sauer U, Oliver SG, Mendes P, Nielsen J, Kell DB: A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology. Nat Biotechnol. 2008 Oct;26(10):1155-60. doi: 10.1038/nbt1492. [PubMed:18846089 ]
Authors unspecified: Ongoing and future developments at the Universal Protein Resource. Nucleic Acids Res. 2011 Jan;39(Database issue):D214-9. doi: 10.1093/nar/gkq1020. Epub 2010 Nov 4. [PubMed:21051339 ]
Scheer M, Grote A, Chang A, Schomburg I, Munaretto C, Rother M, Sohngen C, Stelzer M, Thiele J, Schomburg D: BRENDA, the enzyme information system in 2011. Nucleic Acids Res. 2011 Jan;39(Database issue):D670-6. doi: 10.1093/nar/gkq1089. Epub 2010 Nov 9. [PubMed:21062828 ]

Showing metabocard for 3-Phosphoshikimic acid (MMDBc0032963)

MOL for #<Metabolite:0x00005624ca569e48>

3D MOL for #<Metabolite:0x00005624ca569e48>

3D SDF for #<Metabolite:0x00005624ca569e48>

3D-SDF for #<Metabolite:0x00005624ca569e48>

PDB for #<Metabolite:0x00005624ca569e48>

3D PDB for #<Metabolite:0x00005624ca569e48>

SMILES for #<Metabolite:0x00005624ca569e48>

INCHI for #<Metabolite:0x00005624ca569e48>

Structure for #<Metabolite:0x00005624ca569e48>

3D Structure for #<Metabolite:0x00005624ca569e48>