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Showing NP-Card for Shikimic acid (NP0000998)

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Record Information
Version1.0
Created at2006-05-22 15:12:30 UTC
Updated at2022-04-04 17:56:02 UTC
NP-MRD IDNP0000998
Secondary Accession NumbersNone
Natural Product Identification
Common NameShikimic acid
DescriptionShikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical intermediate in plants and microorganisms. Its name comes from the Japanese flower shikimi (the Japanese star anise, 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.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000998 (Shikimic acid)


  Mrv1652309272007412D          

 12 12  0  0  0  0            999 V2000
10000.442410000.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.1566 9999.7818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.442410001.0203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0114 9997.7176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.581310000.1947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5813 9998.5433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.011310000.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2969 9999.7818    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2969 9998.9567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.0113 9998.5444    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.7258 9998.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7258 9999.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  7  8  1  0  0  0  0
  7 12  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  1 12  1  0  0  0  0
 10  4  1  1  0  0  0
  9  6  1  6  0  0  0
  8  5  1  6  0  0  0
M  END
Download

3D MOL for NP0000998 (Shikimic acid)

HMDB0003070
     RDKit          3D
Shikimic acid
 22 22  0  0  0  0  0  0  0  0999 V2000
    3.1569    1.2230   -0.3238 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6356    0.0855   -0.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -1.0115    0.0899 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2191   -0.0496   -0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5818   -1.2037   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8851   -1.1527   -0.4868 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4843   -2.3836   -0.1987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5756   -0.0433    0.2453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1235   -0.4766    1.4542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6709    1.1405    0.4234 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3698    2.3430    0.4678 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3552    1.1182   -0.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2028   -0.9208    0.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1103   -2.1333   -0.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0156   -0.9299   -1.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494   -2.8580   -1.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4645    0.3468   -0.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7456    0.2296    1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1000    1.0307    1.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928    2.6825    1.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1491    0.9015   -1.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352    2.0615   -0.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12  4  1  0
  3 13  1  0
  5 14  1  0
  6 15  1  6
  7 16  1  0
  8 17  1  6
  9 18  1  0
 10 19  1  1
 11 20  1  0
 12 21  1  0
 12 22  1  0
M  END
Download

3D SDF for NP0000998 (Shikimic acid)


  Mrv1652309272007412D          

 12 12  0  0  0  0            999 V2000
10000.442410000.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.1566 9999.7818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.442410001.0203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0114 9997.7176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.581310000.1947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5813 9998.5433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.011310000.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2969 9999.7818    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2969 9998.9567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.0113 9998.5444    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.7258 9998.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7258 9999.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  7  8  1  0  0  0  0
  7 12  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  1 12  1  0  0  0  0
 10  4  1  1  0  0  0
  9  6  1  6  0  0  0
  8  5  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0000998

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C7H10O5

> <MOLECULAR_WEIGHT>
174.1513

> <EXACT_MASS>
174.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
15.745882820787454

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.70

> <JCHEM_LOGP>
-1.640074077

> <ALOGPS_LOGS>
0.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.02368088868393

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.10331906960995

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2247789599777335

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
38.9603

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-shikimate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000998 (Shikimic acid)

HMDB0003070
     RDKit          3D
Shikimic acid
 22 22  0  0  0  0  0  0  0  0999 V2000
    3.1569    1.2230   -0.3238 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6356    0.0855   -0.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -1.0115    0.0899 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2191   -0.0496   -0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5818   -1.2037   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8851   -1.1527   -0.4868 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4843   -2.3836   -0.1987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5756   -0.0433    0.2453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1235   -0.4766    1.4542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6709    1.1405    0.4234 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3698    2.3430    0.4678 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3552    1.1182   -0.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2028   -0.9208    0.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1103   -2.1333   -0.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0156   -0.9299   -1.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494   -2.8580   -1.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4645    0.3468   -0.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7456    0.2296    1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1000    1.0307    1.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928    2.6825    1.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1491    0.9015   -1.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352    2.0615   -0.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12  4  1  0
  3 13  1  0
  5 14  1  0
  6 15  1  6
  7 16  1  0
  8 17  1  6
  9 18  1  0
 10 19  1  1
 11 20  1  0
 12 21  1  0
 12 22  1  0
M  END
Download

PDB for NP0000998 (Shikimic acid)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8667.4928667.030   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8668.8268666.259   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8667.4928668.571   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8664.8218662.406   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8662.1528667.030   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8662.1528663.947   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8664.8218667.029   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8663.4888666.259   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.4888664.719   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.8218663.949   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8666.1558664.719   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.1558666.259   0.000  0.00  0.00           C+0
CONECT    1    2    3   12                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   10                                                            
CONECT    5    8                                                            
CONECT    6    9                                                            
CONECT    7    8   12                                                       
CONECT    8    7    9    5                                                  
CONECT    9    8   10    6                                                  
CONECT   10    9   11    4                                                  
CONECT   11   10   12                                                       
CONECT   12    7   11    1                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for NP0000998 (Shikimic acid)

COMPND    HMDB0003070
HETATM    1  O1  UNL     1       3.157   1.223  -0.324  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.636   0.086  -0.205  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.429  -1.012   0.090  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.219  -0.050  -0.379  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.582  -1.204  -0.273  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.885  -1.153  -0.487  1.00  0.00           C  
HETATM    7  O3  UNL     1      -1.484  -2.384  -0.199  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.576  -0.043   0.245  1.00  0.00           C  
HETATM    9  O4  UNL     1      -2.123  -0.477   1.454  1.00  0.00           O  
HETATM   10  C6  UNL     1      -0.671   1.140   0.423  1.00  0.00           C  
HETATM   11  O5  UNL     1      -1.370   2.343   0.468  1.00  0.00           O  
HETATM   12  C7  UNL     1       0.355   1.118  -0.687  1.00  0.00           C  
HETATM   13  H1  UNL     1       4.203  -0.921   0.738  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.110  -2.133  -0.043  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.016  -0.930  -1.589  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.649  -2.858  -1.051  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.464   0.347  -0.334  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.746   0.230   1.750  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.100   1.031   1.386  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.393   2.683   1.409  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.149   0.902  -1.659  1.00  0.00           H  
HETATM   22  H10 UNL     1       0.935   2.062  -0.736  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5    5   12
CONECT    5    6   14
CONECT    6    7    8   15
CONECT    7   16
CONECT    8    9   10   17
CONECT    9   18
CONECT   10   11   12   19
CONECT   11   20
CONECT   12   21   22
END
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SMILES for NP0000998 (Shikimic acid)

O[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(O)=O
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INCHI for NP0000998 (Shikimic acid)

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
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View in JSmol
Synonyms
ValueSource
3,4,5-Trihydroxy-1-cyclohexenecarboxylic acidChEBI
3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylic acidChEBI
[3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acidChEBI
L-Shikimic acidChEBI
ShikimateChEBI
3,4,5-Trihydroxy-1-cyclohexenecarboxylateGenerator
3a,4a,5b-Trihydroxy-1-cyclohexene-1-carboxylateGenerator
3a,4a,5b-Trihydroxy-1-cyclohexene-1-carboxylic acidGenerator
3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylateGenerator
3Α,4α,5β-trihydroxy-1-cyclohexene-1-carboxylateGenerator
3Α,4α,5β-trihydroxy-1-cyclohexene-1-carboxylic acidGenerator
[3R-(3a,4a,5b)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylateGenerator
[3R-(3a,4a,5b)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acidGenerator
[3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylateGenerator
[3R-(3Α,4α,5β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylateGenerator
[3R-(3Α,4α,5β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acidGenerator
L-ShikimateGenerator
(-)-ShikimateHMDB
(-)-Shikimic acidHMDB
SkikimateHMDB
Skikimic acidHMDB
Acid, shikimicHMDB
(3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acidHMDB
(-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acidHMDB
Shikimic acidPhytoBank
Chemical FormulaC7H10O5
Average Mass174.1513 Da
Monoisotopic Mass174.05282 Da
IUPAC Name(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
Traditional Name(-)-shikimate
CAS Registry Number138-59-0
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 KeyJXOHGGNKMLTUBP-HSUXUTPPSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-04-04View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-04-04View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Blasia pusillaLOTUS Database
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brainea insignisLOTUS Database
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Callitris columellarisLOTUS Database
Calophyllum brasilienseLOTUS Database
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumKNApSAcK Database
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Castanopsis fissaLOTUS Database
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Cistus incanusLOTUS Database
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cleistopholis patensLOTUS Database
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Corymbia citriodoraLOTUS Database
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma domesticaKNApSAcK Database
Curcuma longaPlant
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dicranopteris linearisLOTUS Database
Dicranopteris pedataKNApSAcK Database
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea bulbiferaLOTUS Database
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Excoecaria cochinchinensisLOTUS Database
Excoecaria cochinchinensis var.viridisKNApSAcK Database
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaKNApSAcK Database
Glycine maxKNApSAcK Database
GossypiumFooDB
Grifola frondosaFooDB
Hedyosmum bonplandianumLOTUS Database
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Hordeum vulgareFooDB
Hydrangea chinensisKNApSAcK Database
Hypericum beaniiKNApSAcK Database
Hypericum laricifoliumLOTUS Database
Hypericum monogynumLOTUS Database
Hyssopus officinalis L.FooDB
Illicium anisatumLOTUS Database
Illicium majusLOTUS Database
Illicium minwanenseKNApSAcK Database
Illicium religiosumKNApSAcK Database
Illicium simonsiiLOTUS Database
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Kielmeyera pumilaLOTUS Database
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Leucopogon parviflorusLOTUS Database
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Liquidambar styracifluaLOTUS Database
Litchi chinensisFooDB
Lotus corniculatusLOTUS Database
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Magnolia denudataLOTUS Database
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumKNApSAcK Database
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Pelargonium reniformeKNApSAcK Database
Pelargonium sidoidesKNApSAcK Database
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Pinus pinasterLOTUS Database
Pinus ponderosaLOTUS Database
Pinus sylvestrisLOTUS Database
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Populus lasiocarpaLOTUS Database
Populus tremulaLOTUS Database
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Pseudocyclosorus esquiroliiLOTUS Database
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Pteridium aquilinumKNApSAcK Database
Punica granatumPlant
Punica granatum L.KNApSAcK Database
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Sapium japonicumLOTUS Database
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sequoiadendron giganteumLOTUS Database
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumKNApSAcK Database
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Stenostomum acreanumLOTUS Database
Streptomyces lincolnensisLOTUS Database
Streptomyces nigraLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Taxus baccataKNApSAcK Database
Terminalia chebulaLOTUS Database
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Trypanosoma bruceiLOTUS Database
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium dunalianumLOTUS Database
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Species Where Detected
Species NameSourceReference
Alicyclobacillus acidocaldariusKNApSAcK Database
Escherichia coliKNApSAcK Database
Streptomyces collinusKNApSAcK Database
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentShikimic 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 FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point186 °CNot Available
Boiling Point400.00 to 401.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility150 mg/mL at 21 °CNot Available
LogP-2.220 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility206 g/LALOGPS
logP-1.7ALOGPS
logP-1.6ChemAxon
logS0.07ALOGPS
pKa (Strongest Acidic)4.1ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.96 m³·mol⁻¹ChemAxon
Polarizability15.75 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003070
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031172
KNApSAcK IDC00001203
Chemspider ID8412
KEGG Compound IDC00493
BioCyc IDSHIKIMATE
BiGG IDNot Available
Wikipedia LinkShikimic_acid
METLIN ID338
PubChem Compound8742
PDB IDNot Available
ChEBI ID16119
Good Scents IDrw1282291
References
General References
  1. 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. [PubMed:15911418 ]
  2. Rose GA: Studies on the chemical nature of urinary chemiluminescence. Br J Urol. 1976 Feb;48(1):61-71. [PubMed:5168 ]
  3. Escamilla-Trevino LL, Shen H, Hernandez T, Yin Y, Xu Y, Dixon RA: Early lignin pathway enzymes and routes to chlorogenic acid in switchgrass (Panicum virgatum L.). Plant Mol Biol. 2014 Mar;84(4-5):565-76. doi: 10.1007/s11103-013-0152-y. Epub 2013 Nov 5. [PubMed:24190737 ]
  4. Liu DF, Ai GM, Zheng QX, Liu C, Jiang CY, Liu LX, Zhang B, Liu YM, Yang C, Liu SJ: Metabolic flux responses to genetic modification for shikimic acid production by Bacillus subtilis strains. Microb Cell Fact. 2014 Mar 14;13(1):40. doi: 10.1186/1475-2859-13-40. [PubMed:24628944 ]
  5. Xiao M, Zhang L, Shi G: [Improvements of shikimic acid production in Escherichia coli with ideal metabolic modification in biosynthetic pathway--a review]. Wei Sheng Wu Xue Bao. 2014 Jan 4;54(1):5-13. [PubMed:24783849 ]
  6. Paley EL: Towards Understanding COVID-19: Molecular Insights, Co-infections, Associated Disorders, and Aging. J Alzheimers Dis Rep. 2021 Jul 20;5(1):571-600. doi: 10.3233/ADR-210010. eCollection 2021. [PubMed:34514341 ]