Showing metabocard for 3-Dehydroshikimic acid (MMDBc0032974)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:29:32 UTC
Update Date2022-08-31 21:54:43 UTC
Metabolite IDMMDBc0032974
Metabolite Identification
Common Name3-Dehydroshikimic acid
Description3-Dehydroshikimic 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
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f923c5a1240>

 
  Mrv0541 02241222172D          
 
 12 12  0  0  1  0            999 V2000
   10.8206   -8.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5362   -8.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1088   -8.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8169   -7.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5362   -9.2988    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1088   -9.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5249   -6.8320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1050   -6.8357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8206   -9.7169    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.2480   -9.7055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3969   -9.7055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8169  -10.5379    0.0000 O   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
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  1  0  0  0
  6 11  2  0  0  0  0
  9 12  1  6  0  0  0
  6  9  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f923c5a1240>

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3D SDF for #<Metabolite:0x00007f923c5a1240>
 
  Mrv0541 02241222172D          
 
 12 12  0  0  1  0            999 V2000
   10.8206   -8.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5362   -8.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1088   -8.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8169   -7.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5362   -9.2988    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1088   -9.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5249   -6.8320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1050   -6.8357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8206   -9.7169    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.2480   -9.7055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3969   -9.7055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8169  -10.5379    0.0000 O   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
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  1  0  0  0
  6 11  2  0  0  0  0
  9 12  1  6  0  0  0
  6  9  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032974

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)/t5-,6-/m1/s1

> <INCHI_KEY>
SLWWJZMPHJJOPH-PHDIDXHHSA-N

> <FORMULA>
C7H8O5

> <MOLECULAR_WEIGHT>
172.1354

> <EXACT_MASS>
172.037173366

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
14.914686507045417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.19

> <JCHEM_LOGP>
-1.024897902666667

> <ALOGPS_LOGS>
-0.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.41661028782423

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2142420075706486

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2670456083440538

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
38.1936

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-dehydroshikimic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f923c5a1240>
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PDB for #<Metabolite:0x00007f923c5a1240>
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      20.198 -15.045   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.534 -15.811   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.870 -15.811   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.192 -13.519   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.534 -17.358   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.870 -17.358   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      21.513 -12.753   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      18.863 -12.760   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      20.198 -18.138   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      22.863 -18.117   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      17.541 -18.117   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      20.192 -19.671   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7    8                                                  
CONECT    5    2    9   10                                                  
CONECT    6    3   11    9                                                  
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    5   12    6                                                  
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for #<Metabolite:0x00007f923c5a1240>
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SMILES for #<Metabolite:0x00007f923c5a1240>
O[C@@H]1CC(=CC(=O)[C@H]1O)C(O)=O
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INCHI for #<Metabolite:0x00007f923c5a1240>
InChI=1S/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)/t5-,6-/m1/s1
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Synonyms
ValueSource
(-)-3-Dehydroshikimic acidChEBI
5-DehydroshikimateChEBI
5-Dehydroshikimic acidChEBI
(-)-3-DehydroshikimateGenerator
3-Dehydroshikimic acidGenerator
3-DehydroshikimateChEBI
Molecular FormulaC7H8O5
Average Mass172.1354
Monoisotopic Mass172.037173366
IUPAC Name(4S,5R)-4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid
Traditional Name3-dehydroshikimic acid
CAS Registry Number27655-56-7
SMILES
O[C@@H]1CC(=CC(=O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)/t5-,6-/m1/s1
InChI KeySLWWJZMPHJJOPH-PHDIDXHHSA-N