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

Plant

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:29:06 UTC

Update Date

2022-08-31 21:49:42 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

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

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	Unknown

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

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:0x0000560be216c8f0>

3D MOL for #<Metabolite:0x0000560be216c8f0>

3D SDF for #<Metabolite:0x0000560be216c8f0>

3D-SDF for #<Metabolite:0x0000560be216c8f0>

PDB for #<Metabolite:0x0000560be216c8f0>

3D PDB for #<Metabolite:0x0000560be216c8f0>

SMILES for #<Metabolite:0x0000560be216c8f0>

INCHI for #<Metabolite:0x0000560be216c8f0>

Structure for #<Metabolite:0x0000560be216c8f0>

3D Structure for #<Metabolite:0x0000560be216c8f0>