NP-MRD: Showing NP-Card for Isochorismic acid (NP0050494)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 21:45:55 UTC

Updated at

2022-04-27 21:45:55 UTC

NP-MRD ID

NP0050494

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isochorismic acid

Description

Isochorismic acid is found in Bacillus subtilis , Catharanthus roseus , Escherichia coli, Galium mollugo, Glycine max , Klebsiella pneumonia and Streptomyces aminophilus.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 10211212162D          

 18 18  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   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
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  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
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  2  0  0  0  0
  5  1  2  0  0  0  0
  6  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
  8 11  1  1  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 10  2  0  0  0  0
 16  5  1  0  0  0  0
  7 16  1  6  0  0  0
  7 17  1  1  0  0  0
  8 18  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050494

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O6/c1-5(9(12)13)16-7-4-2-3-6(8(7)11)10(14)15/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/t7-,8-/m0/s1

> <INCHI_KEY>
NTGWPRCCOQCMGE-YUMQZZPRSA-N

> <FORMULA>
C10H10O6

> <MOLECULAR_WEIGHT>
226.1828

> <EXACT_MASS>
226.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
20.366957284349

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6S)-5-[(1-carboxyeth-1-en-1-yl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid

> <ALOGPS_LOGP>
0.69

> <JCHEM_LOGP>
-0.12549059733333331

> <ALOGPS_LOGS>
-1.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.193366544817536

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3894329236949416

> <JCHEM_PKA_STRONGEST_BASIC>
-3.571763680746476

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
54.31010000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isochorismic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-OCT-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2    3    4                                                       
CONECT    3    2    6                                                       
CONECT    4    2    7                                                       
CONECT    5    1    9   16                                                  
CONECT    6    3    8   10                                                  
CONECT    7    4    8   16   17                                             
CONECT    8    6    7   11   18                                             
CONECT    9    5   12   13                                                  
CONECT   10    6   14   15                                                  
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13    9                                                            
CONECT   14   10                                                            
CONECT   15   10                                                            
CONECT   16    5    7                                                       
CONECT   17    7                                                            
CONECT   18    8                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
Isochorismic acid	Kegg
5-((1-Carboxyethenyl)oxy)-6-hydroxy-1,3-cyclohexadiene-1-carboxylic acid	MeSH
Iso-chorismic acid	MeSH

Chemical Formula

C₁₀H₁₀O₆

Average Mass

226.1828 Da

Monoisotopic Mass

226.04774 Da

IUPAC Name

(5S,6S)-5-[(1-carboxyeth-1-en-1-yl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid

Traditional Name

isochorismic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H10O6/c1-5(9(12)13)16-7-4-2-3-6(8(7)11)10(14)15/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/t7-,8-/m0/s1

InChI Key

NTGWPRCCOQCMGE-YUMQZZPRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bacillus subtilis	Bacteria	KNApSAcK
Catharanthus roseus	Plant	KNApSAcK
Escherichia coli	Bacteria	KNApSAcK
Galium mollugo	Plant	KNApSAcK
Glycine max	Plant	KNApSAcK
Klebsiella pneumoniae	Bacteria	KNApSAcK
Streptomyces aminophilus	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Dicarboxylic acid or derivatives
Secondary alcohol
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

5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid (CHEBI:17582 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.69	ALOGPS
logP	-0.13	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.39	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.31 m³·mol⁻¹	ChemAxon
Polarizability	20.37 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB030944

KNApSAcK ID

C00007614

Chemspider ID

Not Available

KEGG Compound ID

C00885

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

189062

PDB ID

Not Available

ChEBI ID

17582

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isochorismic acid (NP0050494)

MOL for NP0050494 (Isochorismic acid)

3D MOL for NP0050494 (Isochorismic acid)

3D SDF for NP0050494 (Isochorismic acid)

3D-SDF for NP0050494 (Isochorismic acid)

PDB for NP0050494 (Isochorismic acid)

3D PDB for NP0050494 (Isochorismic acid)

SMILES for NP0050494 (Isochorismic acid)

INCHI for NP0050494 (Isochorismic acid)

Structure for NP0050494 (Isochorismic acid)

3D Structure for NP0050494 (Isochorismic acid)