NP-MRD: Showing NP-Card for 4-Amino-4-deoxychorismate (NP0050493)

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Record Information

Version

2.0

Created at

2022-04-27 21:45:52 UTC

Updated at

2022-04-27 21:45:52 UTC

NP-MRD ID

NP0050493

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Amino-4-deoxychorismate

Description

4-Amino-4-deoxychorismate, also known as ADC, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. 4-Amino-4-deoxychorismate is a very strong basic compound (based on its pKa). 4-Amino-4-deoxychorismate exists in both E. 4-Amino-4-deoxychorismate is found in Apis cerana, Escherichia coli, Klebsiella pneumonia, Streptomyces aminophilus and Streptomyces coelicolor. Coli (prokaryote) and yeast (eukaryote).

Structure

MOL SDF PDB SMILES InChI

 
  Mrv0541 02241222142D          
 
 16 16  0  0  1  0            999 V2000
   13.7354  -14.2863    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7354  -13.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0120  -14.7089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4485  -14.6986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0120  -13.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2996  -14.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0086  -15.5301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1574  -14.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2996  -13.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0086  -12.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8740  -14.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1574  -13.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7251  -11.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2921  -11.8160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8740  -15.5197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5830  -14.2794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  6  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
  8 12  2  0  0  0  0
 10 13  1  0  0  0  0
 10 14  2  0  0  0  0
 11 15  1  0  0  0  0
 11 16  2  0  0  0  0
  6  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0050493

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO5/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8H,1,11H2,(H,12,13)(H,14,15)/t7-,8-/m1/s1

> <INCHI_KEY>
OIUJHGOLFKDBSU-HTQZYQBOSA-N

> <FORMULA>
C10H11NO5

> <MOLECULAR_WEIGHT>
225.198

> <EXACT_MASS>
225.063722467

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
20.91348894694996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4R)-4-amino-3-[(1-carboxyeth-1-en-1-yl)oxy]cyclohexa-1,5-diene-1-carboxylic acid

> <ALOGPS_LOGP>
-2.33

> <JCHEM_LOGP>
-2.7948315736268627

> <ALOGPS_LOGS>
-1.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.0640300536636245

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.236193593310046

> <JCHEM_PKA_STRONGEST_BASIC>
9.118419006317595

> <JCHEM_POLAR_SURFACE_AREA>
109.85000000000002

> <JCHEM_REFRACTIVITY>
55.967600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-amino-4-deoxychorismic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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      25.639 -26.668   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.639 -25.122   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.289 -27.457   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      26.971 -27.437   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      24.289 -24.353   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.959 -26.668   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      24.283 -28.990   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      28.294 -26.668   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.959 -25.122   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.283 -22.813   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.631 -27.431   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.294 -25.129   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      25.620 -22.050   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      22.945 -22.057   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      29.631 -28.970   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      30.955 -26.655   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6    7                                                  
CONECT    4    1    8                                                       
CONECT    5    2    9   10                                                  
CONECT    6    3    9                                                       
CONECT    7    3                                                            
CONECT    8    4   11   12                                                  
CONECT    9    5    6                                                       
CONECT   10    5   13   14                                                  
CONECT   11    8   15   16                                                  
CONECT   12    8                                                            
CONECT   13   10                                                            
CONECT   14   10                                                            
CONECT   15   11                                                            
CONECT   16   11                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
ADC	ChEBI
4-Amino-4-deoxychorismic acid	Generator
4-Amino-4-deoxychorismate	Generator

Chemical Formula

C₁₀H₁₁NO₅

Average Mass

225.1980 Da

Monoisotopic Mass

225.06372 Da

IUPAC Name

(3R,4R)-4-amino-3-[(1-carboxyeth-1-en-1-yl)oxy]cyclohexa-1,5-diene-1-carboxylic acid

Traditional Name

4-amino-4-deoxychorismic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H11NO5/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8H,1,11H2,(H,12,13)(H,14,15)/t7-,8-/m1/s1

InChI Key

OIUJHGOLFKDBSU-HTQZYQBOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Escherichia coli	Bacteria	KNApSAcK
Klebsiella pneumoniae	Bacteria	KNApSAcK
Streptomyces aminophilus	Bacteria	KNApSAcK
Streptomyces coelicolor	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Amino acid or derivatives
Amino acid
Carboxylic acid
Amine
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:18198 )

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	-2.3	ALOGPS
logP	-2.8	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.24	ChemAxon
pKa (Strongest Basic)	9.12	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.85 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	55.97 m³·mol⁻¹	ChemAxon
Polarizability	20.91 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB030486

KNApSAcK ID

C00000730

Chemspider ID

Not Available

KEGG Compound ID

C11355

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443142

PDB ID

Not Available

ChEBI ID

18198

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-Amino-4-deoxychorismate (NP0050493)

MOL for NP0050493 (4-Amino-4-deoxychorismate)

3D MOL for NP0050493 (4-Amino-4-deoxychorismate)

3D SDF for NP0050493 (4-Amino-4-deoxychorismate)

3D-SDF for NP0050493 (4-Amino-4-deoxychorismate)

PDB for NP0050493 (4-Amino-4-deoxychorismate)

3D PDB for NP0050493 (4-Amino-4-deoxychorismate)

SMILES for NP0050493 (4-Amino-4-deoxychorismate)

INCHI for NP0050493 (4-Amino-4-deoxychorismate)

Structure for NP0050493 (4-Amino-4-deoxychorismate)

3D Structure for NP0050493 (4-Amino-4-deoxychorismate)