MiMeDB: Showing metabocard for 4-Amino-4-deoxychorismate (MMDBc0030013)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:50:40 UTC

Update Date

2022-08-31 17:38:40 UTC

MiMeDB ID

MMDBc0030013

Metabolite Identification

Common Name

4-Amino-4-deoxychorismate

Description

4-amino-4-deoxychorismate (or ADC) can be classified as a member of the Dicarboxylic Acids and Derivatives. These are organic compounds containing exactly two carboxylic acid groups. ADC is involved in antibiotic biosynthesis. In some antibiotic producers, p-aminobenzoic acid (PABA) or its immediate precursor, 4-amino-4-deoxychorismate (ADC), is involved in primary metabolism and antibiotic biosynthesis. (PMID 19389784 ) In Escherichia coli, the production of PABA is catalyzed by the PabC protein, a beta-lyase that converts 4-amino-4-deoxychorismate (ADC)--the reaction product of the PabA and PabB enzymes--to PABA and pyruvate. (PMID 15500462 ) 4-Amino-4-deoxychorismate lyase (ADCL) is a member of the fold-type IV of PLP dependent enzymes that converts 4-amino-4-deoxychorismate (ADC) to p-aminobenzoate and pyruvate. (PMID 10876155 )

Structure

MOL SDF PDB SMILES InChI

      
  Mrv1652303082006192D          

 18 18  0  0  0  0            999 V2000
    0.3572    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3572    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0717    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    1.2375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.7861   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  1  2  0  0  0  0
  6  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  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
  7 11  1  6  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15 10  1  0  0  0  0
 16  5  1  0  0  0  0
  8 16  1  1  0  0  0
  7 17  1  1  0  0  0
  8 18  1  6  0  0  0
M  CHG  1  13  -1
M  END
> <DATABASE_ID>
MMDBc0030013

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(N)C=CC(=C[C@@]1([H])OC(=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)/p-1/t7-,8-/m1/s1

> <INCHI_KEY>
OIUJHGOLFKDBSU-HTQZYQBOSA-M

> <FORMULA>
C10H10NO5

> <MOLECULAR_WEIGHT>
224.193

> <EXACT_MASS>
224.056446006

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.25339934557646

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(1R,6R)-6-amino-3-carboxycyclohexa-2,4-dien-1-yl]oxy}prop-2-enoate

> <ALOGPS_LOGP>
-1.88

> <JCHEM_LOGP>
-2.7948315736268627

> <ALOGPS_LOGS>
-1.14

> <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>
112.68

> <JCHEM_REFRACTIVITY>
66.80470000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.77e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(1R,6R)-6-amino-3-carboxycyclohexa-2,4-dien-1-yl]oxy}prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-20         0                                  
HETATM    1  C   UNK     0       0.667   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.334  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.334   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.667  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.667   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.001   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.001   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.001  -3.850   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.001   2.310   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      -2.001   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -3.334   2.310   0.000  0.00  0.00           O-1
HETATM   14  O   UNK     0       3.334  -4.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.667  -4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.667   0.770   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       3.334   1.540   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.667   1.540   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2    3    6                                                       
CONECT    3    2    7                                                       
CONECT    4    6    8                                                       
CONECT    5    1    9   16                                                  
CONECT    6    2    4   10                                                  
CONECT    7    3    8   11   17                                             
CONECT    8    4    7   16   18                                             
CONECT    9    5   12   13                                                  
CONECT   10    6   14   15                                                  
CONECT   11    7                                                            
CONECT   12    9                                                            
CONECT   13    9                                                            
CONECT   14   10                                                            
CONECT   15   10                                                            
CONECT   16    5    8                                                       
CONECT   17    7                                                            
CONECT   18    8                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

Synonyms

Value	Source
4-Amino-4-deoxychorismic acid	Generator

Chemical Formula

C₁₀H₁₀NO₅

Average Molecular Weight

224.193

Monoisotopic Molecular Weight

224.056446006

IUPAC Name

2-{[(1R,6R)-6-amino-3-carboxycyclohexa-2,4-dien-1-yl]oxy}prop-2-enoate

Traditional Name

2-{[(1R,6R)-6-amino-3-carboxycyclohexa-2,4-dien-1-yl]oxy}prop-2-enoate

CAS Registry Number

133442-18-9

SMILES

[H][C@@]1(N)C=CC(=C[C@@]1([H])OC(=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)/p-1/t7-,8-/m1/s1

InChI Key

OIUJHGOLFKDBSU-HTQZYQBOSA-M

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

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

dicarboxylic acid monoanion (CHEBI:58406 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	17.7 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-2.8	ChemAxon
logS	-1.1	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	2	ChemAxon
Polar Surface Area	112.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.8 m³·mol⁻¹	ChemAxon
Polarizability	20.25 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-bee4ab08f2487ef7bfac	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-016r-1490000000-ce07381212ca3d6e1621	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bvl-9300000000-bfb080c1e0d50f131b0b	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-1f7090b031c701fc0736	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1190000000-d53fcaa0fd33d000a4ae	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-8900000000-90784b49b917ebf5baf8	2016-09-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Proteobacteria	173	Human Feces; Human ; Pig	Unknown; Metabolic reconstruction;
	Firmicutes	223	Pig ; Human Feces; Human	Metabolic reconstruction;
	Verrucomicrobia	1	Human	Metabolic reconstruction
	Bacteroidetes	108	Human Feces; Human	Metabolic reconstruction
	Actinobacteria	98	Human Feces; Human	Metabolic reconstruction;
	Fusobacteria	15	Human Feces; Human	Metabolic reconstruction
	Euryarchaeota	5	Human Feces; Cattle ; Human	Metabolic reconstruction
	Planctomycetes	1	Human Feces	Metabolic reconstruction
	Thaumarchaeota	1	Human Feces	Metabolic reconstruction
	Synergistetes	1	Human Feces	Metabolic reconstruction
	Crenarchaeota	1	Human Feces	Metabolic reconstruction
Fungi	Ascomycota	3	Human Feces	; Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB		details

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45266632

PDB ID

Not Available

ChEBI ID

58406

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 4-Amino-4-deoxychorismate (MMDBc0030013)

MOL for #<Metabolite:0x0000564abfb7ba00>

3D MOL for #<Metabolite:0x0000564abfb7ba00>

3D SDF for #<Metabolite:0x0000564abfb7ba00>

3D-SDF for #<Metabolite:0x0000564abfb7ba00>

PDB for #<Metabolite:0x0000564abfb7ba00>

3D PDB for #<Metabolite:0x0000564abfb7ba00>

SMILES for #<Metabolite:0x0000564abfb7ba00>

INCHI for #<Metabolite:0x0000564abfb7ba00>

Structure for #<Metabolite:0x0000564abfb7ba00>

3D Structure for #<Metabolite:0x0000564abfb7ba00>