MiMeDB: Showing metabocard for N-(5-phosphoribosyl)-anthranilate (MMDBc0032123)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 02:03:20 UTC

Update Date

2022-08-31 18:30:43 UTC

Metabolite ID

MMDBc0032123

Metabolite Identification

Common Name

N-(5-phosphoribosyl)-anthranilate

Description

N-(5-Phosphoribosyl)-anthranilate is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. N-(5-phosphoribosyl)-anthranilate is invovled in tryptophan biosynthesis. N-(5'-Phosphoribosyl)anthranilate isomerase-indole-3-glycerol-phosphate synthase from Escherichia coli is a monomeric bifunctional enzyme of Mr 49,500 that catalyzes two sequential reactions in the biosynthesis of tryptophan. (PMID 3303031 ) Phosphoribosyl anthranilate isomerase from Thermotoga maritima is an extremely stable and active homodimer. (PMID 8897600 )

Structure

MOL SDF PDB SMILES InChI

  Mrv1652303072020242D          

 23 24  0  0  0  0            999 V2000
   -0.6077   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222   -0.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    0.7633    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    1.5883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4972    0.7633    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.1472    0.7633    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.6077   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2752   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0598   -1.5290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0202   -2.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5051   -3.2360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1952   -2.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0596   -1.7840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896   -3.2360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1101   -3.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4456   -2.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2661   -2.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7510   -2.9773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4155   -3.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5950   -3.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2595   -4.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4390   -4.6572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7444   -5.2384    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 15 20  2  0  0  0  0
M  CHG  3   5  -1   6  -1  23  -1
M  END
> <DATABASE_ID>
MMDBc0032123

> <DATABASE_NAME>
MIME

> <SMILES>
OC1C(O)C(NC2=C(C=CC=C2)C([O-])=O)OC1COP([O-])([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H16NO9P/c14-9-8(5-21-23(18,19)20)22-11(10(9)15)13-7-4-2-1-3-6(7)12(16)17/h1-4,8-11,13-15H,5H2,(H,16,17)(H2,18,19,20)/p-3

> <INCHI_KEY>
PMFMJXPRNJUYMB-UHFFFAOYSA-K

> <FORMULA>
C12H13NO9P

> <MOLECULAR_WEIGHT>
346.209

> <EXACT_MASS>
346.03443874

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.014821716585217

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
-3

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-({3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}amino)benzoate

> <ALOGPS_LOGP>
0.09

> <JCHEM_LOGP>
-0.15358638733333307

> <ALOGPS_LOGS>
-1.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.479601137460893

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2253408707793954

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1194422626628873

> <JCHEM_POLAR_SURFACE_AREA>
174.27

> <JCHEM_REFRACTIVITY>
84.6742

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.15e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-({3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}amino)benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-MAR-20         0                                  
HETATM    1  C   UNK     0      -1.134  -0.885   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.468  -0.115   0.000  0.00  0.00           O+0
HETATM    3  P   UNK     0      -2.468   1.425   0.000  0.00  0.00           P+0
HETATM    4  O   UNK     0      -2.468   2.965   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -0.928   1.425   0.000  0.00  0.00           O-1
HETATM    6  O   UNK     0      -4.008   1.425   0.000  0.00  0.00           O-1
HETATM    7  C   UNK     0      -1.134  -2.425   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.380  -3.330   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.845  -2.854   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.904  -4.795   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.810  -6.041   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.364  -4.795   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.111  -3.330   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       0.541  -6.041   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.072  -5.880   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.698  -4.473   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.230  -4.312   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.135  -5.558   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.509  -6.965   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.977  -7.125   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.351  -8.532   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.819  -8.693   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.256  -9.778   0.000  0.00  0.00           O-1
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7    1    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12    7                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   15                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

Synonyms

Value	Source
N-(5-Phosphoribosyl)-anthranilic acid	Generator

Molecular Formula

C₁₂H₁₃NO₉P

Average Mass

346.209

Monoisotopic Mass

346.03443874

IUPAC Name

2-({3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}amino)benzoate

Traditional Name

2-({3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}amino)benzoate

CAS Registry Number

Not Available

SMILES

OC1C(O)C(NC2=C(C=CC=C2)C([O-])=O)OC1COP([O-])([O-])=O

InChI Identifier

InChI=1S/C12H16NO9P/c14-9-8(5-21-23(18,19)20)22-11(10(9)15)13-7-4-2-1-3-6(7)12(16)17/h1-4,8-11,13-15H,5H2,(H,16,17)(H2,18,19,20)/p-3

InChI Key

PMFMJXPRNJUYMB-UHFFFAOYSA-K

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0009000000-ba91d10082bd2fb49789	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-0009000000-be942d0b329937457b73	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fu-7900000000-8a15ea25fd2c2ed717dc	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-69e13688e52695febbe4	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1009000000-778c77e3318e670312af	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003s-9200000000-3dd565bffbe85a3ee03f	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

Showing metabocard for N-(5-phosphoribosyl)-anthranilate (MMDBc0032123)

MOL for #<Metabolite:0x00007fb7e3ebb9f8>

3D MOL for #<Metabolite:0x00007fb7e3ebb9f8>

3D SDF for #<Metabolite:0x00007fb7e3ebb9f8>

3D-SDF for #<Metabolite:0x00007fb7e3ebb9f8>

PDB for #<Metabolite:0x00007fb7e3ebb9f8>

3D PDB for #<Metabolite:0x00007fb7e3ebb9f8>

SMILES for #<Metabolite:0x00007fb7e3ebb9f8>

INCHI for #<Metabolite:0x00007fb7e3ebb9f8>

Structure for #<Metabolite:0x00007fb7e3ebb9f8>

3D Structure for #<Metabolite:0x00007fb7e3ebb9f8>