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

Description

Belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose phosphates

Alternative Parents

Substituents

Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Benzoic acid or derivatives
Benzoic acid
Benzoyl
Phenylalkylamine
Aniline or substituted anilines
Secondary aliphatic/aromatic amine
Monocyclic benzene moiety
Organic phosphoric acid derivative
Benzenoid
Alkyl phosphate
Phosphoric acid ester
Vinylogous amide
Tetrahydrofuran
Secondary alcohol
Amino acid or derivatives
Amino acid
1,2-diol
Secondary amine
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Alcohol
Amine
Hydrocarbon derivative
Organic nitrogen compound
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a small molecule (N-5-PHOSPHORIBOSYL-ANTHRANILATE )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	21.5 g/L	ALOGPS
logP	0.09	ALOGPS
logP	-0.15	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	1.23	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	174.27 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.67 m³·mol⁻¹	ChemAxon
Polarizability	29.01 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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	splash10-0002-0009000000-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

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

Metabolic Reactions

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
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

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

25245690

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 ]

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

MOL for #<Metabolite:0x00007fdb503e6560>

3D MOL for #<Metabolite:0x00007fdb503e6560>

3D SDF for #<Metabolite:0x00007fdb503e6560>

3D-SDF for #<Metabolite:0x00007fdb503e6560>

PDB for #<Metabolite:0x00007fdb503e6560>

3D PDB for #<Metabolite:0x00007fdb503e6560>

SMILES for #<Metabolite:0x00007fdb503e6560>

INCHI for #<Metabolite:0x00007fdb503e6560>

Structure for #<Metabolite:0x00007fdb503e6560>

3D Structure for #<Metabolite:0x00007fdb503e6560>