MiMeDB: Showing metabocard for N-(5-phospho-beta-D-ribosyl)anthranilic acid (MMDBc0032912)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:27:04 UTC

Update Date

2022-08-31 21:45:33 UTC

Metabolite ID

MMDBc0032912

Metabolite Identification

Common Name

N-(5-phospho-beta-D-ribosyl)anthranilic acid

Description

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241222032D          

 23 24  0  0  1  0            999 V2000
   -0.6078   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078   -1.2991    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0597   -1.7840    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8443   -1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953   -2.5687    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2897   -3.2361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1101   -3.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4457   -2.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2662   -2.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7511   -2.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4155   -3.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5951   -3.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2595   -4.5710    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  0  0  0  0  0  0  0  0  0  0  0
   -1.0203   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2752   -1.7840    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0598   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2314   -0.7221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0160   -0.4672    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8006   -0.2122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7610    0.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2709   -1.2518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032912

> <DATABASE_NAME>
MIME

> <SMILES>
O[C@H]1[C@@H](O)[C@H](NC2=CC=CC=C2C(O)=O)O[C@@H]1COP(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)/t8-,9-,10-,11-/m1/s1

> <INCHI_KEY>
PMFMJXPRNJUYMB-GWOFURMSSA-N

> <FORMULA>
C12H16NO9P

> <MOLECULAR_WEIGHT>
349.2305

> <EXACT_MASS>
349.056267627

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
30.590674563134687

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-1.00

> <JCHEM_LOGP>
-0.15358638733333307

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.479601137460891

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2253408707793971

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1194422626628873

> <JCHEM_POLAR_SURFACE_AREA>
165.77999999999997

> <JCHEM_REFRACTIVITY>
76.08050000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nprat

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -1.135  -0.885   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.135  -2.425   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.111  -3.330   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.576  -2.854   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.365  -4.795   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.541  -6.041   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.072  -5.880   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.699  -4.473   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.230  -4.312   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.135  -5.558   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.509  -6.965   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.978  -7.126   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.351  -8.533   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.819  -8.693   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.256  -9.778   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.905  -4.795   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.380  -3.330   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.845  -2.854   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.165  -1.348   0.000  0.00  0.00           O+0
HETATM   20  P   UNK     0      -5.630  -0.872   0.000  0.00  0.00           P+0
HETATM   21  O   UNK     0      -7.094  -0.396   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -5.154   0.592   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.106  -2.337   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    5   17                                                       
CONECT   17   16    2   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

Synonyms

Value	Source
N-(5'-Phosphoribosyl)anthranilate	ChEBI
N-(5-Phosphoribosyl)anthranilic acid	ChEBI
NPRAT	ChEBI
N-(5-Phospho-beta-D-ribosyl)anthranilate	Kegg
N-(5'-Phosphoribosyl)anthranilic acid	Generator
N-(5-Phosphoribosyl)anthranilate	Generator
N-(5-Phospho-b-D-ribosyl)anthranilate	Generator
N-(5-Phospho-b-D-ribosyl)anthranilic acid	Generator
N-(5-Phospho-β-D-ribosyl)anthranilate	Generator
N-(5-Phospho-β-D-ribosyl)anthranilic acid	Generator
N-(5-phospho-D-Ribosyl)anthranilic acid	Generator
N-(5-Phospho-beta-D-ribosyl)anthranilic acid	Generator

Molecular Formula

C₁₂H₁₆NO₉P

Average Mass

349.2305

Monoisotopic Mass

349.056267627

IUPAC Name

2-{[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]amino}benzoic acid

Traditional Name

nprat

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@@H](O)[C@H](NC2=CC=CC=C2C(O)=O)O[C@@H]1COP(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)/t8-,9-,10-,11-/m1/s1

InChI Key

PMFMJXPRNJUYMB-GWOFURMSSA-N

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

N-glycosyl compound (CHEBI:7091 )
ribose monophosphate (CHEBI:7091 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.5 g/L	ALOGPS
logP	-1	ALOGPS
logP	-0.15	ChemAxon
logS	-2	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	6	ChemAxon
Polar Surface Area	165.78 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	76.08 m³·mol⁻¹	ChemAxon
Polarizability	30.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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 GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_10) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1539000000-afa303df223fc236b2a8	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uej-6796000000-d8aec7db3c63af996744	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2910000000-a2f91d8bb4e2ccda7cd1	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-005a-3904000000-63d42279e1736d1159fd	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9201000000-2cfcddd5b31d906f0cb2	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-b5c17b0df8b3db541b9e	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	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

Not Available

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
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	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

C00007384

Chemspider ID

Not Available

KEGG Compound ID

C04302

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440289

PDB ID

Not Available

ChEBI ID

7091

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Miozzari G, Niederberger P, Hutter R: Tryptophan biosynthesis in Saccharomyces cerevisiae: control of the flux through the pathway. J Bacteriol. 1978 Apr;134(1):48-59. doi: 10.1128/jb.134.1.48-59.1978. [PubMed:348687 ]
Hommel U, Lustig A, Kirschner K: Purification and characterization of yeast anthranilate phosphoribosyltransferase. Eur J Biochem. 1989 Mar 1;180(1):33-40. doi: 10.1111/j.1432-1033.1989.tb14611.x. [PubMed:2651124 ]
Herrgard MJ, Swainston N, Dobson P, Dunn WB, Arga KY, Arvas M, Bluthgen N, Borger S, Costenoble R, Heinemann M, Hucka M, Le Novere N, Li P, Liebermeister W, Mo ML, Oliveira AP, Petranovic D, Pettifer S, Simeonidis E, Smallbone K, Spasic I, Weichart D, Brent R, Broomhead DS, Westerhoff HV, Kirdar B, Penttila M, Klipp E, Palsson BO, Sauer U, Oliver SG, Mendes P, Nielsen J, Kell DB: A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology. Nat Biotechnol. 2008 Oct;26(10):1155-60. doi: 10.1038/nbt1492. [PubMed:18846089 ]
Authors unspecified: Ongoing and future developments at the Universal Protein Resource. Nucleic Acids Res. 2011 Jan;39(Database issue):D214-9. doi: 10.1093/nar/gkq1020. Epub 2010 Nov 4. [PubMed:21051339 ]
Scheer M, Grote A, Chang A, Schomburg I, Munaretto C, Rother M, Sohngen C, Stelzer M, Thiele J, Schomburg D: BRENDA, the enzyme information system in 2011. Nucleic Acids Res. 2011 Jan;39(Database issue):D670-6. doi: 10.1093/nar/gkq1089. Epub 2010 Nov 9. [PubMed:21062828 ]

Showing metabocard for N-(5-phospho-beta-D-ribosyl)anthranilic acid (MMDBc0032912)

MOL for #<Metabolite:0x00007fdb5461fee0>

3D MOL for #<Metabolite:0x00007fdb5461fee0>

3D SDF for #<Metabolite:0x00007fdb5461fee0>

3D-SDF for #<Metabolite:0x00007fdb5461fee0>

PDB for #<Metabolite:0x00007fdb5461fee0>

3D PDB for #<Metabolite:0x00007fdb5461fee0>

SMILES for #<Metabolite:0x00007fdb5461fee0>

INCHI for #<Metabolite:0x00007fdb5461fee0>

Structure for #<Metabolite:0x00007fdb5461fee0>

3D Structure for #<Metabolite:0x00007fdb5461fee0>