MiMeDB: Showing metabocard for 1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate (MMDBc0029956)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:48:15 UTC

Update Date

2022-08-31 17:37:58 UTC

Metabolite ID

MMDBc0029956

Metabolite Identification

Common Name

1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate

Description

1-(2-carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate is a pentose phosphate derivative. It is a substrate for indole-3-glycerol-phosphate synthase (IPGS) (EC 4.1.1.48)which is an enzyme that catalyzes the chemical reaction: 1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate ‚Üµightleftharpoons 1-C-(indol-3-yl)-glycerol 3-phosphate + CO2 + H2O

Structure

MOL SDF PDB SMILES InChI

 
  Mrv0541 02241222112D          
 
 23 23  0  0  1  0            999 V2000
   11.7066  -11.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7066  -10.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4229  -11.9661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9827  -11.9775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9827  -10.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4191  -10.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1355  -11.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2702  -11.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2702  -10.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1355  -10.7193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4153   -9.6075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8518  -11.9624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5643  -11.5492    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.8855  -12.7848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2769  -11.9585    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.5605  -10.7230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9894  -11.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2806  -12.7848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7057  -11.9548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4183  -11.5417    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.7329  -12.2883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1074  -10.7989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2066  -11.2119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  2  0  0  0  0
  6 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  6  0  0  0
 15 17  1  0  0  0  0
 15 18  1  1  0  0  0
 17 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
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029956

> <DATABASE_NAME>
MIME

> <SMILES>
O[C@H](COP(O)(O)=O)[C@@H](O)C(=O)CNC1=C(C=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H16NO9P/c14-9(11(16)10(15)6-22-23(19,20)21)5-13-8-4-2-1-3-7(8)12(17)18/h1-4,10-11,13,15-16H,5-6H2,(H,17,18)(H2,19,20,21)/t10-,11+/m1/s1

> <INCHI_KEY>
QKMBYNRMPRKVTO-MNOVXSKESA-N

> <FORMULA>
C12H16NO9P

> <MOLECULAR_WEIGHT>
349.2305

> <EXACT_MASS>
349.056267627

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
30.76095090784712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(3R,4R)-3,4-dihydroxy-2-oxo-5-(phosphonooxy)pentyl]amino}benzoic acid

> <ALOGPS_LOGP>
-0.91

> <JCHEM_LOGP>
-0.5022199484053262

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.600888907965788

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4783402351175567

> <JCHEM_PKA_STRONGEST_BASIC>
0.2737084817385371

> <JCHEM_POLAR_SURFACE_AREA>
173.62

> <JCHEM_REFRACTIVITY>
77.7189

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.55e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(3R,4R)-3,4-dihydroxy-2-oxo-5-(phosphonooxy)pentyl]amino}benzoic 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      21.852 -21.566   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.852 -20.009   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      23.189 -22.337   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      20.501 -22.358   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.501 -19.245   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.182 -19.238   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.520 -21.566   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.171 -21.566   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.171 -20.009   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      24.520 -20.009   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      23.175 -17.934   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      25.857 -22.330   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.187 -21.559   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      25.920 -23.865   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      28.517 -22.323   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      27.180 -20.016   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      29.847 -21.552   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      28.524 -23.865   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      31.184 -22.316   0.000  0.00  0.00           O+0
HETATM   20  P   UNK     0      32.514 -21.545   0.000  0.00  0.00           P+0
HETATM   21  O   UNK     0      33.101 -22.938   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      31.934 -20.158   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      33.986 -20.929   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10   11                                                  
CONECT    7    3   12                                                       
CONECT    8    4    9                                                       
CONECT    9    5    8                                                       
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12    7   13   14                                                  
CONECT   13   12   15   16                                                  
CONECT   14   12                                                            
CONECT   15   13   17   18                                                  
CONECT   16   13                                                            
CONECT   17   15   19                                                       
CONECT   18   15                                                            
CONECT   19   17   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   46    0
END

Synonyms

Value	Source
1-[(2-Carboxyphenyl)amino]-1-deoxy-5-O-phosphono-D-ribulose	ChEBI
1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphoric acid	Generator
1-(2-carboxyphenylamino)-1'-Deoxy-D-ribulose 5'-phosphate	ChEBI
1-(2-carboxyphenylamino)-1-Deoxy-D-ribulose 5-phosphoric acid	Generator
1-(2-Carboxyphenylamino)-1-deoxyribulose 5-phosphate	MeSH

Molecular Formula

C₁₂H₁₆NO₉P

Average Mass

349.2305

Monoisotopic Mass

349.056267627

IUPAC Name

2-{[(3R,4R)-3,4-dihydroxy-2-oxo-5-(phosphonooxy)pentyl]amino}benzoic acid

Traditional Name

2-{[(3R,4R)-3,4-dihydroxy-2-oxo-5-(phosphonooxy)pentyl]amino}benzoic acid

CAS Registry Number

Not Available

SMILES

O[C@H](COP(O)(O)=O)[C@@H](O)C(=O)CNC1=C(C=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C12H16NO9P/c14-9(11(16)10(15)6-22-23(19,20)21)5-13-8-4-2-1-3-7(8)12(17)18/h1-4,10-11,13,15-16H,5-6H2,(H,17,18)(H2,19,20,21)/t10-,11+/m1/s1

InChI Key

QKMBYNRMPRKVTO-MNOVXSKESA-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
Aminobenzoic acid or derivatives
Aminobenzoic acid
Monosaccharide phosphate
Benzoic acid
Benzoic acid or derivatives
Benzoyl
Phenylalkylamine
Aniline or substituted anilines
Monoalkyl phosphate
Secondary aliphatic/aromatic amine
Alkyl phosphate
Beta-hydroxy ketone
Phosphoric acid ester
Monocyclic benzene moiety
Organic phosphoric acid derivative
Benzenoid
Acyloin
Alpha-hydroxy ketone
Alpha-aminoketone
1,3-aminoalcohol
Vinylogous amide
Ketone
Amino acid or derivatives
Secondary alcohol
Amino acid
1,2-diol
Secondary amine
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organopnictogen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

deoxyribulose phosphate (CHEBI:29112 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.55 g/L	ALOGPS
logP	-0.91	ALOGPS
logP	-0.5	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	1.48	ChemAxon
pKa (Strongest Basic)	0.27	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.62 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	77.72 m³·mol⁻¹	ChemAxon
Polarizability	30.76 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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 GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-5911000000-37b09c66588c632153be	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-0339000000-69722cac0a11d3f77f39	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udm-1921000000-c609a3aa34bcb82cfcfd	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfr-3900000000-a5ab2361731c8e108c8d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a6s-4955000000-a019a420bd68acd6c195	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9410000000-f6a1776a0ae271fef65d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-6a98c0c5e5f9775e0b22	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	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
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

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

C00007450

Chemspider ID

Not Available

KEGG Compound ID

C01302

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

446894

PDB ID

Not Available

ChEBI ID

29112

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Winder CL, Dunn WB, Schuler S, Broadhurst D, Jarvis R, Stephens GM, Goodacre R: Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites. Anal Chem. 2008 Apr 15;80(8):2939-48. doi: 10.1021/ac7023409. Epub 2008 Mar 11. [PubMed:18331064 ]
Keseler IM, Collado-Vides J, Santos-Zavaleta A, Peralta-Gil M, Gama-Castro S, Muniz-Rascado L, Bonavides-Martinez C, Paley S, Krummenacker M, Altman T, Kaipa P, Spaulding A, Pacheco J, Latendresse M, Fulcher C, Sarker M, Shearer AG, Mackie A, Paulsen I, Gunsalus RP, Karp PD: EcoCyc: a comprehensive database of Escherichia coli biology. Nucleic Acids Res. 2011 Jan;39(Database issue):D583-90. doi: 10.1093/nar/gkq1143. Epub 2010 Nov 21. [PubMed:21097882 ]
Kanehisa M, Goto S, Sato Y, Furumichi M, Tanabe M: KEGG for integration and interpretation of large-scale molecular data sets. Nucleic Acids Res. 2012 Jan;40(Database issue):D109-14. doi: 10.1093/nar/gkr988. Epub 2011 Nov 10. [PubMed:22080510 ]

Showing metabocard for 1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate (MMDBc0029956)

MOL for #<Metabolite:0x00007f46c8807350>

3D MOL for #<Metabolite:0x00007f46c8807350>

3D SDF for #<Metabolite:0x00007f46c8807350>

3D-SDF for #<Metabolite:0x00007f46c8807350>

PDB for #<Metabolite:0x00007f46c8807350>

3D PDB for #<Metabolite:0x00007f46c8807350>

SMILES for #<Metabolite:0x00007f46c8807350>

INCHI for #<Metabolite:0x00007f46c8807350>

Structure for #<Metabolite:0x00007f46c8807350>

3D Structure for #<Metabolite:0x00007f46c8807350>