MiMeDB: Showing metabocard for 3-(Imidazol-4-yl)-2-oxopropyl phosphate (MMDBc0049988)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:47:41 UTC

Update Date

2022-09-01 02:17:46 UTC

Metabolite ID

MMDBc0049988

Metabolite Identification

Common Name

3-(Imidazol-4-yl)-2-oxopropyl phosphate

Description

Imidazole acetol-phosphate belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Imidazole acetol-phosphate exists in all living species, ranging from bacteria to plants to humans. Imidazole acetol-phosphate has been detected, but not quantified in, several different foods, such as sparkleberries (Vaccinium arboreum), soy milk, ucuhubas (Virola surinamensis), cornbread, and alaska wild rhubarbs (Polygonum alpinum). This could make imidazole acetol-phosphate a potential biomarker for the consumption of these foods. Imidazole acetol-phosphate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on Imidazole acetol-phosphate.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309042000352D          

 14 14  0  0  0  0            999 V2000
 9999.234510000.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9491 9999.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.662910000.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9491 9999.0097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.3781 9999.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.093410000.2470    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10001.681110000.9602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.8065 9999.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.505610000.9602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.848210000.3289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1808 9999.8439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4357 9999.0593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2607 9999.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5156 9999.8439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
 13 14  2  0  0  0  0
 10 11  2  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 14  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0049988

> <DATABASE_NAME>
MIME

> <SMILES>
OP(O)(=O)OCC(=O)CC1=CNC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C6H9N2O5P/c9-6(3-13-14(10,11)12)1-5-2-7-4-8-5/h2,4H,1,3H2,(H,7,8)(H2,10,11,12)

> <INCHI_KEY>
YCFFMSOLUMRAMD-UHFFFAOYSA-N

> <FORMULA>
C6H9N2O5P

> <MOLECULAR_WEIGHT>
220.1198

> <EXACT_MASS>
220.02490792

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.148917277754943

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[3-(1H-imidazol-4-yl)-2-oxopropoxy]phosphonic acid

> <ALOGPS_LOGP>
-0.90

> <JCHEM_LOGP>
-2.9574821134456775

> <ALOGPS_LOGS>
-1.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.03139600175535

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2314915163527376

> <JCHEM_PKA_STRONGEST_BASIC>
6.647396425017994

> <JCHEM_POLAR_SURFACE_AREA>
112.51

> <JCHEM_REFRACTIVITY>
46.0746

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(1H-imidazol-4-yl)-2-oxopropoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8665.2388667.128   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.5728666.358   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8667.9048667.128   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8666.5728664.818   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8669.2398666.358   0.000  0.00  0.00           O+0
HETATM    6  P   UNK     0    8670.5748667.128   0.000  0.00  0.00           P+0
HETATM    7  O   UNK     0    8669.8058668.459   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8671.9058666.358   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8671.3448668.459   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0    8662.6508667.281   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0    8661.4048666.375   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    8661.8808664.911   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    8663.4208664.911   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.8968666.375   0.000  0.00  0.00           C+0
CONECT    1    2   14                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2    5                                                       
CONECT    4    2                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10   11   14                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   14   12                                                       
CONECT   14   13   10    1                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

Synonyms

Value	Source
3-(Imidazol-4-yl)-2-oxopropyl phosphate	ChEBI
Imidazole-acetol phosphate	ChEBI
3-(Imidazol-4-yl)-2-oxopropyl phosphoric acid	Generator
Imidazole-acetol phosphoric acid	Generator
Imidazole acetol-phosphoric acid	Generator
1-(1H-Imidazol-4-yl)-3-(phosphonooxy)-2-propanone	HMDB
3-(1H-Imidazol-4-yl)-2-oxopropyl dihydrogen phosphate	HMDB
3-(Imidazol-4-yl)-2-oxopropyl dihydrogen phosphate	HMDB
Imidazole acetol phosphate	HMDB
Imidazole acetol-P	HMDB
1-(1H-Imidazol-5-yl)-3-(phosphonooxy)-2-propanone	HMDB

Molecular Formula

C₆H₉N₂O₅P

Average Mass

220.1198

Monoisotopic Mass

220.02490792

IUPAC Name

[3-(1H-imidazol-4-yl)-2-oxopropoxy]phosphonic acid

Traditional Name

3-(1H-imidazol-4-yl)-2-oxopropoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

OP(O)(=O)OCC(=O)CC1=CNC=N1

InChI Identifier

InChI=1S/C6H9N2O5P/c9-6(3-13-14(10,11)12)1-5-2-7-4-8-5/h2,4H,1,3H2,(H,7,8)(H2,10,11,12)

InChI Key

YCFFMSOLUMRAMD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Monoalkyl phosphates

Alternative Parents

Substituents

Monoalkyl phosphate
Azole
Imidazole
Heteroaromatic compound
Ketone
Organoheterocyclic compound
Azacycle
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:16426 )
oxoalkyl phosphate (CHEBI:16426 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	14.9 g/L	ALOGPS
logP	-0.9	ALOGPS
logP	-3	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.23	ChemAxon
pKa (Strongest Basic)	6.65	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	112.51 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	46.07 m³·mol⁻¹	ChemAxon
Polarizability	18.15 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 GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-9200000000-41a681dee161ad4f3e7b	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-3390000000-102fb9b517f2001e0996	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kmi-4950000000-076be23324f875b841dc	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9500000000-99bd6a8eac665bc00868	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-016r-7190000000-c52bfb05c2cd90023536	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-7598c15214a6b2b67038	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-59a5e26dad504ee2412d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-199895f882e036c55087	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-3930000000-3a2cf619e974119e8f24	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pw9-9300000000-f31212a9e65f18dabcb3	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2090000000-bd2937021ad7bda9fa53	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9020000000-af7370fa1a56f74a6fb4	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-8c5fbfcdabecdcd6d55b	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View 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

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
MMDBr0007072	D-erythro-1-(Imidazol-4-yl)glycerol 3-phosphate	3-(Imidazol-4-yl)-2-oxopropyl phosphate	Not Available		VMH	30371894

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	Firmicutes	356	Human feces; Human pleural fluid plaque; Pig ; Human ; Human stool; Human subgingival plaque; Catfish ; Cattle	Metabolic reconstruction
Bacteria	Proteobacteria	487	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Cattle ; Turkey ; Sheep ; Chicken ; River trout	Metabolic reconstruction
Bacteria	Actinobacteria	159	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Cattle	Metabolic reconstruction
Bacteria	Verrucomicrobia	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	101	Human feces; Human appendix biopsy; Human ; Human stool; Human urine; Human gastric fluid; Human saliva; Human supragingival plaque; Human subgingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Fusobacteria	1	Human ; Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	20	Human feces; Human saliva; Human supragingival plaque	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Aquificae	3
Archaea/Archaea	Euryarchaeota	30		Metabolic reconstruction
Archaea/Archaea	Crenarchaeota	13		Metabolic reconstruction
Archaea/Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Chloroflexi	7
Bacteria	Chlorobi	11
Eukaryota/Fungi	Basidiomycota	3	Human feces
Bacteria	Deinococcus-thermus	5
Bacteria	Dictyoglomi	2
Bacteria	Elusimicrobia	1
Bacteria	Cyanobacteria	31	Human
Bacteria	Acidobacteria	2
Bacteria	Spirochaetes	7	Human ; Pig
Bacteria	nah	1
Bacteria	Thermotogae	4
Bacteria	Nitrospirae	1

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
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0012236

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

792

PDB ID

Not Available

ChEBI ID

16426

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Henderson GB, Snell EE: Vitamin B 6 -responsive histidine deficiency in mutants of Salmonella typhimurium. Proc Natl Acad Sci U S A. 1971 Dec;68(12):2903-7. doi: 10.1073/pnas.68.12.2903. [PubMed:4943547 ]
Albritton WL, Levin AP: Some comparative kinetic data on the enzyme imidazoleacetol phosphate:L-glutamate aminotransferase derived from mutant strains of Salmonella typhimurium. J Biol Chem. 1970 May 25;245(10):2525-8. [PubMed:5445798 ]
AMES BN, HORECKER BL: The biosynthesis of histidine: imidazoleacetol phosphate transaminase. J Biol Chem. 1956 May;220(1):113-28. [PubMed:13319331 ]
LEVIN AP, HARTMAN PE: ACTION OF A HISTIDINE ANALOGUE, 1,2,4-TRIAZOLE-3-ALANINE, IN SALMONELLA TYPHIMURIUM. J Bacteriol. 1963 Oct;86:820-8. doi: 10.1128/jb.86.4.820-828.1963. [PubMed:14066480 ]
AMES BN, MITCHELL HK: The biosynthesis of histidine; imidazoleglycerol phosphate, imidazoleacetol phosphate, and histidinol phosphate. J Biol Chem. 1955 Feb;212(2):687-96. [PubMed:14353870 ]

Showing metabocard for 3-(Imidazol-4-yl)-2-oxopropyl phosphate (MMDBc0049988)

MOL for #<Metabolite:0x00007fecd34c2288>

3D MOL for #<Metabolite:0x00007fecd34c2288>

3D SDF for #<Metabolite:0x00007fecd34c2288>

3D-SDF for #<Metabolite:0x00007fecd34c2288>

PDB for #<Metabolite:0x00007fecd34c2288>

3D PDB for #<Metabolite:0x00007fecd34c2288>

SMILES for #<Metabolite:0x00007fecd34c2288>

INCHI for #<Metabolite:0x00007fecd34c2288>

Structure for #<Metabolite:0x00007fecd34c2288>

3D Structure for #<Metabolite:0x00007fecd34c2288>