MiMeDB: Showing metabocard for N-Acetylphosphinothricin (MMDBc0031926)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:55:16 UTC

Update Date

2022-08-31 18:26:30 UTC

Metabolite ID

MMDBc0031926

Metabolite Identification

Common Name

N-Acetylphosphinothricin

Description

N-Acetylphosphinothricin is an intermediate in phosphonate and phosphinate metabolism in E.coli, where the enzyme acetyl-CoA:phosphinothricin N-acetyltransferase catalyzes the reaction acetyl-CoA + phosphinothricin <=> CoA + N-acetylphosphinothricin (KEGG compound: C17952).

Structure

MOL SDF PDB SMILES InChI

 
  Mrv1533006041517192D          
 
 14 13  0  0  1  0            999 V2000
   12.5244   -9.6457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2388   -9.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9533   -9.6457    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.6677   -9.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3822   -9.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0967   -9.2332    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.8111   -9.2332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0967   -8.4083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2388   -8.4083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0967  -10.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0210  -10.5932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7355  -11.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4499  -10.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7355  -11.8306    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  2  9  2  0  0  0  0
  6 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  3 11  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031926

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)N[C@@H](CCP(C)(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H14NO5P/c1-5(9)8-6(7(10)11)3-4-14(2,12)13/h6H,3-4H2,1-2H3,(H,8,9)(H,10,11)(H,12,13)/t6-/m0/s1

> <INCHI_KEY>
VZVQOWUYAAWBCP-LURJTMIESA-N

> <FORMULA>
C7H14NO5P

> <MOLECULAR_WEIGHT>
223.165

> <EXACT_MASS>
223.060959553

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
20.022070302087222

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-acetamido-4-[hydroxy(methyl)phosphoryl]butanoic acid

> <ALOGPS_LOGP>
-1.57

> <JCHEM_LOGP>
-2.2372586006666664

> <ALOGPS_LOGS>
-1.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.124063515674235

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0072970187198487

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8011539575428865

> <JCHEM_POLAR_SURFACE_AREA>
103.69999999999999

> <JCHEM_REFRACTIVITY>
49.104800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-acetamido-4-[hydroxy(methyl)phosphoryl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-15         0                                  
HETATM    1  O   UNK     0      23.379 -18.005   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      24.712 -17.235   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.046 -18.005   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.380 -17.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.713 -18.005   0.000  0.00  0.00           C+0
HETATM    6  P   UNK     0      30.047 -17.235   0.000  0.00  0.00           P+0
HETATM    7  O   UNK     0      31.381 -17.235   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      30.047 -15.695   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      24.712 -15.695   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      30.047 -18.775   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      26.173 -19.774   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      27.506 -20.544   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.840 -19.774   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      27.506 -22.084   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   10                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2                                                            
CONECT   10    6                                                            
CONECT   11   12    3                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

Synonyms

Value	Source
L-N-Acetylphosphinothricin	ChEBI
N-Acetyl-L-glufosinate	ChEBI
N-Acetylphinothricin	ChEBI
N-Acetyl-L-glufosinic acid	Generator
N-Acetyl-L-phosphinothricin	MeSH
N-Ac-PT	MeSH

Molecular Formula

C₇H₁₄NO₅P

Average Mass

223.165

Monoisotopic Mass

223.060959553

IUPAC Name

(2S)-2-acetamido-4-[hydroxy(methyl)phosphoryl]butanoic acid

Traditional Name

(2S)-2-acetamido-4-[hydroxy(methyl)phosphoryl]butanoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@@H](CCP(C)(O)=O)C(O)=O

InChI Identifier

InChI=1S/C7H14NO5P/c1-5(9)8-6(7(10)11)3-4-14(2,12)13/h6H,3-4H2,1-2H3,(H,8,9)(H,10,11)(H,12,13)/t6-/m0/s1

InChI Key

VZVQOWUYAAWBCP-LURJTMIESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Fatty acid
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Organophosphorus compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	14.4 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-2.2	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	2.01	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.7 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	49.1 m³·mol⁻¹	ChemAxon
Polarizability	20.02 Å³	ChemAxon
Number of Rings	0	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 (TMS_3_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-1970000000-f1aea239228c312466cc	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-057r-2910000000-0c54aeb1ff9965c2e4eb	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6t-9700000000-441822e7d07ac1768964	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-2690000000-2b98948cb9dd456607df	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-9740000000-880853b8d72b143338ab	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-570e314b2895522f2590	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

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/Eubacteria	Proteobacteria	2	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown
Bacteria/Eubacteria	Actinobacteria	1
Bacteria	Actinobacteria	2
Bacteria/Eubacteria	Firmicutes	1	Human feces

Exposure Sources

Source Type	Activity	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C17952

BioCyc ID

CPD-9999

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14647097

PDB ID

Not Available

ChEBI ID

131436

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for N-Acetylphosphinothricin (MMDBc0031926)

MOL for #<Metabolite:0x00007f3e1c6bea48>

3D MOL for #<Metabolite:0x00007f3e1c6bea48>

3D SDF for #<Metabolite:0x00007f3e1c6bea48>

3D-SDF for #<Metabolite:0x00007f3e1c6bea48>

PDB for #<Metabolite:0x00007f3e1c6bea48>

3D PDB for #<Metabolite:0x00007f3e1c6bea48>

SMILES for #<Metabolite:0x00007f3e1c6bea48>

INCHI for #<Metabolite:0x00007f3e1c6bea48>

Structure for #<Metabolite:0x00007f3e1c6bea48>

3D Structure for #<Metabolite:0x00007f3e1c6bea48>