MiMeDB: Showing metabocard for 2-Amino-3-oxo-4-phosphonooxybutyrate (MMDBc0029970)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:48:51 UTC

Update Date

2022-08-31 17:38:09 UTC

MiMeDB ID

MMDBc0029970

Metabolite Identification

Common Name

2-Amino-3-oxo-4-phosphonooxybutyrate

Description

2-amino-3-oxo-4-phosphonooxybutyrate is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon)

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 08131209222D          

 14 13  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  3  5  1  6  0  0  0
  6  2  2  0  0  0  0
  7  4  2  0  0  0  0
  8  4  1  0  0  0  0
 12  1  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 13 11  2  0  0  0  0
 13 12  1  0  0  0  0
  3 14  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029970

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H8NO7P/c5-3(4(7)8)2(6)1-12-13(9,10)11/h3H,1,5H2,(H,7,8)(H2,9,10,11)/t3-/m0/s1

> <INCHI_KEY>
LMKSRFWSQAKTOE-VKHMYHEASA-N

> <FORMULA>
C4H8NO7P

> <MOLECULAR_WEIGHT>
213.0826

> <EXACT_MASS>
213.003838127

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
16.02780359883773

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-oxo-4-(phosphonooxy)butanoic acid

> <ALOGPS_LOGP>
-1.75

> <JCHEM_LOGP>
-3.2612596957387257

> <ALOGPS_LOGS>
-1.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
1.8217774845366357

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.0295040721835598

> <JCHEM_PKA_STRONGEST_BASIC>
7.2257721632553915

> <JCHEM_POLAR_SURFACE_AREA>
147.15

> <JCHEM_REFRACTIVITY>
38.109700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-3-oxo-4-(phosphonooxy)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-AUG-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   14  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2   12                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5   14                                             
CONECT    4    3    7    8                                                  
CONECT    5    3                                                            
CONECT    6    2                                                            
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9   13                                                            
CONECT   10   13                                                            
CONECT   11   13                                                            
CONECT   12    1   13                                                       
CONECT   13    9   10   11   12                                             
CONECT   14    3                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

Synonyms

Value	Source
(2S)-2-Amino-3-oxo-4-phosphonooxybutanoate	ChEBI
L-2-Amino-3-oxo-4-phosphonooxybutyrate	ChEBI
(2S)-2-Amino-3-oxo-4-phosphonooxybutanoic acid	Generator
L-2-Amino-3-oxo-4-phosphonooxybutyric acid	Generator
2-Amino-3-oxo-4-phosphonooxybutyric acid	Generator

Chemical Formula

C₄H₈NO₇P

Average Molecular Weight

213.0826

Monoisotopic Molecular Weight

213.003838127

IUPAC Name

(2S)-2-amino-3-oxo-4-(phosphonooxy)butanoic acid

Traditional Name

(2S)-2-amino-3-oxo-4-(phosphonooxy)butanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](N)(C(O)=O)C(=O)COP(O)(O)=O

InChI Identifier

InChI=1S/C4H8NO7P/c5-3(4(7)8)2(6)1-12-13(9,10)11/h3H,1,5H2,(H,7,8)(H2,9,10,11)/t3-/m0/s1

InChI Key

LMKSRFWSQAKTOE-VKHMYHEASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are 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

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Beta-keto acid
Short-chain keto acid
Monoalkyl phosphate
Beta-hydroxy ketone
Keto acid
Monosaccharide
Organic phosphoric acid derivative
Phosphoric acid ester
1,3-dicarbonyl compound
Alkyl phosphate
Alpha-aminoketone
Amino acid
Ketone
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Hydrocarbon derivative
Primary aliphatic amine
Organooxygen compound
Organic oxygen compound
Carbonyl group
Primary amine
Organopnictogen compound
Organic oxide
Organic nitrogen compound
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-amino-3-oxo-4-(phosphonooxy)butanoic acid (CHEBI:64186 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	16.6 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-3.3	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.03	ChemAxon
pKa (Strongest Basic)	7.23	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	147.15 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	38.11 m³·mol⁻¹	ChemAxon
Polarizability	16.03 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 (Non-derivatized) - 70eV, Positive	splash10-0002-9300000000-67f6d576df6ecedda3a5	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0292-4930000000-5d03d45aa354832df1ca	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xs-9800000000-1651e4804966f49060f0	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006t-9100000000-de1b0969b556dea6c460	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03fr-9860000000-4aae0dd934f15993c083	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-4a5986983776a835b113	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-8918b9d07cb95a5132b4	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		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

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Proteobacteria	160	Human Feces; Human	Unknown; Metabolic reconstruction
	Verrucomicrobia	1	Human	Metabolic reconstruction
	Bacteroidetes	116	Human Feces; Human	Metabolic reconstruction
	Synergistetes	1		Metabolic reconstruction
	Firmicutes	160	Human Feces; Human ; Cattle	Metabolic reconstruction
	Actinobacteria	24	Human Feces; Human	Metabolic reconstruction
	Fusobacteria	16	Human Feces; Human	Metabolic reconstruction
	Planctomycetes	1	Human Feces	Metabolic reconstruction
	Euryarchaeota	1	Human Feces	Metabolic reconstruction
Fungi	Ascomycota	1	Human Feces	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

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		details

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

C07335

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441260

PDB ID

Not Available

ChEBI ID

64186

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
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 2-Amino-3-oxo-4-phosphonooxybutyrate (MMDBc0029970)

MOL for #<Metabolite:0x00007f4589685170>

3D MOL for #<Metabolite:0x00007f4589685170>

3D SDF for #<Metabolite:0x00007f4589685170>

3D-SDF for #<Metabolite:0x00007f4589685170>

PDB for #<Metabolite:0x00007f4589685170>

3D PDB for #<Metabolite:0x00007f4589685170>

SMILES for #<Metabolite:0x00007f4589685170>

INCHI for #<Metabolite:0x00007f4589685170>

Structure for #<Metabolite:0x00007f4589685170>

3D Structure for #<Metabolite:0x00007f4589685170>