MiMeDB: Showing metabocard for (2S)-2-amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino}butanoic acid (MMDBc0054852)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:36:23 UTC

Update Date

2022-08-12 20:09:06 UTC

Metabolite ID

MMDBc0054852

Metabolite Identification

Common Name

(2S)-2-amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino}butanoic acid

Description

(2S)-2-amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino}butanoate belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on (2S)-2-amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino}butanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221362D          

 20 20  0  0  1  0            999 V2000
    4.8290   -1.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0188   -0.9098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1285   -2.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7161   -2.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497   -1.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184   -1.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3691   -0.4421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6686   -1.3775    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1792   -0.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3986   -0.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0990    0.3375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0062   -2.0104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4787   -1.5335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9683   -1.0982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7193    0.0256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4492   -1.3775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5884   -0.4421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9387    0.0256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6391   -1.2216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8585   -1.2216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  1  1  0  0  0  0
  8  3  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
  7 11  1  1  0  0  0
 12  4  1  0  0  0  0
 12  5  2  0  0  0  0
 13  2  1  0  0  0  0
  8 13  1  6  0  0  0
 14  5  1  0  0  0  0
 14  6  1  0  0  0  0
 15  9  2  0  0  0  0
 16  9  1  0  0  0  0
 17 10  2  0  0  0  0
 18 10  1  0  0  0  0
  7 19  1  1  0  0  0
  8 20  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054852

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](N)(CCN[C@@]([H])(CC1=CN=CN1)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N4O4/c11-7(9(15)16)1-2-13-8(10(17)18)3-6-4-12-5-14-6/h4-5,7-8,13H,1-3,11H2,(H,12,14)(H,15,16)(H,17,18)/t7-,8-/m0/s1

> <INCHI_KEY>
PQUPEWJRDBYFHU-YUMQZZPRSA-N

> <FORMULA>
C10H16N4O4

> <MOLECULAR_WEIGHT>
256.262

> <EXACT_MASS>
256.117155011

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
25.164152392663652

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-5-yl)ethyl]amino}butanoic acid

> <JCHEM_LOGP>
-6.855103767914

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.044798246596292

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2886027551380383

> <JCHEM_PKA_STRONGEST_BASIC>
10.279283346197483

> <JCHEM_POLAR_SURFACE_AREA>
141.32999999999998

> <JCHEM_REFRACTIVITY>
61.478699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-4-{[(1S)-1-carboxy-2-(3H-imidazol-4-yl)ethyl]amino}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       9.014  -1.989   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.502  -1.698   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.973  -3.736   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.337  -4.497   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.279  -2.241   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.461  -3.445   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.022  -0.825   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.981  -2.571   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.534  -1.116   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.477  -1.116   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       9.518   0.630   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      -0.012  -3.753   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       6.494  -2.862   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       1.808  -2.050   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      12.543   0.048   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      12.039  -2.571   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.965  -0.825   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.485   0.048   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0      10.526  -2.280   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       3.469  -2.280   0.000  0.00  0.00           H+0
CONECT    1    2    7                                                       
CONECT    2    1   13                                                       
CONECT    3    6    8                                                       
CONECT    4    6   12                                                       
CONECT    5   12   14                                                       
CONECT    6    3    4   14                                                  
CONECT    7    1    9   11   19                                             
CONECT    8    3   10   13   20                                             
CONECT    9    7   15   16                                                  
CONECT   10    8   17   18                                                  
CONECT   11    7                                                            
CONECT   12    4    5                                                       
CONECT   13    2    8                                                       
CONECT   14    5    6                                                       
CONECT   15    9                                                            
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   10                                                            
CONECT   19    7                                                            
CONECT   20    8                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

Synonyms

Value	Source
(2S)-2-Amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino}butanoic acid	Generator

Molecular Formula

C₁₀H₁₆N₄O₄

Average Mass

256.262

Monoisotopic Mass

256.117155011

IUPAC Name

(2S)-2-amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-5-yl)ethyl]amino}butanoic acid

Traditional Name

(2S)-2-amino-4-{[(1S)-1-carboxy-2-(3H-imidazol-4-yl)ethyl]amino}butanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CCN[C@@]([H])(CC1=CN=CN1)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C10H16N4O4/c11-7(9(15)16)1-2-13-8(10(17)18)3-6-4-12-5-14-6/h4-5,7-8,13H,1-3,11H2,(H,12,14)(H,15,16)(H,17,18)/t7-,8-/m0/s1

InChI Key

PQUPEWJRDBYFHU-YUMQZZPRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Histidine and derivatives

Alternative Parents

Substituents

Histidine or derivatives
L-alpha-amino acid
Alpha-amino acid
Imidazolyl carboxylic acid derivative
Aralkylamine
Amino fatty acid
Fatty acyl
Dicarboxylic acid or derivatives
Heteroaromatic compound
Imidazole
Azole
Amino acid
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-6.9	ChemAxon
pKa (Strongest Acidic)	1.29	ChemAxon
pKa (Strongest Basic)	10.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	141.33 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	61.48 m³·mol⁻¹	ChemAxon
Polarizability	25.16 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 (TMS_4_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	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	Proteobacteria	3	Human

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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134820210

PDB ID

Not Available

ChEBI ID

Not Available

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 (2S)-2-amino-4-{[(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino}butanoic acid (MMDBc0054852)

MOL for #<Metabolite:0x00007fdaf6252988>

3D MOL for #<Metabolite:0x00007fdaf6252988>

3D SDF for #<Metabolite:0x00007fdaf6252988>

3D-SDF for #<Metabolite:0x00007fdaf6252988>

PDB for #<Metabolite:0x00007fdaf6252988>

3D PDB for #<Metabolite:0x00007fdaf6252988>

SMILES for #<Metabolite:0x00007fdaf6252988>

INCHI for #<Metabolite:0x00007fdaf6252988>

Structure for #<Metabolite:0x00007fdaf6252988>

3D Structure for #<Metabolite:0x00007fdaf6252988>