MiMeDB: Showing metabocard for N(2)-citryl-N(6)-acetyl-N(6)-hydroxy-L-lysine (MMDBc0056179)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:18:50 UTC

Update Date

2022-08-12 20:09:37 UTC

Metabolite ID

MMDBc0056179

Metabolite Identification

Common Name

N(2)-citryl-N(6)-acetyl-N(6)-hydroxy-L-lysine

Description

N(alpha)-citryl-N(epsilon)-acetyl-N(epsilon)-hydroxylysine(3-), also known as N(2)-citryl-N(6)-acetyl-N(6)-hydroxy-L-lysine, 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. Based on a literature review a small amount of articles have been published on N(alpha)-citryl-N(epsilon)-acetyl-N(epsilon)-hydroxylysine(3-).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222182D          

 27 26  0  0  1  0            999 V2000
   -1.3502   -0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604    0.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502    0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7004    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -0.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4009    1.8709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8608    3.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -0.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106    0.7796    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8608    1.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507    3.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7806    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9104    2.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1308    2.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507    1.4032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700   -1.4032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1308    0.4677    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.7806    4.3655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106    2.9623    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.5908   -0.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -0.6236    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.0663    3.7307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5340    2.3804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3513    2.3804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700    0.7796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9705    0.1559    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  8  1  1  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  1  0  0  0  0
 14  6  1  0  0  0  0
 14  7  1  0  0  0  0
 14 13  1  0  0  0  0
  9 15  1  1  0  0  0
 15 10  2  0  0  0  0
 16  5  1  0  0  0  0
 16  8  1  0  0  0  0
 17  8  2  0  0  0  0
 10 18  1  4  0  0  0
 19 11  2  0  0  0  0
 20 11  1  0  0  0  0
 21 12  2  0  0  0  0
 22 12  1  0  0  0  0
 23 13  2  0  0  0  0
 24 13  1  0  0  0  0
 25 14  1  0  0  0  0
 26 16  1  0  0  0  0
  9 27  1  1  0  0  0
M  CHG  3  18  -1  20  -1  22  -1
M  END


  Mrv1652306172222182D          

 27 26  0  0  1  0            999 V2000
   -1.3502   -0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604    0.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502    0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7004    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -0.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4009    1.8709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8608    3.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -0.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106    0.7796    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8608    1.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507    3.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7806    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9104    2.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1308    2.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507    1.4032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700   -1.4032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1308    0.4677    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.7806    4.3655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106    2.9623    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.5908   -0.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -0.6236    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.0663    3.7307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5340    2.3804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3513    2.3804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700    0.7796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9705    0.1559    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  8  1  1  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  1  0  0  0  0
 14  6  1  0  0  0  0
 14  7  1  0  0  0  0
 14 13  1  0  0  0  0
  9 15  1  1  0  0  0
 15 10  2  0  0  0  0
 16  5  1  0  0  0  0
 16  8  1  0  0  0  0
 17  8  2  0  0  0  0
 10 18  1  4  0  0  0
 19 11  2  0  0  0  0
 20 11  1  0  0  0  0
 21 12  2  0  0  0  0
 22 12  1  0  0  0  0
 23 13  2  0  0  0  0
 24 13  1  0  0  0  0
 25 14  1  0  0  0  0
 26 16  1  0  0  0  0
  9 27  1  1  0  0  0
M  CHG  3  18  -1  20  -1  22  -1
M  END
> <DATABASE_ID>
MMDBc0056179

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H22N2O10/c1-8(17)16(26)5-3-2-4-9(12(21)22)15-10(18)6-14(25,13(23)24)7-11(19)20/h9,25-26H,2-7H2,1H3,(H,15,18)(H,19,20)(H,21,22)(H,23,24)/p-3/t9-,14?/m0/s1

> <INCHI_KEY>
HPOPJZNNZCIWFX-CUVJYRNJSA-K

> <FORMULA>
C14H19N2O10

> <MOLECULAR_WEIGHT>
375.312

> <EXACT_MASS>
375.10561556

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.78861391828012

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
-3

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(3,4-dicarboxy-3-hydroxy-1-oxidobutylidene)amino]-6-(N-hydroxyacetamido)hexanoate

> <JCHEM_LOGP>
-1.3558381350000004

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.7665706256079488

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1040899367662993

> <JCHEM_PKA_STRONGEST_BASIC>
0.8647904746578982

> <JCHEM_POLAR_SURFACE_AREA>
213.74999999999997

> <JCHEM_REFRACTIVITY>
114.1881

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(3,4-dicarboxy-3-hydroxy-1-oxidobutylidene)amino]-6-(N-hydroxyacetamido)hexanoate

> <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      -2.520  -0.873   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.033   0.582   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.520   0.873   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.041   1.746   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.512  -0.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.082   3.492   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.073   6.403   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.008  -1.164   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.553   1.455   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.073   2.328   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.561   6.694   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.057   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.033   5.452   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.578   4.948   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       7.561   2.619   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0      -0.504  -2.619   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.578   0.873   0.000  0.00  0.00           O-1
HETATM   19  O   UNK     0       7.057   8.149   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.553   5.530   0.000  0.00  0.00           O-1
HETATM   21  O   UNK     0       8.569  -0.291   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.049  -1.164   0.000  0.00  0.00           O-1
HETATM   23  O   UNK     0      11.324   6.964   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      12.197   4.443   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.122   4.443   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -0.504   1.455   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       5.545   0.291   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    9                                                       
CONECT    5    3   16                                                       
CONECT    6   10   14                                                       
CONECT    7   11   14                                                       
CONECT    8    1   16   17                                                  
CONECT    9    4   12   15   27                                             
CONECT   10    6   15   18                                                  
CONECT   11    7   19   20                                                  
CONECT   12    9   21   22                                                  
CONECT   13   14   23   24                                                  
CONECT   14    6    7   13   25                                             
CONECT   15    9   10                                                       
CONECT   16    5    8   26                                                  
CONECT   17    8                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   11                                                            
CONECT   21   12                                                            
CONECT   22   12                                                            
CONECT   23   13                                                            
CONECT   24   13                                                            
CONECT   25   14                                                            
CONECT   26   16                                                            
CONECT   27    9                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

Synonyms

Value	Source
N(2)-Citryl-N(6)-acetyl-N(6)-hydroxy-L-lysine	ChEBI
N(alpha)-Citryl-N(epsilon)-acetyl-N(epsilon)-hydroxylysine trianion	ChEBI
N(a)-Citryl-N(epsilon)-acetyl-N(epsilon)-hydroxylysine trianion	Generator
N(Α)-citryl-N(epsilon)-acetyl-N(epsilon)-hydroxylysine trianion	Generator
N(a)-Citryl-N(epsilon)-acetyl-N(epsilon)-hydroxylysine(3-)	Generator
N(Α)-citryl-N(epsilon)-acetyl-N(epsilon)-hydroxylysine(3-)	Generator

Molecular Formula

C₁₄H₁₉N₂O₁₀

Average Mass

375.312

Monoisotopic Mass

375.10561556

IUPAC Name

(2S)-2-[(3,4-dicarboxy-3-hydroxy-1-oxidobutylidene)amino]-6-(N-hydroxyacetamido)hexanoate

Traditional Name

(2S)-2-[(3,4-dicarboxy-3-hydroxy-1-oxidobutylidene)amino]-6-(N-hydroxyacetamido)hexanoate

CAS Registry Number

Not Available

SMILES

[H][C@@](CCCCN(O)C(C)=O)(N=C([O-])CC(O)(CC([O-])=O)C(O)=O)C([O-])=O

InChI Identifier

InChI=1S/C14H22N2O10/c1-8(17)16(26)5-3-2-4-9(12(21)22)15-10(18)6-14(25,13(23)24)7-11(19)20/h9,25-26H,2-7H2,1H3,(H,15,18)(H,19,20)(H,21,22)(H,23,24)/p-3/t9-,14?/m0/s1

InChI Key

HPOPJZNNZCIWFX-CUVJYRNJSA-K

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
Tricarboxylic acid or derivatives
Fatty amide
N-acyl-amine
Fatty acyl
Tertiary alcohol
Acetamide
Acetohydroxamic acid
Secondary carboxylic acid amide
Hydroxamic acid
Carboxamide group
Carboxylic acid
Organic oxide
Organopnictogen compound
Alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tricarboxylic acid trianion (CHEBI:63796 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-1.4	ChemAxon
pKa (Strongest Acidic)	3.1	ChemAxon
pKa (Strongest Basic)	0.86	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	213.75 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	114.19 m³·mol⁻¹	ChemAxon
Polarizability	33.79 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	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	2	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool

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

Not Available

Chemspider ID

27471300

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56928008

PDB ID

Not Available

ChEBI ID

63796

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(2)-citryl-N(6)-acetyl-N(6)-hydroxy-L-lysine (MMDBc0056179)

MOL for #<Metabolite:0x00007fecd96d12a8>

3D MOL for #<Metabolite:0x00007fecd96d12a8>

3D SDF for #<Metabolite:0x00007fecd96d12a8>

3D-SDF for #<Metabolite:0x00007fecd96d12a8>

PDB for #<Metabolite:0x00007fecd96d12a8>

3D PDB for #<Metabolite:0x00007fecd96d12a8>

SMILES for #<Metabolite:0x00007fecd96d12a8>

INCHI for #<Metabolite:0x00007fecd96d12a8>

Structure for #<Metabolite:0x00007fecd96d12a8>

3D Structure for #<Metabolite:0x00007fecd96d12a8>