MiMeDB: Showing metabocard for L-Ala-D-Glu-meso-A2pm (MMDBc0030197)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:58:00 UTC

Update Date

2022-08-31 17:40:36 UTC

Metabolite ID

MMDBc0030197

Metabolite Identification

Common Name

L-Ala-D-Glu-meso-A2pm

Description

L-ala-D-glu-meso-a2pm is a member of the chemical class known as Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05311207092D          

 31 30  0  0  0  0            999 V2000
   10.1490    4.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979    3.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5877    4.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9379    4.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4485    5.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6384    5.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8789    4.8196    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0476    3.4164    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7481    4.3519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9886    5.9110    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0983    4.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0688    4.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7186    6.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4190    5.4433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3177    2.6369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2882    4.9755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7987    5.7551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3683    4.0401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5287    4.3519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6974    2.9487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9675    4.3519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8283    3.4164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4780    2.9487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9084    6.8465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2587    7.3142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3388    4.1960    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7776    4.1960    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2080    3.7283    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1785    6.0669    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
  6  5  1  0  0  0  0
  7  1  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
  7 16  1  6  0  0  0
  8 17  1  6  0  0  0
  9 18  1  1  0  0  0
 18 11  2  0  0  0  0
 10 19  1  1  0  0  0
 19 12  2  0  0  0  0
 11 20  1  4  0  0  0
 12 21  1  4  0  0  0
 22 13  2  0  0  0  0
 23 13  1  0  0  0  0
 24 14  2  0  0  0  0
 25 14  1  0  0  0  0
 26 15  2  0  0  0  0
 27 15  1  0  0  0  0
  7 28  1  6  0  0  0
  8 29  1  6  0  0  0
  9 30  1  1  0  0  0
 10 31  1  1  0  0  0
M  END


  Mrv0541 05311207092D          

 31 30  0  0  0  0            999 V2000
   10.1490    4.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979    3.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5877    4.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9379    4.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4485    5.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6384    5.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8789    4.8196    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0476    3.4164    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7481    4.3519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9886    5.9110    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0983    4.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0688    4.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0181    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7186    6.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4190    5.4433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3177    2.6369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2882    4.9755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7987    5.7551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3683    4.0401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5287    4.3519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6974    2.9487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9675    4.3519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8283    3.4164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4780    2.9487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9084    6.8465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2587    7.3142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3388    4.1960    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7776    4.1960    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2080    3.7283    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1785    6.0669    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
  6  5  1  0  0  0  0
  7  1  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
  7 16  1  6  0  0  0
  8 17  1  6  0  0  0
  9 18  1  1  0  0  0
 18 11  2  0  0  0  0
 10 19  1  1  0  0  0
 19 12  2  0  0  0  0
 11 20  1  4  0  0  0
 12 21  1  4  0  0  0
 22 13  2  0  0  0  0
 23 13  1  0  0  0  0
 24 14  2  0  0  0  0
 25 14  1  0  0  0  0
 26 15  2  0  0  0  0
 27 15  1  0  0  0  0
  7 28  1  6  0  0  0
  8 29  1  6  0  0  0
  9 30  1  1  0  0  0
 10 31  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030197

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H26N4O8/c1-7(16)12(21)19-10(15(26)27)5-6-11(20)18-9(14(24)25)4-2-3-8(17)13(22)23/h7-10H,2-6,16-17H2,1H3,(H,18,20)(H,19,21)(H,22,23)(H,24,25)(H,26,27)/t7-,8+,9-,10+/m0/s1

> <INCHI_KEY>
FMNCPUGORYYCEM-QCLAVDOMSA-N

> <FORMULA>
C15H26N4O8

> <MOLECULAR_WEIGHT>
390.3889

> <EXACT_MASS>
390.175063828

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
37.826119524219536

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,6S)-2-amino-6-{[(4R)-4-{[(2S)-2-amino-1-hydroxypropylidene]amino}-4-carboxy-1-hydroxybutylidene]amino}heptanedioic acid

> <ALOGPS_LOGP>
-3.71

> <JCHEM_LOGP>
-5.669918056461695

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.367249884332346

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9136490459727824

> <JCHEM_PKA_STRONGEST_BASIC>
9.851624304304286

> <JCHEM_POLAR_SURFACE_AREA>
229.11999999999998

> <JCHEM_REFRACTIVITY>
90.068

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,6S)-2-amino-6-{[(4R)-4-{[(2S)-2-amino-1-hydroxypropylidene]amino}-4-carboxy-1-hydroxybutylidene]amino}heptanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-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  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   28  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    8                                                       
CONECT    4    2    9                                                       
CONECT    5    6   10                                                       
CONECT    6    5   11                                                       
CONECT    7    1   12   16   28                                             
CONECT    8    3   13   17   29                                             
CONECT    9    4   14   18   30                                             
CONECT   10    5   15   19   31                                             
CONECT   11    6   18   20                                                  
CONECT   12    7   19   21                                                  
CONECT   13    8   22   23                                                  
CONECT   14    9   24   25                                                  
CONECT   15   10   26   27                                                  
CONECT   16    7                                                            
CONECT   17    8                                                            
CONECT   18    9   11                                                       
CONECT   19   10   12                                                       
CONECT   20   11                                                            
CONECT   21   12                                                            
CONECT   22   13                                                            
CONECT   23   13                                                            
CONECT   24   14                                                            
CONECT   25   14                                                            
CONECT   26   15                                                            
CONECT   27   15                                                            
CONECT   28    7                                                            
CONECT   29    8                                                            
CONECT   30    9                                                            
CONECT   31   10                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   60    0
END

Synonyms

Value	Source
Tri-dap	MeSH
(2R,6S)-2-Amino-6-{[(4R)-4-{[(2S)-2-amino-1-hydroxypropylidene]amino}-4-carboxy-1-hydroxybutylidene]amino}heptanedioate	Generator

Molecular Formula

C₁₅H₂₆N₄O₈

Average Mass

390.3889

Monoisotopic Mass

390.175063828

IUPAC Name

(2R,6S)-2-amino-6-{[(4R)-4-{[(2S)-2-amino-1-hydroxypropylidene]amino}-4-carboxy-1-hydroxybutylidene]amino}heptanedioic acid

Traditional Name

(2R,6S)-2-amino-6-{[(4R)-4-{[(2S)-2-amino-1-hydroxypropylidene]amino}-4-carboxy-1-hydroxybutylidene]amino}heptanedioic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H26N4O8/c1-7(16)12(21)19-10(15(26)27)5-6-11(20)18-9(14(24)25)4-2-3-8(17)13(22)23/h7-10H,2-6,16-17H2,1H3,(H,18,20)(H,19,21)(H,22,23)(H,24,25)(H,26,27)/t7-,8+,9-,10+/m0/s1

InChI Key

FMNCPUGORYYCEM-QCLAVDOMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Gamma-glutamyl alpha-amino acid
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alanine or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
D-alpha-amino acid
Tricarboxylic acid or derivatives
Amino fatty acid
Fatty acyl
Fatty amide
N-acyl-amine
Secondary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Amino acid
Carboxylic acid
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Amine
Organopnictogen compound
Organic oxygen compound
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	0.27 g/L	ALOGPS
logP	-3.7	ALOGPS
logP	-5.7	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	1.91	ChemAxon
pKa (Strongest Basic)	9.85	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	229.12 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	90.07 m³·mol⁻¹	ChemAxon
Polarizability	37.83 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

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated 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	1	Human ; Human feces; Human feces; pleural fluid plaque; bal	Unknown

Exposure Sources

Other Exposures

Source Type	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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25203562

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van der Werf MJ, Overkamp KM, Muilwijk B, Coulier L, Hankemeier T: Microbial metabolomics: toward a platform with full metabolome coverage. Anal Biochem. 2007 Nov 1;370(1):17-25. doi: 10.1016/j.ab.2007.07.022. Epub 2007 Aug 1. [PubMed:17765195 ]
Keseler IM, Collado-Vides J, Santos-Zavaleta A, Peralta-Gil M, Gama-Castro S, Muniz-Rascado L, Bonavides-Martinez C, Paley S, Krummenacker M, Altman T, Kaipa P, Spaulding A, Pacheco J, Latendresse M, Fulcher C, Sarker M, Shearer AG, Mackie A, Paulsen I, Gunsalus RP, Karp PD: EcoCyc: a comprehensive database of Escherichia coli biology. Nucleic Acids Res. 2011 Jan;39(Database issue):D583-90. doi: 10.1093/nar/gkq1143. Epub 2010 Nov 21. [PubMed:21097882 ]

Showing metabocard for L-Ala-D-Glu-meso-A2pm (MMDBc0030197)

MOL for #<Metabolite:0x00007f12408363b0>

3D MOL for #<Metabolite:0x00007f12408363b0>

3D SDF for #<Metabolite:0x00007f12408363b0>

3D-SDF for #<Metabolite:0x00007f12408363b0>

PDB for #<Metabolite:0x00007f12408363b0>

3D PDB for #<Metabolite:0x00007f12408363b0>

SMILES for #<Metabolite:0x00007f12408363b0>

INCHI for #<Metabolite:0x00007f12408363b0>

Structure for #<Metabolite:0x00007f12408363b0>

3D Structure for #<Metabolite:0x00007f12408363b0>