MiMeDB: Showing metabocard for N6-Acetyl-LL-2,6-diaminoheptanedioate (MMDBc0049868)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:45:09 UTC

Update Date

2022-09-01 02:16:45 UTC

Metabolite ID

MMDBc0049868

Metabolite Identification

Common Name

N6-Acetyl-LL-2,6-diaminoheptanedioate

Description

N-acetyl-L,L-DAP 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 very few articles have been published on N-acetyl-L,L-DAP.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304302200452D          

 16 15  0  0  1  0            999 V2000
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2849    3.3809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    3.7934    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.7125    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  CHG  2  12  -1  15  -1
M  END
> <DATABASE_ID>
MMDBc0049868

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H16N2O5/c1-5(12)11-7(9(15)16)4-2-3-6(10)8(13)14/h6-7H,2-4,10H2,1H3,(H,11,12)(H,13,14)(H,15,16)/p-2/t6-,7-/m0/s1

> <INCHI_KEY>
KYVLWJXMCBZDRL-BQBZGAKWSA-L

> <FORMULA>
C9H14N2O5

> <MOLECULAR_WEIGHT>
230.221

> <EXACT_MASS>
230.091368719

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.029881777919122

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,6S)-2-amino-6-acetamidoheptanedioate

> <ALOGPS_LOGP>
-0.68

> <JCHEM_LOGP>
-3.546177306982192

> <ALOGPS_LOGS>
-0.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.9028673828804936

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0174103857764285

> <JCHEM_PKA_STRONGEST_BASIC>
9.526534205250046

> <JCHEM_POLAR_SURFACE_AREA>
135.38

> <JCHEM_REFRACTIVITY>
74.7574

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.99e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-acetyl-L,L-DAP

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-APR-22         0                                  
HETATM    1  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.596   6.311   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       6.930   4.001   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      13.598   6.311   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O-1
HETATM   13  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.264   6.311   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.597   7.081   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0       6.930   7.081   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    5   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

Synonyms

Not Available

Molecular Formula

C₉H₁₄N₂O₅

Average Mass

230.221

Monoisotopic Mass

230.091368719

IUPAC Name

(2S,6S)-2-amino-6-acetamidoheptanedioate

Traditional Name

N-acetyl-L,L-DAP

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H16N2O5/c1-5(12)11-7(9(15)16)4-2-3-6(10)8(13)14/h6-7H,2-4,10H2,1H3,(H,11,12)(H,13,14)(H,15,16)/p-2/t6-,7-/m0/s1

InChI Key

KYVLWJXMCBZDRL-BQBZGAKWSA-L

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
Alpha-amino acid
L-alpha-amino acid
Medium-chain fatty acid
Amino fatty acid
Dicarboxylic acid or derivatives
Fatty acid
Fatty acyl
Acetamide
Carboxamide group
Carboxylic acid salt
Secondary carboxylic acid amide
Amino acid
Carboxylic acid
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxide
Organic nitrogen compound
Carbonyl group
Amine
Organic oxygen compound
Hydrocarbon derivative
Organic anion
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	49.9 g/L	ALOGPS
logP	-0.68	ALOGPS
logP	-3.5	ChemAxon
logS	-0.73	ALOGPS
pKa (Strongest Acidic)	2.02	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	135.38 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	74.76 m³·mol⁻¹	ChemAxon
Polarizability	22.03 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

Not Available

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

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0006924	N6-Acetyl-LL-2,6-diaminoheptanedioate	LL-2,6-Diaminoheptanedioate	Not Available	VMH	30371894
MMDBr0008084	Oxoglutaric acid	N_Acetyl_L_2_amino_6_oxopimelate	Not Available	VMH	30371894
MMDBr0008533	N6-Acetyl-LL-2,6-diaminoheptanedioate	LL-2,6-Diaminoheptanedioate	Not Available	VMH	30371894

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	Firmicutes	293	Human feces; Human pleural fluid plaque; Pig ; Human ; Human supragingival plaque; Human saliva; Cattle ; Human subgingival plaque	Metabolic reconstruction
Bacteria	Proteobacteria	65	Human feces; Human sputum; Human ; Human pleural fluid plaque; Human stool	Metabolic reconstruction
Bacteria	Bacteroidetes	10	Human feces; Human appendix biopsy	Metabolic reconstruction
Bacteria	Actinobacteria	55	Human feces; Human ; Human supragingival plaque	Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction

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
Human Feces	Detected but not Quantified									HMDB

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

26333128

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

51351649

PDB ID

Not Available

ChEBI ID

Not Available

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 ]

Showing metabocard for N6-Acetyl-LL-2,6-diaminoheptanedioate (MMDBc0049868)

MOL for #<Metabolite:0x00007fececc8a808>

3D MOL for #<Metabolite:0x00007fececc8a808>

3D SDF for #<Metabolite:0x00007fececc8a808>

3D-SDF for #<Metabolite:0x00007fececc8a808>

PDB for #<Metabolite:0x00007fececc8a808>

3D PDB for #<Metabolite:0x00007fececc8a808>

SMILES for #<Metabolite:0x00007fececc8a808>

INCHI for #<Metabolite:0x00007fececc8a808>

Structure for #<Metabolite:0x00007fececc8a808>

3D Structure for #<Metabolite:0x00007fececc8a808>