MiMeDB: Showing metabocard for LL-2,6-Diaminoheptanedioate (MMDBc0049924)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:46:23 UTC

Update Date

2022-12-15 22:52:19 UTC

Metabolite ID

MMDBc0049924

Metabolite Identification

Common Name

LL-2,6-Diaminoheptanedioate

Description

LL-2,6-Diaminoheptanedioate, also known as diaminopimelic acid or DAPA, is a lysine-like amino acid derivative that is a key component of the bacterial cell wall. DAPA is incorporated or integrated into peptidoglycan of gram negative bacteria and is the attachment point for Braun's lipoprotein (BLP or Murein Lipoprotein). BLP is found in gram-negative cell walls and is one of the most abundant membrane proteins. BLP is bound at its C-terminal end (a lysine) by a covalent bond to the peptidoglycan layer (specifically to diaminopimelic acid molecules) and is embedded in the outer membrane by its hydrophobic head (a cysteine with lipids attached). BLP tightly links the two layers and provides structural integrity to the bacterial outer membrane. Diaminopimelic acid can be found in human urine or feces due to the lysis or enzymatic breakdown of gram negative gut microbes.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309042000222D          

 13 12  0  0  1  0            999 V2000
    7.2849    3.3809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  1  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
    5.8559    2.5559    0.0000 C   0  0  0  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
    4.4270    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4270    3.3809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 O   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  0  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
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0049924

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H14N2O4/c8-4(6(10)11)2-1-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1

> <INCHI_KEY>
GMKMEZVLHJARHF-WHFBIAKZSA-N

> <FORMULA>
C7H14N2O4

> <MOLECULAR_WEIGHT>
190.1971

> <EXACT_MASS>
190.095356946

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.933170312561906

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,6S)-2,6-diaminoheptanedioic acid

> <ALOGPS_LOGP>
-4.13

> <JCHEM_LOGP>
-5.545367993935247

> <ALOGPS_LOGS>
-1.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.585040505515717

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8470749826619342

> <JCHEM_PKA_STRONGEST_BASIC>
9.827564769536531

> <JCHEM_POLAR_SURFACE_AREA>
126.64000000000001

> <JCHEM_REFRACTIVITY>
43.63940000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diamino-pimelic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  N   UNK     0      13.598   6.311   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       8.264   6.311   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.596   4.771   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       6.930   2.461   0.000  0.00  0.00           O+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+0
HETATM   13  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    2   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

COMPND    HMDB0001370
HETATM    1  N1  UNL     1      -3.203  -0.540  -1.056  1.00  0.00           N  
HETATM    2  C1  UNL     1      -2.263  -0.506   0.071  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.945   0.074  -0.372  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.000   0.096   0.794  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.370   0.632   0.401  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.026  -0.204  -0.676  1.00  0.00           C  
HETATM    7  N2  UNL     1       2.179  -1.550  -0.171  1.00  0.00           N  
HETATM    8  C6  UNL     1       3.380   0.414  -0.913  1.00  0.00           C  
HETATM    9  O1  UNL     1       4.396  -0.279  -0.657  1.00  0.00           O  
HETATM   10  O2  UNL     1       3.504   1.694  -1.394  1.00  0.00           O  
HETATM   11  C7  UNL     1      -2.830   0.170   1.223  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.344   0.164   2.359  1.00  0.00           O  
HETATM   13  O4  UNL     1      -4.028   0.889   1.027  1.00  0.00           O  
HETATM   14  H1  UNL     1      -3.295   0.371  -1.515  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.977  -1.336  -1.681  1.00  0.00           H  
HETATM   16  H3  UNL     1      -2.069  -1.581   0.319  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.174   1.096  -0.753  1.00  0.00           H  
HETATM   18  H5  UNL     1      -0.518  -0.484  -1.236  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.091  -0.904   1.204  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.410   0.836   1.544  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.316   1.693   0.150  1.00  0.00           H  
HETATM   22  H9  UNL     1       2.009   0.527   1.309  1.00  0.00           H  
HETATM   23  H10 UNL     1       1.450  -0.188  -1.626  1.00  0.00           H  
HETATM   24  H11 UNL     1       1.977  -2.282  -0.894  1.00  0.00           H  
HETATM   25  H12 UNL     1       3.126  -1.724   0.235  1.00  0.00           H  
HETATM   26  H13 UNL     1       3.946   2.428  -0.829  1.00  0.00           H  
HETATM   27  H14 UNL     1      -4.713   0.492   0.423  1.00  0.00           H  
CONECT    1    2   14   15
CONECT    2    3   11   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7    8   23
CONECT    7   24   25
CONECT    8    9    9   10
CONECT   10   26
CONECT   11   12   12   13
CONECT   13   27
END

Synonyms

Value	Source
(S,S)-2,6-Diaminopimelic acid	ChEBI
(S-(R,r))-2,6-diaminoheptanedioic acid	ChEBI
L,L-2,6-Diaminopimelic acid	ChEBI
LL-2,6-Diaminoheptanedioate	ChEBI
LL-2,6-Diaminopimelate	ChEBI
LL-2,6-Diaminopimelic acid	Kegg
(S,S)-2,6-Diaminopimelate	Generator
(S-(R,r))-2,6-diaminoheptanedioate	Generator
L,L-2,6-Diaminopimelate	Generator
LL-2,6-Diaminoheptanedioic acid	Generator
Diaminopimelate	Generator
( (R,s)-2,6-diamino-heptanedioate	HMDB
( (R,s)-2,6-diamino-heptanedioic acid	HMDB
(2R,6S)-2,6-diamino-Heptanedioate	HMDB
(2R,6S)-2,6-diamino-Heptanedioic acid	HMDB
(R,s)-2,6-diamino-heptanedioate	HMDB
(R,s)-2,6-diamino-heptanedioic acid	HMDB
2,6-diamino-Heptanedioate	HMDB
2,6-diamino-Heptanedioic acid	HMDB
2,6-Diaminoheptanedioate	HMDB
2,6-Diaminoheptanedioic acid	HMDB
2,6-Diaminopimelate	HMDB
2,6-Diaminopimelic acid	HMDB, MeSH
a,A'-diaminopimelate	HMDB
a,A'-diaminopimelic acid	HMDB
a,e-Diaminopimelate	HMDB
a,e-Diaminopimelic acid	HMDB
D,L-Diaminopimelate	HMDB
D,L-meso-Diaminoheptanedioate	HMDB
D,L-meso-Diaminoheptanedioic acid	HMDB
DAPA	HMDB
DL-2,6-Diaminoheptanedioate	HMDB
DL-2,6-Diaminoheptanedioic acid	HMDB
DL-2,6-Diaminopimelate	HMDB
DL-2,6-Diaminopimelic acid	HMDB
L,L-2,6-Diaminoheptanedioate	HMDB
L,L-2,6-Diaminoheptanedioic acid	HMDB
L,L-Diaminopimelate	HMDB
meso-1-alpha,epsilon-Diaminopimelate	HMDB
meso-2,6-diamino-Heptanedioate	HMDB
meso-2,6-diamino-Heptanedioic acid	HMDB
meso-2,6-Diaminoheptanedioate	HMDB
meso-2,6-Diaminoheptanedioic acid	HMDB
meso-alpha,Alpha'-diaminopimelate	HMDB
meso-alpha,Alpha'-diaminopimelic acid	HMDB
meso-alpha,epsilon-Diaminopimelate	HMDB
meso-alpha,epsilon-Diaminopimelic acid	HMDB
meso-Diaminoheptanedioate	HMDB
meso-Diaminoheptanedioic acid	HMDB
meso-Diaminopimelate	HMDB
Acid, diaminopimelic	MeSH, HMDB
2,6 Diaminopimelic acid	MeSH, HMDB
Acid, 2,6-diaminopimelic	MeSH, HMDB
Diamino-pimelate	Generator, HMDB
Diaminopimelic acid	MeSH

Molecular Formula

C₇H₁₄N₂O₄

Average Mass

190.1971

Monoisotopic Mass

190.095356946

IUPAC Name

(2S,6S)-2,6-diaminoheptanedioic acid

Traditional Name

diamino-pimelic acid

CAS Registry Number

583-93-7

SMILES

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

InChI Identifier

InChI=1S/C7H14N2O4/c8-4(6(10)11)2-1-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1

InChI Key

GMKMEZVLHJARHF-WHFBIAKZSA-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
Medium-chain fatty acid
Amino fatty acid
Dicarboxylic acid or derivatives
Fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Organopnictogen compound
Organic nitrogen compound
Amine
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2,6-diaminopimelic acid (CHEBI:16026 )
Dicarboxylic acids (LMFA01170102 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	14.1 g/L	ALOGPS
logP	-4.1	ALOGPS
logP	-5.5	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	9.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	126.64 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	43.64 m³·mol⁻¹	ChemAxon
Polarizability	18.93 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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-0umi-1950000000-749403a0eb6d05c7903e	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-0uk9-1980000000-1b092f9141e7549bee24	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0umi-1950000000-749403a0eb6d05c7903e	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0uk9-1980000000-1b092f9141e7549bee24	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dm-9500000000-5d0aafd0747a1090e055	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-014i-4590000000-b941e92697a8b7800912	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004l-0900000000-d85213bd7ac426f10cd7	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9100000000-add590f1b216bdb40334	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-de98ed3bb8c48b6f9852	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-2c8a0ca138ef6ea5ef43	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-003r-9600000000-19f54d2417fe44d0eba3	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-e8b0bbffeaa501a6fedd	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-91296097628a67dd97ef	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-e5c4e034dcab0695e0ce	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-002r-0900000000-2a19445fee9eade1d538	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-f44538bc8ae3a51cbbc6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-003r-9700000000-3baa36a29b4ed6172da0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-1900000000-cf39d89ce72ac9ddaf51	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0200-6900000000-6f21b7798408480c1bfc	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9300000000-6e778092666f89ff4211	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-28fbb202ae5558af7594	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-004i-1900000000-8a1ee3da7fbe94f840c2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-8caae42eda716644fdc1	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0005-1900000000-be94a16bee7fad24d5d9	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-5900000000-896859ce722942f9dd68	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006t-9200000000-50c1b5a4f7b19e8ff0db	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-5ecd829b51ba774883f6	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1900000000-53b7aee01233b5b73d3e	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9400000000-2cc35eb21a44b2d472b5	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0079-0900000000-a0ce1f9601e9b8d83ccf	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dj-6900000000-cc22f522673c5549366c	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Urine

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
MMDBr0006985	LL-2,6-Diaminoheptanedioate	L-Glutamic acid	Not Available	VMH	30371894
MMDBr0007300	LL-2,6-Diaminoheptanedioate	Meso-2,6-Diaminoheptanedioate	Not Available	VMH	30371894
MMDBr0007566	N-Succinyl-LL-2,6-diaminoheptanedioate	LL-2,6-Diaminoheptanedioate	Not Available	VMH	30371894
MMDBr0008516	L-Glutamic acid	LL-2,6-Diaminoheptanedioate	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	448	Human feces; Human pleural fluid plaque; Pig ; Human ; Human supragingival plaque; Human saliva; Cattle ; Human stool; Human subgingival plaque; Catfish	Metabolic reconstruction
Bacteria	Proteobacteria	554	Human feces; Human sputum; Human ; Human pleural fluid plaque; Human stool; Human unknown; Pig ; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Cattle ; River trout ; Rat ; Sheep ; Chicken ; Human subgingival plaque; American dog tick ; Turkey ; Dog ; Lion	Metabolic reconstruction
Bacteria	Bacteroidetes	131	Human feces; Human appendix biopsy; Human ; Human stool; Human urine; Human gastric fluid; Human saliva; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Actinobacteria	153	Human feces; Human ; Human sputum; Human pleural fluid plaque; Human dental plaque; Human nasopharyngeal swab; Human bronchial brush; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Tenericutes	2	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	8	Human feces; Pig ; Human	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1		Metabolic reconstruction
Bacteria	Cyanobacteria	34	Human
Bacteria	Aquificae	2
Archaea/Archaea	Euryarchaeota	11		Metabolic reconstruction
Bacteria	Chlamydiae	10	Human ; Sheep ; Cat
Bacteria	Chlorobi	1
Bacteria	Elusimicrobia	1
Bacteria	Gemmatimonadetes	1
Bacteria	nah	1
Bacteria	Thermotogae	1
Bacteria	Chloroflexi	3

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Urine	Detected and Quantified	0.08	0.03	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	11262151
Human Blood	Detected but not Quantified							HMDB

External Links

HMDB ID

HMDB0001370

DrugBank ID

DB03590

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Diaminopimelic acid

METLIN ID

352

PubChem Compound

439283

PDB ID

Not Available

ChEBI ID

16026

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Hamaker BR, Rivera K, Morales E, Graham GG: Effect of dietary fiber and starch on fecal composition in preschool children consuming maize, amaranth, or cassava flours. J Pediatr Gastroenterol Nutr. 1991 Jul;13(1):59-66. doi: 10.1097/00005176-199107000-00011. [PubMed:1656007 ]
Ladesic B, Tomasic J, Kveder S, Hrsak I: The metabolic fate of 14C-labeled immunoadjuvant peptidoglycan monomer. II. In vitro studies. Biochim Biophys Acta. 1981 Nov 18;678(1):12-7. doi: 10.1016/0304-4165(81)90042-8. [PubMed:6118181 ]
Borruat G, Roten CA, Fay LB, Karamata D: A high-performance liquid chromatography method for the detection of diaminopimelic acid in urine. Anal Biochem. 2001 Apr 1;291(1):11-6. doi: 10.1006/abio.2001.5016. [PubMed:11262151 ]
Iida S, Taniguchi H, Kageyama A, Yazawa K, Chibana H, Murata S, Nomura F, Kroppenstedt RM, Mikami Y: Gordonia otitidis sp. nov., isolated from a patient with external otitis. Int J Syst Evol Microbiol. 2005 Sep;55(Pt 5):1871-1876. doi: 10.1099/ijs.0.63282-0. [PubMed:16166681 ]

Showing metabocard for LL-2,6-Diaminoheptanedioate (MMDBc0049924)

MOL for #<Metabolite:0x00007fdb71637cd0>

3D MOL for #<Metabolite:0x00007fdb71637cd0>

3D SDF for #<Metabolite:0x00007fdb71637cd0>

3D-SDF for #<Metabolite:0x00007fdb71637cd0>

PDB for #<Metabolite:0x00007fdb71637cd0>

3D PDB for #<Metabolite:0x00007fdb71637cd0>

SMILES for #<Metabolite:0x00007fdb71637cd0>

INCHI for #<Metabolite:0x00007fdb71637cd0>

Structure for #<Metabolite:0x00007fdb71637cd0>

3D Structure for #<Metabolite:0x00007fdb71637cd0>