Showing metabocard for N(6)-[(indole-3-yl)acetyl]-L-lysine (MMDBc0056199)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-06-17 20:19:20 UTC
Update Date2022-08-12 20:09:37 UTC
Metabolite IDMMDBc0056199
Metabolite Identification
Common NameN(6)-[(indole-3-yl)acetyl]-L-lysine
DescriptionN(6)-[(indol-3-yl)acetyl]-L-lysine, also known as indole-3-acetyl-epsilon-lysine or iaa-lysine, 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. Based on a literature review very few articles have been published on N(6)-[(indol-3-yl)acetyl]-L-lysine.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007fd5cdbe9420>

  Mrv1652306172222192D          

 23 24  0  0  1  0            999 V2000
   -5.7455    6.1714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5525    6.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6696    3.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3840    3.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4906    5.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9551    3.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1045    5.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0985    3.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2419    3.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7101    3.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9564    3.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0426    4.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406    3.9532    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8496    4.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5275    3.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4738    3.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406    4.7782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8130    3.5407    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2621    4.2307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5275    4.7782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883    3.9532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4738    2.7157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406    3.1282    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12  5  2  0  0  0  0
 12 11  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  2  0  0  0  0
 14 12  1  0  0  0  0
 15  9  1  0  0  0  0
 16 13  1  0  0  0  0
 13 17  1  1  0  0  0
 18  8  1  4  0  0  0
 18 15  2  0  0  0  0
 19 10  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  2  0  0  0  0
 22 16  1  0  0  0  0
 13 23  1  1  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fd5cdbe9420>

Download
3D SDF for #<Metabolite:0x00007fd5cdbe9420>
  Mrv1652306172222192D          

 23 24  0  0  1  0            999 V2000
   -5.7455    6.1714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5525    6.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6696    3.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3840    3.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4906    5.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9551    3.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1045    5.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0985    3.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2419    3.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7101    3.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9564    3.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0426    4.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406    3.9532    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8496    4.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5275    3.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4738    3.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406    4.7782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8130    3.5407    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2621    4.2307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5275    4.7782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883    3.9532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4738    2.7157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406    3.1282    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12  5  2  0  0  0  0
 12 11  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  2  0  0  0  0
 14 12  1  0  0  0  0
 15  9  1  0  0  0  0
 16 13  1  0  0  0  0
 13 17  1  1  0  0  0
 18  8  1  4  0  0  0
 18 15  2  0  0  0  0
 19 10  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  2  0  0  0  0
 22 16  1  0  0  0  0
 13 23  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0056199

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](N)(CCCCN=C(O)CC1=CNC2=CC=CC=C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H21N3O3/c17-13(16(21)22)6-3-4-8-18-15(20)9-11-10-19-14-7-2-1-5-12(11)14/h1-2,5,7,10,13,19H,3-4,6,8-9,17H2,(H,18,20)(H,21,22)/t13-/m0/s1

> <INCHI_KEY>
FKIGOUKDKBOZID-ZDUSSCGKSA-N

> <FORMULA>
C16H21N3O3

> <MOLECULAR_WEIGHT>
303.362

> <EXACT_MASS>
303.158291548

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.72381565321608

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-6-{[1-hydroxy-2-(1H-indol-3-yl)ethylidene]amino}hexanoic acid

> <JCHEM_LOGP>
-1.37455438868291

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.210894035388955

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.111773822325156

> <JCHEM_PKA_STRONGEST_BASIC>
9.527049704049404

> <JCHEM_POLAR_SURFACE_AREA>
111.7

> <JCHEM_REFRACTIVITY>
83.5834

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-6-{[1-hydroxy-2-(1H-indol-3-yl)ethylidene]amino}hexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007fd5cdbe9420>
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PDB for #<Metabolite:0x00007fd5cdbe9420>
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     -10.725  11.520   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.231  11.840   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.117   7.379   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.450   6.609   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.249  10.055   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.783   6.609   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -13.262  10.696   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.784   7.379   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.785   6.609   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -12.525   6.753   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -11.119   7.379   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -11.280   8.911   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.449   7.379   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -12.786   9.231   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.451   7.379   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.885   6.609   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -0.449   8.919   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -7.118   6.609   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0     -13.556   7.897   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -8.451   8.919   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.218   7.379   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.885   5.069   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0      -0.449   5.839   0.000  0.00  0.00           H+0
CONECT    1    2    5                                                       
CONECT    2    1    7                                                       
CONECT    3    4    6                                                       
CONECT    4    3    8                                                       
CONECT    5    1   12                                                       
CONECT    6    3   13                                                       
CONECT    7    2   14                                                       
CONECT    8    4   18                                                       
CONECT    9   11   15                                                       
CONECT   10   11   19                                                       
CONECT   11    9   10   12                                                  
CONECT   12    5   11   14                                                  
CONECT   13    6   16   17   23                                             
CONECT   14    7   12   19                                                  
CONECT   15    9   18   20                                                  
CONECT   16   13   21   22                                                  
CONECT   17   13                                                            
CONECT   18    8   15                                                       
CONECT   19   10   14                                                       
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22   16                                                            
CONECT   23   13                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

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3D PDB for #<Metabolite:0x00007fd5cdbe9420>
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SMILES for #<Metabolite:0x00007fd5cdbe9420>
[H][C@](N)(CCCCN=C(O)CC1=CNC2=CC=CC=C12)C(O)=O
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INCHI for #<Metabolite:0x00007fd5cdbe9420>
InChI=1S/C16H21N3O3/c17-13(16(21)22)6-3-4-8-18-15(20)9-11-10-19-14-7-2-1-5-12(11)14/h1-2,5,7,10,13,19H,3-4,6,8-9,17H2,(H,18,20)(H,21,22)/t13-/m0/s1
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Synonyms
ValueSource
N6-[(indol-3-yl)Acetyl]-L-lysineChEBI
N6-[(Indole-3-yl)acetyl]-L-lysineChEBI
Indole-3-acetyl-epsilon-lysineMeSH
IAA-lysineMeSH
Indoleacetic acid-lysineMeSH
Molecular FormulaC16H21N3O3
Average Mass303.362
Monoisotopic Mass303.158291548
IUPAC Name(2S)-2-amino-6-{[1-hydroxy-2-(1H-indol-3-yl)ethylidene]amino}hexanoic acid
Traditional Name(2S)-2-amino-6-{[1-hydroxy-2-(1H-indol-3-yl)ethylidene]amino}hexanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(CCCCN=C(O)CC1=CNC2=CC=CC=C12)C(O)=O
InChI Identifier
InChI=1S/C16H21N3O3/c17-13(16(21)22)6-3-4-8-18-15(20)9-11-10-19-14-7-2-1-5-12(11)14/h1-2,5,7,10,13,19H,3-4,6,8-9,17H2,(H,18,20)(H,21,22)/t13-/m0/s1
InChI KeyFKIGOUKDKBOZID-ZDUSSCGKSA-N