MiMeDB: Showing metabocard for Indole-3-acetyl-epsilon-L-lysine (MMDBc0000982)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 18:40:20 UTC

Update Date

2022-08-31 06:17:27 UTC

Metabolite ID

MMDBc0000982

Metabolite Identification

Common Name

Indole-3-acetyl-epsilon-L-lysine

Description

SCHEMBL4290912 belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Based on a literature review very few articles have been published on SCHEMBL4290912.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305142120402D          

 22 23  0  0  0  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  0  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
  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
 17 13  1  0  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
M  END
> <DATABASE_ID>
MMDBc0000982

> <DATABASE_NAME>
MIME

> <SMILES>
NC(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)

> <INCHI_KEY>
FKIGOUKDKBOZID-UHFFFAOYSA-N

> <FORMULA>
C16H21N3O3

> <MOLECULAR_WEIGHT>
303.362

> <EXACT_MASS>
303.158291548

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.85126431028602

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.54

> <JCHEM_LOGP>
-1.37455438868291

> <ALOGPS_LOGS>
-3.65

> <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

> <ALOGPS_SOLUBILITY>
6.85e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-21         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
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                                                  
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                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

Synonyms

Not Available

Molecular Formula

C₁₆H₂₁N₃O₃

Average Mass

303.362

Monoisotopic Mass

303.158291548

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

NC(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)

InChI Key

FKIGOUKDKBOZID-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
3-alkylindole
Indole
Indole or derivatives
Medium-chain fatty acid
Amino fatty acid
Heterocyclic fatty acid
Substituted pyrrole
Benzenoid
Fatty acid
Fatty acyl
Pyrrole
Heteroaromatic compound
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Azacycle
Organoheterocyclic compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.068 g/L	ALOGPS
logP	-0.54	ALOGPS
logP	-1.4	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	2.11	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	111.7 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	83.58 m³·mol⁻¹	ChemAxon
Polarizability	32.85 Å³	ChemAxon
Number of Rings	2	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

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

Not Available

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		Metabolic reconstruction

Exposure Sources

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

2590971

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3344370

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Indole-3-acetyl-epsilon-L-lysine (MMDBc0000982)

MOL for #<Metabolite:0x00007fdb4c736200>

3D MOL for #<Metabolite:0x00007fdb4c736200>

3D SDF for #<Metabolite:0x00007fdb4c736200>

3D-SDF for #<Metabolite:0x00007fdb4c736200>

PDB for #<Metabolite:0x00007fdb4c736200>

3D PDB for #<Metabolite:0x00007fdb4c736200>

SMILES for #<Metabolite:0x00007fdb4c736200>

INCHI for #<Metabolite:0x00007fdb4c736200>

Structure for #<Metabolite:0x00007fdb4c736200>

3D Structure for #<Metabolite:0x00007fdb4c736200>