MiMeDB: Showing metabocard for (indol-3-yl)acetyl-L-aspartic acid (MMDBc0055019)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:39:58 UTC

Update Date

2022-08-12 20:09:11 UTC

Metabolite ID

MMDBc0055019

Metabolite Identification

Common Name

(indol-3-yl)acetyl-L-aspartic acid

Description

(indol-3-yl)acetyl-L-aspartate, also known as indole-3-acetyl-aspartic acid, belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom (indol-3-yl)acetyl-L-aspartate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on (indol-3-yl)acetyl-L-aspartate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221392D          

 22 23  0  0  1  0            999 V2000
   -1.2345    6.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4894    7.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7865    5.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2964    7.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2610    4.5776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1175    3.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284    5.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2610    5.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5935    5.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8485    6.6722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8320    2.9276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5465    4.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4031    2.9276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8320    2.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6735    6.6722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5465    3.3401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8320    4.5776    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.3114    3.3401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4031    2.1026    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.1175    1.6901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5465    1.6901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1175    2.5151    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  3  2  0  0  0  0
  9  8  1  0  0  0  0
 10  4  2  0  0  0  0
 10  9  1  0  0  0  0
 11  6  1  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 14 11  1  0  0  0  0
 15  7  1  0  0  0  0
 15 10  1  0  0  0  0
 11 16  1  6  0  0  0
 16 12  2  0  0  0  0
 12 17  1  4  0  0  0
 18 13  2  0  0  0  0
 19 13  1  0  0  0  0
 20 14  2  0  0  0  0
 21 14  1  0  0  0  0
 11 22  1  6  0  0  0
M  CHG  2  17  -1  19  -1
M  END
> <DATABASE_ID>
MMDBc0055019

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H14N2O5/c17-12(16-11(14(20)21)6-13(18)19)5-8-7-15-10-4-2-1-3-9(8)10/h1-4,7,11,15H,5-6H2,(H,16,17)(H,18,19)(H,20,21)/p-2/t11-/m0/s1

> <INCHI_KEY>
VAFNMNRKDDAKRM-NSHDSACASA-L

> <FORMULA>
C14H12N2O5

> <MOLECULAR_WEIGHT>
288.26

> <EXACT_MASS>
288.075718654

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.144756009805555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-3-carboxy-3-{[2-(1H-indol-3-yl)-1-oxidoethylidene]amino}propanoate

> <JCHEM_LOGP>
1.3510293180000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.107045325177408

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7838484566284816

> <JCHEM_PKA_STRONGEST_BASIC>
0.8470146158425496

> <JCHEM_POLAR_SURFACE_AREA>
128.64

> <JCHEM_REFRACTIVITY>
93.694

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-carboxy-3-{[2-(1H-indol-3-yl)-1-oxidoethylidene]amino}propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

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      -2.304  11.814   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.780  13.279   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.335  10.670   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.287  13.599   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.087   8.545   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.086   6.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.333  10.990   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.087  10.085   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.841  10.990   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.317  12.455   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.420   5.465   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.753   7.775   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.752   5.465   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.420   3.925   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -6.857  12.455   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -4.753   6.235   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0      -3.420   8.545   0.000  0.00  0.00           O-1
HETATM   18  O   UNK     0       0.581   6.235   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.752   3.925   0.000  0.00  0.00           O-1
HETATM   20  O   UNK     0      -2.086   3.155   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.753   3.155   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0      -2.086   4.695   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    9                                                       
CONECT    4    2   10                                                       
CONECT    5    8   12                                                       
CONECT    6   11   13                                                       
CONECT    7    8   15                                                       
CONECT    8    5    7    9                                                  
CONECT    9    3    8   10                                                  
CONECT   10    4    9   15                                                  
CONECT   11    6   14   16   22                                             
CONECT   12    5   16   17                                                  
CONECT   13    6   18   19                                                  
CONECT   14   11   20   21                                                  
CONECT   15    7   10                                                       
CONECT   16   11   12                                                       
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21   14                                                            
CONECT   22   11                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

Synonyms

Value	Source
Indole-3-acetyl-aspartate	ChEBI
Indole-3-acetyl-aspartate(2-)	ChEBI
Indole-3-acetylaspartate	ChEBI
N-(Indole-3-acetyl)aspartate(2-)	ChEBI
Indole-3-acetyl-aspartic acid	Generator
Indole-3-acetyl-aspartic acid(2-)	Generator
Indole-3-acetylaspartic acid	Generator
N-(Indole-3-acetyl)aspartic acid(2-)	Generator
(indol-3-yl)Acetyl-L-aspartic acid	Generator

Molecular Formula

C₁₄H₁₂N₂O₅

Average Mass

288.26

Monoisotopic Mass

288.075718654

IUPAC Name

(3S)-3-carboxy-3-{[2-(1H-indol-3-yl)-1-oxidoethylidene]amino}propanoate

Traditional Name

(3S)-3-carboxy-3-{[2-(1H-indol-3-yl)-1-oxidoethylidene]amino}propanoate

CAS Registry Number

Not Available

SMILES

[H][C@@](CC([O-])=O)(N=C([O-])CC1=CNC2=CC=CC=C12)C(O)=O

InChI Identifier

InChI=1S/C14H14N2O5/c17-12(16-11(14(20)21)6-13(18)19)5-8-7-15-10-4-2-1-3-9(8)10/h1-4,7,11,15H,5-6H2,(H,16,17)(H,18,19)(H,20,21)/p-2/t11-/m0/s1

InChI Key

VAFNMNRKDDAKRM-NSHDSACASA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Aspartic acid and derivatives

Alternative Parents

Substituents

Aspartic acid or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Dicarboxylic acid or derivatives
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Carboxamide group
Carboxylic acid salt
Secondary carboxylic acid amide
Azacycle
Carboxylic acid
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organic anion
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
logP	1.35	ChemAxon
pKa (Strongest Acidic)	3.78	ChemAxon
pKa (Strongest Basic)	0.85	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.64 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	93.69 m³·mol⁻¹	ChemAxon
Polarizability	27.14 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

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

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

5296528

KEGG Compound ID

Not Available

BioCyc ID

INDOLE-3-ACETYL-ASP

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6921620

PDB ID

Not Available

ChEBI ID

133482

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (indol-3-yl)acetyl-L-aspartic acid (MMDBc0055019)

MOL for #<Metabolite:0x00007fecb3082490>

3D MOL for #<Metabolite:0x00007fecb3082490>

3D SDF for #<Metabolite:0x00007fecb3082490>

3D-SDF for #<Metabolite:0x00007fecb3082490>

PDB for #<Metabolite:0x00007fecb3082490>

3D PDB for #<Metabolite:0x00007fecb3082490>

SMILES for #<Metabolite:0x00007fecb3082490>

INCHI for #<Metabolite:0x00007fecb3082490>

Structure for #<Metabolite:0x00007fecb3082490>

3D Structure for #<Metabolite:0x00007fecb3082490>