NP-MRD: Showing NP-Card for L-N-(1H-Indol-3-ylacetyl)aspartic acid (NP0049188)

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Record Information

Version

2.0

Created at

2022-03-17 21:08:30 UTC

Updated at

2022-03-17 21:08:30 UTC

NP-MRD ID

NP0049188

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-N-(1H-Indol-3-ylacetyl)aspartic acid

Description

L-N-(1H-Indol-3-ylacetyl)aspartic acid, also known as aspartic acid, N-(indol-3-ylacetyl)- (7ci) or indole-3-acetylasparaginic 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. L-N-(1H-Indol-3-ylacetyl)aspartic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, L-N-(1H-Indol-3-ylacetyl)aspartic acid has been detected, but not quantified in, a few different foods, such as garden tomato (var.), Opium poppies, and pulses. L-N-(1H-Indol-3-ylacetyl)aspartic acid is found in Gleditschia triacanthos, Glycine max. , Lupinus angustifolius , Magnolia sp., Papaver somniferum and Solanum lycopersicum . This could make L-N-(1H-indol-3-ylacetyl)aspartic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241218012D          

 21 22  0  0  0  0            999 V2000
    2.1443    0.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -0.3229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1443   -0.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059   -1.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7394   -2.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9303   -2.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7686   -1.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3344   -0.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3344    0.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7686    0.6470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7686    1.3753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4968    1.8609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4961    0.2436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7679    0.6470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2021    0.0003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1220    1.8609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6063    1.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3344    1.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0627    1.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4675    0.9711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6292    2.3459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 17  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0049188

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC(NC(=O)CC1=CNC2=C1C=CC=C2)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)

> <INCHI_KEY>
VAFNMNRKDDAKRM-UHFFFAOYSA-N

> <FORMULA>
C14H14N2O5

> <MOLECULAR_WEIGHT>
290.2714

> <EXACT_MASS>
290.090271568

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
28.18168812826304

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[2-(1H-indol-3-yl)acetamido]butanedioic acid

> <ALOGPS_LOGP>
1.04

> <JCHEM_LOGP>
0.531425191

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.520219862773287

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7408154764353134

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6883227075491307

> <JCHEM_POLAR_SURFACE_AREA>
119.49000000000001

> <JCHEM_REFRACTIVITY>
71.7849

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[2-(1H-indol-3-yl)acetamido]butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       4.003   0.604   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       4.908  -0.603   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.003  -1.811   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.304  -3.322   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.247  -4.379   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.737  -3.926   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.435  -2.416   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.491  -1.359   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.491   0.152   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.435   1.208   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.435   2.567   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.794   3.474   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.793   0.455   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.433   1.208   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.377   0.001   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       0.228   3.474   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -1.132   2.718   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.491   3.625   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.850   3.172   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.606   1.813   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.908   4.379   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    3    7    9                                                  
CONECT    9    1    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14   13   15   17                                                  
CONECT   15   14                                                            
CONECT   16   11   17                                                       
CONECT   17   14   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
L-N-(1H-indol-3-Ylacetyl)aspartate	Generator
(Indole-3-acetyl)aspartic acid	HMDB
(Indoleacetyl)aspartic acid	HMDB
3-Indolylacetyl-L-aspartic acid	HMDB
Aspartic acid, N-(indol-3-ylacetyl)- (7ci)	HMDB
Aspartic acid, N-(indol-3-ylacetyl)-, L- (8ci)	HMDB
Indole-3-acetyl-L-aspartic acid	HMDB
Indole-3-acetylasparaginic acid	HMDB
Indoleacetylaspartate	HMDB
Indolyl-3-aspartic acid	HMDB
L-Aspartic acid, N-indol-3-ylacetyl- (6ci)	HMDB
N-(1H-indol-3-Ylacetyl)-L-aspartic acid	HMDB
2-{[1-hydroxy-2-(1H-indol-3-yl)ethylidene]amino}butanedioate	Generator

Chemical Formula

C₁₄H₁₄N₂O₅

Average Mass

290.2714 Da

Monoisotopic Mass

290.09027 Da

IUPAC Name

2-[2-(1H-indol-3-yl)acetamido]butanedioic acid

Traditional Name

2-[2-(1H-indol-3-yl)acetamido]butanedioic acid

CAS Registry Number

2456-73-7

SMILES

OC(=O)CC(NC(=O)CC1=CNC2=C1C=CC=C2)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)

InChI Key

VAFNMNRKDDAKRM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Gleditschia triacanthos	-	KNApSAcK
Glycine max.	Plant	KNApSAcK
Lupinus angustifolius	Plant	KNApSAcK
Magnolia sp.	Plant	KNApSAcK
Papaver somniferum	Plant	KNApSAcK
Solanum lycopersicum	Plant	KNApSAcK
Solanum lycopersicum var. lycopersicum	FooDB	KNAPSACK

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-alpha amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Dicarboxylic acid or derivatives
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid
Azacycle
Organoheterocyclic compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aspartic acid derivative (CHEBI:86909 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.04	ALOGPS
logP	0.53	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.74	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	119.49 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	71.78 m³·mol⁻¹	ChemAxon
Polarizability	28.18 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

External Links

HMDB ID

HMDB0038666

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018065

KNApSAcK ID

C00000117

Chemspider ID

3845644

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4656408

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for L-N-(1H-Indol-3-ylacetyl)aspartic acid (NP0049188)

MOL for NP0049188 (L-N-(1H-Indol-3-ylacetyl)aspartic acid)

3D MOL for NP0049188 (L-N-(1H-Indol-3-ylacetyl)aspartic acid)

3D SDF for NP0049188 (L-N-(1H-Indol-3-ylacetyl)aspartic acid)

3D-SDF for NP0049188 (L-N-(1H-Indol-3-ylacetyl)aspartic acid)

PDB for NP0049188 (L-N-(1H-Indol-3-ylacetyl)aspartic acid)

3D PDB for NP0049188 (L-N-(1H-Indol-3-ylacetyl)aspartic acid)

SMILES for NP0049188 (L-N-(1H-Indol-3-ylacetyl)aspartic acid)

INCHI for NP0049188 (L-N-(1H-Indol-3-ylacetyl)aspartic acid)

Structure for NP0049188 (L-N-(1H-Indol-3-ylacetyl)aspartic acid)

3D Structure for NP0049188 (L-N-(1H-Indol-3-ylacetyl)aspartic acid)