NP-MRD: Showing NP-Card for N-Malonyltryptophan (NP0049430)

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Record Information

Version

2.0

Created at

2022-03-17 21:12:26 UTC

Updated at

2022-03-17 21:12:26 UTC

NP-MRD ID

NP0049430

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Malonyltryptophan

Description

N-Malonyltryptophan belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. A tryptophan derivative resulting from the formal condensation of the alpha-amino group of tryptophan with malonic acid. N-Malonyltryptophan is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, N-Malonyltryptophan has been detected, but not quantified in, several different foods, such as garden tomato, herbs and spices, opium poppies, and pulses. N-Malonyltryptophan is found in Ephedra distachya, Gleditschia triacanthos, Lupinus angustifolius , Magnolia sp., Medicago sativa , Melilotus albus and Papaver somniferum . N-Malonyltryptophan was first documented in 2011 (PMID: 21958116). This could make N-malonyltryptophan a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241209412D          

 21 22  0  0  0  0            999 V2000
   -1.6957   -0.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2802   -0.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0765   -0.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2897   -1.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7065   -1.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9103   -1.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2171   -2.0416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5762   -1.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8719   -0.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4222   -0.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4015   -0.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8141   -0.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6393   -0.8176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8141    0.6112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6393    0.6112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0519   -0.1024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4015   -1.5328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0519    1.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8771    1.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2897    2.0416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2897    0.6112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1  9  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 12 13  2  0  0  0  0
 12 17  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049430

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H14N2O5/c17-12(6-13(18)19)16-11(14(20)21)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>
OVEAWSPZRGBTSS-UHFFFAOYSA-N

> <FORMULA>
C14H14N2O5

> <MOLECULAR_WEIGHT>
290.2714

> <EXACT_MASS>
290.090271568

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.89197540605339

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-carboxyacetamido)-3-(1H-indol-3-yl)propanoic acid

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
0.8874520950000001

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.205958104902131

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5150888337811983

> <JCHEM_PKA_STRONGEST_BASIC>
-6.053641428002946

> <JCHEM_POLAR_SURFACE_AREA>
119.49

> <JCHEM_REFRACTIVITY>
71.9907

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2-carboxyacetamido)-3-(1H-indol-3-yl)propanoic 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      -3.165  -1.485   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.256  -0.394   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.743  -0.794   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.141  -2.281   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.052  -3.369   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.566  -2.971   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -2.272  -3.811   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.076  -2.841   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.628  -1.403   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.788  -0.112   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.749  -0.191   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.520  -1.526   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.060  -1.526   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       1.520   1.141   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       3.060   1.141   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.830  -0.191   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.749  -2.861   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.830   2.476   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.371   2.476   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.141   3.811   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.141   1.141   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    1    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15                                                            
CONECT   17   12                                                            
CONECT   18   15   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
2-(2-Carboxyacetamido)-3-(1H-indol-3-yl)propanoic acid	ChEBI
N-Malonyl-tryptophan	ChEBI
2-(2-Carboxyacetamido)-3-(1H-indol-3-yl)propanoate	Generator
2-[(2-Carboxy-1-hydroxyethylidene)amino]-3-(1H-indol-3-yl)propanoate	Generator

Chemical Formula

C₁₄H₁₄N₂O₅

Average Mass

290.2714 Da

Monoisotopic Mass

290.09027 Da

IUPAC Name

2-(2-carboxyacetamido)-3-(1H-indol-3-yl)propanoic acid

Traditional Name

2-(2-carboxyacetamido)-3-(1H-indol-3-yl)propanoic acid

CAS Registry Number

29399-11-9

SMILES

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

InChI Identifier

InChI=1S/C14H14N2O5/c17-12(6-13(18)19)16-11(14(20)21)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

OVEAWSPZRGBTSS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ephedra distachya	LOTUS Database	35616633
Gleditschia triacanthos	-	KNApSAcK
Lupinus angustifolius	Plant	KNApSAcK
Magnolia sp.	Plant	KNApSAcK
Medicago sativa	Plant	KNApSAcK
Melilotus albus	Plant	KNApSAcK
Papaver somniferum	Plant	KNApSAcK
Solanum lycopersicum	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Indolyl carboxylic acid derivative
3-alkylindole
Indole
Indole or derivatives
Dicarboxylic acid or derivatives
Substituted pyrrole
Benzenoid
1,3-dicarbonyl compound
Heteroaromatic compound
Pyrrole
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Carboxylic acid
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	1.1	ALOGPS
logP	0.89	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.52	ChemAxon
pKa (Strongest Basic)	-6.1	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	71.99 m³·mol⁻¹	ChemAxon
Polarizability	27.89 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

HMDB0039500

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019107

KNApSAcK ID

C00000118

Chemspider ID

4371010

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5199636

PDB ID

Not Available

ChEBI ID

142268

Good Scents ID

Not Available

References

General References

Vallverdu-Queralt A, Medina-Remon A, Casals-Ribes I, Amat M, Lamuela-Raventos RM: A metabolomic approach differentiates between conventional and organic ketchups. J Agric Food Chem. 2011 Nov 9;59(21):11703-10. doi: 10.1021/jf202822s. Epub 2011 Oct 11. [PubMed:21958116 ]

Showing NP-Card for N-Malonyltryptophan (NP0049430)

MOL for NP0049430 (N-Malonyltryptophan)

3D MOL for NP0049430 (N-Malonyltryptophan)

3D SDF for NP0049430 (N-Malonyltryptophan)

3D-SDF for NP0049430 (N-Malonyltryptophan)

PDB for NP0049430 (N-Malonyltryptophan)

3D PDB for NP0049430 (N-Malonyltryptophan)

SMILES for NP0049430 (N-Malonyltryptophan)

INCHI for NP0049430 (N-Malonyltryptophan)

Structure for NP0049430 (N-Malonyltryptophan)

3D Structure for NP0049430 (N-Malonyltryptophan)