NP-MRD: Showing NP-Card for (2s)-2-[(2-carboxy-1-hydroxyethylidene)amino]-3-(1h-indol-3-yl)propanoic acid (NP0255775)

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Record Information

Version

2.0

Created at

2022-09-07 20:23:05 UTC

Updated at

2022-09-07 20:23:05 UTC

NP-MRD ID

NP0255775

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-[(2-carboxy-1-hydroxyethylidene)amino]-3-(1h-indol-3-yl)propanoic acid

Description

N-(Carboxyacetyl)-L-tryptophan belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. (2s)-2-[(2-carboxy-1-hydroxyethylidene)amino]-3-(1h-indol-3-yl)propanoic acid is found in Ephedra distachya. Based on a literature review very few articles have been published on N-(Carboxyacetyl)-L-tryptophan.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -2.4766    2.4141   -0.2624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3984    1.6657    0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5264    2.2197    0.7154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2984    0.1972   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3260   -0.3188    0.9183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6359   -0.1097    2.2580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2477   -0.9283    0.6369 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8337   -1.1963   -0.7266 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5316   -1.8312   -0.7598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5835   -1.0177   -0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1495   -1.2275    1.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0793   -0.2845    1.2763 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1612    0.5482    0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9569    1.6367    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230    2.3157   -1.1770 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8910    1.8954   -2.1286 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1092    0.7935   -1.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2220    0.0929   -0.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928   -2.1988   -1.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6720   -2.6289   -2.4610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8325   -2.7127   -0.5364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5065    3.0512    1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3089   -0.2378    0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9758   -0.0297   -1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7911    0.8402    2.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8837   -0.2385   -1.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4529   -2.7931   -0.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8373   -2.1038   -1.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9148   -2.0110    1.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633   -0.2085    2.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6878    1.9854    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4192    3.1879   -1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7975    2.4351   -3.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3886    0.4552   -2.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1620   -3.6574   -0.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  8 19  1  0
 19 21  1  0
 19 20  2  0
 18 10  1  0
 18 13  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  8 26  1  6
  9 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 21 35  1  0
M  END


  Mrv1652309072222232D          

 21 22  0  0  1  0            999 V2000
   -2.3020   -5.0184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470   -4.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990   -3.6207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.9238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  4  0  0  0
  5  7  2  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 10 18  1  0  0  0  0
 13 18  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255775

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC(O)=N[C@@H](CC1=CNC2=CC=CC=C12)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)/t11-/m0/s1

> <INCHI_KEY>
OVEAWSPZRGBTSS-NSHDSACASA-N

> <FORMULA>
C14H14N2O5

> <MOLECULAR_WEIGHT>
290.275

> <EXACT_MASS>
290.090271559

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.104679667306918

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-[(2-carboxy-1-hydroxyethylidene)amino]-3-(1H-indol-3-yl)propanoic acid

> <JCHEM_LOGP>
1.707056222

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.220235400118477

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.528737387197959

> <JCHEM_PKA_STRONGEST_BASIC>
0.8702334327063493

> <JCHEM_POLAR_SURFACE_AREA>
122.98

> <JCHEM_REFRACTIVITY>
72.51239999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2-carboxy-1-hydroxyethylidene)amino]-3-(1H-indol-3-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0      -4.297  -9.368   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.821  -7.903   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.852  -6.759   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.315  -7.583   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.869  -4.974   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      -0.333  -5.798   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.887  -3.189   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.411  -1.724   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.393  -3.509   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   10   13                                                  
CONECT   19    8   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

Not Available

Chemical Formula

C₁₄H₁₄N₂O₅

Average Mass

290.2750 Da

Monoisotopic Mass

290.09027 Da

IUPAC Name

(2S)-2-[(2-carboxy-1-hydroxyethylidene)amino]-3-(1H-indol-3-yl)propanoic acid

Traditional Name

(2S)-2-[(2-carboxy-1-hydroxyethylidene)amino]-3-(1H-indol-3-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CC(O)=N[C@@H](CC1=CNC2=CC=CC=C12)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)/t11-/m0/s1

InChI Key

OVEAWSPZRGBTSS-NSHDSACASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ephedra distachya	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon 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-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Indolyl carboxylic acid derivative
3-alkylindole
Indole
Indole or derivatives
Dicarboxylic acid or derivatives
Substituted pyrrole
1,3-dicarbonyl compound
Benzenoid
Pyrrole
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Organoheterocyclic compound
Azacycle
Organic oxide
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
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	1.71	ChemAxon
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	0.87	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	122.98 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	72.51 m³·mol⁻¹	ChemAxon
Polarizability	28.1 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

57568174

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15160194

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-[(2-carboxy-1-hydroxyethylidene)amino]-3-(1h-indol-3-yl)propanoic acid (NP0255775)

MOL for NP0255775 ((2s)-2-[(2-carboxy-1-hydroxyethylidene)amino]-3-(1h-indol-3-yl)propanoic acid)

3D MOL for NP0255775 ((2s)-2-[(2-carboxy-1-hydroxyethylidene)amino]-3-(1h-indol-3-yl)propanoic acid)

3D SDF for NP0255775 ((2s)-2-[(2-carboxy-1-hydroxyethylidene)amino]-3-(1h-indol-3-yl)propanoic acid)

3D-SDF for NP0255775 ((2s)-2-[(2-carboxy-1-hydroxyethylidene)amino]-3-(1h-indol-3-yl)propanoic acid)

PDB for NP0255775 ((2s)-2-[(2-carboxy-1-hydroxyethylidene)amino]-3-(1h-indol-3-yl)propanoic acid)

3D PDB for NP0255775 ((2s)-2-[(2-carboxy-1-hydroxyethylidene)amino]-3-(1h-indol-3-yl)propanoic acid)

SMILES for NP0255775 ((2s)-2-[(2-carboxy-1-hydroxyethylidene)amino]-3-(1h-indol-3-yl)propanoic acid)

INCHI for NP0255775 ((2s)-2-[(2-carboxy-1-hydroxyethylidene)amino]-3-(1h-indol-3-yl)propanoic acid)

Structure for NP0255775 ((2s)-2-[(2-carboxy-1-hydroxyethylidene)amino]-3-(1h-indol-3-yl)propanoic acid)

3D Structure for NP0255775 ((2s)-2-[(2-carboxy-1-hydroxyethylidene)amino]-3-(1h-indol-3-yl)propanoic acid)