NP-MRD: Showing NP-Card for (2s)-2-amino-3-(1h-indol-3-yl)propanimidic acid (NP0284693)

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Record Information

Version

2.0

Created at

2022-09-09 12:31:30 UTC

Updated at

2022-09-09 12:31:30 UTC

NP-MRD ID

NP0284693

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-amino-3-(1h-indol-3-yl)propanimidic acid

Description

Tryptophanamide belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine. Tryptophanamide is a very strong basic compound (based on its pKa). (2s)-2-amino-3-(1h-indol-3-yl)propanimidic acid is found in Daphnia pulex. An amino acid amide that is the carboxamide of L-tryptophan.

Structure

MOL SDF PDB SMILES InChI

LTN
  Mrv0541 02231217452D          

 16 17  0  0  0  0            999 V2000
    0.4738   -0.8957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3331   -1.0672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8852   -0.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302    0.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1544    0.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1544    1.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8689    0.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1151    0.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302    1.6654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8689    1.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5833    0.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5833    1.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5881   -1.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0360   -2.4649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3950   -2.0233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1527   -0.5118    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2 13  1  0  0  0  0
  2 16  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  2  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  2  0  0  0  0
  8  9  1  0  0  0  0
 10 12  2  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0284693

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](N)(CC1=CNC2=C1C=CC=C2)C(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H13N3O/c12-9(11(13)15)5-7-6-14-10-4-2-1-3-8(7)10/h1-4,6,9,14H,5,12H2,(H2,13,15)/t9-/m0/s1

> <INCHI_KEY>
JLSKPBDKNIXMBS-VIFPVBQESA-N

> <FORMULA>
C11H13N3O

> <MOLECULAR_WEIGHT>
203.2404

> <EXACT_MASS>
203.105862053

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
21.54754236117587

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-amino-3-(1H-indol-3-yl)propanamide

> <ALOGPS_LOGP>
0.35

> <JCHEM_LOGP>
0.3694344323333335

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.79051814205109

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.949795138253851

> <JCHEM_PKA_STRONGEST_BASIC>
7.966191419613276

> <JCHEM_POLAR_SURFACE_AREA>
84.9

> <JCHEM_REFRACTIVITY>
58.02500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-tryptophanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LTN                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       0.884  -1.672   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -0.622  -1.992   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.652  -0.848   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.176   0.617   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.288   1.093   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.288   2.633   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.622   0.323   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.082   1.863   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.176   3.109   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.622   3.403   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.955   1.093   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.955   2.633   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.098  -3.457   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.067  -4.601   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0      -2.604  -3.777   0.000  0.00  0.00           N+0
HETATM   16  H   UNK     0      -0.285  -0.955   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   13   16                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    9   10                                                  
CONECT    7    5   11                                                       
CONECT    8    4    9                                                       
CONECT    9    6    8                                                       
CONECT   10    6   12                                                       
CONECT   11    7   12                                                       
CONECT   12   10   11                                                       
CONECT   13    2   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    2                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
(S)-alpha-Amino-1H-indole-3-propionamide	ChEBI
L-Tryptophan amide	ChEBI
(S)-a-Amino-1H-indole-3-propionamide	Generator
(S)-Α-amino-1H-indole-3-propionamide	Generator
Tryptophanamide, (S)-isomer	MeSH
Tryptophanamide, (+-)-isomer	MeSH
Tryptophanamide monohydrochloride, (S)-isomer	MeSH
Tryptophanamide	MeSH

Chemical Formula

C₁₁H₁₃N₃O

Average Mass

203.2404 Da

Monoisotopic Mass

203.10586 Da

IUPAC Name

(2S)-2-amino-3-(1H-indol-3-yl)propanamide

Traditional Name

L-tryptophanamide

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CC1=CNC2=C1C=CC=C2)C(N)=O

InChI Identifier

InChI=1S/C11H13N3O/c12-9(11(13)15)5-7-6-14-10-4-2-1-3-8(7)10/h1-4,6,9,14H,5,12H2,(H2,13,15)/t9-/m0/s1

InChI Key

JLSKPBDKNIXMBS-VIFPVBQESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Daphnia pulex	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Tryptamines and derivatives

Alternative Parents

Substituents

Alpha-amino acid amide
Triptan
Alpha-amino acid or derivatives
3-alkylindole
Indole
Aralkylamine
Fatty amide
Substituted pyrrole
Fatty acyl
Benzenoid
Pyrrole
Heteroaromatic compound
Amino acid or derivatives
Carboxamide group
Primary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

amino acid amide (CHEBI:16533 )
tryptophan derivative (CHEBI:16533 )

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	0.35	ALOGPS
logP	0.37	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	15.95	ChemAxon
pKa (Strongest Basic)	7.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	84.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	58.02 m³·mol⁻¹	ChemAxon
Polarizability	21.55 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

DB04537

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00977

BioCyc ID

CPD-584

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439356

PDB ID

Not Available

ChEBI ID

16533

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-amino-3-(1h-indol-3-yl)propanimidic acid (NP0284693)

MOL for NP0284693 ((2s)-2-amino-3-(1h-indol-3-yl)propanimidic acid)

3D MOL for NP0284693 ((2s)-2-amino-3-(1h-indol-3-yl)propanimidic acid)

3D SDF for NP0284693 ((2s)-2-amino-3-(1h-indol-3-yl)propanimidic acid)

3D-SDF for NP0284693 ((2s)-2-amino-3-(1h-indol-3-yl)propanimidic acid)

PDB for NP0284693 ((2s)-2-amino-3-(1h-indol-3-yl)propanimidic acid)

3D PDB for NP0284693 ((2s)-2-amino-3-(1h-indol-3-yl)propanimidic acid)

SMILES for NP0284693 ((2s)-2-amino-3-(1h-indol-3-yl)propanimidic acid)

INCHI for NP0284693 ((2s)-2-amino-3-(1h-indol-3-yl)propanimidic acid)

Structure for NP0284693 ((2s)-2-amino-3-(1h-indol-3-yl)propanimidic acid)

3D Structure for NP0284693 ((2s)-2-amino-3-(1h-indol-3-yl)propanimidic acid)