NP-MRD: Showing NP-Card for Tryptophanamide (NP0333351)

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Record Information

Version

2.0

Created at

2024-06-03 19:04:50 UTC

Updated at

2024-09-03 04:22:01 UTC

NP-MRD ID

NP0333351

Natural Product DOI

https://doi.org/10.57994/2711

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tryptophanamide

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 was first documented in 2018 (PMID: 30413031). Based on a literature review a significant number of articles have been published on Tryptophanamide (PMID: 36095307) (PMID: 38444395) (PMID: 36275105) (PMID: 33946050) (PMID: 32810781) (PMID: 31612007).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02152321402D          

 15 16  0  0  0  0            999 V2000
    2.2428   -2.5916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    0.0000 C   0  0  0  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
    1.1809   -3.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -4.1608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 12  1  0  0  0  0
  7 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333351

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CC1=CNC2=CC=CC=C12)C(N)=O

> <INCHI_IDENTIFIER>
InChI=1/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)

> <INCHI_KEY>
JLSKPBDKNIXMBS-UHFFFAOYNA-N

> <FORMULA>
C11H13N3O

> <MOLECULAR_WEIGHT>
203.245

> <EXACT_MASS>
203.105862051

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.54430537259975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
0.3694344323333335

> <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>
58.02500000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
tryptophan amide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-FEB-23         0                                  
HETATM    1  N   UNK     0       4.187  -4.838   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.680  -5.158   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.204  -6.622   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.235  -7.767   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       0.698  -6.943   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    4    7                                                  
CONECT   13    2   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₃N₃O

Average Mass

203.2450 Da

Monoisotopic Mass

203.10586 Da

IUPAC Name

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

Traditional Name

tryptophan amide

CAS Registry Number

Not Available

SMILES

NC(CC1=CNC2=CC=CC=C12)C(N)=O

InChI Identifier

InChI=1/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)

InChI Key

JLSKPBDKNIXMBS-UHFFFAOYNA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-03	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-03	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-03	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-03	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, D₂O, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-03	View Spectrum

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as tryptamines and derivatives. These 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

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	0.37	ChemAxon
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	21.54 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hendra R, Salib MN, Molinski TF: Spiroisoxazoline Inhibitors of Acetylcholinesterase from Pseudoceratina verrucosa. Quantitative Chiroptical Analysis of Configurational Heterogeneity, and Total Synthesis of (+/-)-Methyl Purpuroceratate C. J Nat Prod. 2022 Sep 23;85(9):2207-2216. doi: 10.1021/acs.jnatprod.2c00595. Epub 2022 Sep 12. [PubMed:36095307 ]
Di X, Rouger C, Hardardottir I, Freysdottir J, Molinski TF, Tasdemir D, Omarsdottir S: 6-Bromoindole Derivatives from the Icelandic Marine Sponge Geodia barretti: Isolation and Anti-Inflammatory Activity. Mar Drugs. 2018 Nov 8;16(11):437. doi: 10.3390/md16110437. [PubMed:30413031 ]
Liu Y, Li L, Feng J, Wan B, Tu Q, Cai W, Jin F, Tang G, Rodrigues LR, Zhang X, Yin J, Zhang Y: Modulation of chronic obstructive pulmonary disease progression by antioxidant metabolites from Pediococcus pentosaceus: enhancing gut probiotics abundance and the tryptophan-melatonin pathway. Gut Microbes. 2024 Jan-Dec;16(1):2320283. doi: 10.1080/19490976.2024.2320283. Epub 2024 Mar 6. [PubMed:38444395 ]
Khanikar RR, Kalita P, Narzary M, Basumatary D, Bharati AJ, Priyadarshi A, Swaminathan R, Bailung H, Sankaranarayanan K: Cold atmospheric plasma driven self-assembly in serum proteins: insights into the protein aggregation to biomaterials. RSC Adv. 2022 Sep 15;12(40):26211-26219. doi: 10.1039/d2ra04318a. eCollection 2022 Sep 12. [PubMed:36275105 ]
Deng Y, Shuai P, Wang H, Zhang S, Li J, Du M, Huang P, Qu C, Huang L: Untargeted metabolomics for uncovering plasma biological markers of wet age-related macular degeneration. Aging (Albany NY). 2021 May 4;13(10):13968-14000. doi: 10.18632/aging.203006. Epub 2021 May 4. [PubMed:33946050 ]
Kumaran R, Gayathri S, Augustine Arul Prasad T, Dhenadhayalan N, Keerthiga R, Sureka S, Jeevitha K, Karthick P: Fluorescence and quantum mechanical approach on the interaction of amides and their role on the stability and coexistence of the rotamer conformations of L-tryptophan in aqueous solution. Spectrochim Acta A Mol Biomol Spectrosc. 2020 Dec 15;243:118791. doi: 10.1016/j.saa.2020.118791. Epub 2020 Aug 3. [PubMed:32810781 ]
Yu X, Bao Y, Meng X, Wang S, Li T, Chang X, Xu W, Yang G, Bo T: Multi-pathway integrated adjustment mechanism of licorice flavonoids presenting anti-inflammatory activity. Oncol Lett. 2019 Nov;18(5):4956-4963. doi: 10.3892/ol.2019.10793. Epub 2019 Sep 4. [PubMed:31612007 ]
Moriya Y, Kogame A, Tagawa Y, Morohashi A, Kondo T, Asahi S, Benet LZ: The Enhancement of Subcutaneous First-Pass Metabolism Causes Nonlinear Pharmacokinetics of TAK-448 after a Single Subcutaneous Administration to Rats. Drug Metab Dispos. 2019 Sep;47(9):1004-1012. doi: 10.1124/dmd.119.087148. Epub 2019 Jun 14. [PubMed:31201213 ]
Molina-Bolivar JA, Galisteo-Gonzalez F, Ruiz CC, Medina-O'Donnell M, Martinez A, Parra A: Maslinic acid conjugate with 7-amino-4-methylcoumarin as probe to monitor the temperature dependent conformational changes of human serum albumin by FRET. Spectrochim Acta A Mol Biomol Spectrosc. 2019 May 5;214:161-169. doi: 10.1016/j.saa.2019.02.014. Epub 2019 Feb 11. [PubMed:30776717 ]
Moriya Y, Kogame A, Tagawa Y, Morohashi A, Kondo T, Asahi S: Investigation of disposition for TAK-448, a synthetic peptide of kisspeptin analog, in rats and dogs using the radiolabeled TAK-448 suitable for pharmacokinetic study. Xenobiotica. 2019 Jul;49(7):833-839. doi: 10.1080/00498254.2018.1499152. Epub 2018 Sep 12. [PubMed:30044673 ]

Showing NP-Card for Tryptophanamide (NP0333351)

MOL for NP0333351 (Tryptophanamide)

3D MOL for NP0333351 (Tryptophanamide)

3D SDF for NP0333351 (Tryptophanamide)

3D-SDF for NP0333351 (Tryptophanamide)

PDB for NP0333351 (Tryptophanamide)

3D PDB for NP0333351 (Tryptophanamide)

SMILES for NP0333351 (Tryptophanamide)

INCHI for NP0333351 (Tryptophanamide)

Structure for NP0333351 (Tryptophanamide)

3D Structure for NP0333351 (Tryptophanamide)