MiMeDB: Showing metabocard for N-acetyl-D-tryptophan (MMDBc0054578)

Microbial

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:19:08 UTC

Update Date

2025-10-07 16:04:19 UTC

Metabolite ID

MMDBc0054578

Metabolite Identification

Common Name

N-acetyl-D-tryptophan

Description

N-acetyl-D-tryptophan is a member of the amino acid derivative chemical class, specifically an N-acetylated form of the amino acid D-tryptophan. Its chemical structure features an acetyl group attached to the nitrogen atom of the tryptophan side chain, influencing its solubility and biological activity. In the realm of biochemistry, N-acetyl-D-tryptophan is involved in various metabolic pathways, serving as a significant metabolite in brain tissue where it is part of a complex network of biochemical interactions. For instance, studies have identified N-acetyl-D-tryptophan among other metabolites that are differentially regulated in brain tissue, highlighting its potential role in neurochemical processes (PMID:39844704 ). Additionally, it has been recognized in the context of flocculation processes, where it, along with other N-acetylated amino acids, was identified for the first time as secreted flocculants (PMID:40701379 ). This suggests that N-acetyl-D-tryptophan may play a role in cellular interactions and responses, although the specific biological significance of these pathways remains to be fully elucidated.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241222372D          

 18 19  0  0  1  0            999 V2000
    0.7145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8347    1.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6551    1.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9840    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1401    0.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8045    0.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -0.6674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13  1  1  0  0  0  0
  1  2  1  6  0  0  0
  2 15  1  0  0  0  0
  3  7  1  0  0  0  0
  4  3  1  0  0  0  0
  1  4  1  0  0  0  0
  5  3  2  0  0  0  0
 12  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  9  2  0  0  0  0
 12  9  1  0  0  0  0
 11 10  1  0  0  0  0
 14 13  1  0  0  0  0
 16 13  2  0  0  0  0
 18 15  1  0  0  0  0
 17 15  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054578

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)N[C@H](CC1=CNC2=CC=CC=C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H14N2O3/c1-8(16)15-12(13(17)18)6-9-7-14-11-5-3-2-4-10(9)11/h2-5,7,12,14H,6H2,1H3,(H,15,16)(H,17,18)/t12-/m1/s1

> <INCHI_KEY>
DZTHIGRZJZPRDV-GFCCVEGCSA-N

> <FORMULA>
C13H14N2O3

> <MOLECULAR_WEIGHT>
246.2619

> <EXACT_MASS>
246.100442324

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.8489235767553

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.45

> <JCHEM_LOGP>
0.9952236489999997

> <ALOGPS_LOGS>
-2.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.369297636096736

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.118377727694558

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4777090919661933

> <JCHEM_POLAR_SURFACE_AREA>
82.19

> <JCHEM_REFRACTIVITY>
65.6466

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-acetyl-D-tryptophan

> <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       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.425   2.653   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.798   1.246   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.956   2.814   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.703   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.862   1.568   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.235   0.161   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -2.798  -1.246   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
CONECT    1   13    2    4                                                  
CONECT    2    1   15                                                       
CONECT    3    7    4    5                                                  
CONECT    4    3    1                                                       
CONECT    5    3   12                                                       
CONECT    6    7    8                                                       
CONECT    7    3    6    9                                                  
CONECT    8    6   10                                                       
CONECT    9    7   11   12                                                  
CONECT   10    8   11                                                       
CONECT   11    9   10                                                       
CONECT   12    5    9                                                       
CONECT   13    1   14   16                                                  
CONECT   14   13                                                            
CONECT   15    2   18   17                                                  
CONECT   16   13                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

Synonyms

Value	Source
Acetyltryptophan	MeSH
N-Acetyltryptophanate sodium	MeSH
N-Acetyltryptophan	MeSH

Molecular Formula

C₁₃H₁₄N₂O₃

Average Mass

246.2619

Monoisotopic Mass

246.100442324

IUPAC Name

(2R)-2-acetamido-3-(1H-indol-3-yl)propanoic acid

Traditional Name

N-acetyl-D-tryptophan

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@H](CC1=CNC2=CC=CC=C12)C(O)=O

InChI Identifier

InChI=1S/C13H14N2O3/c1-8(16)15-12(13(17)18)6-9-7-14-11-5-3-2-4-10(9)11/h2-5,7,12,14H,6H2,1H3,(H,15,16)(H,17,18)/t12-/m1/s1

InChI Key

DZTHIGRZJZPRDV-GFCCVEGCSA-N

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
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Azacycle
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

D-tryptophan derivative (CHEBI:16734 )
N-acetyl-D-amino acid (CHEBI:16734 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.49 g/L	ALOGPS
logP	1.45	ALOGPS
logP	1	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.12	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	82.19 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.65 m³·mol⁻¹	ChemAxon
Polarizability	24.85 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9460000000-937bf2ebdeba4febf4d2	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f6t-0390000000-bee3f00676dbb20cddc3	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pb9-0960000000-ffc38c580062532632f8	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0900000000-5e314622f2cf80867542	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1290000000-2f09bb4277a17573a1d4	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfs-6890000000-cf484d59c551e83dba23	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mo-9500000000-49f44fec5a91f601a9b4	2016-09-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)		2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental)		2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0026117	D-Tryptophan	N-acetyl-D-tryptophan	D-amino-acid N-acetyltransferase HPA3	Acetylation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Deinococcus-thermus	1
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C03137

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439917

PDB ID

Not Available

ChEBI ID

16734

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for N-acetyl-D-tryptophan (MMDBc0054578)

MOL for #<Metabolite:0x00007fadcee41398>

3D MOL for #<Metabolite:0x00007fadcee41398>

3D SDF for #<Metabolite:0x00007fadcee41398>

3D-SDF for #<Metabolite:0x00007fadcee41398>

PDB for #<Metabolite:0x00007fadcee41398>

3D PDB for #<Metabolite:0x00007fadcee41398>

SMILES for #<Metabolite:0x00007fadcee41398>

INCHI for #<Metabolite:0x00007fadcee41398>

Structure for #<Metabolite:0x00007fadcee41398>

3D Structure for #<Metabolite:0x00007fadcee41398>