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

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:19:08 UTC

Update Date

2022-08-12 20:09:01 UTC

Metabolite ID

MMDBc0054578

Metabolite Identification

Common Name

N-acetyl-D-tryptophan

Description

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

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

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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	Deinococcus-thermus	1
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

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

References

Synthesis Reference

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:0x00007fdb4c2f5420>

3D MOL for #<Metabolite:0x00007fdb4c2f5420>

3D SDF for #<Metabolite:0x00007fdb4c2f5420>

3D-SDF for #<Metabolite:0x00007fdb4c2f5420>

PDB for #<Metabolite:0x00007fdb4c2f5420>

3D PDB for #<Metabolite:0x00007fdb4c2f5420>

SMILES for #<Metabolite:0x00007fdb4c2f5420>

INCHI for #<Metabolite:0x00007fdb4c2f5420>

Structure for #<Metabolite:0x00007fdb4c2f5420>

3D Structure for #<Metabolite:0x00007fdb4c2f5420>