MiMeDB: Showing metabocard for N-Methyltryptophan (MMDBc0000726)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:53:37 UTC

Update Date

2022-08-31 06:11:39 UTC

Metabolite ID

MMDBc0000726

Metabolite Identification

Common Name

N-Methyltryptophan

Description

N(alpha)-methyl-L-tryptophan, also known as L-abrine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. N(alpha)-methyl-L-tryptophan is a very strong basic compound (based on its pKa). N(alpha)-methyl-L-tryptophan exists in all living organisms, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

 
  Mrv1652304021923582D          
 
 16 17  0  0  1  0            999 V2000
    7.5075  -10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5075  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2921  -11.8049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7771  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2921  -10.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7930  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0785  -10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0785  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7930  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2929   -9.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0082   -9.2414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0098   -8.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7125   -8.0123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2826   -7.9946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7094   -9.6483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4111   -9.2450    0.0000 C   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
  1  5  1  0  0  0  0
  1  6  2  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
  2  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 11 15  1  1  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000726

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N2O2/c1-13-11(12(15)16)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,11,13-14H,6H2,1H3,(H,15,16)/t11-/m0/s1

> <INCHI_KEY>
CZCIKBSVHDNIDH-NSHDSACASA-N

> <FORMULA>
C12H14N2O2

> <MOLECULAR_WEIGHT>
218.2518

> <EXACT_MASS>
218.105527702

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.99041669366013

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-(1H-indol-3-yl)-2-(methylamino)propanoic acid

> <ALOGPS_LOGP>
0.41

> <JCHEM_LOGP>
-0.8624855431895604

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.156484631505773

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.158616853111793

> <JCHEM_PKA_STRONGEST_BASIC>
10.642934922385205

> <JCHEM_POLAR_SURFACE_AREA>
65.11999999999999

> <JCHEM_REFRACTIVITY>
60.9774

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-methyl-L-tryptophan

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-APR-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-19         0                                  
HETATM    1  C   UNK     0      14.014 -20.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.014 -21.560   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      15.479 -22.036   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      16.384 -20.790   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.479 -19.544   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.680 -19.250   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.347 -20.020   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.347 -21.560   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.680 -22.330   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.480 -18.018   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.815 -17.251   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.818 -15.711   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      18.130 -14.956   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      15.461 -14.923   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0      18.124 -18.010   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      19.434 -17.257   0.000  0.00  0.00           C+0
CONECT    1    2    5    6                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    1   10                                                  
CONECT    6    1    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    2                                                       
CONECT   10    5   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

Synonyms

Value	Source
Abrine	ChEBI
L-Abrine	ChEBI
N-Methyl-L-tryptophan	ChEBI
N-Methyl-L-tryptophane	Kegg
N(a)-Methyl-L-tryptophan	Generator
N(Α)-methyl-L-tryptophan	Generator

Molecular Formula

C₁₂H₁₄N₂O₂

Average Mass

218.2518

Monoisotopic Mass

218.105527702

IUPAC Name

(2S)-3-(1H-indol-3-yl)-2-(methylamino)propanoic acid

Traditional Name

N-methyl-L-tryptophan

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H14N2O2/c1-13-11(12(15)16)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,11,13-14H,6H2,1H3,(H,15,16)/t11-/m0/s1

InChI Key

CZCIKBSVHDNIDH-NSHDSACASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are 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

L-alpha-amino acids

Alternative Parents

Substituents

3-alkylindole
L-alpha-amino acid
Indole
Indole or derivatives
Aralkylamine
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Amino acid
Azacycle
Organoheterocyclic compound
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-methyl-L-alpha-amino acid (CHEBI:15334 )
L-tryptophan derivative (CHEBI:15334 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.72 g/L	ALOGPS
logP	0.41	ALOGPS
logP	-0.86	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	2.16	ChemAxon
pKa (Strongest Basic)	10.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	65.12 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	60.98 m³·mol⁻¹	ChemAxon
Polarizability	22.99 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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 (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-0690000000-a98666c8a9c61813cca1	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0920000000-ab8dc3dd7978cc5d46a4	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-0900000000-48c7477e906b07bfa8a3	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1490000000-b7526370209f477b3d36	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00y0-6940000000-4054acf237567c27741b	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-3900000000-de5b7cdf2b6da100100a	2019-02-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	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	Bacteroidetes	1	Human appendix biopsy; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Proteobacteria	49	Human ; Human feces

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

HMDB0240319

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00001331

Chemspider ID

Not Available

KEGG Compound ID

C02983

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

160511

PDB ID

Not Available

ChEBI ID

15334

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-Methyltryptophan (MMDBc0000726)

MOL for #<Metabolite:0x00007fdb4c892450>

3D MOL for #<Metabolite:0x00007fdb4c892450>

3D SDF for #<Metabolite:0x00007fdb4c892450>

3D-SDF for #<Metabolite:0x00007fdb4c892450>

PDB for #<Metabolite:0x00007fdb4c892450>

3D PDB for #<Metabolite:0x00007fdb4c892450>

SMILES for #<Metabolite:0x00007fdb4c892450>

INCHI for #<Metabolite:0x00007fdb4c892450>

Structure for #<Metabolite:0x00007fdb4c892450>

3D Structure for #<Metabolite:0x00007fdb4c892450>