MiMeDB: Showing metabocard for 7-chloro-L-tryptophan (MMDBc0054298)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:05:26 UTC

Update Date

2022-09-01 02:28:22 UTC

Metabolite ID

MMDBc0054298

Metabolite Identification

Common Name

7-chloro-L-tryptophan

Description

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05041402112D          

 17 18  0  0  1  0            999 V2000
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    2.0361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1659    1.4230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3440    2.9922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0150    3.4338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2700    2.6492    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  2  1  0  0  0  0
  7  6  1  0  0  0  0
  8  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  7  2  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
  9 13  1  1  0  0  0
 14  5  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
 16 11  1  0  0  0  0
  9 17  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054298

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](N)(CC1=CNC2=C1C=CC=C2Cl)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H11ClN2O2/c12-8-3-1-2-7-6(5-14-10(7)8)4-9(13)11(15)16/h1-3,5,9,14H,4,13H2,(H,15,16)/t9-/m0/s1

> <INCHI_KEY>
DMQFGLHRDFQKNR-VIFPVBQESA-N

> <FORMULA>
C11H11ClN2O2

> <MOLECULAR_WEIGHT>
238.67

> <EXACT_MASS>
238.050905313

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.39463834100242

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-(7-chloro-1H-indol-3-yl)propanoic acid

> <ALOGPS_LOGP>
-0.47

> <JCHEM_LOGP>
-0.48196116841515063

> <ALOGPS_LOGS>
-2.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.068343530785057

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.145768111719404

> <JCHEM_PKA_STRONGEST_BASIC>
9.395264482056405

> <JCHEM_POLAR_SURFACE_AREA>
79.11

> <JCHEM_REFRACTIVITY>
61.007600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-chlorotryptophan

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   13  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    7                                                       
CONECT    3    1    8                                                       
CONECT    4    6    9                                                       
CONECT    5    6   14                                                       
CONECT    6    4    5    7                                                  
CONECT    7    2    6   10                                                  
CONECT    8    3   10   12                                                  
CONECT    9    4   11   13   17                                             
CONECT   10    7    8   14                                                  
CONECT   11    9   15   16                                                  
CONECT   12    8                                                            
CONECT   13    9                                                            
CONECT   14    5   10                                                       
CONECT   15   11                                                            
CONECT   16   11                                                            
CONECT   17    9                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

Synonyms

Value	Source
7-Chlorotryptophan	ChEBI

Molecular Formula

C₁₁H₁₁ClN₂O₂

Average Mass

238.67

Monoisotopic Mass

238.050905313

IUPAC Name

(2S)-2-amino-3-(7-chloro-1H-indol-3-yl)propanoic acid

Traditional Name

7-chlorotryptophan

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CC1=CNC2=C1C=CC=C2Cl)C(O)=O

InChI Identifier

InChI=1S/C11H11ClN2O2/c12-8-3-1-2-7-6(5-14-10(7)8)4-9(13)11(15)16/h1-3,5,9,14H,4,13H2,(H,15,16)/t9-/m0/s1

InChI Key

DMQFGLHRDFQKNR-VIFPVBQESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
3-alkylindole
Indole
Aralkylamine
Aryl chloride
Aryl halide
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Organopnictogen compound
Primary aliphatic amine
Primary amine
Amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:47356 )
L-tryptophan derivative (CHEBI:47356 )
7-chlorotryptophan (CHEBI:47356 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.6 g/L	ALOGPS
logP	-0.47	ALOGPS
logP	-0.48	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	2.15	ChemAxon
pKa (Strongest Basic)	9.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.11 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	61.01 m³·mol⁻¹	ChemAxon
Polarizability	23.39 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_3_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0076-0970000000-6e646dc38f2170e19a51	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-989a7ccccfb567fce121	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-0900000000-964591700d2640e9e4b0	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-2090000000-3d0d9143670c69305c11	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9360000000-3b24a48695a6bcf91f1f	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fk9-9600000000-da3eef768c20cf318fbe	2019-02-23	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	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	Actinobacteria	1
Bacteria	Proteobacteria	2	Human ; Human subgingival plaque

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

C19687

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3081936

PDB ID

Not Available

ChEBI ID

47356

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 7-chloro-L-tryptophan (MMDBc0054298)

MOL for #<Metabolite:0x00007fdb445e5ed0>

3D MOL for #<Metabolite:0x00007fdb445e5ed0>

3D SDF for #<Metabolite:0x00007fdb445e5ed0>

3D-SDF for #<Metabolite:0x00007fdb445e5ed0>

PDB for #<Metabolite:0x00007fdb445e5ed0>

3D PDB for #<Metabolite:0x00007fdb445e5ed0>

SMILES for #<Metabolite:0x00007fdb445e5ed0>

INCHI for #<Metabolite:0x00007fdb445e5ed0>

Structure for #<Metabolite:0x00007fdb445e5ed0>

3D Structure for #<Metabolite:0x00007fdb445e5ed0>