6-chloro-L-tryptophan (CHEBI:140077)

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CHEBI:140077 - 6-chloro-L-tryptophan

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ChEBI Name	6-chloro-L-tryptophan

ChEBI ID	CHEBI:140077

ChEBI ASCII Name	6-chloro-L-tryptophan

Definition	A non-proteinogenic L-α-amino acid that is L-tryptophan in which the hydrogen at position 6 on the indole ring has been replaced by a chlorine.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:47157

Supplier Information	ChemicalBook:CB0399395, eMolecules:28294244, ZINC000002020167

Download	Molfile XML SDF

more structures >>

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27 28 0 0 0 0 999 V2000

-1.9680 4.0660 5.9840 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.2730 2.8630 5.6000 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.1460 1.6160 5.8740 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.3790 0.3620 6.0180 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.8480 -0.1720 7.2250 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.8560 0.2470 8.5710 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.2000 -1.3640 6.8960 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.3380 -1.5390 5.5370 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.0490 -0.5000 4.9980 C 0 0 0 0 0 0 0 0 0 0 0 0

0.4430 -2.1630 7.8490 C 0 0 0 0 0 0 0 0 0 0 0 0

0.4220 -1.7280 9.1770 C 0 0 0 0 0 0 0 0 0 0 0 0

1.1970 -2.6760 10.3890 Cl 0 0 0 0 0 0 0 0 0 0 0 0

-0.2170 -0.5420 9.5350 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.8430 2.9200 4.1410 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.5070 3.4740 3.2710 O 0 0 0 0 0 0 0 0 0 0 0 0

0.3400 2.3170 3.8720 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.2650 4.7080 5.2690 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.9650 4.3430 6.9510 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3570 2.8340 6.2010 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7470 1.7930 6.7890 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9080 1.5330 5.0710 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.3490 1.1680 8.8660 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0290 -2.3210 5.0140 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.2570 -0.4690 3.9370 H 0 0 0 0 0 0 0 0 0 0 0 0

0.9380 -3.0840 7.5580 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.2280 -0.2110 10.5710 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6190 2.3580 2.9340 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 17 1 0 0 0 0

1 18 1 0 0 0 0

2 3 1 0 0 0 0

2 14 1 0 0 0 0

2 19 1 0 0 0 0

3 4 1 0 0 0 0

3 20 1 0 0 0 0

3 21 1 0 0 0 0

4 5 4 0 0 0 0

4 9 4 0 0 0 0

5 6 4 0 0 0 0

5 7 4 0 0 0 0

6 13 4 0 0 0 0

6 22 1 0 0 0 0

7 8 4 0 0 0 0

7 10 4 0 0 0 0

8 9 4 0 0 0 0

8 23 1 0 0 0 0

9 24 1 0 0 0 0

10 11 4 0 0 0 0

10 25 1 0 0 0 0

11 12 1 0 0 0 0

11 13 4 0 0 0 0

13 26 1 0 0 0 0

14 15 2 0 0 0 0

14 16 1 0 0 0 0

16 27 1 0 0 0 0

M END): 17 ms

reading 27 atoms

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Formula

C11H11ClN2O2

Net Charge

Average Mass

238.671

Monoisotopic Mass

238.05091

InChI

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

InChIKey

FICLVQOYKYBXFN-VIFPVBQESA-N

SMILES

C1(=CNC2=C1C=CC(=C2)Cl)C[C@@H](C(=O)O)N

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	6-chloro-L-tryptophan (CHEBI:140077) is a L-tryptophan derivative (CHEBI:47994) 6-chloro-L-tryptophan (CHEBI:140077) is a non-proteinogenic L-α-amino acid (CHEBI:83822) 6-chloro-L-tryptophan (CHEBI:140077) is a organochlorine compound (CHEBI:36683) 6-chloro-L-tryptophan (CHEBI:140077) is tautomer of 6-chloro-L-tryptophan zwitterion (CHEBI:139335)

Incoming	6-chloro-L-tryptophan zwitterion (CHEBI:139335) is tautomer of 6-chloro-L-tryptophan (CHEBI:140077)

IUPAC Name

6-chloro-L-tryptophan

Synonyms	Sources
(2S)-2-amino-3-(6-chloro-1H-indol-3-yl)propanoic acid	PDBeChem
6-chlorotryptophan	ChEBI

Manual Xrefs	Databases
6CW	PDBeChem
CPD-20612	MetaCyc
View more database links

Registry Number	Type	Source
9854848	Reaxys Registry Number	Reaxys

Citations

Chee SMQ, Wongsantichon J, Siau J, Thean D, Ferrer F, Robinson RC, Lane DP, Brown CJ, Ghadessy FJ (2017)
Structure-activity studies of Mdm2/Mdm4-binding stapled peptides comprising non-natural amino acids.
PloS one 12, e0189379 [PubMed:29228061]
[show Abstract]

Fukushima T, Sugiura A, Furuta I, Iwasa S, Iizuka H, Ichiba H, Onozato M, Hikawa H, Yokoyama Y (2015)
Enantiomeric Separation of Monosubstituted Tryptophan Derivatives and Metabolites by HPLC with a Cinchona Alkaloid-Based Zwitterionic Chiral Stationary Phase and Its Application to the Evaluation of the Optical Purity of Synthesized 6-Chloro-l-Tryptophan.
International journal of tryptophan research : IJTR 8, 1-5 [PubMed:25624766]
[show Abstract]

Hintersteiner M, Kimmerlin T, Garavel G, Schindler T, Bauer R, Meisner NC, Seifert JM, Uhl V, Auer M (2009)
A highly potent and cellularly active beta-peptidic inhibitor of the p53/hDM2 interaction.
Chembiochem : a European journal of chemical biology 10, 994-998 [PubMed:19267375]
[show Abstract]

Kwon I, Tirrell DA (2007)
Site-specific incorporation of tryptophan analogues into recombinant proteins in bacterial cells.
Journal of the American Chemical Society 129, 10431-10437 [PubMed:17685515]
[show Abstract]

Fasan R, Dias RL, Moehle K, Zerbe O, Obrecht D, Mittl PR, Grütter MG, Robinson JA (2006)
Structure-activity studies in a family of beta-hairpin protein epitope mimetic inhibitors of the p53-HDM2 protein-protein interaction.
Chembiochem : a European journal of chemical biology 7, 515-526 [PubMed:16511824]
[show Abstract]

Naritsin DB, Saito K, Markey SP, Chen CY, Heyes MP (1995)
Metabolism of L-tryptophan to kynurenate and quinolinate in the central nervous system: effects of 6-chlorotryptophan and 4-chloro-3-hydroxyanthranilate.
Journal of neurochemistry 65, 2217-2226 [PubMed:7595510]
[show Abstract]

Parli CJ, Krieter P, Schmidt B (1980)
Metabolism of 6-chlorotryptophan to 4-chloro-3-hydroxyanthranilic acid: a potent inhibitor of 3-hydroxyanthranilic acid oxidase.
Archives of biochemistry and biophysics 203, 161-166 [PubMed:6893263]

Last Modified

12 February 2018

CHEBI:140077 - 6-chloro-L-tryptophan

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