L-lanthionine (CHEBI:21347)

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CHEBI:21347 - L-lanthionine

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ChEBI Name	L-lanthionine

ChEBI ID	CHEBI:21347

ChEBI ASCII Name	L-lanthionine

Definition	The L-enantiomer of lanthionine.

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

Supplier Information	eMolecules:6882610, ZINC000001730666

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

85F - Ideal conformer

Mrv1927 09132112523D

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Time for openFile(85F - Ideal conformer

Mrv1927 09132112523D

25 24 0 0 0 0 999 V2000

2.8140 1.3250 -1.0790 N 0 0 1 0 0 0 0 0 0 0 0 0

2.7140 0.4770 0.1170 C 0 0 1 0 0 0 0 0 0 0 0 0

1.4180 -0.3340 0.0610 C 0 0 1 0 0 0 0 0 0 0 0 0

0.0000 0.7950 0.0010 S 0 0 0 0 0 0 0 0 0 0 0 0

-1.4180 -0.3340 -0.0610 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.7140 0.4770 -0.1170 C 0 0 2 0 0 0 0 0 0 0 0 0

-2.8140 1.3230 1.0800 N 0 0 1 0 0 0 0 0 0 0 0 0

-3.8920 -0.4610 -0.1680 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.2420 -1.0360 -1.3290 O 0 0 0 0 0 0 0 0 0 0 0 0

-4.5220 -0.6950 0.8360 O 0 0 0 0 0 0 0 0 0 0 0 0

3.8920 -0.4610 0.1670 C 0 0 0 0 0 0 0 0 0 0 0 0

4.5220 -0.6940 -0.8370 O 0 0 0 0 0 0 0 0 0 0 0 0

4.2420 -1.0380 1.3280 O 0 0 0 0 0 0 0 0 0 0 0 0

3.6290 1.9180 -1.0350 H 0 0 0 0 0 0 0 0 0 0 0 0

2.8180 0.7660 -1.9190 H 0 0 0 0 0 0 0 0 0 0 0 0

2.7110 1.1050 1.0080 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4210 -0.9620 -0.8300 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3450 -0.9630 0.9480 H 0 0 0 0 0 0 0 0 0 0 0 0

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-2.7110 1.1060 -1.0070 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.6290 1.9170 1.0370 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.8180 0.7630 1.9190 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.0050 -1.6300 -1.3120 H 0 0 0 0 0 0 0 0 0 0 0 0

5.0050 -1.6320 1.3110 H 0 0 0 0 0 0 0 0 0 0 0 0

12 11 2 0 0 0 0

11 2 1 0 0 0 0

11 13 1 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 1 0 0 0 0

5 6 1 0 0 0 0

7 6 1 0 0 0 0

6 8 1 0 0 0 0

8 10 2 0 0 0 0

8 9 1 0 0 0 0

1 14 1 0 0 0 0

1 15 1 0 0 0 0

2 16 1 1 0 0 0

3 17 1 0 0 0 0

3 18 1 0 0 0 0

5 19 1 0 0 0 0

5 20 1 0 0 0 0

6 21 1 6 0 0 0

7 22 1 0 0 0 0

7 23 1 0 0 0 0

9 24 1 0 0 0 0

13 25 1 0 0 0 0

M END): 18 ms

reading 25 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

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25 atoms created

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Wikipedia	License
Lanthionine is a nonproteinogenic amino acid with the chemical formula (HOOC-CH(NH2)-CH2-S-CH2-CH(NH2)-COOH). It is typically formed by a cysteine residue and a dehydrated serine residue. Despite its name, lanthionine does not contain the element lanthanum.
Read full article at Wikipedia

Formula

C6H12N2O4S

Net Charge

Average Mass

208.230

Monoisotopic Mass

208.05178

InChI

InChI=1S/C6H12N2O4S/c7-3(5(9)10)1-13-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1

InChIKey

DWPCPZJAHOETAG-IMJSIDKUSA-N

SMILES

N[C@@H](CSC[C@H](N)C(O)=O)C(O)=O

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 )

Biological Role(s):	bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. (via lanthionine )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	L-lanthionine (CHEBI:21347) is a L-alanine derivative (CHEBI:83943) L-lanthionine (CHEBI:21347) is a lanthionine (CHEBI:25013) L-lanthionine (CHEBI:21347) is a non-proteinogenic L-α-amino acid (CHEBI:83822) L-lanthionine (CHEBI:21347) is tautomer of L-lanthionine dizwitterion (CHEBI:178193)

Incoming	L-lanthionine dizwitterion (CHEBI:178193) is tautomer of L-lanthionine (CHEBI:21347)

IUPAC Names

(2R,2'R)-3,3'-sulfanediylbis(2-aminopropanoic acid)

L-lanthionine

Synonyms	Sources
(R)-S-(2-amino-2-carboxyethyl)-L-cysteine	ChEBI
(R,R)-2,6-diamino-4-thiaheptanedioic acid	ChEBI
(R,R)-3,3'-thiobis-(2-aminopropanoic acid)	ChEBI
(R,R)-bis(2-amino-2-carboxyethyl)sulfide	ChEBI
3,3'-thiobis-L-alanine	ChEBI
3,3'-thiodi-L-alanine	MetaCyc
β,β'-thiodi-L-alanine	MetaCyc

Manual Xrefs	Databases
85F	PDBeChem
88959	ChemSpider
CPD-3736	MetaCyc
HMDB0240656	HMDB
Lanthionine	Wikipedia
View more database links

Registry Number	Type	Source
922-55-4	CAS Registry Number	ChemIDplus

Citations

Mothersole RG, Billett CR, Saini G, Mothersole MK, Darbyshire AL, Wolthers KR (2020)
S224 Presents a Catalytic Trade-off in PLP-Dependent l-Lanthionine Synthase from Fusobacterium nucleatum.
Biochemistry 59, 4250-4261 [PubMed:33112129]
[show Abstract]

Feldeková E, Solichová K, Horáčková Š, Kumherová M, Kyselka J (2020)
The impact of L-lanthionine supplementation on the production of nisin by lactococci
Eur Food Res Technol. 246, 845-851 [Agricola:IND606859743]
[show Abstract]

Mothersole RG, Wolthers KR (2019)
Structural and Kinetic Insight into the Biosynthesis of H₂S and l-Lanthionine from l-Cysteine by a Pyridoxal l-Phosphate-Dependent Enzyme from Fusobacterium nucleatum.
Biochemistry 58, 3592-3603 [PubMed:31398016]
[show Abstract]

Ricci G, Federici G, Lucente G, Achilli M, Cavallini D (1982)
L-lanthionine oxidation by snake venom L-amino acid oxidase.
Physiological chemistry and physics 14, 193-199 [PubMed:7185053]
[show Abstract]

Harpp DN, Gleason JG (1971)
Preparation and mass spectral properties of cystine and lanthionine derivatives. A novel synthesis of L-lanthionine by selective desulfurization.
The Journal of organic chemistry 36, 73-80 [PubMed:5543047]

Rao DR, Ennor AH, Thorpe B (1966)
The occurrence of L-lanthionine in the amino-acid pool of insects.
Biochemical and biophysical research communications 22, 163-168 [PubMed:5948138]

Sloane NH, Unich KG (1966)
Studies on amino acids in embryonic tissue. I. L-Lanthionine, a naturally occurring amino acid in the chick embryo.
Biochemistry 5, 2658-2665 [PubMed:6007887]

Last Modified

13 September 2021

CHEBI:21347 - L-lanthionine

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