Lanthionine (BioDeep_00000169991)
Secondary id: BioDeep_00000899057, BioDeep_00001872245
human metabolite Chemicals and Drugs Toxin Antibiotics
代谢物信息卡片
(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}propanoic acid
化学式: C6H12N2O4S (208.05177519999998)
中文名称: DL-羊毛硫氨酸, L-羊毛硫氨酸
谱图信息:
最多检出来源 Homo sapiens(blood) 8.57%
Reviewed
Last reviewed on 2024-06-29.
Cite this Page
Lanthionine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/lanthionine (retrieved
2024-11-25) (BioDeep RN: BioDeep_00000169991). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
分子结构信息
SMILES: C(C(C(=O)O)N)SCC(C(=O)O)N
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
描述信息
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.
Lanthionine belongs to the class of organic compounds known as L-cysteine-S-conjugates. These are compounds containing L-cysteine where the thio-group is conjugated. Lanthionine is a uremic toxin (PMID: 30087103).
In 1941, lanthionine was first isolated by treating wool with sodium carbonate. It was found to be a sulfur-containing amino acid; accordingly it was given the name lanthionine [wool (Latin: Lana), sulfur (Greek: theîon)].[1] Lanthionine was first synthesized by alkylation of cysteine with β-chloroalanine.[2] Lanthionines are found widely in nature. They have been isolated from human hair, lactalbumin, and feathers. Lanthionines have also been found in bacterial cell walls and are the components of a group of gene-encoded peptide antibiotics called lantibiotics, which includes nisin (a food preservative), subtilin, epidermin (effective against Staphylococcus and Streptococcus), and ancovenin (an enzyme inhibitor).[3][4]
L-Lanthionine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=922-55-4 (retrieved 2024-06-29) (CAS RN: 922-55-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
同义名列表
19 个代谢物同义名
(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}propanoic acid; S-[(2R)-2-Amino-2-carboxyethyl]-L-cysteine; (R,R)-2,6-Diamino-4-thiaheptanedioic acid; (R,R)-3,3-Thiobis-(2-aminopropanoic acid); (R,R)-Bis(2-amino-2-carboxyethyl)sulphide; (R)-S-(2-Amino-2-carboxyethyl)-L-cysteine; (R,R)-Bis(2-amino-2-carboxyethyl)sulfide; (R,R)-2,6-Diamino-4-thiaheptanedioate; (R,R)-3,3-Thiobis-(2-aminopropanoate); N-(2-Amino-2-carboxyethyl)-D-cysteine; Lanthionine, (L)-(R)-isomer; beta,Beta-thiodi-L-alanine; Β,beta-thiodi-L-alanine; b,Beta-thiodi-L-alanine; 3,3-Thiobis-L-alanine; 3,3-Thiodi-L-alanine; 3,3-Thiodialanine; L-Lanthionine; Lanthionine
数据库引用编号
8 个数据库交叉引用编号
- ChEBI: CHEBI:21347
- PubChem: 98504
- HMDB: HMDB0240656
- Wikipedia: Lanthionine
- MetaCyc: CPD-3736
- chemspider: 88959
- CAS: 922-55-4
- RefMet: Lanthionine
分类词条
相关代谢途径
Reactome(4)
BioCyc(0)
PlantCyc(0)
代谢反应
12 个相关的代谢反应过程信息。
Reactome(12)
- Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Amino acid and derivative metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Sulfur amino acid metabolism:
H2O + L-Cystathionine ⟶ 2OBUTA + L-Cys + ammonia - Degradation of cysteine and homocysteine:
H2O + HCYS ⟶ 2OBUTA + H2S + ammonia - Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Amino acid and derivative metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Sulfur amino acid metabolism:
H2O + L-Cystathionine ⟶ 2OBUTA + L-Cys + ammonia - Degradation of cysteine and homocysteine:
H2O + HCYS ⟶ 2OBUTA + H2S + ammonia - Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Amino acid and derivative metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Sulfur amino acid metabolism:
H2O + L-Cystathionine ⟶ 2OBUTA + L-Cys + ammonia - Degradation of cysteine and homocysteine:
H2O + HCYS ⟶ 2OBUTA + H2S + ammonia
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Michelle R Denburg, Yunwen Xu, Alison G Abraham, Josef Coresh, Jingsha Chen, Morgan E Grams, Harold I Feldman, Paul L Kimmel, Casey M Rebholz, Eugene P Rhee, Ramachandran S Vasan, Bradley A Warady, Susan L Furth. Metabolite Biomarkers of CKD Progression in Children.
Clinical journal of the American Society of Nephrology : CJASN.
2021 08; 16(8):1178-1189. doi:
10.2215/cjn.00220121. [PMID: 34362785] - Hamada Saad, Saefuddin Aziz, Matthias Gehringer, Markus Kramer, Jan Straetener, Anne Berscheid, Heike Brötz-Oesterhelt, Harald Gross. Nocathioamides, Uncovered by a Tunable Metabologenomic Approach, Define a Novel Class of Chimeric Lanthipeptides.
Angewandte Chemie (International ed. in English).
2021 07; 60(30):16472-16479. doi:
10.1002/anie.202102571. [PMID: 33991039] - Alessandra Fortunata Perna, Luigi Russo, Vittoria D'Esposito, Pietro Formisano, Dario Bruzzese, Carmela Vigorito, Annapaola Coppola, Patrizia Lombari, Domenico Russo, Diego Ingrosso. Lanthionine, a Novel Uremic Toxin, in the Vascular Calcification of Chronic Kidney Disease: The Role of Proinflammatory Cytokines.
International journal of molecular sciences.
2021 Jun; 22(13):. doi:
10.3390/ijms22136875. [PMID: 34206780] - Brian J Koos, Jeffrey A Gornbein. Early pregnancy metabolites predict gestational diabetes mellitus: implications for fetal programming.
American journal of obstetrics and gynecology.
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10.1016/j.ajog.2020.07.050. [PMID: 32739399] - Pawel Namsolleck, Alan Richardson, Gert N Moll, Axel Mescheder. LP2, the first lanthipeptide GPCR agonist in a human pharmacokinetics and safety study.
Peptides.
2021 02; 136(?):170468. doi:
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Molecular immunology.
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