(2R,3R,4R)-2-Amino-4-hydroxy-3-methylpentanoic acid (BioDeep_00000000239)
Secondary id: BioDeep_00000265384, BioDeep_00000902013, BioDeep_00001867478, BioDeep_00001891744
human metabolite PANOMIX_OTCML-2023 Endogenous
代谢物信息卡片
化学式: C6H13NO3 (147.0895)
中文名称: 4-羟基异亮氨酸, (4S)-4-羟基-L-异亮氨酸, 4-羟基-L-异亮氨酸, 羟基异亮氨酸
谱图信息:
最多检出来源 Homo sapiens(otcml) 24.48%
分子结构信息
SMILES: CC(C(C)O)C(C(=O)O)N
InChI: InChI=1S/C6H13NO3/c1-3(4(2)8)5(7)6(9)10/h3-5,8H,7H2,1-2H3,(H,9,10)
描述信息
(4S)-4-hydroxy-L-isoleucine is an L-isoleucine derivative that is L-isoleucine bearing a (4S)-hydroxy substituent. It has a role as a plant metabolite. It is an amino alcohol, a L-isoleucine derivative and a non-proteinogenic L-alpha-amino acid. It is a tautomer of a (4S)-4-hydroxy-L-isoleucine zwitterion.
See also: Fenugreek seed (part of).
L-Ribo-2-Amino-4-hydroxy-3-methylpentanoic acid is found in herbs and spices. L-Ribo-2-Amino-4-hydroxy-3-methylpentanoic acid is a major constituent of Trigonella foenum-graecum (fenugreek
(2S,3R,4S)-4-Hydroxyisoleucine is an orally active compound isolated from Trigonella foenum-graecum, with anti-diabetes and anti-diabetic nephropathy activity[1].
(2S,3R,4S)-4-Hydroxyisoleucine is an orally active compound isolated from Trigonella foenum-graecum, with anti-diabetes and anti-diabetic nephropathy activity[1].
4-Hydroxyisoleucine (4-?Hydroxy-?L-?isoleucine) is an amino acid which can be extracted and purified from fenugreek seeds. 4-Hydroxyisoleucine (4-?Hydroxy-?L-?isoleucine) displays an insulinotropic activity of great interest[1].
4-Hydroxyisoleucine (4-?Hydroxy-?L-?isoleucine) is an amino acid which can be extracted and purified from fenugreek seeds. 4-Hydroxyisoleucine (4-?Hydroxy-?L-?isoleucine) displays an insulinotropic activity of great interest[1].
同义名列表
35 个代谢物同义名
(2S,3R,4S)-2-Amino-4-hydroxy-3-methylpentanoic acid (H-L-Ile(4-OH)-OH); (4S)-4-Hydroxy-L-isoleucine, from fenugreek seed, >=98.0\\% (TLC); 4-HYDROXYISOLEUCINE (CONSTITUENT OF FENUGREEK SEED) [DSC]; rel-(2S,3R,4S)-2-Amino-4-hydroxy-3-methylpentanoic acid; rel-(2S,3R,4S)-2-Amino-4-hydroxy-3-methylpentanoicacid; (2S,3R,4S)-2-Amino-4-hydroxy-3-methyl-pentanoic acid; (2R,3R,4R)-2-Amino-4-hydroxy-3-methylpentanoic acid; 4-HYDROXYISOLEUCINE (CONSTITUENT OF FENUGREEK SEED); (2S,3R,4S)-2-amino-4-hydroxy-3-methylpentanoic acid; L-Ribonic acid, 2-amino-2,3,5-trideoxy-3-methyl-; (2R,3R,4R)-2-Amino-4-hydroxy-3-methylpentanoate; 2-amino-2,3,5-trideoxy-3-methyl-L-ribonic acid; 2-amino-4-hydroxy-3-methylpentanoic acid; 2-Amino-4-hydroxy-3-methylpentanoate; (2S,3S,4R)-gamma-hydroxyisoleucine; (2S,3R,4S)-4-hydroxy-L-isoleucine; (2S,3R,4S)-4-HYDROXYISOLEUCINE; 4-HYDROXYISOLEUCINE (USP-RS); 4-HYDROXYISOLEUCINE [USP-RS]; OSCCDBFHNMXNME-YUPRTTJUSA-N; (4S)-4-Hydroxy-L-isoleucine; (4S)-Hydroxy-L-isoleucine; 4-HYDROXYISOLEUCINE, (+)-; HYDROXYISOLEUCINE [INCI]; (4S)-4-hydroxyisoleucine; 4-HYDROXY-L-ISOLEUCINE; 4-Hydroxyisoleucine; Hydroxyisoleucine; UNII-4SWT01T54O; D-xylo-Form; 4SWT01T54O; 4-OH-Ile; Adyvia; 4-Hydroxy-L-isoleucine; 4-?Hydroxy-?L-?isoleucine
数据库引用编号
25 个数据库交叉引用编号
- ChEBI: CHEBI:172410
- ChEBI: CHEBI:79079
- ChEBI: CHEBI:78247
- KEGG: C20802
- PubChem: 6918732
- PubChem: 354197
- HMDB: HMDB0029449
- ChEMBL: CHEMBL508094
- MeSH: (2S,3S,4R)-gamma-hydroxyisoleucine
- ChemIDplus: 0055399934
- chemspider: 2054036
- chemspider: 314416
- CAS: 1044661-15-5
- CAS: 1219387-79-7
- CAS: 781658-23-9
- CAS: 55399-93-4
- CAS: 50764-07-3
- medchemexpress: HY-W010271
- medchemexpress: HY-N6858
- PMhub: MS000028180
- PubChem: 254741269
- LOTUS: LTS0269789
- wikidata: Q105198778
- LOTUS: LTS0078799
- wikidata: Q27147705
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
4 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
- Geetika Wadhwa, Kowthavarapu Venkata Krishna, Rajeev Taliyan, Neeraj Tandon, Satyapal Singh Yadav, Dipankar Banerjee, Avinash Narwaria, Chandrakant Katiyar, Sunil Kumar Dubey. A novel UPLC-MS/MS method for simultaneous quantification of trigonelline, 4-hydroxyisoleucine, and diosgenin from Trigonella foenum-graecum extract: Application to pharmacokinetic study in healthy and type 2 diabetic rats.
Biomedical chromatography : BMC.
2022 Feb; 36(2):e5275. doi:
10.1002/bmc.5275. [PMID: 34738247] - Pragati Singh, Sharmeen Ishteyaque, Ramanand Prajapati, Karan Singh Yadav, Rupali Singh, Akhilesh Kumar, Sharad Sharma, Tadigoppula Narender, Madhav Nilakanth Mugale. Assessment of antidiabetic effect of 4-HIL in type 2 diabetic and healthy Sprague Dawley rats.
Human & experimental toxicology.
2022 Jan; 41(?):9603271211061873. doi:
10.1177/09603271211061873. [PMID: 35072544] - Maryam Mohammad-Sadeghipour, Mehdi Mahmoodi, Mojgan Noroozi Karimabad, Mohammad Reza Mirzaei, Mohammad Reza Hajizadeh. Diosgenin and 4-Hydroxyisoleucine from Fenugreek Are Regulators of Genes Involved in Lipid Metabolism in The Human Colorectal Cancer Cell Line SW480.
Cell journal.
2021 Jan; 22(4):514-522. doi:
10.22074/cellj.2021.6751. [PMID: 32347045] - Cong Zhou, Rui Chen, Feng Gao, Jiaoyue Zhang, Furong Lu. 4-Hydroxyisoleucine relieves inflammation through iRhom2-dependent pathway in co-cultured macrophages and adipocytes with LPS stimulation.
BMC complementary medicine and therapies.
2020 Dec; 20(1):373. doi:
10.1186/s12906-020-03166-1. [PMID: 33298044] - Brenden Barco, Yoseph Kim, Nicole K Clay. Expansion of a core regulon by transposable elements promotes Arabidopsis chemical diversity and pathogen defense.
Nature communications.
2019 08; 10(1):3444. doi:
10.1038/s41467-019-11406-3. [PMID: 31371717] - Anaguiven Avalos-Soriano, Ricardo De la Cruz-Cordero, Jorge L Rosado, Teresa Garcia-Gasca. 4-Hydroxyisoleucine from Fenugreek (Trigonella foenum-graecum): Effects on Insulin Resistance Associated with Obesity.
Molecules (Basel, Switzerland).
2016 Nov; 21(11):. doi:
10.3390/molecules21111596. [PMID: 27879673] - Nikita Naicker, Savania Nagiah, Alisa Phulukdaree, Anil Chuturgoon. Trigonella foenum-graecum Seed Extract, 4-Hydroxyisoleucine, and Metformin Stimulate Proximal Insulin Signaling and Increase Expression of Glycogenic Enzymes and GLUT2 in HepG2 Cells.
Metabolic syndrome and related disorders.
2016 Mar; 14(2):114-20. doi:
10.1089/met.2015.0081. [PMID: 26835874] - Feng Gao, Liumeng Jian, Mohammad Ishraq Zafar, Wen Du, Qin Cai, Raja Adeel Shafqat, Furong Lu. 4-Hydroxyisoleucine improves insulin resistance in HepG2 cells by decreasing TNF-α and regulating the expression of insulin signal transduction proteins.
Molecular medicine reports.
2015 Nov; 12(5):6555-60. doi:
10.3892/mmr.2015.4298. [PMID: 26352439] - Scott Fuller, Jacqueline M Stephens. Diosgenin, 4-hydroxyisoleucine, and fiber from fenugreek: mechanisms of actions and potential effects on metabolic syndrome.
Advances in nutrition (Bethesda, Md.).
2015 Mar; 6(2):189-97. doi:
10.3945/an.114.007807. [PMID: 25770257] - Feng Gao, Wen Du, Mohammad Ishraq Zafar, Raja Adeel Shafqat, Liumeng Jian, Qin Cai, Furong Lu. 4-Hydroxyisoleucine ameliorates an insulin resistant-like state in 3T3-L1 adipocytes by regulating TACE/TIMP3 expression.
Drug design, development and therapy.
2015; 9(?):5727-36. doi:
10.2147/dddt.s92355. [PMID: 26527864] - Arun Kumar Rawat, Venkateswarlu Korthikunta, Sudeep Gautam, Savita Pal, Narender Tadigoppula, Akhilesh Kumar Tamrakar, Arvind Kumar Srivastava. 4-Hydroxyisoleucine improves insulin resistance by promoting mitochondrial biogenesis and act through AMPK and Akt dependent pathway.
Fitoterapia.
2014 Dec; 99(?):307-17. doi:
10.1016/j.fitote.2014.10.006. [PMID: 25454462] - Hai Yu, Meng Wu, Fu-Rong Lu, Jing Xie, Na Zheng, You Qin, Feng Gao, Wen Du, Liu-Meng Jian. [Effect of Trigonella foenum-graecum 4-hydroxyisoleucine on high-glucose induced insulin resistance in 3T3-L1 adipocytes of mice].
Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine.
2013 Oct; 33(10):1394-9. doi:
. [PMID: 24432687] - Natasha Jaiswal, Chandan K Maurya, K Venkateswarlu, P Sukanya, Arvind K Srivastava, Tadigoppula Narender, Akhilesh K Tamrakar. 4-Hydroxyisoleucine stimulates glucose uptake by increasing surface GLUT4 level in skeletal muscle cells via phosphatidylinositol-3-kinase-dependent pathway.
European journal of nutrition.
2012 Oct; 51(7):893-8. doi:
10.1007/s00394-012-0374-9. [PMID: 22610671] - Mohammed R Haeri, Hamidreza Khalatbari Limaki, Christopher J Branford White, Kenneth N White. Non-insulin dependent anti-diabetic activity of (2S, 3R, 4S) 4-hydroxyisoleucine of fenugreek (Trigonella foenum graecum) in streptozotocin-induced type I diabetic rats.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2012 May; 19(7):571-4. doi:
10.1016/j.phymed.2012.01.004. [PMID: 22397995] - James E Thomas, Manjula Bandara, Ee Lynn Lee, Darcy Driedger, Surya Acharya. Biochemical monitoring in fenugreek to develop functional food and medicinal plant variants.
New biotechnology.
2011 Feb; 28(2):110-7. doi:
10.1016/j.nbt.2010.09.001. [PMID: 20851781] - Lucie Jetté, Laurent Harvey, Karen Eugeni, Nigel Levens. 4-Hydroxyisoleucine: a plant-derived treatment for metabolic syndrome.
Current opinion in investigational drugs (London, England : 2000).
2009 Apr; 10(4):353-8. doi:
. [PMID: 19337956] - Mohammad Reza Haeri, Mohammad Izaddoost, Mohammad Reza Shams Ardekani, Mohammad Rahbani Nobar, Kenneth N White. The effect of fenugreek 4-hydroxyisoleucine on liver function biomarkers and glucose in diabetic and fructose-fed rats.
Phytotherapy research : PTR.
2009 Jan; 23(1):61-4. doi:
10.1002/ptr.2557. [PMID: 18680121] - D Slivka, J Cuddy, W Hailes, S Harger, B Ruby. Glycogen resynthesis and exercise performance with the addition of fenugreek extract (4-hydroxyisoleucine) to post-exercise carbohydrate feeding.
Amino acids.
2008 Aug; 35(2):439-44. doi:
10.1007/s00726-007-0580-6. [PMID: 17710365] - Tadigoppula Narender, Anju Puri, Shweta, Tanvir Khaliq, Rashmi Saxena, Geetika Bhatia, Ramesh Chandra. 4-hydroxyisoleucine an unusual amino acid as antidyslipidemic and antihyperglycemic agent.
Bioorganic & medicinal chemistry letters.
2006 Jan; 16(2):293-6. doi:
10.1016/j.bmcl.2005.10.003. [PMID: 16246556] - B C Ruby, S E Gaskill, D Slivka, S G Harger. The addition of fenugreek extract (Trigonella foenum-graecum) to glucose feeding increases muscle glycogen resynthesis after exercise.
Amino acids.
2005 Feb; 28(1):71-6. doi:
10.1007/s00726-004-0143-z. [PMID: 15719265] - Christophe Broca, Vincent Breil, Céline Cruciani-Guglielmacci, Michèle Manteghetti, Christine Rouault, Michel Derouet, Salwa Rizkalla, Bernard Pau, Pierre Petit, Gérard Ribes, Alain Ktorza, René Gross, Gérard Reach, Mohammed Taouis. Insulinotropic agent ID-1101 (4-hydroxyisoleucine) activates insulin signaling in rat.
American journal of physiology. Endocrinology and metabolism.
2004 Sep; 287(3):E463-71. doi:
10.1152/ajpendo.00163.2003. [PMID: 15082420] - Zecharia Madar, Aliza H Stark. New legume sources as therapeutic agents.
The British journal of nutrition.
2002 Dec; 88 Suppl 3(?):S287-92. doi:
10.1079/bjn2002719. [PMID: 12498629] - C Broca, M Manteghetti, R Gross, Y Baissac, M Jacob, P Petit, Y Sauvaire, G Ribes. 4-Hydroxyisoleucine: effects of synthetic and natural analogues on insulin secretion.
European journal of pharmacology.
2000 Mar; 390(3):339-45. doi:
10.1016/s0014-2999(00)00030-3. [PMID: 10708743] - Y Sauvaire, P Petit, C Broca, M Manteghetti, Y Baissac, J Fernandez-Alvarez, R Gross, M Roye, A Leconte, R Gomis, G Ribes. 4-Hydroxyisoleucine: a novel amino acid potentiator of insulin secretion.
Diabetes.
1998 Feb; 47(2):206-10. doi:
10.2337/diab.47.2.206. [PMID: 9519714]
