Trans-4-hydroxyproline (BioDeep_00000000265)

 

Secondary id: BioDeep_00000229679, BioDeep_00000269144

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid

化学式: C5H9NO3 (131.0582404)
中文名称: L-羟基脯氨酸, L-羟脯氨酸, 羟脯氨酸
谱图信息: 最多检出来源 Homo sapiens(blood) 1.01%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Trans-4-hydroxyproline. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/trans-4-hydroxyproline (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000000265). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1C(CNC1C(=O)O)O
InChI: InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1

描述信息

Trans-4-hydroxy-L-proline is an optically active form of 4-hydroxyproline having L-trans-configuration. It has a role as a human metabolite, a plant metabolite and a mouse metabolite. It is a tautomer of a trans-4-hydroxy-L-proline zwitterion.
Hydroxyproline is a neutral heterocyclic protein amino acid. It is found in collagen and as such it is common in many gelatin products. Hydroxyproline is mostly used as a diagnostic marker of bone turnover and liver fibrosis. Therapeutically, hydroxyproline is being studied as an an experimental medicine but is approved in France as a combination topical gel product called Cicactive for small, superficial wounds.
Hydroxyproline is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
Hydroxyproline is a nonessential amino acid derivative formed during post-translational protein modification through hydroxylation of the amino acid proline by the enzyme prolyl hydroxylase which requires vitamin C as a co-factor. Hydroxyproline is a major component of the protein collagen and plays a key role in the stability of the collagen triple helix. It can be used as an indicator to determine the amount of collagen. Increased hydroxyproline levels in the urine and/or serum are normally associated with degradation of connective tissue. Vitamin C deficiency decreases the conversion of proline to hydroxyproline, which leads to reduced collagen stability.
4-Hydroxyproline (or hydroxyproline or Hyp) is a major component of the protein collagen. Hydroxyproline is produced by hydroxylation of the amino acid proline and is, therefore, a post-translationally modified amino acid. Hydroxyproline and proline play key roles for collagen stability. In particular, they permit the sharp twisting of the collagen helix. Hydroxyproline is found in few proteins other than collagen. The only other mammalian protein which includes hydroxyproline is elastin. For this reason, hydroxyproline content has been used as an indicator to determine collagen and/or gelatin amount in tissue or biological samples. Increased serum and urine levels of hydroxyproline have been found in Pagets disease Hydroxyproline (Hyp) content in biological fluids is used as a parameter of collagen catabolism, especially bone resorption or tissue degradation. Bedridden and elderly individuals show significantly elevated serum levels of hydroxyproline in comparison to normal, active individuals Elevated levels of urinary hydroxyproline are also indicative of muscle damage Increased reactive oxygen species (ROS) are also known to accelerate collagen degradation. Hydroxyproline levels increase in cases of depression and stress (A3486, A3487, A3488, A3489).
See also: Hydroxyproline; niacinamide (component of); Hydroxyproline; octinoxate (component of) ... View More ...
4-Hydroxyproline (hydroxyproline or Hyp) is a major component of the protein collagen. Hydroxyproline is produced by hydroxylation of the amino acid proline and is, therefore, a post-translationally modified, non-essential amino acid. Hydroxyproline and proline play key roles in collagen stability. In particular, they permit the sharp twisting of the collagen helix. Hydroxyproline is found in few proteins other than collagen. The only other mammalian protein which includes hydroxyproline is elastin. For this reason, hydroxyproline content has been used as an indicator to determine collagen and/or gelatin amount in tissue or biological samples. Increased serum and urine levels of hydroxyproline have been found in Pagets disease (PMID: 436278). Hydroxyproline (Hyp) content in biological fluids is used as a parameter of collagen catabolism, especially bone resorption or tissue degradation. Bedridden and elderly individuals show significantly elevated serum levels of hydroxyproline in comparison to normal, active individuals (PMID: 10706420). Elevated levels of urinary hydroxyproline are also indicative of muscle damage (PMID: 21988268). Increased reactive oxygen species (ROS) are also known to accelerate collagen degradation. Hydroxyproline levels increase in cases of depression and stress (PMID: 21483218). 4-Hydroxyproline is found to be associated with Alzheimers disease, and also hydroxyprolinemia and iminoglycinuria which are both inborn errors of metabolism. 4-Hydroxyproline is also involved in metabolic disorders such as hyperprolinemia type I, hyperornithinemia with gyrate atrophy (HOGA), L-arginine:glycine amidinotransferase deficiency, creatine deficiency, and guanidinoacetate methyltransferase deficiency. A deficiency in ascorbic acid can result in impaired hydroxyproline formation (PubChem). trans-4-Hydroxy-L-proline is a biomarker for the consumption of processed meat.
Constituent of proteins [DFC]. 4-hydroxyproline is a biomarker for the consumption of processed meat
An optically active form of 4-hydroxyproline having L-trans-configuration.
L-Hydroxyproline, one of the hydroxyproline (Hyp) isomers, is a useful chiral building block in the production of many pharmaceuticals.
L-Hydroxyproline, one of the hydroxyproline (Hyp) isomers, is a useful chiral building block in the production of many pharmaceuticals.

同义名列表

103 个代谢物同义名

Hydroxyproline, Pharmaceutical Secondary Standard; Certified Reference Material; trans-4-Hydroxy-L-proline, BioReagent, suitable for cell culture, >=98.5\\%; trans-4-Hydroxy-L-proline, microbial, cell culture tested; trans-4-Hydroxy-L-proline, Vetec(TM) reagent grade, 99\\%; (2S,4R)-(-)-4-Hydroxy-2-Pyrrolidinecarboxylic Acid; (2S,4R)-rel-4-Hydroxypyrrolidine-2-carboxylic acid; trans-4-Hydroxy-L-proline, BioXtra, >=99.0\\% (NT); (2S, 4R)-4-hydroxy-2-pyrrolidine-carboxylic acid; 4-(R)-hydroxy-pyrrolidine-2-(S)-carboxylic acid; (2S, 4R)-4-hydroxy-2-pyrrolidinecarboxylic acid; (2S,4R)-4-hydroxy-pyrrolidine-2-carboxylic acid; (2S,4R)-4-hydroxy-2-pyrrolidinecarboxylic acid; (2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid; trans-4-Hydroxy-L-proline, analytical standard; 4(R)-Hydroxy-2(S)-pyrrolidinecarboxylic acid; (2S,4R)-4-Hydroxy-2-pyrrolidinecarboxylate; (-)-4-Hydroxy-2-pyrrolidinecarboxylic acid; L-Hydroxyproline;trans-4-Hydroxy-L-Proline; Ohui Wrinkle Science Wrinkle Repair Eye; (2S,4R)-2-carboxy-4-hydroxypyrrolidine; 4-Hydroxy-2-pyrrolidinecarboxylic acid; O Hui Wrinkle Science Wrinkle Repair; L-Proline, 4-hydroxy-, trans- (9CI); N-methyl-trans-4-hydroxy-L-proline; trans-4-Hydroxy-L-proline, >=99\\%; (2S,4R)-trans-4-hydroxyproline; L-Proline, 4-hydroxy-, trans-; (2S,4R)-(-)-4-Hydroxyproline; L-Proline, 4-hydroxy-, (4R)-; (2s,4r)-4-hydroxy-l-proline; trans-4-hydroxy-(L)-proline; PMMYEEVYMWASQN-DMTCNVIQSA-N; trans-4-hydroxyl-l-proline; (2S, 4R)-4-hydroxy-proline; (R)-4-Hydroxy-(S)-proline; trans-4-hydroxy(L)proline; Proline, 4-hydroxy- (VAN); 4-trans-Hydroxy-L-proline; trans-4-hydroxy-L-proline; L-trans-4-hydroxy-proline; trans-L-4-hydroxy-proline; (2S, 4R)-4-hydroxyproline; trans-4-D-Hydroxyproline; trans-4-hydroxyL-proline; Trans4-hydroxy-L-proline; L-trans-4-Hydroxyproline; trans-L-4-hydroxyproline; (2S,4R)-4-hydroxyproline; (4R)-4-hydroxy-L-proline; L-threo-4-hydroxyproline; L-4-transhydroxyproline; (R)-4-Hydroxy-L-proline; trans-hydroxy-L-proline; HYDROXYPROLINE [WHO-DD]; trans-4-hydroxy-proline; Proline, 4-hydroxy-, L-; trans-L-Hydroxyproline; trans-4-Hydroxyproline; .delta.-Hydroxyproline; HYDROXYPROLINE [INCI]; 4-Hydroxy-(S)-proline; L-Proline, 4-hydroxy-; Hydroxyproline (VAN); trans-Hydroxyproline; L-Hydroxyproline,(S); delta-Hydroxyproline; 4(R)-hydroxyproline; (4r)-hydroxyproline; 4-Hydroxy-L-proline; HYDROXYPROLINE [MI]; Proline, 4-hydroxy-; 4-L-Hydroxyproline; (S)-Hydroxyproline; L-4-hydroxyproline; Hydroxyproline,(l); hydroxy-L-proline; Ls-Hydroxyproline; L-Hydroxyproline;; L-Proline, trans-; 4-hydroxyproline; 4 HYDROXYPROLINE; trans-oxyproline; L-Hydroxyproline; Δ-hydroxyproline; hydroxy-proline; UNII-RMB44WO89X; L-Hydroxyprolin; H-trans-Hyp-OH; Hydroxyproline; hydroxiproline; NCI60_004102; oxyproline; RMB44WO89X; Oxaceprol; NSC 46704; LUMISTOR; H-Hyp-OH; L-Hypro; NMH-Pro; Hypro; Hyp; Hydroxyproline; L-Hydroxyproline,BioReagent, suitable for cell culture



数据库引用编号

28 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

43 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(2)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(40)

PharmGKB(0)

2 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

  • Shengdi Hu, Wenliang He, Guoyao Wu. Hydroxyproline in animal metabolism, nutrition, and cell signaling. Amino acids. 2022 Apr; 54(4):513-528. doi: 10.1007/s00726-021-03056-x. [PMID: 34342708]
  • Sebastian Kwiatkowski, Maria Bozko, Michal Zarod, Apolonia Witecka, Kubra Kocdemir, Adam K Jagielski, Jakub Drozak. Recharacterization of the mammalian cytosolic type 2 (R)-β-hydroxybutyrate dehydrogenase as 4-oxo-l-proline reductase (EC 1.1.1.104). The Journal of biological chemistry. 2022 03; 298(3):101708. doi: 10.1016/j.jbc.2022.101708. [PMID: 35150746]
  • Pedro Everson Alexandre de Aquino, Jéssica Rabelo Bezerra, Tyciane de Souza Nascimento, Juliete Tavares, Ítalo Rosal Lustosa, Adriano José Maia Chaves Filho, Melina Mottin, Danielle Macêdo Gaspar, Geanne Matos de Andrade, Kelly Rose Tavares Neves, Giuseppe Biagini, Edilberto Rocha Silveira, Glauce Socorro de Barros Viana. A Proline Derivative-Enriched Fraction from Sideroxylon obtusifolium Protects the Hippocampus from Intracerebroventricular Pilocarpine-Induced Injury Associated with Status Epilepticus in Mice. International journal of molecular sciences. 2020 Jun; 21(11):. doi: 10.3390/ijms21114188. [PMID: 32545390]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • David T Thwaites, Catriona M H Anderson. The SLC36 family of proton-coupled amino acid transporters and their potential role in drug transport. British journal of pharmacology. 2011 Dec; 164(7):1802-16. doi: 10.1111/j.1476-5381.2011.01438.x. [PMID: 21501141]
  • Bah Moustapha, Gutiérrez-Avella Dora Marina, Fuentes-Ordaz Raúl, Castañeda-Moreno Raquel, Martínez Mahinda. Chemical constituents of the Mexican mistletoe (Psittacanthus calyculatus). Molecules (Basel, Switzerland). 2011 Nov; 16(11):9397-403. doi: 10.3390/molecules16119397. [PMID: 22071447]
  • Jifeng Gu, Nianzu Chen, Guoqiang Ding, Zhen Zhang. Determination of oxaceprol in rat plasma by LC-MS/MS and its application in a pharmacokinetic study. Journal of pharmaceutical and biomedical analysis. 2011 Jan; 54(1):173-8. doi: 10.1016/j.jpba.2010.08.011. [PMID: 20832228]
  • Gao-Xue Wang, You-Tao Liu, Fu-Yuan Li, Hong-Tao Gao, Yi Lei, Xiao-Lin Liu. Immunostimulatory activities of Bacillus simplex DR-834 to carp (Cyprinus carpio). Fish & shellfish immunology. 2010 Sep; 29(3):378-87. doi: 10.1016/j.fsi.2010.03.014. [PMID: 20472068]
  • Ricky R Lareu, Dimitrios I Zeugolis, Mohammad Abu-Rub, Abhay Pandit, Michael Raghunath. Essential modification of the Sircol Collagen Assay for the accurate quantification of collagen content in complex protein solutions. Acta biomaterialia. 2010 Aug; 6(8):3146-51. doi: 10.1016/j.actbio.2010.02.004. [PMID: 20144751]
  • I Cetin Ozturk, Kadir Batcioglu, Fikret Karatas, Ersoy Hazneci, Metin Genc. Comparison of plasma malondialdehyde, glutathione, glutathione peroxidase, hydroxyproline and selenium levels in patients with vitiligo and healthy controls. Indian journal of dermatology. 2008; 53(3):106-10. doi: 10.4103/0019-5154.39577. [PMID: 19882005]
  • James J Clayton. Nutraceuticals in the management of osteoarthritis. Orthopedics. 2007 08; 30(8):624-9; quiz 630. doi: 10.3928/01477447-20070801-13. [PMID: 17727018]
  • Jane K Kay, John R Roche, Chel E Moore, Lance H Baumgard. Effects of dietary conjugated linoleic acid on production and metabolic parameters in transition dairy cows grazing fresh pasture. The Journal of dairy research. 2006 Aug; 73(3):367-77. doi: 10.1017/s0022029906001944. [PMID: 16836800]
  • Tammo Winkler. Comments on 'Piperidone derivative from Dalbergia sympathetica'. Magnetic resonance in chemistry : MRC. 2006 May; 44(5):571-2. doi: 10.1002/mrc.1783. [PMID: 16425210]
  • Cornelle R Parker, Penelope J Blackwell, Anthony J Freemont, David J Hosking. Biochemical measurements in the prediction of histologic subtype of renal transplant bone disease in women. American journal of kidney diseases : the official journal of the National Kidney Foundation. 2002 Aug; 40(2):385-96. doi: 10.1053/ajkd.2002.34535. [PMID: 12148113]