Trans-4-hydroxyproline (BioDeep_00000000265)

 

Secondary id: BioDeep_00000000731, BioDeep_00000229679, BioDeep_00000269144

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


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

化学式: C5H9NO3 (131.0582)
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(feces) 12.45%

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 2024-12-22) (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

105 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; Hydroxyproline; Hydroxyproline



数据库引用编号

36 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)

52 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。

亚细胞结构定位 关联基因列表
Cytoplasm 8 ALB, BGLAP, CALCA, COL1A1, CTNNB1, HIF1A, MAPK14, SKP1
Endoplasmic reticulum membrane 1 SPP1
Nucleus 7 ALB, CTNNB1, HIF1A, MAPK14, MMP2, PCNA, SKP1
cytosol 6 AGPS, ALB, CTNNB1, HIF1A, MAPK14, SKP1
dendrite 1 BGLAP
nuclear body 2 HIF1A, PCNA
centrosome 4 ALB, CTNNB1, PCNA, SKP1
nucleoplasm 5 CTNNB1, HIF1A, MAPK14, PCNA, SKP1
RNA polymerase II transcription regulator complex 1 HIF1A
Cell membrane 4 CTNNB1, ITGAM, SPP1, TNF
lamellipodium 1 CTNNB1
Multi-pass membrane protein 1 SPP1
Synapse 1 CTNNB1
cell cortex 1 CTNNB1
cell junction 1 CTNNB1
cell surface 3 HRG, ITGAM, TNF
glutamatergic synapse 2 CTNNB1, MAPK14
Golgi apparatus 2 ALB, SPP1
Golgi membrane 1 INS
neuronal cell body 2 CALCA, TNF
presynaptic membrane 1 CTNNB1
plasma membrane 6 CTNNB1, HRG, ITGAM, MMP2, SPP1, TNF
terminal bouton 1 CALCA
Membrane 4 AGPS, COL1A1, CTNNB1, ITGAM
basolateral plasma membrane 1 CTNNB1
extracellular exosome 8 ALB, CTNNB1, HRG, ITGAM, MMP9, PCNA, PEPD, SPP1
endoplasmic reticulum 1 ALB
extracellular space 11 ALB, BGLAP, CALCA, COL1A1, INS, ITGAM, MMP2, MMP9, PTH, SPP1, TNF
perinuclear region of cytoplasm 2 CTNNB1, SPP1
Schaffer collateral - CA1 synapse 1 CTNNB1
adherens junction 1 CTNNB1
apicolateral plasma membrane 1 CTNNB1
bicellular tight junction 1 CTNNB1
mitochondrion 3 AGPS, MAPK14, MMP2
protein-containing complex 3 ALB, CTNNB1, HIF1A
Single-pass type I membrane protein 1 ITGAM
Secreted 6 ALB, BGLAP, CALCA, HRG, INS, SPP1
extracellular region 13 ALB, BGLAP, CALCA, COL1A1, ELN, HRG, INS, MAPK14, MMP2, MMP9, PTH, SPP1, TNF
hippocampal mossy fiber to CA3 synapse 1 CALCA
anchoring junction 1 ALB
transcription regulator complex 1 CTNNB1
motile cilium 1 HIF1A
external side of plasma membrane 2 ITGAM, TNF
Secreted, extracellular space, extracellular matrix 3 COL1A1, ELN, MMP9
perikaryon 1 BGLAP
Z disc 1 CTNNB1
beta-catenin destruction complex 1 CTNNB1
Wnt signalosome 1 CTNNB1
axon cytoplasm 1 HIF1A
apical part of cell 1 CTNNB1
cell-cell junction 1 CTNNB1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 BGLAP
postsynaptic membrane 1 CTNNB1
Membrane raft 2 ITGAM, TNF
Cytoplasm, cytoskeleton 1 CTNNB1
focal adhesion 1 CTNNB1
Cell junction, adherens junction 1 CTNNB1
flotillin complex 1 CTNNB1
extracellular matrix 2 ELN, MMP2
Peroxisome 1 AGPS
collagen trimer 1 COL1A1
peroxisomal matrix 1 AGPS
peroxisomal membrane 1 AGPS
collagen-containing extracellular matrix 5 COL1A1, ELN, HRG, MMP2, MMP9
secretory granule 1 COL1A1
fascia adherens 1 CTNNB1
lateral plasma membrane 1 CTNNB1
nuclear speck 2 HIF1A, MAPK14
sarcomere 1 MMP2
ciliary basal body 1 ALB
chromatin 2 HIF1A, PCNA
cell projection 1 SPP1
phagocytic cup 1 TNF
cell periphery 1 CTNNB1
Cytoplasm, cytoskeleton, cilium basal body 1 CTNNB1
centriole 1 ALB
spindle pole 3 ALB, CTNNB1, MAPK14
nuclear replication fork 1 PCNA
chromosome, telomeric region 1 PCNA
blood microparticle 2 ALB, HRG
postsynaptic density, intracellular component 1 CTNNB1
microvillus membrane 1 CTNNB1
Endomembrane system 1 CTNNB1
endosome lumen 1 INS
specific granule membrane 1 ITGAM
tertiary granule membrane 1 ITGAM
Nucleus speckle 1 HIF1A
euchromatin 2 CTNNB1, HIF1A
replication fork 1 PCNA
Peroxisome membrane 1 AGPS
plasma membrane raft 1 ITGAM
ficolin-1-rich granule lumen 2 MAPK14, MMP9
secretory granule lumen 2 INS, MAPK14
Golgi lumen 2 BGLAP, INS
endoplasmic reticulum lumen 5 ALB, BGLAP, COL1A1, INS, SPP1
PcG protein complex 1 SKP1
male germ cell nucleus 1 PCNA
platelet alpha granule lumen 2 ALB, HRG
tertiary granule lumen 1 MMP9
transport vesicle 1 INS
[Isoform 1]: Secreted, extracellular space, extracellular matrix 1 MMP2
beta-catenin-TCF complex 1 CTNNB1
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
neuronal dense core vesicle 1 CALCA
presynaptic active zone cytoplasmic component 1 CTNNB1
nuclear lamina 1 PCNA
protein-DNA complex 1 CTNNB1
catenin complex 1 CTNNB1
integrin complex 1 ITGAM
cyclin-dependent protein kinase holoenzyme complex 1 PCNA
elastic fiber 1 ELN
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
collagen type I trimer 1 COL1A1
integrin alphaM-beta2 complex 1 ITGAM
SCF ubiquitin ligase complex 1 SKP1
PCNA complex 1 PCNA
PCNA-p21 complex 1 PCNA
replisome 1 PCNA
beta-catenin-TCF7L2 complex 1 CTNNB1
beta-catenin-ICAT complex 1 CTNNB1
Scrib-APC-beta-catenin complex 1 CTNNB1
ciliary transition fiber 1 ALB
Cul7-RING ubiquitin ligase complex 1 SKP1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


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]