Chloroacetaldehyde (BioDeep_00000006318)
Secondary id: BioDeep_00001868083
human metabolite Endogenous blood metabolite
代谢物信息卡片
Chloroacetaldehyde hydrate
化学式: C2H3ClO (77.9872418)
中文名称: 一氯乙醛
谱图信息:
最多检出来源 Homo sapiens(blood) 0.03%
分子结构信息
SMILES: C(C=O)Cl
InChI: InChI=1S/C2H3ClO/c3-1-2-4/h2H,1H2
描述信息
Being bifunctional, chloroacetaldehyde is a versatile precursor to many heterocyclic compounds. It condenses with thiourea derivatives to give aminothiazoles. This reaction was once important as a precursor to sulfathiazole, one of the first sulfa drugs. Chloroacetaldehyde is the organic compound with the formula ClCH2CHO. Like some related compounds, it is highly electrophilic reagent and a potentially dangerous alkylating agent. The compound is not normally encountered in the anhydrous form, but rather as the hydrate (acetal), ClCH2CH(OH)2. Chloroacetaldehyde is a useful intermediate in the synthesis, e.g. of 2-aminothiazole or many pharmaceutical compounds. Another use is to facilitate bark removal from tree trunks.
同义名列表
数据库引用编号
13 个数据库交叉引用编号
- ChEBI: CHEBI:27871
- KEGG: C06754
- PubChem: 33
- HMDB: HMDB0013860
- Metlin: METLIN66522
- ChEMBL: CHEMBL506976
- Wikipedia: Chloroacetaldehyde
- CAS: 107-20-0
- PMhub: MS000019342
- PubChem: 8975
- 3DMET: B01043
- NIKKAJI: J4.060F
- RefMet: Chloroacetaldehyde
分类词条
相关代谢途径
Reactome(0)
PlantCyc(0)
代谢反应
12 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(7)
- 1,2-dichloroethane degradation:
1,2-dichloroethane + H2O ⟶ 2-chloroethanol + H+ + chloride - 1,2-dichloroethane degradation:
H2O + chloroacetate ⟶ H+ + chloride + glycolate - 1,2-dichloroethane degradation:
H2O + chloroacetate ⟶ H+ + chloride + glycolate - 1,2-dichloroethane degradation:
1,2-dichloroethane + H2O ⟶ 2-chloroethanol + H+ + chloride - 1,2-dichloroethane degradation:
1,2-dichloroethane + H2O ⟶ 2-chloroethanol + H+ + chloride - 1,2-dichloroethane degradation:
H2O + chloroacetate ⟶ H+ + chloride + glycolate - 1,2-dichloroethane degradation:
H2O + NAD+ + chloroacetaldehyde ⟶ H+ + NADH + chloroacetate
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(4)
- Ifosfamide Action Pathway:
Ifosfamide + Oxygen + Water ⟶ 2-Dechloroethylifosfamide + 3-Dechloroethylifosfamide + Chloroacetaldehyde + Hydrogen peroxide - Ifosfamide Metabolism Pathway:
Ifosfamide + Oxygen + Water ⟶ 2-Dechloroethylifosfamide + 3-Dechloroethylifosfamide + Chloroacetaldehyde + Hydrogen peroxide - Cyclophosphamide Action Pathway:
Aldophosphamide + Glutathione ⟶ 4-Glutathionyl cyclophosphamide + Water - Cyclophosphamide Metabolism Pathway:
Aldophosphamide + Glutathione ⟶ 4-Glutathionyl cyclophosphamide + Water
PharmGKB(1)
- Cyclophosphamide Pathway, Pharmacokinetics:
cyclophosphamide ⟶ 3-dechloroethyl ifosfamide + chloroacetaldehyde
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
- Li Chen, Xiaojuan Xiong, Xingyun Hou, Hua Wei, Jianxiu Zhai, Tianyi Xia, Xiaobin Gong, Shouhong Gao, Ge Feng, Xia Tao, Feng Zhang, Wansheng Chen. Wuzhi capsule regulates chloroacetaldehyde pharmacokinetics behaviour and alleviates high-dose cyclophosphamide-induced nephrotoxicity and neurotoxicity in rats.
Basic & clinical pharmacology & toxicology.
2019 Aug; 125(2):142-151. doi:
10.1111/bcpt.13211. [PMID: 30793490] - Le Yang, Chenyang Yan, Feng Zhang, Bo Jiang, Shouhong Gao, Youtian Liang, Lifeng Huang, Wansheng Chen. Effects of ketoconazole on cyclophosphamide metabolism: evaluation of CYP3A4 inhibition effect using the in vitro and in vivo models.
Experimental animals.
2018 Feb; 67(1):71-82. doi:
10.1538/expanim.17-0048. [PMID: 29129847] - Jianxiu Zhai, Feng Zhang, Shouhong Gao, Li Chen, Ge Feng, Jun Yin, Wansheng Chen. Schisandra chinensis extract decreases chloroacetaldehyde production in rats and attenuates cyclophosphamide toxicity in liver, kidney and brain.
Journal of ethnopharmacology.
2018 Jan; 210(?):223-231. doi:
10.1016/j.jep.2017.08.020. [PMID: 28821392] - Lisanne C Anders, Anna L Lang, Anwar Anwar-Mohamed, Amanda N Douglas, Adrienne M Bushau, Keith Cameron Falkner, Bradford G Hill, Nikole L Warner, Gavin E Arteel, Matt Cave, Craig J McClain, Juliane I Beier. Vinyl Chloride Metabolites Potentiate Inflammatory Liver Injury Caused by LPS in Mice.
Toxicological sciences : an official journal of the Society of Toxicology.
2016 06; 151(2):312-23. doi:
10.1093/toxsci/kfw045. [PMID: 26962056] - Eric Leclerc, Jeremy Hamon, Frederic Yves Bois. Investigation of ifosfamide and chloroacetaldehyde renal toxicity through integration of in vitro liver-kidney microfluidic data and pharmacokinetic-system biology models.
Journal of applied toxicology : JAT.
2016 Feb; 36(2):330-9. doi:
10.1002/jat.3191. [PMID: 26152902] - Andreas Benesic, Gerald Schwerdt, Isabell Hennemeier, Christoph Sauvant, Sigrid Mildenberger, Michael Gekle. The nephrotoxic Ifosfamide-metabolite chloroacetaldehyde interferes with renal extracellular matrix homeostasis.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology.
2014; 33(4):1106-16. doi:
10.1159/000358680. [PMID: 24732969] - Stephanie L MacAllister, Nicolas Martin-Brisac, Vincent Lau, Kai Yang, Peter J O'Brien. Acrolein and chloroacetaldehyde: an examination of the cell and cell-free biomarkers of toxicity.
Chemico-biological interactions.
2013 Feb; 202(1-3):259-66. doi:
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Analytical sciences : the international journal of the Japan Society for Analytical Chemistry.
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Oxidative medicine and cellular longevity.
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Genome biology.
2011 Oct; 12(10):R106. doi:
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Journal of experimental botany.
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Cancer research and treatment.
2010 Dec; 42(4):244-6. doi:
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Human & experimental toxicology.
2010 Jun; 29(6):507-12. doi:
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Canadian journal of physiology and pharmacology.
2010 Apr; 88(4):448-55. doi:
10.1139/y10-023. [PMID: 20555413] - Agnieszka M Maciejewska, Karol P Ruszel, Jadwiga Nieminuszczy, Joanna Lewicka, Beata Sokołowska, Elzbieta Grzesiuk, Jarosław T Kuśmierek. Chloroacetaldehyde-induced mutagenesis in Escherichia coli: the role of AlkB protein in repair of 3,N(4)-ethenocytosine and 3,N(4)-alpha-hydroxyethanocytosine.
Mutation research.
2010 Feb; 684(1-2):24-34. doi:
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Journal of ethnopharmacology.
2010 Feb; 127(2):335-40. doi:
10.1016/j.jep.2009.10.036. [PMID: 19897023] - Burhan Knouzy, Laurence Dubourg, Gabriel Baverel, Christian Michoudet. Targets of chloroacetaldehyde-induced nephrotoxicity.
Toxicology in vitro : an international journal published in association with BIBRA.
2010 Feb; 24(1):99-107. doi:
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International journal of molecular sciences.
2010; 11(12):5339-47. doi:
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BMC neuroscience.
2009 Sep; 10(?):111. doi:
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Chirality.
2009 Jul; 21(7):674-80. doi:
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Plant molecular biology.
2009 Jul; 70(5):535-46. doi:
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Expert opinion on drug safety.
2009 Mar; 8(2):155-68. doi:
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Biochemistry.
2009 Feb; 48(4):800-9. doi:
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Biopolymers.
2009; 92(2):116-23. doi:
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Plant physiology.
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Purinergic signalling.
2008 Jun; 4(2):139-46. doi:
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Cancer research.
2008 Jun; 68(11):4142-9. doi:
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Pediatric nephrology (Berlin, Germany).
2008 Apr; 23(4):611-8. doi:
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Translational research : the journal of laboratory and clinical medicine.
2007 Jul; 150(1):51-7. doi:
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Pediatric nephrology (Berlin, Germany).
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Xenobiotica; the fate of foreign compounds in biological systems.
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Pediatric nephrology (Berlin, Germany).
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Kidney international.
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Cancer research.
2006 Aug; 66(15):7824-31. doi:
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Chirality.
2006 Jun; 18(6):398-405. doi:
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Pediatric nephrology (Berlin, Germany).
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Nature structural & molecular biology.
2005 Oct; 12(10):855-60. doi:
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Pediatric nephrology (Berlin, Germany).
2005 Jul; 20(7):872-85. doi:
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Medycyna wieku rozwojowego.
2005 Jul; 9(3 Pt 2):579-92. doi:
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Canadian journal of physiology and pharmacology.
2005 Jun; 83(6):499-508. doi:
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Journal of the American Chemical Society.
2005 Jan; 127(3):836-7. doi:
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Acta biochimica Polonica.
2005; 52(1):149-65. doi:
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The Journal of laboratory and clinical medicine.
2004 Dec; 144(6):285-93. doi:
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Electrophoresis.
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2004 Apr; 18(6):728-30. doi:
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BMC genomics.
2004 Mar; 5(1):19. doi:
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