1,3-Benzenediol (BioDeep_00000002919)
Secondary id: BioDeep_00000395744, BioDeep_00000871131
human metabolite PANOMIX_OTCML-2023 Endogenous Volatile Flavor Compounds
代谢物信息卡片
Resorcinol, monocopper (2+) salt
化学式: C6H6O2 (110.0367776)
中文名称: 间苯二酚标准溶液, 间苯二酚
谱图信息:
最多检出来源 Viridiplantae(plant) 0.3%
分子结构信息
SMILES: C1=CC(=CC(=C1)O)O
InChI: InChI=1S/C6H6O2/c7-5-2-1-3-6(8)4-5/h1-4,7-8H
描述信息
1,3-Benzenediol, also known as resorcin or m-hydroquinone, belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3. 1,3-Benzenediol exists in all living organisms, ranging from bacteria to humans. 1,3-Benzenediol is a creamy, hawthorn, and musty tasting compound. 1,3-Benzenediol has been detected, but not quantified, in several different foods, such as alcoholic beverages, cereals and cereal products, coffee and coffee products, eggplants, and java plums. This could make 1,3-benzenediol a potential biomarker for the consumption of these foods. 1,3-Benzenediol is a potentially toxic compound. In addition, exogenous ochronosis is associated with prolonged exposure to resorcinol . Data regarding the specific mechanisms of action of resorcinol does not appear to be readily accessible in the literature. Nevertheless, the role played by iodide ions in the irreversible inactivation of the enzymes is not yet fully elucidated . Resorcinol works by helping to remove hard, scaly, or roughened skin. In particular, it appears that resorcinol indicated for treating acne, dermatitis, or eczema in various skin care topical applications and peels revolves around the compounds ability to precipitate cutaneous proteins from the treated skin . In LPO and TPO, the resulting π-cation radical of the porphyrin can isomerize to a radical cation with the radical in an aromatic side chain of the enzyme . In vitro and in vivo studies have demonstrated that resorcinol can inhibit peroxidases in the thyroid and subsequently block the synthesis of thyroid hormones and cause goiter .
Present in roasted barley, cane molasses, coffee, beer and wine. Flavouring ingredient. 1,3-Benzenediol is found in many foods, some of which are cereals and cereal products, coffee and coffee products, alcoholic beverages, and java plum.
D - Dermatologicals > D10 - Anti-acne preparations > D10A - Anti-acne preparations for topical use
S - Sensory organs > S01 - Ophthalmologicals > S01A - Antiinfectives
C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent
同义名列表
23 个代谢物同义名
Resorcinol, monocopper (2+) salt; Resorcinol disodium salt; 1,3-Dihydroxy-benzene; 1,3-Dihydroxybenzene; 1,3-Dihydroxybenzol; m-Dihydroxybenzene; m-Hydroxy-phenol; Benzene-1,3-Diol; 1,3-Benzenediol; Resorcinol, 8ci; m-Hydroxyphenol; 3-Hydroxyphenol; m-Dioxybenzene; m-Hydroquinone; m-Benzenediol; Resorcinol; Resorcine; Rezorsine; FEMA 3589; Resorzin; Resorcin; Resorcinol; Resorcinol
数据库引用编号
24 个数据库交叉引用编号
- ChEBI: CHEBI:27810
- KEGG: C01751
- KEGGdrug: D00133
- PubChem: 5054
- HMDB: HMDB0032037
- Metlin: METLIN43324
- DrugBank: DB11085
- ChEMBL: CHEMBL24147
- Wikipedia: Resorcinol
- MetaCyc: CPD-623
- KNApSAcK: C00002671
- foodb: FDB008738
- chemspider: 4878
- CAS: 26982-54-7
- CAS: 108-46-3
- PMhub: MS000006938
- PubChem: 4884
- PDB-CCD: RCO
- 3DMET: B00342
- NIKKAJI: J2.863K
- RefMet: Resorcinol
- KNApSAcK: 27810
- LOTUS: LTS0035614
- wikidata: Q408865
分类词条
相关代谢途径
Reactome(0)
BioCyc(5)
PlantCyc(0)
代谢反应
6 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(6)
- γ-resorcylate degradation I:
γ-resorcylate + H+ ⟶ CO2 + resorcinol - resorcinol degradation:
O2 + hydroxyquinol ⟶ 2-maleylacetate + H+ - γ-resorcylate degradation II:
O2 + hydroxyquinol ⟶ 2-maleylacetate + H+ - resorcinol degradation:
H+ + NADH + O2 + resorcinol ⟶ 1,2,4-benzenetriol + H2O + NAD+ - superpathway of aromatic compound degradation:
O2 + protocatechuate ⟶ 3-carboxy-cis,cis-muconate + H+ - resorcinol degradation:
H+ + NADPH + O2 + resorcinol ⟶ H2O + NADP+ + hydroxyquinol
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
12 个相关的物种来源信息
- 171929 - Anacardium occidentale: 10.1021/JF00002A039
- 84009 - Arctostaphylos uva-ursi: 10.1016/S0021-9673(01)89414-0
- 241862 - Bagassa guianensis: 10.1016/J.PHYTOCHEM.2010.06.020
- 4047 - Coriandrum sativum: 10.1016/J.ARABJC.2013.12.011
- 1766648 - Dothiorella vidmadera: 10.1021/ACS.JAFC.7B05248
- 9606 - Homo sapiens: -
- 65561 - Hypericum perforatum: 10.1055/S-2007-969352
- 3496 - Maclura pomifera: 10.1007/BF02859211
- 77113 - Nuphar lutea: 10.1007/BF02029542
- 53809 - Oxalis pes-caprae: 10.1021/NP0702786
- 38942 - Quercus robur: 10.1055/S-2007-969352
- 552636 - Xanthium strumarium var. canadense: 10.1021/NP50041A038
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
- Eva Arrebola, Francesca R Aprile, Claudia E Calderón, Antonio de Vicente, Francisco M Cazorla. Insecticidal features displayed by the beneficial rhizobacterium Pseudomonas chlororaphis PCL1606.
International microbiology : the official journal of the Spanish Society for Microbiology.
2022 Nov; 25(4):679-689. doi:
10.1007/s10123-022-00253-w. [PMID: 35670867] - Anna Jeżewska, Dorota Kondej. [Resorcinol - determination method in the workplace air].
Medycyna pracy.
2022 Apr; 73(2):135-142. doi:
10.13075/mp.5893.01150. [PMID: 35373783] - Andrew S Elder, John N Coupland, Ryan J Elias. Effect of alkyl chain length on the antioxidant activity of alkylresorcinol homologues in bulk oils and oil-in-water emulsions.
Food chemistry.
2021 Jun; 346(?):128885. doi:
10.1016/j.foodchem.2020.128885. [PMID: 33429298] - Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
Cell reports.
2021 04; 35(4):109040. doi:
10.1016/j.celrep.2021.109040. [PMID: 33910017] - Stanislas Nsanzamahoro, Ying Zhang, Wei-Feng Wang, Yu-Zhu Ding, Yan-Ping Shi, Jun-Li Yang. Fluorescence 'turn-on' of silicon-containing nanoparticles for the determination of resorcinol.
Mikrochimica acta.
2021 01; 188(2):46. doi:
10.1007/s00604-021-04700-9. [PMID: 33483779] - Miroslav Sisa, Marcela Dvorakova, Veronika Temml, Veronika Jarosova, Tomas Vanek, Premysl Landa. Synthesis, inhibitory activity and in silico docking of dual COX/5-LOX inhibitors with quinone and resorcinol core.
European journal of medicinal chemistry.
2020 Oct; 204(?):112620. doi:
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Biomaterials science.
2020 Mar; 8(6):1622-1637. doi:
10.1039/c9bm01089k. [PMID: 31967622] - Md Shahinozzaman, Takahiro Ishii, Mohammad A Halim, Md Amzad Hossain, Md Tofazzal Islam, Shinkichi Tawata. Cytotoxic and anti-inflammatory resorcinol and alkylbenzoquinone derivatives from the leaves of Ardisia sieboldii.
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Journal of proteome research.
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2013 Dec; 141(4):3546-51. doi:
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Analytical chemistry.
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PloS one.
2012; 7(2):e31261. doi:
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PloS one.
2012; 7(6):e38534. doi:
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Analytical and bioanalytical chemistry.
2012 Jan; 402(1):405-12. doi:
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AoB PLANTS.
2012; 2012(?):pls008. doi:
10.1093/aobpla/pls008. [PMID: 22593822] - Luisa M Ostertag, Niamh O'Kennedy, Graham W Horgan, Paul A Kroon, Garry G Duthie, Baukje de Roos. In vitro anti-platelet effects of simple plant-derived phenolic compounds are only found at high, non-physiological concentrations.
Molecular nutrition & food research.
2011 Nov; 55(11):1624-36. doi:
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Fitoterapia.
2011 Oct; 82(7):1137-9. doi:
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Journal of ethnopharmacology.
2011 Sep; 137(1):620-5. doi:
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Journal of Asian natural products research.
2011 Aug; 13(8):734-43. doi:
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Andrologia.
2011 Aug; 43(4):273-7. doi:
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Bioorganic & medicinal chemistry letters.
2011 May; 21(10):2945-8. doi:
10.1016/j.bmcl.2011.03.060. [PMID: 21511472] - Poonam Yadav, Nalini V Purohit. Synthesis and biological evaluation of some novel 3,4-disubstituted isocoumarins.
Indian journal of pharmaceutical sciences.
2011 Mar; 73(2):171-8. doi:
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BMC pulmonary medicine.
2011 Feb; 11(?):12. doi:
10.1186/1471-2466-11-12. [PMID: 21345191] - Annett Braune, Michael Blaut. Deglycosylation of puerarin and other aromatic C-glucosides by a newly isolated human intestinal bacterium.
Environmental microbiology.
2011 Feb; 13(2):482-94. doi:
10.1111/j.1462-2920.2010.02352.x. [PMID: 20946528] - Daniel W Bergner, Theresa B Kuhlenschmidt, William P Hanafin, Lawrence D Firkins, Mark S Kuhlenschmidt. Inhibition of rotavirus infectivity by a neoglycolipid receptor mimetic.
Nutrients.
2011 02; 3(2):228-44. doi:
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Phytotherapy research : PTR.
2011 Feb; 25(2):271-6. doi:
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International journal of biological sciences.
2011; 7(8):1161-70. doi:
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Planta medica.
2011 Jan; 77(1):60-5. doi:
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Marine drugs.
2011; 9(7):1187-209. doi:
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Current medicinal chemistry.
2011; 18(7):1085-99. doi:
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Chemistry & biodiversity.
2010 Dec; 7(12):2901-7. doi:
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Plant physiology.
2010 Nov; 154(3):1514-31. doi:
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Journal of agricultural and food chemistry.
2010 Oct; 58(19):10410-8. doi:
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Phytochemistry.
2010 Oct; 71(14-15):1708-13. doi:
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Journal of medicine and life.
2010 Oct; 3(4):437-43. doi:
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Bioorganic & medicinal chemistry.
2010 Sep; 18(17):6538-46. doi:
10.1016/j.bmc.2010.06.077. [PMID: 20692173] - Manjiri Joshi, Ranjitkumar Patil. Estimation and comparative study of serum total sialic acid levels as tumor markers in oral cancer and precancer.
Journal of cancer research and therapeutics.
2010 Jul; 6(3):263-6. doi:
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Phytochemistry.
2010 Jul; 71(10):1032-9. doi:
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Phytochemistry.
2010 Jul; 71(10):1059-67. doi:
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European journal of histochemistry : EJH.
2010 May; 54(2):e23. doi:
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Tropical doctor.
2010 Apr; 40(2):100-3. doi:
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Bioorganic & medicinal chemistry.
2010 Apr; 18(7):2464-73. doi:
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Biochemistry research international.
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Journal of environmental sciences (China).
2010; 22(2):192-7. doi:
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Molecular cancer.
2009 Dec; 8(?):116. doi:
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Oxidative medicine and cellular longevity.
2009 Nov; 2(5):270-8. doi:
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Polski merkuriusz lekarski : organ Polskiego Towarzystwa Lekarskiego.
2009 Aug; 27(158):101-4. doi:
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Journal of chemical ecology.
2009 Aug; 35(8):980-96. doi:
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European journal of pharmacology.
2009 Jul; 614(1-3):128-36. doi:
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Annals of Indian Academy of Neurology.
2009 Jul; 12(3):162-6. doi:
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Biophysical journal.
2009 Apr; 96(8):3140-53. doi:
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Rapid communications in mass spectrometry : RCM.
2009 Mar; 23(6):737-44. doi:
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Phytomedicine : international journal of phytotherapy and phytopharmacology.
2009 Mar; 16(2-3):262-4. doi:
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Journal of agricultural and food chemistry.
2009 Feb; 57(4):1195-203. doi:
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PloS one.
2009; 4(5):e5353. doi:
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Critical care (London, England).
2009; 13(6):R182. doi:
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Journal of experimental botany.
2009; 60(7):2107-17. doi:
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Genome biology.
2009; 10(1):205. doi:
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Biology of reproduction.
2008 Dec; 79(6):1153-9. doi:
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