Hexahydrocurcumin (BioDeep_00000000788)
Secondary id: BioDeep_00001867550
human metabolite PANOMIX_OTCML-2023 Antitumor activity natural product
代谢物信息卡片
化学式: C21H26O6 (374.1729)
中文名称: 六氢姜黄素
谱图信息:
最多检出来源 Viridiplantae(plant) 26.2%
分子结构信息
SMILES: COc(c1)c(O)ccc(CCC(O)CC(=O)CCc(c2)cc(OC)c(O)c2)1
InChI: InChI=1S/C21H26O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h5-6,9-12,16,22,24-25H,3-4,7-8,13H2,1-2H3
描述信息
Hexahydrocurcumin is a member of the class of compounds known as curcuminoids. Curcuminoids are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group. Hexahydrocurcumin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Hexahydrocurcumin can be found in ginger, which makes hexahydrocurcumin a potential biomarker for the consumption of this food product.
Hexahydrocurcumin is a diarylheptanoid.
Hexahydrocurcumin is a natural product found in Zingiber officinale with data available.
[Raw Data] CBA88_Hexahydrocurcum_pos_40eV.txt
[Raw Data] CBA88_Hexahydrocurcum_neg_20eV.txt
[Raw Data] CBA88_Hexahydrocurcum_pos_10eV.txt
[Raw Data] CBA88_Hexahydrocurcum_neg_10eV.txt
[Raw Data] CBA88_Hexahydrocurcum_pos_20eV.txt
[Raw Data] CBA88_Hexahydrocurcum_pos_50eV.txt
[Raw Data] CBA88_Hexahydrocurcum_neg_40eV.txt
[Raw Data] CBA88_Hexahydrocurcum_neg_30eV.txt
[Raw Data] CBA88_Hexahydrocurcum_neg_50eV.txt
[Raw Data] CBA88_Hexahydrocurcum_pos_30eV.txt
Hexahydrocurcumin is one of the major metabolites of curcumin and a selective, orally active COX-2 inhibitor. Hexahydrocurcumin is inactive against COX-1. Hexahydrocurcumin has antioxidant, anticancer and anti-inflammatory activities[1][2].
Hexahydrocurcumin is one of the major metabolites of curcumin and a selective, orally active COX-2 inhibitor. Hexahydrocurcumin is inactive against COX-1. Hexahydrocurcumin has antioxidant, anticancer and anti-inflammatory activities[1][2].
同义名列表
13 个代谢物同义名
(RS)-5-Hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone; 3-Heptanone, 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-; 5-hydroxy-1,7-bis(4-hydroxy-3-methoxy-phenyl)heptan-3-one; 5-hydroxy-1,7-bis(4-hydroxy-3-methoxylphenyl)-3-heptanone; 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone; 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one; 1,7-Bis(4-hydroxy-3-methoxyphenyl)-5-heptanol-3-one; Hexahydrocurcumin, analytical standard; Curcumin, hexahydro-; Hexahydrocurcumin; UNII-RNL5XJ2BA7; MEGxp0_001211; RNL5XJ2BA7
数据库引用编号
27 个数据库交叉引用编号
- ChEBI: CHEBI:81358
- KEGG: C17826
- PubChem: 96024124
- PubChem: 5318039
- HMDB: HMDB0302135
- Metlin: METLIN71920
- ChEMBL: CHEMBL479650
- MeSH: hexahydrocurcumin
- ChemIDplus: 0036062052
- KNApSAcK: C00035640
- foodb: FDB001897
- chemspider: 4476682
- CAS: 36062-05-2
- MoNA: FIO01046
- MoNA: FIO01040
- MoNA: FIO01047
- MoNA: FIO01045
- MoNA: FIO01043
- MoNA: FIO01048
- MoNA: FIO01044
- MoNA: FIO01042
- MoNA: FIO01041
- MoNA: FIO01039
- medchemexpress: HY-N0929
- PMhub: MS000026125
- NIKKAJI: J445.265H
- LOTUS: LTS0000795
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)
25 个相关的物种来源信息
- 94326 - Alpinia: LTS0000795
- 199623 - Alpinia officinarum: 10.1055/S-2005-873176
- 199623 - Alpinia officinarum: LTS0000795
- 199623 - Alpinia officinarum Hance: -
- 99568 - Curcuma: LTS0000795
- 136217 - Curcuma Longa L.: -
- 136222 - Curcuma xanthorrhiza: 10.1248/CPB.35.3298
- 136222 - Curcuma xanthorrhiza: LTS0000795
- 2759 - Eukaryota: LTS0000795
- 9606 - Homo sapiens: -
- 4447 - Liliopsida: LTS0000795
- 3398 - Magnoliopsida: LTS0000795
- 33090 - Plants: -
- 35493 - Streptophyta: LTS0000795
- 58023 - Tracheophyta: LTS0000795
- 33090 - Viridiplantae: LTS0000795
- 4650 - Zingiber: LTS0000795
- 94328 - Zingiber officinale:
- 94328 - Zingiber officinale: 10.1021/NP800555Y
- 94328 - Zingiber officinale: 10.1248/CPB.39.120
- 94328 - Zingiber officinale: 10.1248/CPB.40.387
- 94328 - Zingiber officinale: LTS0000795
- 94328 - Zingiber officinale Rosc.: -
- 94328 - Zingiber Officinale Roscoe: -
- 4642 - Zingiberaceae: LTS0000795
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
- Pranglada Jearjaroen, Phakkawat Thangwong, Chainarong Tocharus, Waraluck Chaichompoo, Apichart Suksamrarn, Jiraporn Tocharus. Hexahydrocurcumin attenuated demyelination and improved cognitive impairment in chronic cerebral hypoperfusion rats.
Inflammopharmacology.
2023 Dec; ?(?):. doi:
10.1007/s10787-023-01406-7. [PMID: 38153537] - Ruopeng Li, Qinghe Liang, Qin Yang, Wenqi Dai, Yao Xiao, Hudan Pan, Zhongde Zhang, Liang Liu, Xiaojuan Li. Hexahydrocurcumin from Zingiberis rhizoma attenuates lipopolysaccharide-induced acute pneumonia through JAK1/STAT3 signaling pathway.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2023 Oct; 122(?):155141. doi:
10.1016/j.phymed.2023.155141. [PMID: 37837898] - Yi-Hsiung Lin, Shwu-Jiuan Sheu, Wangta Liu, Yun-Tzu Hsu, Chen-Xi He, Chang-Yi Wu, Kuo-Jen Chen, Po-Yen Lee, Chien-Chih Chiu, Kai-Chun Cheng. Retinal protective effect of curcumin metabolite hexahydrocurcumin against blue light-induced RPE damage.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2023 Feb; 110(?):154606. doi:
10.1016/j.phymed.2022.154606. [PMID: 36584606] - Qianwen Guo, Wenbin Li, Rong Wang, Jiazhong Li, Ruxue Zhang, Xiaojing Zhang, Zihan Wang. Screening of activators of 2,3-diphosphoglycerate mutase from traditional Chinese herb medicines.
Zhejiang da xue xue bao. Yi xue ban = Journal of Zhejiang University. Medical sciences.
2022 Aug; 51(4):430-437. doi:
10.3724/zdxbyxb-2022-0178. [PMID: 37202106] - Luckika Panthiya, Jiraporn Tocharus, Amnart Onsa-Ard, Waraluck Chaichompoo, Apichart Suksamrarn, Chainarong Tocharus. Hexahydrocurcumin ameliorates hypertensive and vascular remodeling in L-NAME-induced rats.
Biochimica et biophysica acta. Molecular basis of disease.
2022 03; 1868(3):166317. doi:
10.1016/j.bbadis.2021.166317. [PMID: 34883248] - Corinne Vanucci-Bacqué, Florence Bedos-Belval. Anti-inflammatory activity of naturally occuring diarylheptanoids - A review.
Bioorganic & medicinal chemistry.
2021 02; 31(?):115971. doi:
10.1016/j.bmc.2020.115971. [PMID: 33422907] - Toshio Niwa, Shin-Ichiro Yokoyama, Mika Mochizuki, Toshihiko Osawa. Production of Optically Active Hexahydrocurcumin by Human Intestinal Bacterium in Vitro.
Biological & pharmaceutical bulletin.
2021; 44(1):136-139. doi:
10.1248/bpb.b20-00584. [PMID: 33390541] - Yiyuan Huang, Shijie Cao, Qiang Zhang, Hongyang Zhang, Yuqi Fan, Feng Qiu, Ning Kang. Biological and pharmacological effects of hexahydrocurcumin, a metabolite of curcumin.
Archives of biochemistry and biophysics.
2018 05; 646(?):31-37. doi:
10.1016/j.abb.2018.03.030. [PMID: 29596797] - Gary N Asher, Ying Xie, Ruin Moaddel, Mitesh Sanghvi, Katina S S Dossou, Angela D M Kashuba, Robert S Sandler, Roy L Hawke. Randomized Pharmacokinetic Crossover Study Comparing 2 Curcumin Preparations in Plasma and Rectal Tissue of Healthy Human Volunteers.
Journal of clinical pharmacology.
2017 02; 57(2):185-193. doi:
10.1002/jcph.806. [PMID: 27503249] - Feng Zhao, Yudian Gong, Yuan Hu, Minghui Lu, Jing Wang, Jianxin Dong, Daquan Chen, Lei Chen, Fenghua Fu, Feng Qiu. Curcumin and its major metabolites inhibit the inflammatory response induced by lipopolysaccharide: translocation of nuclear factor-κB as potential target.
Molecular medicine reports.
2015 Apr; 11(4):3087-93. doi:
10.3892/mmr.2014.3079. [PMID: 25502175] - Kiyotaka Nakagawa, Jean-Marc Zingg, Sharon H Kim, Michael J Thomas, Gregory G Dolnikowski, Angelo Azzi, Teruo Miyazawa, Mohsen Meydani. Differential cellular uptake and metabolism of curcuminoids in monocytes/macrophages: regulatory effects on lipid accumulation.
The British journal of nutrition.
2014 Jul; 112(1):8-14. doi:
10.1017/s0007114514000567. [PMID: 24725345] - Feng Li, Viriya Nitteranon, Xiaozhen Tang, Jin Liang, Guodong Zhang, Kirk L Parkin, Qiuhui Hu. In vitro antioxidant and anti-inflammatory activities of 1-dehydro-[6]-gingerdione, 6-shogaol, 6-dehydroshogaol and hexahydrocurcumin.
Food chemistry.
2012 Nov; 135(2):332-7. doi:
10.1016/j.foodchem.2012.04.145. [PMID: 22868095] - Huei-Ping Dong, Rei-Cheng Yang, I-Chun Chunag, Li-Ju Huang, Hsing-Tan Li, Hsin-Liang Chen, Chung-Yi Chen. Inhibitory effect of hexahydrocurcumin on human platelet aggregation.
Natural product communications.
2012 Jul; 7(7):883-4. doi:
NULL. [PMID: 22908571] - Chatchawan Changtam, Poonpilas Hongmanee, Apichart Suksamrarn. Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity.
European journal of medicinal chemistry.
2010 Oct; 45(10):4446-57. doi:
10.1016/j.ejmech.2010.07.003. [PMID: 20691508] - Chatchawan Changtam, Harry P de Koning, Hasan Ibrahim, M Sohail Sajid, Matthew K Gould, Apichart Suksamrarn. Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
European journal of medicinal chemistry.
2010 Mar; 45(3):941-56. doi:
10.1016/j.ejmech.2009.11.035. [PMID: 20004045]
