Hydrastine (BioDeep_00000003599)

 

Secondary id: BioDeep_00001869316

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


3-((5R)-6-methyl(5,6,7,8-tetrahydro-2H-1,3-dioxoleno[4,5-g]isoquinolin-5-yl))( 3S)-6,7-dimethoxy-3-hydroisobenzofuran-1-one

化学式: C21H21NO6 (383.1369)
中文名称: 北美黄连碱, 白毛莨碱, 金印草素, (1R,9S)-(-)-β-羟基
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 86.84%

分子结构信息

SMILES: CN1CCC2=CC3=C(C=C2C1C4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OCO3
InChI: InChI=1S/C21H21NO6/c1-22-7-6-11-8-15-16(27-10-26-15)9-13(11)18(22)19-12-4-5-14(24-2)20(25-3)17(12)21(23)28-19/h4-5,8-9,18-19H,6-7,10H2,1-3H3

描述信息

Hydrastine is a member of isoquinolines. It has a role as a metabolite.
Hydrastine is a natural product found in Hydrastis canadensis, Fumaria indica, and other organisms with data available.
See also: Goldenseal (part of).
A natural product found in Hydrastis canadensis.
Origin: Plant; SubCategory_DNP: Isoquinoline alkaloids, Benzylisoquinoline alkaloids
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.582
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.578
Hydrastine is a natural alkaloid which is present in Hydrastis canadensis and other plants of the ranunculaceae family.

同义名列表

60 个代谢物同义名

3-((5R)-6-methyl(5,6,7,8-tetrahydro-2H-1,3-dioxoleno[4,5-g]isoquinolin-5-yl))( 3S)-6,7-dimethoxy-3-hydroisobenzofuran-1-one; (S)-6,7-DIMETHOXY-3-(R)-(6-METHYL-5,6,7,8-TETRAHYDRO-(1,3)DIOXOLO(4,5-G)ISOQUINOLIN-5-YL)ISOBENZOFURAN-1(3H)-ONE; (S)-6,7-dimethoxy-3-((R)-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)isobenzofuran-1(3H)-one; (S)-6,7-Dimethoxy-3-(R)-(6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)isobenzofuran-1(3H)-one; (3S)-6,7-dimethoxy-3-[(5R)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-isobenzofuran-1-one; (3S)-6,7-dimethoxy-3-[(5R)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one; 6,7-Dimethoxy-3-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinoline-5-yl)-1(3H)-isobenzo furan; PHTHALIDE (S)-6,7-DIMETHOXY-3-(R)-(5,6,7,8-TETRAHYDRO-6-METHYL-1,3-DIOXOLO(4,5-G)ISOQUINOLIN-5-YL)-; 6,7-dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-, (3S)-; Phthalide, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-; Hydrastine, United States Pharmacopeia (USP) Reference Standard; hydrastine hydrochloride, (S-(R*,S*))-isomer; HYDRASTINE (CONSTITUENT OF GOLDENSEAL) [DSC]; 4-27-00-06833 (Beilstein Handbook Reference); HYDRASTINE (CONSTITUENT OF GOLDENSEAL); (1R,9S)-b-Hydrastine(-)-b-Hydrastine; hydrastine, (R-(R*,S*))-isomer; hydrastine, (R-(R*,R*))-isomer; (1R,9S)-(-)- beta -Hydrastine; (1R,9S)-(-)-.beta.-Hydrastine; (1R,9S)-(-)-beta-Hydrastine; (1R,9S)-beta-Hydrastine; (-)-.BETA.-Hydrastine; (+/-)-beta-Hydrastine; (1R,9S)-b-Hydrastine; HYDRASTINE (1R, 9S); HYDRASTINE (USP-RS); (-)-beta-Hydrastine; (+/-)-|A-Hydrastine; HYDRASTINE [WHO-DD]; HYDRASTINE [USP-RS]; (+)-B-HYDRASTINEHCL; (+/-)-β-hydrastine; HYDRASTINE (1R 9S); (-)-|A-Hydrastine; Prestwick2_000581; Prestwick0_000581; Prestwick3_000581; Prestwick1_000581; Hydrastine [USP]; (-)-B-Hydrastine; HYDRASTINE [MI]; beta-hydrastine; (-)-Hydrastine; BPBio1_000466; Tox21_200686; l-Hydrastine; NCI60_003057; Hydrastine; 1ST157723; isocoryne; Hydrastin; 1R,9S-HYDRASTINE; (+)-beta-Hydrastine; 6,7-Dimethoxy-3-(6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-2-benzofuran-1(3H)-one; (-)-alpha-Hydrastine; beta-Hydrastine; (-)-β-Hydrastine; (1R,9S)-β-Hydrastine; (-)-alpha-Hydrastine



数据库引用编号

37 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

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)

90 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 13 ABCB1, CCND1, CCND3, CDK2, CDK4, CDK6, CYP2C9, CYP2D6, CYP3A4, ELANE, LIMK1, PAK4, STMN2
Peripheral membrane protein 2 CYP1B1, STMN2
Endoplasmic reticulum membrane 5 CYP1B1, CYP2C9, CYP2D6, CYP3A4, CYP3A5
Nucleus 8 CCND1, CCND3, CDK2, CDK4, CDK6, DNTT, LIMK1, MMP2
cytosol 10 CCND1, CCND3, CDK2, CDK4, CDK6, DNTT, ELANE, LIMK1, PAK4, STMN2
phagocytic vesicle 1 ELANE
centrosome 4 CCND1, CCND3, CDK2, CDK6
nucleoplasm 6 CCND1, CCND3, CDK2, CDK4, CDK6, DNTT
Cell membrane 2 ABCB1, SLC29A4
Cytoplasmic side 1 STMN2
lamellipodium 2 LIMK1, STMN2
Multi-pass membrane protein 3 ABCB1, SLC19A3, SLC29A4
cell surface 2 ABCB1, ELANE
glutamatergic synapse 1 LIMK1
Golgi apparatus 2 PAK4, STMN2
growth cone 1 STMN2
neuronal cell body 1 STMN2
postsynapse 1 LIMK1
Presynapse 1 SLC29A4
endosome 2 CDK2, STMN2
plasma membrane 6 ABCB1, CYP2C9, ICAM3, MMP2, SLC19A3, SLC29A4
Membrane 10 ABCB1, CYP1B1, CYP2D6, CYP3A4, CYP3A5, ICAM3, LIMK1, SLC19A3, SLC29A4, STMN2
apical plasma membrane 2 ABCB1, SLC29A4
basolateral plasma membrane 1 SLC29A4
extracellular exosome 3 ABCB1, ELANE, ICAM3
endoplasmic reticulum 1 CYP2D6
extracellular space 2 ELANE, MMP2
perinuclear region of cytoplasm 1 STMN2
adherens junction 1 PAK4
bicellular tight junction 2 CCND1, CDK4
mitochondrion 3 CYP1B1, CYP2D6, MMP2
intracellular membrane-bounded organelle 5 CYP1B1, CYP2C9, CYP2D6, CYP3A4, CYP3A5
Microsome membrane 5 CYP1B1, CYP2C9, CYP2D6, CYP3A4, CYP3A5
Single-pass type I membrane protein 1 ICAM3
extracellular region 2 ELANE, MMP2
Single-pass membrane protein 1 CYP2D6
transcription regulator complex 2 CDK2, CDK4
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 2 CDK2, CDK6
Nucleus membrane 2 CCND1, CDK4
nuclear membrane 2 CCND1, CDK4
nucleolus 1 CDK4
Apical cell membrane 2 ABCB1, SLC29A4
Cell projection, lamellipodium 2 LIMK1, STMN2
Cytoplasm, perinuclear region 1 STMN2
Cytoplasm, cytoskeleton 1 LIMK1
focal adhesion 2 LIMK1, PAK4
extracellular matrix 1 MMP2
collagen-containing extracellular matrix 2 ELANE, MMP2
secretory granule 1 ELANE
nuclear speck 1 LIMK1
ruffle 1 CDK6
sarcomere 1 MMP2
neuron projection 2 LIMK1, STMN2
chromatin 1 CDK4
cytoskeleton 1 LIMK1
chromosome, telomeric region 1 CDK2
nuclear envelope 1 CDK2
euchromatin 1 DNTT
nuclear matrix 1 DNTT
transcription repressor complex 2 CCND1, ELANE
male germ cell nucleus 2 CDK2, LIMK1
specific granule lumen 1 ELANE
[Isoform 1]: Secreted, extracellular space, extracellular matrix 1 MMP2
azurophil granule lumen 1 ELANE
Cajal body 1 CDK2
external side of apical plasma membrane 1 ABCB1
condensed chromosome 1 CDK2
Cytoplasmic vesicle, phagosome 1 ELANE
Nucleus, Cajal body 1 CDK2
X chromosome 1 CDK2
Y chromosome 1 CDK2
cyclin-dependent protein kinase holoenzyme complex 5 CCND1, CCND3, CDK2, CDK4, CDK6
cyclin E1-CDK2 complex 1 CDK2
cyclin E2-CDK2 complex 1 CDK2
cyclin D1-CDK4 complex 2 CCND1, CDK4
cyclin D2-CDK4 complex 1 CDK4
cyclin D3-CDK4 complex 2 CCND3, CDK4
cyclin A2-CDK2 complex 1 CDK2
cyclin D1-CDK6 complex 2 CCND1, CDK6
cyclin A1-CDK2 complex 1 CDK2
cyclin D3-CDK6 complex 2 CCND3, CDK6
cyclin D2-CDK6 complex 1 CDK6


文献列表

  • Manead Khin, Nadja B Cech, Joshua J Kellogg, Lindsay K Caesar. Chemical Evaluation of the Effects of Storage Conditions on the Botanical Goldenseal using Marker-based and Metabolomics Approaches. The Yale journal of biology and medicine. 2020 06; 93(2):265-275. doi: . [PMID: 32607087]
  • Phuong Mai Le, Clément Milande, Estelle Martineau, Patrick Giraudeau, Jonathan Farjon. Quantification of natural products in herbal supplements: A combined NMR approach applied on goldenseal. Journal of pharmaceutical and biomedical analysis. 2019 Feb; 165(?):155-161. doi: 10.1016/j.jpba.2018.11.062. [PMID: 30544050]
  • Bingyu Guo, Xiaodong Li, Shuai Song, Meng Chen, Maosheng Cheng, Dongmei Zhao, Feng Li. (-)-β-hydrastine suppresses the proliferation and invasion of human lung adenocarcinoma cells by inhibiting PAK4 kinase activity. Oncology reports. 2016 Apr; 35(4):2246-56. doi: 10.3892/or.2016.4594. [PMID: 26821251]
  • Xinwen Wang, Hao-Jie Zhu, Juliana Munoz, Bill J Gurley, John S Markowitz. An ex vivo approach to botanical-drug interactions: a proof of concept study. Journal of ethnopharmacology. 2015 Apr; 163(?):149-56. doi: 10.1016/j.jep.2015.01.021. [PMID: 25623616]
  • Prem K Gupta, Gary Barone, Bill J Gurley, E Kim Fifer, Howard P Hendrickson. Hydrastine pharmacokinetics and metabolism after a single oral dose of goldenseal (Hydrastis canadensis) to humans. Drug metabolism and disposition: the biological fate of chemicals. 2015 Apr; 43(4):534-52. doi: 10.1124/dmd.114.059410. [PMID: 25609220]
  • Daniel J Warner, Hongming Chen, Louis-David Cantin, J Gerry Kenna, Simone Stahl, Clare L Walker, Tobias Noeske. Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification. Drug metabolism and disposition: the biological fate of chemicals. 2012 Dec; 40(12):2332-41. doi: 10.1124/dmd.112.047068. [PMID: 22961681]
  • Nadja B Cech, Hiyas A Junio, Laynez W Ackermann, Jeffrey S Kavanaugh, Alexander R Horswill. Quorum quenching and antimicrobial activity of goldenseal (Hydrastis canadensis) against methicillin-resistant Staphylococcus aureus (MRSA). Planta medica. 2012 Sep; 78(14):1556-61. doi: 10.1055/s-0032-1315042. [PMID: 22814821]
  • Phurpa Wangchuk, Paul A Keller, Stephen G Pyne, Anthony C Willis, Sumalee Kamchonwongpaisan. Antimalarial alkaloids from a Bhutanese traditional medicinal plant Corydalis dubia. Journal of ethnopharmacology. 2012 Aug; 143(1):310-3. doi: 10.1016/j.jep.2012.06.037. [PMID: 22796506]
  • Michelle L Dawes, Thomas Brettell. Analysis of goldenseal, Hydrastis canadensis L., and related alkaloids in urine using HPLC with UV detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Jan; 880(1):114-8. doi: 10.1016/j.jchromb.2011.11.026. [PMID: 22177787]
  • Katsunori Yamaura, Maki Shimada, Noriyuki Nakayama, Koichi Ueno. Protective effects of goldenseal (Hydrastis canadensis L.) on acetaminophen-induced hepatotoxicity through inhibition of CYP2E1 in rats. Pharmacognosy research. 2011 Oct; 3(4):250-5. doi: 10.4103/0974-8490.89745. [PMID: 22224048]
  • Keivan A Ettefagh, Johnna T Burns, Hiyas A Junio, Glenn W Kaatz, Nadja B Cech. Goldenseal (Hydrastis canadensis L.) extracts synergistically enhance the antibacterial activity of berberine via efflux pump inhibition. Planta medica. 2011 May; 77(8):835-40. doi: 10.1055/s-0030-1250606. [PMID: 21157683]
  • James A Douglas, John M Follett, Graeme A Parmenter, Catherine E Sansom, Nigel B Perry, Ray A Littler. Seasonal variation of biomass and bioactive alkaloid content of goldenseal, Hydrastis canadensis. Fitoterapia. 2010 Oct; 81(7):925-8. doi: 10.1016/j.fitote.2010.06.006. [PMID: 20550958]
  • Deepak Singla, Arun Sharma, Jasjit Kaur, Bharat Panwar, Gajendra P S Raghava. BIAdb: a curated database of benzylisoquinoline alkaloids. BMC pharmacology. 2010 Mar; 10(?):4. doi: 10.1186/1471-2210-10-4. [PMID: 20205728]
  • Prem K Gupta, Martha Hubbard, Bill Gurley, Howard P Hendrickson. Validation of a liquid chromatography-tandem mass spectrometric assay for the quantitative determination of hydrastine and berberine in human serum. Journal of pharmaceutical and biomedical analysis. 2009 May; 49(4):1021-6. doi: 10.1016/j.jpba.2009.01.036. [PMID: 19269122]
  • Paula N Brown, Mark C Roman. Determination of hydrastine and berberine in goldenseal raw materials, extracts, and dietary supplements by high-performance liquid chromatography with UV: collaborative study. Journal of AOAC International. 2008 Jul; 91(4):694-701. doi: . [PMID: 18727526]
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  • Amy S Etheridge, Sherry R Black, Purvi R Patel, James So, James M Mathews. An in vitro evaluation of cytochrome P450 inhibition and P-glycoprotein interaction with goldenseal, Ginkgo biloba, grape seed, milk thistle, and ginseng extracts and their constituents. Planta medica. 2007 Jul; 73(8):731-41. doi: 10.1055/s-2007-981550. [PMID: 17611934]
  • Matthias Unger, Stefanie Laug, Ulrike Holzgrabe. Capillary zone electrophoresis as a tool for the quality control of goldenseal extracts. Electrophoresis. 2005 Jun; 26(12):2430-6. doi: 10.1002/elps.200410322. [PMID: 15912542]
  • Catherine E McNamara, Nigel B Perry, John M Follett, Graeme A Parmenter, James A Douglas. A new glucosyl feruloyl quinic acid as a potential marker for roots and rhizomes of goldenseal, Hydrastis canadensis. Journal of natural products. 2004 Nov; 67(11):1818-22. doi: 10.1021/np049868j. [PMID: 15568768]
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  • Parnali Chatterjee, Michael R Franklin. Human cytochrome p450 inhibition and metabolic-intermediate complex formation by goldenseal extract and its methylenedioxyphenyl components. Drug metabolism and disposition: the biological fate of chemicals. 2003 Nov; 31(11):1391-7. doi: 10.1124/dmd.31.11.1391. [PMID: 14570772]
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  • M Goel, U P Singh, R N Jha, V B Pandey, M B Pandey. Individual and combined effect of (+/-)-alpha-hydrastine and (+/-)-beta-hydrastine on spore germination of some fungi. Folia microbiologica. 2003; 48(3):363-8. doi: 10.1007/bf02931368. [PMID: 12879748]
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