4-Methylumbelliferone (BioDeep_00000000248)

 

Secondary id: BioDeep_00000000258, BioDeep_00000398406, BioDeep_00000406716, BioDeep_00000860368, BioDeep_00000863311

natural product human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


7-Hydroxy-4-methylcoumarin|4-Methylumbelliferone

化学式: C10H8O3 (176.0473)
中文名称: 7-羟基-4-甲基香豆素, 4-甲基伞形酮, 羟甲香豆素, 胆通
谱图信息: 最多检出来源 Viridiplantae(plant) 16.21%

分子结构信息

SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)O
InChI: InChI=1/C10H8O3/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5,11H,1H3

描述信息

Beta-methylumbelliferone appears as colorless crystals. Insoluble in water. (NTP, 1992)
4-methylumbelliferone is a hydroxycoumarin that is umbelliferone substituted by a methyl group at position 4. It has a role as an antineoplastic agent and a hyaluronic acid synthesis inhibitor. It is functionally related to an umbelliferone.
Hymecromone is a natural product found in Ferula fukanensis, Dalbergia volubilis, and other organisms with data available.
4-methylumbelliferone is a metabolite found in or produced by Saccharomyces cerevisiae.
A coumarin derivative possessing properties as a spasmolytic, choleretic and light-protective agent. It is also used in ANALYTICAL CHEMISTRY TECHNIQUES for the determination of NITRIC ACID.
4-methylumbelliferone is a substrate for: Liver carboxylesterase 1, Cocaine esterase, and S-formylglutathione hydrolase.
A - Alimentary tract and metabolism > A05 - Bile and liver therapy > A05A - Bile therapy
A hydroxycoumarin that is umbelliferone substituted by a methyl group at position 4.
COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials
C78272 - Agent Affecting Nervous System > C29698 - Antispasmodic Agent
D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS
Acquisition and generation of the data is financially supported in part by CREST/JST.
4-Methylumbelliferone is a hyaluronic acid biosynthesis inhibitor with antitumoral and antimetastatic effects.
4-Methylumbelliferone is a hyaluronic acid biosynthesis inhibitor with antitumoral and antimetastatic effects.

同义名列表

106 个代谢物同义名

7-Hydroxy-4-methylcoumarin|4-Methylumbelliferone; 5-18-01-00439 (Beilstein Handbook Reference); 2H-1-Benzopyren-2-one, 7-hydroxy-4-methyl-; 2H-1-Benzopyran, 7-hydroxy-4-methyl-2-oxo-; 2H-1-Benzopyran-2-one, 7-hydroxy-4-methyl-; 7H-1-Benzopyran-7-one, 2-hydroxy-4-methyl-; 2H-1-Benzopyran-2-one,7-hydroxy-4-methyl-; 7-Hydroxy-4-methyl-2H-1-benzopyran-2-one; 7-Hydroxy-4-methyl-2-oxo-2H-1-benzopyran; 7-Hydroxy-4-methyl-2H-chromen-2-one #; 7-Hydroxy-4-methyl-2-oxo-3-chromene; 4-HYDROXYNAPHTHALEN-1-YLMETHYLAMINE; 2-Hydroxy-4-methyl-7H-chromen-7-one; 7-Hydroxy-4-methyl-2H-chromen-2-one; 7-Hydroxy-4-methyl-2H-2-chromenone; 7-hydroxy-4-methyl-chromen-2-one; 7-hydroxy-4-methylchromen-2-one; Hymecromone [USAN:INN:BAN:JAN]; 4-Methylumbelliferone, >=98\\%; Coumarin, 7-hydroxy-4-methyl-; 7-hydroxy-4-methyl-2-coumarin; 4-Methyl-7-hydroxyl Coumarin; 4-Methylumbelliferon [Czech]; 7-hydroxy-4-methyl coumarine; 4-Methylumbelliferone (4-MU); 7-hydroxy-4-methyl coumarin; 7-hydroxy-4-methyl-coumarin; 7 Hydroxy 4 methyl coumarin; Methylumbelliferone, .beta.; Hymecromone (JP17/USAN/INN); 4-Methyl-7-hydroxy-coumarin; 4-methyl-7-hydroxy-cumarin; HYMECROMONE [EP MONOGRAPH]; .beta.-Methylumbelliferone; 7-hydroxy-4-methyl-coumari; 7-HYDROXY-4-METHYLCOUMARIN; 4-Methyl-7-hydroxycoumarin; METHYLUMBELLIFERONE, BETA; Himecromona [INN-Spanish]; Hymecromonum [INN-Latin]; beta-Methylumbelliferone; Umbelliferone, 4-methyl-; Coumarin derivative, 3b; 4-Methyl-umbelliferone; 4-methyl umbelliferone; Β-methylumbelliferone; A-Methylumbelliferone; 4-Methylumbelliferone; 4 Methylumbelliferone; b-Methylumbelliferone; 4-Methylumbelliferon; HYMECROMONE [WHO-DD]; HYMECROMONE [MART.]; Methylumbelliferone; WLN: T66 BOVJ E1 IQ; HYMECROMONE [USAN]; Prestwick1_000901; Prestwick2_000901; Prestwick3_000901; HYMECROMONE [INN]; Imecromone [DCIT]; HYMECROMONE [JAN]; Prestwick0_000901; Maybridge1_002078; Cantabiline (TN); HYMECROMONE [MI]; Hymecromohe,(S); UNII-3T5NG4Q468; Tox21_110385_1; BPBio1_000818; MEGxp0_001898; ACon1_002401; NCI60_042099; Tox21_110385; Tox21_300915; Hymecromonum; Himecromona; Cantabiline; Cholspasmin; Cholonerton; Hymecromone; Resocyanine; CAS-90-33-5; Coumarin 4; Hymechrome; Hymecromon; Cumarote-C; Cantabilin; 3T5NG4Q468; Imecromone; AI3-08085; Bilicante; Mendiaxon; Cholestil; Biliton H; Bilcolic; Eurogale; Crodimon; Himecol; Medilla; LM 94; LM-94; 4-MU; 4MU; ZZ1; 4-Methylumbelliferone



数据库引用编号

48 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)

23 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 7 AIMP2, CASP3, CTNNB1, HAS1, HMMR, HYAL2, TLR4
Golgi apparatus, trans-Golgi network membrane 1 HAS3
Endosome membrane 1 TLR4
Endoplasmic reticulum membrane 9 HAS2, UGT1A1, UGT1A10, UGT1A3, UGT1A6, UGT1A7, UGT1A8, UGT1A9, UGT2B7
Nucleus 4 AIMP2, CASP3, CTNNB1, HAS3
cytosol 6 AIMP2, CASP3, CD44, CTNNB1, HMMR, HYAL2
centrosome 2 CTNNB1, HMMR
nucleoplasm 2 CASP3, CTNNB1
RNA polymerase II transcription regulator complex 1 HYAL2
Cell membrane 6 CD44, CTNNB1, HAS2, HAS3, HYAL2, TLR4
lamellipodium 1 CTNNB1
Multi-pass membrane protein 4 HAS1, HAS2, HAS3, SLC45A2
Golgi apparatus membrane 2 HAS2, HAS3
Synapse 1 CTNNB1
cell cortex 1 CTNNB1
cell junction 1 CTNNB1
cell surface 4 CD44, HMMR, HYAL2, TLR4
glutamatergic synapse 2 CASP3, CTNNB1
Golgi apparatus 4 CD44, HAS1, HAS2, HAS3
Golgi membrane 3 HAS2, HAS3, HYAL2
neuronal cell body 1 CASP3
presynaptic membrane 1 CTNNB1
Cytoplasm, cytosol 1 AIMP2
Lysosome 2 HAS2, HYAL2
plasma membrane 9 CD44, CTNNB1, HAS1, HAS2, HAS3, HMMR, HYAL2, TLR4, UGT1A1
Membrane 16 AIMP2, CD44, CTNNB1, HAS1, HAS3, HMMR, SLC45A2, TLR4, UGT1A1, UGT1A10, UGT1A3, UGT1A6, UGT1A7, UGT1A8, UGT1A9, UGT2B7
apical plasma membrane 2 CD44, HYAL2
basolateral plasma membrane 2 CD44, CTNNB1
extracellular exosome 2 CD44, CTNNB1
endoplasmic reticulum 8 HYAL2, UGT1A1, UGT1A10, UGT1A3, UGT1A6, UGT1A7, UGT1A8, UGT1A9
extracellular space 1 IL6
perinuclear region of cytoplasm 4 CTNNB1, HYAL2, TLR4, UGT1A1
Schaffer collateral - CA1 synapse 1 CTNNB1
adherens junction 1 CTNNB1
apicolateral plasma membrane 1 CTNNB1
bicellular tight junction 1 CTNNB1
protein-containing complex 1 CTNNB1
intracellular membrane-bounded organelle 1 UGT1A6
postsynaptic density 1 CASP3
Single-pass type I membrane protein 2 CD44, TLR4
Secreted 2 CD44, IL6
extracellular region 2 CD44, IL6
Single-pass membrane protein 9 CD44, UGT1A1, UGT1A10, UGT1A3, UGT1A6, UGT1A7, UGT1A8, UGT1A9, UGT2B7
transcription regulator complex 1 CTNNB1
external side of plasma membrane 2 HYAL2, TLR4
Extracellular vesicle 1 HAS2
Z disc 1 CTNNB1
beta-catenin destruction complex 1 CTNNB1
cytoplasmic vesicle 2 HAS2, HYAL2
microtubule cytoskeleton 1 HMMR
Wnt signalosome 1 CTNNB1
Melanosome membrane 1 SLC45A2
Early endosome 2 HAS3, TLR4
apical part of cell 1 CTNNB1
cell-cell junction 1 CTNNB1
vesicle 1 HAS2
postsynaptic membrane 1 CTNNB1
Cytoplasm, perinuclear region 1 UGT1A1
Membrane raft 1 HYAL2
Cytoplasm, cytoskeleton 1 CTNNB1
Cytoplasm, cytoskeleton, spindle 1 HMMR
focal adhesion 2 CD44, CTNNB1
spindle 1 HMMR
Cell junction, adherens junction 1 CTNNB1
flotillin complex 1 CTNNB1
fascia adherens 1 CTNNB1
lateral plasma membrane 1 CTNNB1
Cell projection, ruffle 1 TLR4
ruffle 1 TLR4
receptor complex 1 TLR4
cell projection 1 CD44
phagocytic cup 1 TLR4
cell periphery 1 CTNNB1
cytoskeleton 1 HMMR
Cytoplasm, cytoskeleton, cilium basal body 1 CTNNB1
spindle pole 1 CTNNB1
postsynaptic density, intracellular component 1 CTNNB1
Lipid-anchor, GPI-anchor 1 HYAL2
microvillus membrane 1 CTNNB1
Endomembrane system 1 CTNNB1
microvillus 2 CD44, HYAL2
Cell projection, microvillus 1 CD44
euchromatin 1 CTNNB1
lipopolysaccharide receptor complex 1 TLR4
hyaluranon cable 1 HAS3
plasma membrane raft 1 HAS2
secretory granule membrane 1 CD44
endoplasmic reticulum lumen 1 IL6
endocytic vesicle 1 HYAL2
beta-catenin-TCF complex 1 CTNNB1
presynaptic active zone cytoplasmic component 1 CTNNB1
protein-DNA complex 1 CTNNB1
death-inducing signaling complex 1 CASP3
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
catenin complex 1 CTNNB1
lamellipodium membrane 1 CD44
macrophage migration inhibitory factor receptor complex 1 CD44
interleukin-6 receptor complex 1 IL6
endoplasmic reticulum chaperone complex 1 UGT1A1
beta-catenin-TCF7L2 complex 1 CTNNB1
cytochrome complex 1 UGT1A1
beta-catenin-ICAT complex 1 CTNNB1
Scrib-APC-beta-catenin complex 1 CTNNB1


文献列表

  • Noreen Halimani, Mikhail Nesterchuk, Alexandra A Tsitrina, Marat Sabirov, Irina N Andreichenko, Nataliya O Dashenkova, Elizaveta Petrova, Alexey M Kulikov, Timofei S Zatsepin, Roman A Romanov, Arsen S Mikaelyan, Yuri V Kotelevtsev. Knockdown of Hyaluronan synthase 2 suppresses liver fibrosis in mice via induction of transcriptomic changes similar to 4MU treatment. Scientific reports. 2024 02; 14(1):2797. doi: 10.1038/s41598-024-53089-x. [PMID: 38307876]
  • Alexandra A Tsitrina, Noreen Halimani, Irina N Andreichenko, Marat Sabirov, Mikhail Nesterchuk, Nataliya O Dashenkova, Roman Romanov, Elena V Bulgakova, Arsen Mikaelyan, Yuri Kotelevtsev. 4-Methylumbelliferone Targets Revealed by Public Data Analysis and Liver Transcriptome Sequencing. International journal of molecular sciences. 2023 Jan; 24(3):. doi: 10.3390/ijms24032129. [PMID: 36768453]
  • Joelle I Rosser, Nadine Nagy, Riya Goel, Gernot Kaber, Sally Demirdjian, Jamie Saxena, Jennifer B Bollyky, Adam R Frymoyer, Ana E Pacheco-Navarro, Elizabeth B Burgener, Jayakumar Rajadas, Zhe Wang, Olga Arbach, Colleen E Dunn, Anissa Kalinowski, Carlos E Milla, Paul L Bollyky. Oral hymecromone decreases hyaluronan in human study participants. The Journal of clinical investigation. 2022 05; 132(9):. doi: 10.1172/jci157983. [PMID: 35499083]
  • Shuai Yang, Yun Ling, Fang Zhao, Wei Li, Zhigang Song, Lu Wang, Qiuting Li, Mengxing Liu, Ying Tong, Lu Chen, Daoping Ru, Tongsheng Zhang, Kaicheng Zhou, Baolong Zhang, Peng Xu, Zhicong Yang, Wenxuan Li, Yuanlin Song, Jianqing Xu, Tongyu Zhu, Fei Shan, Wenqiang Yu, Hongzhou Lu. Hymecromone: a clinical prescription hyaluronan inhibitor for efficiently blocking COVID-19 progression. Signal transduction and targeted therapy. 2022 03; 7(1):91. doi: 10.1038/s41392-022-00952-w. [PMID: 35304437]
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  • Jennifer L McKimm-Breschkin, Susan Barrett, Charley McKenzie-Kludas, Julie McAuley, Victor A Streltsov, Stephen G Withers. Passaging of an influenza A(H1N1)pdm09 virus in a difluoro sialic acid inhibitor selects for a novel, but unfit I106M neuraminidase mutant. Antiviral research. 2019 09; 169(?):104542. doi: 10.1016/j.antiviral.2019.104542. [PMID: 31233807]
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