Orsellinic_acid (BioDeep_00000000130)

 

Secondary id: BioDeep_00000264833

PANOMIX_OTCML-2023 Marine Natural Products


代谢物信息卡片


6-Methyl-beta-resorcylic acid; Orcinolcarboxylic acid

化学式: C8H8O4 (168.0423)
中文名称: 2,4-二羟基-6-甲基苯甲酸, 苔色酸
谱图信息: 最多检出来源 Homo sapiens(otcml) 7.82%

分子结构信息

SMILES: C1(C(=O)O)C(O)=CC(O)=CC=1C
InChI: InChI=1S/C8H8O4/c1-4-2-5(9)3-6(10)7(4)8(11)12/h2-3,9-10H,1H3,(H,11,12)

描述信息

O-orsellinic acid is a dihydroxybenzoic acid that is 2,4-dihydroxybenzoic acid in which the hydrogen at position 6 is replaced by a methyl group. It has a role as a metabolite, a marine metabolite and a fungal metabolite. It is a dihydroxybenzoic acid and a member of resorcinols. It is a conjugate acid of an o-orsellinate.
2,4-Dihydroxy-6-methylbenzoic acid is a natural product found in Nidularia pulvinata, Hypoxylon rubiginosum, and other organisms with data available.
A dihydroxybenzoic acid that is 2,4-dihydroxybenzoic acid in which the hydrogen at position 6 is replaced by a methyl group.
Orsellinic acid is a compound produced by Lecanoric acid treated with alcohols. Lecanoric acid is a lichen depside isolated from a Parmotrema tinctorum specimen[1].

同义名列表

38 个代谢物同义名

6-Methyl-beta-resorcylic acid; Orcinolcarboxylic acid; 6-Methyl--resorcylic acid; Orcinolcarboxylic acid; 2,4-Dihydroxy-6-methylbenzenecarboxylic acid; Benzoic acid, 2,4-dihydroxy-6-methyl-; 2,4-Dihydroxy-6-methyl benzoic acid; 2,4-dihydroxy-6-methyl-benzoic acid; 2,4-Dihydroxy-6-methylbenzoic acid; 4,6-Dihydroxy-2-methylbenzoic acid; .beta.-Resorcylic acid, 6-methyl-; 6-Methyl-.beta.-resorcylic acid; 2,4-Dihydroxy-6-methylbenzoate; 4,6-Dihydroxy-o-toluic acid; 6-Methyl- -resorcylic acid; O-ORSELLINIC ACID [MI]; Orcinolcarboxylic acid; o-Orsellinic acid; Spectrum4_001598; Spectrum5_000316; Spectrum2_000305; Spectrum3_001284; UNII-11XLA0494B; orsellinic acid; Orsellinsaeure; Orsellinicacid; Orsellic acid; MEGxm0_000096; DivK1c_006216; KBio2_006210; KBio2_003642; KBio2_001074; KBio3_002107; KBio1_001160; Orsellinate; 11XLA0494B; Orsellinic; 6X7; Orsellinate; Orsellinic acid



数据库引用编号

20 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)

17 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 8 ALOX5, CASP3, CASP7, CAT, FDPS, FNTA, PTPRF, TYR
Peripheral membrane protein 2 ALOX5, CTSK
Endosome membrane 1 GPR135
Endoplasmic reticulum membrane 1 PTGES
Nucleus 4 CASP3, CASP7, SINHCAF, TAL1
cytosol 8 ALOX5, CASP3, CASP7, CAT, DHODH, FDPS, FNTA, LIPE
nucleoplasm 7 ALOX5, CASP3, CASP7, CTSK, DHODH, FDPS, TAL1
Cell membrane 6 CD69, CTSK, GPR135, GPRC5A, LIPE, PTAFR
Multi-pass membrane protein 4 GPR135, GPRC5A, PTAFR, PTGES
glutamatergic synapse 1 CASP3
lysosomal membrane 1 GAA
mitochondrial inner membrane 1 DHODH
neuronal cell body 2 CASP3, PTPRF
Cytoplasm, cytosol 3 ALOX5, CASP7, LIPE
Lysosome 3 CTSK, GAA, TYR
endosome 1 GPR135
plasma membrane 8 CD69, CTSK, FNTA, GAA, GPR135, GPRC5A, PTAFR, PTPRF
Membrane 8 CAT, DHODH, FDPS, GAA, LIPE, PTAFR, PTGES, PTPRF
apical plasma membrane 1 CTSK
caveola 1 LIPE
extracellular exosome 5 BMP3, CAT, GAA, GPRC5A, PTPRF
Lysosome membrane 1 GAA
extracellular space 4 ALOX5, BMP3, CASP7, CTSK
lysosomal lumen 2 CTSK, GAA
perinuclear region of cytoplasm 3 ALOX5, PTGES, TYR
mitochondrion 2 CAT, DHODH
protein-containing complex 2 CAT, CD69
intracellular membrane-bounded organelle 5 CAT, CTSK, GAA, GPRC5A, TYR
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 TYR
Secreted 3 BMP3, CTSK, GAA
extracellular region 5 ALOX5, BMP3, CAT, CTSK, GAA
Single-pass membrane protein 2 DHODH, PTPRF
mitochondrial matrix 2 CAT, FDPS
Extracellular side 1 CTSK
transcription regulator complex 1 TAL1
Nucleus membrane 1 ALOX5
nuclear membrane 1 ALOX5
external side of plasma membrane 2 CD69, CTSK
nucleolus 1 GPRC5A
Melanosome membrane 1 TYR
Golgi-associated vesicle 1 TYR
Single-pass type II membrane protein 1 CD69
vesicle 1 GPRC5A
Apical cell membrane 1 CTSK
Cytoplasm, perinuclear region 2 ALOX5, PTGES
Mitochondrion inner membrane 1 DHODH
focal adhesion 1 CAT
Peroxisome 2 CAT, FDPS
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
receptor complex 1 GPRC5A
neuron projection 1 PTPRF
chromatin 1 TAL1
microtubule associated complex 1 FNTA
Secreted, extracellular space 1 CASP7
nuclear envelope 1 ALOX5
Nucleus envelope 1 ALOX5
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
Cytoplasmic vesicle membrane 1 GPRC5A
tertiary granule membrane 2 GAA, PTAFR
Melanosome 1 TYR
ficolin-1-rich granule lumen 2 ALOX5, CAT
secretory granule lumen 2 ALOX5, CAT
secretory granule membrane 1 PTAFR
nuclear matrix 1 ALOX5
azurophil granule membrane 1 GAA
Nucleus matrix 1 ALOX5
nuclear envelope lumen 2 ALOX5, PTGES
Sin3-type complex 1 SINHCAF
ficolin-1-rich granule membrane 1 GAA
death-inducing signaling complex 1 CASP3
catalase complex 1 CAT
endolysosome lumen 1 CTSK
Nucleus intermembrane space 1 ALOX5
autolysosome lumen 1 GAA
CAAX-protein geranylgeranyltransferase complex 1 FNTA
protein farnesyltransferase complex 1 FNTA


文献列表

  • Feng Ju, Qi-Xuan Kuang, Qing-Zhou Li, Li-Jun Huang, Wen-Xiu Guo, Lei-Qiang Gong, Yi-Fei Dai, Lun Wang, Yu-Cheng Gu, Dong Wang, Yun Deng, Da-Le Guo. Aureonitol Analogues and Orsellinic Acid Esters Isolated from Chaetomium elatum and Their Antineuroinflammatory Activity. Journal of natural products. 2021 12; 84(12):3044-3054. doi: 10.1021/acs.jnatprod.1c00783. [PMID: 34846889]
  • Hui Tao, Ikuro Abe. Enzymology and biosynthesis of the orsellinic acid derived medicinal meroterpenoids. Current opinion in biotechnology. 2021 06; 69(?):52-59. doi: 10.1016/j.copbio.2020.11.016. [PMID: 33383296]
  • Mohsen Vaez, Seyed Javad Davarpanah. New Insights into the Biological Activity of Lichens: Bioavailable Secondary Metabolites of Umbilicaria decussata as Potential Anticoagulants. Chemistry & biodiversity. 2021 May; 18(5):e2100080. doi: 10.1002/cbdv.202100080. [PMID: 33773025]
  • Guo-Dong Chen, Dan Hu, Mei-Juan Huang, Jia Tang, Xiao-Xia Wang, Jian Zou, Jun Xie, Wei-Guang Zhang, Liang-Dong Guo, Xin-Sheng Yao, Ikuro Abe, Hao Gao. Sporormielones A-E, bioactive novel C-C coupled orsellinic acid derivative dimers, and their biosynthetic origin. Chemical communications (Cambridge, England). 2020 Apr; 56(33):4607-4610. doi: 10.1039/d0cc00855a. [PMID: 32211655]
  • Godwin U Ebiloma, Teresa Díaz Ayuga, Emmanuel O Balogun, Lucía Abad Gil, Anne Donachie, Marcel Kaiser, Tomás Herraiz, Daniel K Inaoka, Tomoo Shiba, Shigeharu Harada, Kiyoshi Kita, Harry P de Koning, Christophe Dardonville. Inhibition of trypanosome alternative oxidase without its N-terminal mitochondrial targeting signal (ΔMTS-TAO) by cationic and non-cationic 4-hydroxybenzoate and 4-alkoxybenzaldehyde derivatives active against T. brucei and T. congolense. European journal of medicinal chemistry. 2018 Apr; 150(?):385-402. doi: 10.1016/j.ejmech.2018.02.075. [PMID: 29544150]
  • Po-Wei Yu, Ting-Yu Cho, Ruey-Fen Liou, Shean-Shong Tzean, Tzong-Huei Lee. Identification of the orsellinic acid synthase PKS63787 for the biosynthesis of antroquinonols in Antrodia cinnamomea. Applied microbiology and biotechnology. 2017 Jun; 101(11):4701-4711. doi: 10.1007/s00253-017-8196-6. [PMID: 28255687]
  • Andrea N L Batista, José Roberto A Dos Santos-Pinto, João M Batista, Tatiana M Souza-Moreira, Mariana M Santoni, Cleslei F Zanelli, Massuo J Kato, Silvia N López, Mario S Palma, Maysa Furlan. The Combined Use of Proteomics and Transcriptomics Reveals a Complex Secondary Metabolite Network in Peperomia obtusifolia. Journal of natural products. 2017 05; 80(5):1275-1286. doi: 10.1021/acs.jnatprod.6b00827. [PMID: 28422496]
  • Changlei Sun, Feng Liu, Jie Sun, Jia Li, Xiao Wang. Optimisation and establishment of separation conditions of organic acids from Usnea longissima Ach. by pH-zone-refining counter-current chromatography: Discussion of the eluotropic sequence. Journal of chromatography. A. 2016 Jan; 1427(?):96-101. doi: 10.1016/j.chroma.2015.12.016. [PMID: 26686561]
  • Yayue Liu, Qin Yang, Guoping Xia, Hongbo Huang, Hanxiang Li, Lin Ma, Yongjun Lu, Lei He, Xuekui Xia, Zhigang She. Polyketides with α-Glucosidase Inhibitory Activity from a Mangrove Endophytic Fungus, Penicillium sp. HN29-3B1. Journal of natural products. 2015 Aug; 78(8):1816-22. doi: 10.1021/np500885f. [PMID: 26230970]
  • Simon Hartung Jørgensen, Rasmus John Norman Frandsen, Kristian Fog Nielsen, Erik Lysøe, Teis Esben Sondergaard, Reinhard Wimmer, Henriette Giese, Jens Laurids Sørensen. Fusarium graminearum PKS14 is involved in orsellinic acid and orcinol synthesis. Fungal genetics and biology : FG & B. 2014 Sep; 70(?):24-31. doi: 10.1016/j.fgb.2014.06.008. [PMID: 25011010]
  • Christopher J Johnson, James P Bennett, Steven M Biro, Juan Camilo Duque-Velasquez, Cynthia M Rodriguez, Richard A Bessen, Tonie E Rocke. Degradation of the disease-associated prion protein by a serine protease from lichens. PloS one. 2011 May; 6(5):e19836. doi: 10.1371/journal.pone.0019836. [PMID: 21589935]
  • Naoki Iwata, Susumu Kitanaka. New cannabinoid-like chromane and chromene derivatives from Rhododendron anthopogonoides. Chemical & pharmaceutical bulletin. 2011; 59(11):1409-12. doi: 10.1248/cpb.59.1409. [PMID: 22041081]
  • Tatjana Mitrović, Slaviša Stamenković, Vladimir Cvetković, Svetlana Tošić, Milan Stanković, Ivana Radojević, Olgica Stefanović, Ljiljana Comić, Dragana Dačić, Milena Curčić, Snežana Marković. Antioxidant, antimicrobial and antiproliferative activities of five lichen species. International journal of molecular sciences. 2011; 12(8):5428-48. doi: 10.3390/ijms12085428. [PMID: 21954369]
  • Danielle Bogo, Maria Fatima Cepa de Matos, Neli Kika Honda, Elenir Curi Pontes, Patricia Midori Oguma, Evelyn Cristina Silva da Santos, João Ernesto de Carvalho, Auro Nomizo. In vitro antitumour activity of orsellinates. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2010 Jan; 65(1-2):43-8. doi: 10.1515/znc-2010-1-208. [PMID: 20355320]
  • Imke Schmitt, H Thorsten Lumbsch. Ancient horizontal gene transfer from bacteria enhances biosynthetic capabilities of fungi. PloS one. 2009; 4(2):e4437. doi: 10.1371/journal.pone.0004437. [PMID: 19212443]
  • Cory S Harris, Fan Mo, Lamiaa Migahed, Leonid Chepelev, Pierre S Haddad, James S Wright, William G Willmore, John T Arnason, Steffany A L Bennett. Plant phenolics regulate neoplastic cell growth and survival: a quantitative structure-activity and biochemical analysis. Canadian journal of physiology and pharmacology. 2007 Nov; 85(11):1124-38. doi: 10.1139/y07-101. [PMID: 18066115]
  • Scott D Ryan, Cory S Harris, Fan Mo, Haemi Lee, Sheng T Hou, Nicolas G Bazan, Pierre S Haddad, John T Arnason, Steffany A L Bennett. Platelet activating factor-induced neuronal apoptosis is initiated independently of its G-protein coupled PAF receptor and is inhibited by the benzoate orsellinic acid. Journal of neurochemistry. 2007 Oct; 103(1):88-97. doi: 10.1111/j.1471-4159.2007.04740.x. [PMID: 17877634]
  • Pedro J M Abreu, Yonghong Liu. Ozoroalide, a new macrolide from Ozoroa insignis. Fitoterapia. 2007 Jul; 78(5):388-9. doi: 10.1016/j.fitote.2007.04.001. [PMID: 17553631]
  • Karina J Malquichagua Salazar, Guillermo E Delgado Paredes, Luis Ripalda Lluncor, Maria Claudia Max Young, Massuo Jorge Kato. Chromenes of polyketide origin from Peperomia villipetiola. Phytochemistry. 2005 Mar; 66(5):573-9. doi: 10.1016/j.phytochem.2005.01.003. [PMID: 15721950]
  • C Qiu, Y Ding. [Studies on chemical constituents of Umbilicaria esculenta (Miyoshi) minks]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2001 Sep; 26(9):608-10. doi: . [PMID: 12776427]