UsnicAcid (BioDeep_00000230930)
Main id: BioDeep_00000007878
PANOMIX_OTCML-2023
代谢物信息卡片
化学式: C18H16O7 (344.0896)
中文名称: (+)-地衣酸, (-)-松萝酸, 松萝酸
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC1=C(C(=C2C(=C1O)C3(C(=CC(=C(C3=O)C(=O)C)O)O2)C)C(=O)C)O
InChI: InChI=1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,21-23H,1-4H3/t18-/m1/s1
描述信息
(-)-usnic acid is the (-)-enantiomer of usnic acid. It has a role as an EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor. It is a conjugate acid of a (-)-usnic acid(2-). It is an enantiomer of a (+)-usnic acid.
Usnic acid is a furandione found uniquely in lichen that is used widely in cosmetics, deodorants, toothpaste and medicinal creams as well as some herbal products. Taken orally, usnic acid can be toxic and has been linked to instances of clinically apparent, acute liver injury.
(-)-Usnic acid is a natural product found in Dactylina arctica, Evernia divaricata, and other organisms with data available.
The (-)-enantiomer of usnic acid.
(+)-Usnic acid is isolated from isolated from lichens, binds at the ATP-binding pocket of mTOR, and inhibits mTORC1/2 activity. (+)-Usnic acid inhibits the phosphorylation of mTOR downstream effectors: Akt (Ser473), 4EBP1, S6K, induces autophay, with anti-cancer activity[1]. (+)-Usnic acid possesses antimicrobial activity against a number of planktonic gram-positive bacteria, including Staphylococcus aureus, Enterococcus faecalis, and Enterococcus faecium[2].
(+)-Usnic acid is isolated from isolated from lichens, binds at the ATP-binding pocket of mTOR, and inhibits mTORC1/2 activity. (+)-Usnic acid inhibits the phosphorylation of mTOR downstream effectors: Akt (Ser473), 4EBP1, S6K, induces autophay, with anti-cancer activity[1]. (+)-Usnic acid possesses antimicrobial activity against a number of planktonic gram-positive bacteria, including Staphylococcus aureus, Enterococcus faecalis, and Enterococcus faecium[2].
(+)-Usnic acid is isolated from isolated from lichens, binds at the ATP-binding pocket of mTOR, and inhibits mTORC1/2 activity. (+)-Usnic acid inhibits the phosphorylation of mTOR downstream effectors: Akt (Ser473), 4EBP1, S6K, induces autophay, with anti-cancer activity[1]. (+)-Usnic acid possesses antimicrobial activity against a number of planktonic gram-positive bacteria, including Staphylococcus aureus, Enterococcus faecalis, and Enterococcus faecium[2].
(+)-Usnic acid is isolated from isolated from lichens, binds at the ATP-binding pocket of mTOR, and inhibits mTORC1/2 activity. (+)-Usnic acid inhibits the phosphorylation of mTOR downstream effectors: Akt (Ser473), 4EBP1, S6K, induces autophay, with anti-cancer activity[1]. (+)-Usnic acid possesses antimicrobial activity against a number of planktonic gram-positive bacteria, including Staphylococcus aureus, Enterococcus faecalis, and Enterococcus faecium[2].
同义名列表
25 个代谢物同义名
(2R)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(13),3,6,9,11-pentaen-5-one; (R)-1,1-(1,7,9-trihydroxy-8,9b-dimethyl-3-oxo-3,9b-dihydrodibenzo[b,d]furan-2,6-diyl)diethanone; (9aR)-4,8-diacetyl-1,3,9-trihydroxy-2,9a-dimethyl-7-oxo-9a-hydrobenzo[2,1-d]be nzo[b]furan; (9bS)-2,6-diacetyl-3,7,9-trihydroxy-8,9b-dimethyldibenzo[b,d]furan-1(9bH)-one; (9bR)-2,6-diacetyl-1,7,9-trihydroxy-8,9b-dimethyldibenzo[b,d]furan-3(9bH)-one; 1(9BH)-DIBENZOFURANONE, 2,6-DIACETYL-3,7,9-TRIHYDROXY-8,9B-DIMETHYL-, (9BS)-; 1(9BH)-DIBENZOFURANONE, 2,6-DIACETYL-3,7,9-TRIHYDROXY-8,9B-DIMETHYL-, (S)-; 2,6-diacetyl-3,7,9-trihydroxy-8,9b-dimethyldibenzo[b,d]furan-1(9bH)-one; (9bS)-2,6-diacetyl-3,7,9-trihydroxy-8,9b-dimethyldibenzofuran-1-one; (-)-TRANS-45-BIS(IODOMETHYL)-2,2-DIMETHYL-13-DIOXOLANE; (+)-Usniacin (D-Usnic acid); (S)-(-)-USNIC ACID; USNIC ACID, (S)-; (+)-Usnic acid; (S)-Usnic acid; (-)-Usnic acid; USNIC ACID, L-; (+)-Usniacin; d-Usnic acid; usniacin-(+); SMP1_000308; Usnic acid; (S)-usnate; UsnicAcid; (-)-Usnic acid
数据库引用编号
17 个数据库交叉引用编号
- ChEBI: CHEBI:122
- KEGG: C10101
- PubChem: 442614
- ChEMBL: CHEMBL1454474
- ChEMBL: CHEMBL461903
- LipidMAPS: LMPK13060002
- KNApSAcK: C00002413
- chemspider: 109399
- CAS: 882883-26-3
- CAS: 7562-61-0
- CAS: 6159-66-6
- medchemexpress: HY-N0656A
- MetaboLights: MTBLC122
- PubChem: 12287
- 3DMET: B03540
- NIKKAJI: J136.434K
- KNApSAcK: 122
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)
24 个相关的物种来源信息
- 180472 - Asahinea chrysantha:
- 413831 - Asahinea scholanderi: 10.1007/BF00579953
- 184092 - Cladonia convoluta:
- 184101 - Cladonia foliacea:
- 174045 - Cladonia stellaris:
- 112443 - Dactylina arctica:
- 281306 - Dolichousnea longissima:
- 136276 - Evernia divaricata: 10.1016/S0031-9422(00)84857-8
- 336071 - Evernia mesomorpha: 10.1016/S0031-9422(00)84857-8
- 87257 - Evernia prunastri:
- 411583 - Hypotrachyna caraccensis: 10.1016/S0031-9422(00)86850-8
- 145978 - Ophioparma ventosa:
- 37463 - Phoma: 10.1016/J.PHYTOCHEM.2007.10.031
- 33090 - Plants: -
- 416941 - Protousnea magellanica: 10.1021/NP50052A031
- 859455 - Ramalina calicaris: 10.1016/0305-1978(86)90023-2
- 643230 - Ramalina hierrensis: 10.1055/S-2006-961433
- 350623 - Stereocaulon alpinum: 10.1021/NP070464B
- 83480 - Thamnolia vermicularis: 10.1007/BF00570191
- 192176 - Usnea dasopoga: 10.1002/(SICI)1099-0690(199907)1999:7<1719::AID-EJOC1719>3.0.CO;2-U
- 362615 - Usnea lapponica: 10.1016/0031-9422(93)85097-B
- 983630 - Xanthoparmelia camtschadalis: 10.1016/S0367-326X(98)00033-1
- 983642 - Xanthoparmelia vagans: 10.1007/BF00630129
- 33090 - 松萝: -
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
- Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products.
ACS pharmacology & translational science.
2023 May; 6(5):683-701. doi:
10.1021/acsptsci.2c00194. [PMID: 37200814] - Anna A Shtro, Vladimir V Zarubaev, Olga A Luzina, Dmitry N Sokolov, Oleg I Kiselev, Nariman F Salakhutdinov. Novel derivatives of usnic acid effectively inhibiting reproduction of influenza A virus.
Bioorganic & medicinal chemistry.
2014 Dec; 22(24):6826-36. doi:
10.1016/j.bmc.2014.10.033. [PMID: 25464881] - Dmitriy N Sokolov, Vladimir V Zarubaev, Anna A Shtro, Marina P Polovinka, Olga A Luzina, Nina I Komarova, Nariman F Salakhutdinov, Oleg I Kiselev. Anti-viral activity of (-)- and (+)-usnic acids and their derivatives against influenza virus A(H1N1)2009.
Bioorganic & medicinal chemistry letters.
2012 Dec; 22(23):7060-4. doi:
10.1016/j.bmcl.2012.09.084. [PMID: 23099095]
