FA 14:1 (BioDeep_00000229652)
Main id: BioDeep_00000000627
human metabolite PANOMIX_OTCML-2023
代谢物信息卡片
化学式: C14H26O2 (226.1933)
中文名称: 肉豆蔻酸, 肉豆蔻油酸
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C(/C=C\CCCC)CCCCCCC(=O)O
InChI: InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5-
描述信息
Myristoleic acid, a cytotoxic component in the extract from Serenoa repens, induces apoptosis and necrosis in human prostatic LNCaP cells[1].
Myristoleic acid, a cytotoxic component in the extract from Serenoa repens, induces apoptosis and necrosis in human prostatic LNCaP cells[1].
同义名列表
数据库引用编号
17 个数据库交叉引用编号
- ChEBI: CHEBI:27781
- KEGG: C08322
- PubChem: 5281119
- HMDB: HMDB02000
- ChEMBL: CHEMBL456732
- LipidMAPS: LMFA01030051
- CAS: 544-64-9
- MoNA: MT000070
- PubChem: 10520
- KNApSAcK: C00001229
- PDB-CCD: MYZ
- 3DMET: B02166
- NIKKAJI: J11.362J
- medchemexpress: HY-113332
- KNApSAcK: 27781
- LOTUS: LTS0078418
- wikidata: Q58221
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)
48 个相关的物种来源信息
- 9646 - Ailuropoda melanoleuca: 10.1371/JOURNAL.PONE.0143417
- 53852 - Cassia fistula:
- 508996 - Cassia javanica: 10.21608/BFSA.1985.75705
- 252529 - Citrullus colocynthis: 10.1055/S-0028-1099467
- 4672 - Dioscorea: 10.19026/AJFST.11.2408
- 308281 - Diplotaxis harra: 10.1002/(SICI)1099-1573(199906)13:4<329::AID-PTR458>3.0.CO;2-U
- 33136 - Epilobium dodonaei: 10.1007/BF00579976
- 1078594 - Erucaria microcarpa: 10.1002/(SICI)1099-1573(199906)13:4<329::AID-PTR458>3.0.CO;2-U
- 3039 - Euglena gracilis: 10.3389/FBIOE.2021.662655
- 3617 - Fagopyrum esculentum: 10.1007/BF00579976
- 1007786 - Gladiolus italicus: 10.21608/BFSA.1985.75886
- 3635 - Gossypium hirsutum: 10.1016/S0031-9422(97)00265-3
- 9606 - Homo sapiens:
- 9606 - Homo sapiens: -
- 141487 - Hoya australis: 10.1016/S0031-9422(00)82606-0
- 52832 - Hoya bella: 10.1016/S0031-9422(00)82606-0
- 206228 - Hoya cinnamomifolia: 10.1016/S0031-9422(00)82606-0
- 1167121 - Hoya coronaria: 10.1016/S0031-9422(00)82606-0
- 206229 - Hoya crassipes: 10.1016/S0031-9422(00)82606-0
- 206232 - Hoya diversifolia: 10.1016/S0031-9422(00)82606-0
- 2058639 - Hoya fraterna: 10.1016/S0031-9422(00)82606-0
- 2058643 - Hoya imperialis: 10.1016/S0031-9422(00)82606-0
- 365762 - Hoya lacunosa: 10.1016/S0031-9422(00)82606-0
- 2058646 - Hoya latifolia: 10.1016/S0031-9422(00)82606-0
- 945165 - Hoya longifolia: 10.1016/S0031-9422(00)82606-0
- 1167151 - Hoya macrophylla: 10.1016/S0031-9422(00)82606-0
- 206240 - Hoya multiflora: 10.1016/S0031-9422(00)82606-0
- 206243 - Hoya obovata: 10.1016/S0031-9422(00)82606-0
- 1167167 - Hoya ovalifolia: 10.1016/S0031-9422(00)82606-0
- 1167174 - Hoya pseudolanceolata: 10.1016/S0031-9422(00)82606-0
- 2058661 - Hoya shepherdii: 10.1016/S0031-9422(00)82606-0
- 365776 - Hoya tsangii: 10.1016/S0031-9422(00)82606-0
- 75948 - Lactuca saligna: 10.3109/13880209209054625
- 51089 - Myristica fragrans Houtt.: -
- 487997 - Persicaria hydropiperoides: 10.3390/MOLECULES191119220
- 488003 - Persicaria minor: 10.3390/MOLECULES191119220
- 1155347 - Persicaria mitis: 10.3390/MOLECULES191119220
- 268906 - Salvia fruticosa: 10.1016/S0367-326X(01)00327-6
- 13676 - Scomber japonicus: 10.1246/BCSJ.59.3709
- 138017 - Senegalia catechu: 10.5962/BHL.TITLE.108605
- 875646 - Senegalia polyacantha: 10.5962/BHL.TITLE.108605
- 72401 - Senna didymobotrya: 10.21608/BFSA.1985.75705
- 346999 - Senna siamea: 10.21608/BFSA.1985.75705
- 1883 - Streptomyces: 10.3389/FMICB.2018.01302
- 50225 - Taraxacum officinale: 10.1007/BF00579976
- 57577 - Trifolium pratense: 10.1007/BF00579976
- 1144522 - Tritrichomonas foetus: 10.1016/0305-0491(85)90353-0
- 56690 - Tritrichomonas suis: 10.1016/0305-0491(85)90353-0
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
- Alexander Y Starikov, Roman A Sidorov, Kirill S Mironov, Dmitry A Los. The Specificities of Lysophosphatidic Acid Acyltransferase and Fatty Acid Desaturase Determine the High Content of Myristic and Myristoleic Acids in Cyanobacterium sp. IPPAS B-1200.
International journal of molecular sciences.
2024 Jan; 25(2):. doi:
10.3390/ijms25020774
. [PMID: 38255848] - Shang-Zhen Li, Ning-Ning Zhang, Xing Yang, Tian-Qing Huang, Yang Lin, Zheng-Meng Jiang, Yongxiang Yi, E-Hu Liu. Nobiletin Ameliorates Nonalcoholic Fatty Liver Disease by Regulating Gut Microbiota and Myristoleic Acid Metabolism.
Journal of agricultural and food chemistry.
2023 May; ?(?):. doi:
10.1021/acs.jafc.2c08637
. [PMID: 37139957] - Sami Kazaz, Romane Miray, Sébastien Baud. Acyl-Acyl Carrier Protein Desaturases and Plant Biotic Interactions.
Cells.
2021 03; 10(3):. doi:
10.3390/cells10030674
. [PMID: 33803674] - Lin-Hu Quan, Chuanhai Zhang, Meng Dong, Jun Jiang, Hongde Xu, Chunlong Yan, Xiaomeng Liu, Huiqiao Zhou, Hanlin Zhang, Li Chen, Fei-Liang Zhong, Zhao-Bo Luo, Sin-Man Lam, Guanghou Shui, Donghao Li, Wanzhu Jin. Myristoleic acid produced by enterococci reduces obesity through brown adipose tissue activation.
Gut.
2020 07; 69(7):1239-1247. doi:
10.1136/gutjnl-2019-319114
. [PMID: 31744910] - Yanglin Ding, Jian Lv, Yiting Shi, Junping Gao, Jian Hua, Chunpeng Song, Zhizhong Gong, Shuhua Yang. EGR2 phosphatase regulates OST1 kinase activity and freezing tolerance in Arabidopsis.
The EMBO journal.
2019 01; 38(1):. doi:
10.15252/embj.201899819
. [PMID: 30429206] - Ranajay Saha, Samuel Verbanic, Irene A Chen. Lipid vesicles chaperone an encapsulated RNA aptamer.
Nature communications.
2018 06; 9(1):2313. doi:
10.1038/s41467-018-04783-8
. [PMID: 29899431] - Lauren O'Neil, Kathryn Andenoro, Isabella Pagano, Laura Carroll, Leah Langer, Zachary Dell, Davina Perera, Bradley W Treece, Frank Heinrich, Mathias Lösche, John F Nagle, Stephanie Tristram-Nagle. HIV-1 matrix-31 membrane binding peptide interacts differently with membranes containing PS vs. PI(4,5)P2.
Biochimica et biophysica acta.
2016 12; 1858(12):3071-3081. doi:
10.1016/j.bbamem.2016.09.010
. [PMID: 27641491] - Jun-Oh Kwon, Won Jong Jin, Bongjun Kim, Hong-Hee Kim, Zang Hee Lee. Myristoleic acid inhibits osteoclast formation and bone resorption by suppressing the RANKL activation of Src and Pyk2.
European journal of pharmacology.
2015 Dec; 768(?):189-98. doi:
10.1016/j.ejphar.2015.10.053
. [PMID: 26528796] - Gregory F Pirrone, Lori A Emert-Sedlak, Thomas E Wales, Thomas E Smithgall, Michael S Kent, John R Engen. Membrane-Associated Conformation of HIV-1 Nef Investigated with Hydrogen Exchange Mass Spectrometry at a Langmuir Monolayer.
Analytical chemistry.
2015 Jul; 87(14):7030-5. doi:
10.1021/acs.analchem.5b01725
. [PMID: 26133569] - Gregory F Pirrone, Briana C Vernon, Michael S Kent, John R Engen. Hydrogen Exchange Mass Spectrometry of Proteins at Langmuir Monolayers.
Analytical chemistry.
2015 Jul; 87(14):7022-9. doi:
10.1021/acs.analchem.5b01724
. [PMID: 26134943] - Hiroko Yamamoto, Daisuke Tachibana, Go Tajima, Yosuke Shigematsu, Takashi Hamasaki, Akemi Tanaka, Masayasu Koyama. Successful management of pregnancy with very-long-chain acyl-coenzyme A dehydrogenase deficiency.
The journal of obstetrics and gynaecology research.
2015 Jul; 41(7):1126-8. doi:
10.1111/jog.12672
. [PMID: 25655073] - N Scotti, L Sannino, A Idoine, P Hamman, A De Stradis, P Giorio, L Maréchal-Drouard, R Bock, T Cardi. The HIV-1 Pr55 gag polyprotein binds to plastidial membranes and leads to severe impairment of chloroplast biogenesis and seedling lethality in transplastomic tobacco plants.
Transgenic research.
2015 Apr; 24(2):319-31. doi:
10.1007/s11248-014-9845-5
. [PMID: 25348481] - Xuehui Feng, Wan Shi, Xuejun Wang, Mark P Running. In vitro myristoylation assay of Arabidopsis proteins.
Methods in molecular biology (Clifton, N.J.).
2013; 1043(?):135-9. doi:
10.1007/978-1-62703-532-3_14
. [PMID: 23913043] - Soo Chan Lee, Sabrina N Schmidtke, Lawrence J Dangott, Brian D Shaw. Aspergillus nidulans ArfB plays a role in endocytosis and polarized growth.
Eukaryotic cell.
2008 Aug; 7(8):1278-88. doi:
10.1128/ec.00039-08
. [PMID: 18539885] - Oliver Batistic, Nadav Sorek, Stefanie Schültke, Shaul Yalovsky, Jörg Kudla. Dual fatty acyl modification determines the localization and plasma membrane targeting of CBL/CIPK Ca2+ signaling complexes in Arabidopsis.
The Plant cell.
2008 May; 20(5):1346-62. doi:
10.1105/tpc.108.058123
. [PMID: 18502848] - S P Foster. The effects of topical application of various fatty acids on pheromone and glandular lipid biosynthesis in the moth Heliothis virescens.
Insect biochemistry and molecular biology.
2004 May; 34(5):467-75. doi:
10.1016/j.ibmb.2004.02.007
. [PMID: 15110868] - Ryuzo Hanada, Tsuneo Tatara, Yasuhide Iwao. Antagonizing potencies of saturated and unsaturated long-chain free fatty acids to isoflurane in goldfish.
Journal of anesthesia.
2004; 18(2):89-93. doi:
10.1007/s00540-003-0216-2
. [PMID: 15127255] - Martin M Hanczyc, Shelly M Fujikawa, Jack W Szostak. Experimental models of primitive cellular compartments: encapsulation, growth, and division.
Science (New York, N.Y.).
2003 Oct; 302(5645):618-22. doi:
10.1126/science.1089904
. [PMID: 14576428] - Pilar Sánchez-Blázquez, Isabel De Antonio, Carlos Montero, Javier Garzón. Exogenous myristoylated-G(i2)alpha subunits of GTP-binding proteins are mitogens following their internalization by astrocytes in culture.
Brain research. Molecular brain research.
2003 Jan; 110(1):15-26. doi:
10.1016/s0169-328x(02)00554-5
. [PMID: 12573529] - K Iguchi, N Okumura, S Usui, H Sajiki, K Hirota, K Hirano. Myristoleic acid, a cytotoxic component in the extract from Serenoa repens, induces apoptosis and necrosis in human prostatic LNCaP cells.
The Prostate.
2001 Apr; 47(1):59-65. doi:
10.1002/pros.1047
. [PMID: 11304730] - J Jiang, A Wolk, B Vessby. Relation between the intake of milk fat and the occurrence of conjugated linoleic acid in human adipose tissue.
The American journal of clinical nutrition.
1999 Jul; 70(1):21-7. doi:
10.1093/ajcn/70.1.21
. [PMID: 10393134] - D Wang, T J Girard, T P Kasten, R M LaChance, M A Miller-Wideman, R C Durley. Inhibitory activity of unsaturated fatty acids and anacardic acids toward soluble tissue factor-factor VIIa complex.
Journal of natural products.
1998 Nov; 61(11):1352-5. doi:
10.1021/np980117p
. [PMID: 9834151] - N R Simonsen, J Fernandez-Crehuet Navajas, J M Martin-Moreno, J J Strain, J K Huttunen, B C Martin, M Thamm, A F Kardinaal, P van't Veer, F J Kok, L Kohlmeier. Tissue stores of individual monounsaturated fatty acids and breast cancer: the EURAMIC study. European Community Multicenter Study on Antioxidants, Myocardial Infarction, and Breast Cancer.
The American journal of clinical nutrition.
1998 Jul; 68(1):134-41. doi:
10.1093/ajcn/68.1.134
. [PMID: 9665107] - E B Cahoon, S J Coughlan, J Shanklin. Characterization of a structurally and functionally diverged acyl-acyl carrier protein desaturase from milkweed seed.
Plant molecular biology.
1997 Apr; 33(6):1105-10. doi:
10.1023/a:1005821007291
. [PMID: 9154992] - Y J Duan, S Murase, J Okuda, A Tamura, I Miwa. Stimulatory effect of fatty acid treatment on glucose utilization in human erythrocytes.
Biochimica et biophysica acta.
1997 Feb; 1334(1):89-97. doi:
10.1016/s0304-4165(96)00075-x
. [PMID: 9042369] - F Hanakam, G Gerisch, S Lotz, T Alt, A Seelig. Binding of hisactophilin I and II to lipid membranes is controlled by a pH-dependent myristoyl-histidine switch.
Biochemistry.
1996 Aug; 35(34):11036-44. doi:
10.1021/bi960789j
. [PMID: 8780505] - D R Smith, D A Knabe, H R Cross, S B Smith. A diet containing myristoleic plus palmitoleic acids elevates plasma cholesterol in young growing swine.
Lipids.
1996 Aug; 31(8):849-58. doi:
10.1007/bf02522980
. [PMID: 8869887] - G Mamalakis, A Kafatos, S Board. Type A behavior and adipose tissue linoleic acid: implications for stress management.
Journal of the American College of Nutrition.
1994 Jun; 13(3):292-7. doi:
10.1080/07315724.1994.10718411
. [PMID: 8077579]