Queuine (BioDeep_00000004692)
Secondary id: BioDeep_00001868931
human metabolite
代谢物信息卡片
化学式: C12H15N5O3 (277.1175)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(blood) 36.11%
分子结构信息
SMILES: C1=CC(C(C1NCC2=CNC3=C2C(=O)NC(=N3)N)O)O
InChI: InChI=1S/C12H15N5O3/c13-12-16-10-8(11(20)17-12)5(4-15-10)3-14-6-1-2-7(18)9(6)19/h1-2,4,6-7,9,14,18-19H,3H2,(H4,13,15,16,17,20)/t6-,7-,9+/m0/s1
描述信息
Queuine is a highly modified derivative of guanine found in the first position of the anticodon of the transfer RNAs for asp, asn, his and tyr. The original transcripts of these tRNAs contain guanine in this position. All organisms with the exception of yeast and mycoplasma contain queuine. Bacteria synthesize queuine but it cannot be synthesized by higher mammals. Significant amounts of free queuine are present in common plant and animal food products. (PMID 9016755) [HMDB]
Queuine is a highly modified derivative of guanine found in the first position of the anticodon of the transfer RNAs for asp, asn, his and tyr. The original transcripts of these tRNAs contain guanine in this position. All organisms with the exception of yeast and mycoplasma contain queuine. Bacteria synthesize queuine but it cannot be synthesized by higher mammals. Significant amounts of free queuine are present in common plant and animal food products. (PMID 9016755).
同义名列表
8 个代谢物同义名
2-Amino-5-((((1S,4S,5R)-4,5-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-1,7-dihydro-4H-pyrrolo(2,3-D)pyrimidin-4-one; 5-({[(1R,4R,5S)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-2-imino-1H,2H,3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one; 5-({[(1R,4R,5S)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-2-imino-1H,3H,7H-pyrrolo[2,3-d]pyrimidin-4-one; 7-(3,4-trans-4,5-cis-Dihydroxy-1-cyclopenten-3-ylaminomethyl)-7-deazaguanine; SCHEMBL19929101; Queuine; Base Q; Queuine
数据库引用编号
19 个数据库交叉引用编号
- ChEBI: CHEBI:17433
- KEGG: C01449
- PubChem: 135521726
- PubChem: 135398670
- PubChem: 53477731
- HMDB: HMDB0001495
- Metlin: METLIN6279
- DrugBank: DB14732
- Wikipedia: Queuine
- MetaCyc: QUEUINE
- foodb: FDB022654
- CAS: 69565-92-0
- CAS: 72496-59-4
- PMhub: MS000017248
- PubChem: 4626
- PDB-CCD: QEI
- NIKKAJI: J40.715A
- RefMet: Queuine
- KNApSAcK: 17433
分类词条
相关代谢途径
BioCyc(0)
PlantCyc(0)
代谢反应
5 个相关的代谢反应过程信息。
Reactome(3)
- Metabolism of RNA:
Editosome for C to U editing + H2O ⟶ C to U edited ApoB RNA:Editosome complex + ammonia - tRNA processing:
H2O ⟶ ammonia - tRNA modification in the nucleus and cytosol:
H2O ⟶ ammonia
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(2)
- PreQ0 Metabolism:
S-Adenosylmethionine ⟶ Adenine + Hydrogen Ion + L-Methionine + epoxyqueuosine - PreQ0 Metabolism:
S-Adenosylmethionine ⟶ Adenine + Hydrogen Ion + L-Methionine + epoxyqueuosine
PharmGKB(0)
2 个相关的物种来源信息
- 3039 - Euglena gracilis: 10.3389/FBIOE.2021.662655
- 9606 - Homo sapiens: -
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
- Patricia Richard, Lucie Kozlowski, Hélène Guillorit, Patrice Garnier, Nicole C McKnight, Antoine Danchin, Xavier Manière. Queuine, a bacterial-derived hypermodified nucleobase, shows protection in in vitro models of neurodegeneration.
PloS one.
2021; 16(8):e0253216. doi:
10.1371/journal.pone.0253216. [PMID: 34379627] - Bruce N Ames. Prolonging healthy aging: Longevity vitamins and proteins.
Proceedings of the National Academy of Sciences of the United States of America.
2018 10; 115(43):10836-10844. doi:
10.1073/pnas.1809045115. [PMID: 30322941] - Claire Fergus, Dominic Barnes, Mashael A Alqasem, Vincent P Kelly. The queuine micronutrient: charting a course from microbe to man.
Nutrients.
2015 Apr; 7(4):2897-929. doi:
10.3390/nu7042897. [PMID: 25884661] - Tatsiana Rakovich, Coilin Boland, Ilana Bernstein, Vimbai M Chikwana, Dirk Iwata-Reuyl, Vincent P Kelly. Queuosine deficiency in eukaryotes compromises tyrosine production through increased tetrahydrobiopterin oxidation.
The Journal of biological chemistry.
2011 Jun; 286(22):19354-63. doi:
10.1074/jbc.m111.219576. [PMID: 21487017] - C Pathak, Manjula Vinayak. Modulation of lactate dehydrogenase isozymes by modified base queuine.
Molecular biology reports.
2005 Sep; 32(3):191-6. doi:
10.1007/s11033-004-6941-2. [PMID: 16172920] - W Langgut, T Reisser. Involvement of protein kinase C in the control of tRNA modification with queuine in HeLa cells.
Nucleic acids research.
1995 Jul; 23(13):2488-91. doi:
10.1093/nar/23.13.2488. [PMID: 7630726] - T Reisser, W Langgut, H Kersten. The nutrient factor queuine protects HeLa cells from hypoxic stress and improves metabolic adaptation to oxygen availability.
European journal of biochemistry.
1994 May; 221(3):979-86. doi:
10.1111/j.1432-1033.1994.tb18814.x. [PMID: 8181481] - T Reisser, A Eicher, W Langgut. Mitogenic stimulation of HeLa cells increases the activity of the anoxic stress protein, LDH 6/k: suppression by queuine.
Biochemical and biophysical research communications.
1993 Dec; 197(3):1319-25. doi:
10.1006/bbrc.1993.2621. [PMID: 8280149] - W Langgut, T Reisser, H Kersten. Queuine modulates growth of HeLa cells depending on oxygen availability.
BioFactors (Oxford, England).
1990 Oct; 2(4):245-9. doi:
NULL. [PMID: 2282142] - L Szabo, S Nishimura, W R Farkas. Possible involvement of queuine in oxidative metabolism.
BioFactors (Oxford, England).
1988 Oct; 1(3):241-4. doi:
. [PMID: 3256323] - Y Kuchino, Y Kimura, H Akimoto, H Nomura, N Kamei, S Nishimura. Monoclonal antibodies to queuine.
Nucleic acids symposium series.
1985; ?(16):221-3. doi:
. [PMID: 4088873] - U Gündüz, J R Katze. Queuine salvage in mammalian cells. Evidence that queuine is generated from queuosine 5'-phosphate.
The Journal of biological chemistry.
1984 Jan; 259(2):1110-3. doi:
10.1016/s0021-9258(17)43573-3. [PMID: 6319378] - Y Kuchino, M Matsumoto, M Hosoda, H Hoshino, S Nishimura. Effect of queuine on protein biosynthesis in mammalian cells.
Nucleic acids symposium series.
1984; ?(15):29-32. doi:
. [PMID: 6097883] - J R Katze, W T Beck, C S Cheng, J A McCloskey. Why is tumor tRNA hypomodified with respect to Q nucleoside?.
Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer.
1983; 84(?):146-59. doi:
10.1007/978-3-642-81947-6_10. [PMID: 6405458] - J R Katze, B Basile, J A McCloskey. Queuine, a modified base incorporated posttranscriptionally into eukaryotic transfer RNA: wide distribution in nature.
Science (New York, N.Y.).
1982 Apr; 216(4541):55-6. doi:
10.1126/science.7063869. [PMID: 7063869]
