Compound: PSEUDOURIDINE
SMILES: O=c1[nH]c(=O)c([C@@H]2O[C@H](CO)[C@H]([C@H]2O)O)c[nH]1
InChIKey: PTJWIQPHWPFNBW-GBNDHIKLSA-N
Synonyms: PSEUDOURIDINE, 1445-07-4, psi-Uridine, 5-(beta-D-Ribofuranosyl)uracil, 7R0R6H6KEG, 2,4(1H,3H)-Pyrimidinedione, 5-beta-D-ribofuranosyl-, CHEBI:17802, 5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidine-2,4-dione, NSC-162405, 5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione, 5-((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-1H-pyrimidine-2,4-dione, 5-((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione, RefChem:177010, 978-484-6, beta-Pseudouridine, Pseudouridine C, 5-((2S,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione, 5-Ribosyluracil, MFCD00038458, pseudo uridine, 2,4(1H,3H)-Pyrimidinedione, 5-.beta.-D-ribofuranosyl-, NSC 162405, Pseudouridin, b-Pseudouridine, (1S)-1,4-Anhydro-1-(2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)-D-ribitol, (1S)-1,4-anhydro-1-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-D-ribitol, 5-[(2~{S},3~{R},4~{S},5~{R})-5-(hydroxymethyl)-3,4-bis(oxidanyl)oxolan-2-yl]-1~{H}-pyrimidine-2,4-dione, beta-D-Pseudouridine, 5-b-d-ribofuranosyl-uracil, y-Uridine, NSC162405, psi (Synthetic), b-D-Pseudouridine, FJF, beta-delta-Pseudouridine, 5-beta-D-Ribofuranosyl-2,4(1H,3H)-Pyrimidinedione, Pseudouridine (Synthetic), UNII-7R0R6H6KEG, SCHEMBL64635, 5-(b-D-Ribofuranosyl)uracil, 5-(beta-D-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione, orb1307838, CHEMBL3144027, 5-(b-delta-Ribofuranosyl)uracil, 5-beta-delta-ribofuranosyl-Uracil, PTJWIQPHWPFNBW-GBNDHIKLSA-N, GLXC-24088, EX-A3663, MSK167122, AKOS022185210, EBC-616088, NP11297, 5-[(2S,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)-oxolan-2-yl]-1H-pyrimidine-2,4-dione, 5-(.BETA.-D-RIBOFURANOSYL)URACIL, 5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-pyrimidine-2,4-dione, AC-32344, AS-35037, BP-58830, SY235127, 5-(beta-D-Ribofuranosyl)uracil (Synthetic), DB-418733, HY-113061, CS-0059468, NS00014796, P2396, P2939, C02067, F808110, Q420445, Uracil, 5-beta-D-ribofuranosyl- (6CI,7CI,8CI), W-201269, 2,4(1H,3H)-Pyrimidinedione, 5-|A-D-ribofuranosyl-, 2,4(1H,3H)-Pyrimidinedione, 5-beta-D-ribofuranosyl, 5-beta-D-Ribofuranosyl-2,4(1H,3H)-pyrimidinedione (Synthetic), (1S)-1,4-Anhydro-1-(2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)-D-ribitol (Synthetic), 5-b-D-ribofuranosyl-2,4(1H,3H)-Pyrimidinedione, 5-|A-D-ribofuranosyluracil, D-ribitol, 1,4-anhydro-1-C-(1,2,3,4-tetrahydro-2,4-dioxo-5-pyrimidinyl)-, (1S)-, 5-[rac-(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-pyrimidine-2,4-dione
Theoretical properties:
molecular_formula: C9H12N2O6
molecular_weight: 244.20 g/mol
exact_mass: 244.06953611 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 2
heavy_atom_count: 17
topological_polar_surface_area: 128 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Pseudouridine is a C-glycosyl pyrimidine that consists of uracil having a beta-D-ribofuranosyl residue attached at position 5. The C-glycosyl isomer of the nucleoside uridine. It has a role as a fundamental metabolite.", "chebi": "A <em>C</em>-glycosyl pyrimidine that consists of uracil having a \u03b2-<small>D</small>-ribofuranosyl residue attached at position 5. The <em>C</em>-glycosyl isomer of the nucleoside uridine.", "chembl": "Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Pseudouridine (5-ribosyluracil, abbreviated by the Greek letter psi- \u03a8) is an isomer of the nucleoside uridine in which the uracil is attached via a carbon-carbon instead of a nitrogen-carbon glycosidic bond.\nPseudouridine is the most abundant RNA modification in cellular RNA and one of over 100 chemically distinct modifications that may affect translation or other functions of RNA. Pseudouridine is the C5-glycoside isomer of uridine that contains a C-C bond between C1 of the ribose sugar and C5 of uracil, rather than usual C1-N1 bond found in uridine. Uridine is converted to pseudouridine by rotating the uridine molecule 180\u00b0 across its N3-C6 axis. The C-C bond gives it more rotational freedom and conformational flexibility. In addition, pseudouridine has an extra hydrogen bond donor at the N1 position.\nPseudouridine is a ubiquitous constituent of structural RNA (transfer (tRNA), ribosomal (rRNA), small nuclear (snRNA), and small nucleolar (snoRNA)), and present in messenger RNA (mRNA), across the three phylogenetic domains of life and was the first discovered. It accounts for 4% of the nucleotides in yeast tRNA. This base modification is able to stabilize RNA and improve base stacking by forming additional hydrogen bonds with water through its extra amino group. There are 11 pseudouridines in Escherichia coli rRNA, 30 in yeast cytoplasmic rRNA and a single modification in mitochondrial 21S rRNA, and about 100 pseudouridines in human rRNA, indicating that the extent of pseudouridylation increases with the complexity of an organism. Pseudouridine was also detected in the Leishmania donovani genome. 18 pseudouridine modification sites were detected in the peptidyl transferase entry site and in the mRNA entry tunnel in protein translation. These modifications in the parasite lead to increased protein synthesis and growth rate.\nPseudouridine in rRNA and tRNA has been shown to fine-tune and stabilize the regional structure and help maintain their functions in mRNA decoding, ribosome assembly, processing and translation. Pseudouridine in snRNA has been shown to enhance spliceosomal RNA-pre-mRNA interaction to facilitate splicing regulation."}