Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-02-26 21:23:25 UTC |
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HMDB ID | HMDB0001495 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Queuine |
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Description | 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 ). |
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Structure | |
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Synonyms | Value | Source |
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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 | HMDB | 7-(3,4-trans-4,5-cis-Dihydroxy-1-cyclopenten-3-ylaminomethyl)-7-deazaguanine | HMDB | Base Q | HMDB |
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Chemical Formula | C12H15N5O3 |
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Average Molecular Weight | 277.2792 |
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Monoisotopic Molecular Weight | 277.117489371 |
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IUPAC Name | 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 |
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Traditional Name | 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 |
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CAS Registry Number | 72496-59-4 |
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SMILES | O[C@@H]1C=C[C@@H](NCC2=CNC3=C2C(=O)NC(=N)N3)[C@@H]1O |
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InChI Identifier | 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+/m1/s1 |
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InChI Key | WYROLENTHWJFLR-BHNWBGBOSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as pyrrolo[2,3-d]pyrimidines. These are aromatic heteropolycyclic compounds containing a pyrrolo[2,3-d]pyrimidine ring system, which is an pyrrolopyrimidine isomers having the 3 ring nitrogen atoms at the 1-, 5-, and 7-positions. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pyrrolopyrimidines |
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Sub Class | Pyrrolo[2,3-d]pyrimidines |
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Direct Parent | Pyrrolo[2,3-d]pyrimidines |
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Alternative Parents | |
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Substituents | - Pyrrolo[2,3-d]pyrimidine
- Aminopyrimidine
- Pyrimidone
- Aralkylamine
- Pyrimidine
- Substituted pyrrole
- Pyrrole
- Heteroaromatic compound
- Vinylogous amide
- 1,2-diol
- Secondary alcohol
- Secondary amine
- Secondary aliphatic amine
- Azacycle
- Alcohol
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Amine
- Hydrocarbon derivative
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Source: Biological location: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-05mk-5090000000-652d0769b52b975c5157 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-0pkc-9008300000-f8b2fbd8eff39e3fc559 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01t9-0490000000-fb52b5c6a2d47b051994 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-0930000000-fbf4852f9df58f0e7c7a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-2900000000-e9fb13544e19e8acbdc5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0290000000-d43c7510712f48a509a9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-002e-5690000000-c52e490ff589e882ed09 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0007-6900000000-80c4828f9526f8918043 | Spectrum |
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Synthesis Reference | Akimoto, Hiroshi; Imamiya, Eiko; Hitaka, Takenori; Nomura, Hiroaki; Nishimura, Susumu. Synthesis of queuine, the base of naturally occurring hypermodified nucleoside (queuosine), and its analogs. Journal of the Chemical Society, Perkin Transactions 1: Org |
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