Showing Compound Queuine (FDB022654)

Record Information

Version

1.0

Creation date

2011-09-21 00:17:29 UTC

Update date

2015-07-21 06:57:17 UTC

Primary ID

FDB022654

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Queuine

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) [HMDB]

CAS Number

72496-59-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
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
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
7-(3,4-trans-4,5-cis-dihydroxy-1-cyclopenten-3-ylaminomethyl)-7-deazaguanine	hmdb
Base Q	HMDB
Queuine	hmdb

Showing 1 to 6 of 6 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.31 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-0.71	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.11	ChemAxon
pKa (Strongest Basic)	7.43	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	133.26 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.45 m³·mol⁻¹	ChemAxon
Polarizability	27.42 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C12H15N5O3

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

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

InChI Key

WYROLENTHWJFLR-BHNWBGBOSA-N

Isomeric SMILES

O[C@@H]1C=C[C@@H](NCC2=CNC3=C2C(=O)NC(=N)N3)[C@@H]1O

Average Molecular Weight

277.2792

Monoisotopic Molecular Weight

277.117489371

Classification

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolopyrimidines

Sub Class

Pyrrolo[2,3-d]pyrimidines

Direct Parent

Pyrrolo[2,3-d]pyrimidines

Alternative Parents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Tissue and substructures:

Placenta

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Queuine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05mk-5090000000-652d0769b52b975c5157	Spectrum
Predicted GC-MS	Queuine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0pkc-9008300000-f8b2fbd8eff39e3fc559	Spectrum
Predicted GC-MS	Queuine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Queuine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-0490000000-fb52b5c6a2d47b051994	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0930000000-fbf4852f9df58f0e7c7a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-2900000000-e9fb13544e19e8acbdc5	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0290000000-d43c7510712f48a509a9	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002e-5690000000-c52e490ff589e882ed09	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0007-6900000000-80c4828f9526f8918043	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-0490000000-237adb25ec0428e0dd22	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03fr-0980000000-51b408b7c28c2878bc58	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-0910000000-0bc9779e624e8314aab5	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0970000000-89efef47c25a5bb1e162	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01r2-0890000000-06643dd86a98e7fb7a9e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-3900000000-062fe840765b80e24461	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

30776547

ChEMBL ID

Not Available

KEGG Compound ID

C01449

Pubchem Compound ID

53477731

Pubchem Substance ID

Not Available

ChEBI ID

17433

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01495

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Queuine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Queuine (FDB022654)

Structure for FDB022654 (Queuine)