MiMeDB: Showing metabocard for Queuine (MMDBc0029663)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:36:36 UTC

Update Date

2024-04-30 19:40:18 UTC

Metabolite ID

MMDBc0029663

Metabolite Identification

Common Name

Queuine

Description

Queuine is a member of the chemical class known as Aminocyclitols and Derivatives. These are cyclitols with at least one hydroxyl group replace by an amino group. Queuine (Q) is a hypermodified base found in the first (or wobble) position of the anticodon of tRNAs specific for Asn, Asp, His, and Tyr, in most eukaryotes and prokaryotes. The nucleoside of queuine is queuosine. Queuine is not found in the tRNA of archaea; however, a related 7-deazaguanine derivative, the nucleoside of which is archaeosine, occurs in different tRNA position, the dihydrouridine loop, and in tRNAs with more specificities. (WikiPedia)

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0001495
     RDKit          3D
Queuine
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.8116    1.4162   -0.4075 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6955    0.8232   -0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8012    1.4979    0.6765 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5853    0.9793    0.8837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7487    1.5901    1.6273 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2858   -0.2286    0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1554   -0.9036    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2375   -0.5734    0.7454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9660   -0.4431   -0.5595 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2870   -0.4680   -0.5469 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1277    0.2694   -1.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9665    1.1133   -0.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7445    1.0319    0.5176 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9309    1.0689    1.2654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9744   -0.2314    0.7673 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8453   -1.2897    1.1033 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3247   -1.9861   -0.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6049   -1.9481   -1.0304 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2289   -0.9022   -0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449   -0.3550   -0.6810 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0279    2.3843   -0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0312    2.4018    1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5601   -1.4807    1.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2197    0.2937    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4128    0.3408   -1.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5982   -1.6249   -0.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0968    0.1833   -2.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7383    1.7417   -1.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1107    1.9077    0.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7129    0.6703    2.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2450   -0.0337    1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7347   -1.0568    0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5425   -2.6847   -0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0520   -2.6725   -1.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1683   -0.8311   -1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  7 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
 19  6  2  0
 15 10  1  0
  1 21  1  0
  3 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  6
 11 27  1  0
 12 28  1  0
 13 29  1  1
 14 30  1  0
 15 31  1  1
 16 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
M  END


  Mrv0541 02231219102D          

 20 22  0  0  1  0            999 V2000
   14.4296  -14.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2501  -14.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7350  -13.7983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5925  -12.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9281  -13.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0940  -13.3567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.4216  -13.2172    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.3149  -14.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7072  -12.8047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6005  -13.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3149  -15.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8860  -15.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1715  -15.4163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2871  -13.1852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7720  -12.9594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8860  -14.1788    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6005  -15.4163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1753  -12.8817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6209  -11.9843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0294  -15.4163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  2  2  0  0  0  0
  2  7  1  0  0  0  0
  3  5  1  0  0  0  0
  3 14  1  0  0  0  0
  4  5  2  0  0  0  0
  4 15  1  0  0  0  0
  5  8  1  0  0  0  0
  6 14  1  1  0  0  0
  6  9  1  0  0  0  0
  7 18  1  6  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
  9 19  1  6  0  0  0
 10 16  1  0  0  0  0
 10 15  1  0  0  0  0
 11 20  2  0  0  0  0
 11 17  1  0  0  0  0
 12 13  2  0  0  0  0
 12 16  1  0  0  0  0
 12 17  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029663

> <DATABASE_NAME>
MIME

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

> <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

> <FORMULA>
C12H15N5O3

> <MOLECULAR_WEIGHT>
277.2792

> <EXACT_MASS>
277.117489371

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
27.421324559474105

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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

> <ALOGPS_LOGP>
-1.10

> <JCHEM_LOGP>
-0.7080790420000003

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.315302687246323

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.113981815998383

> <JCHEM_PKA_STRONGEST_BASIC>
7.432771199202244

> <JCHEM_POLAR_SURFACE_AREA>
133.26000000000002

> <JCHEM_REFRACTIVITY>
83.45299999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001495
     RDKit          3D
Queuine
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.8116    1.4162   -0.4075 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6955    0.8232   -0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8012    1.4979    0.6765 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5853    0.9793    0.8837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7487    1.5901    1.6273 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2858   -0.2286    0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1554   -0.9036    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2375   -0.5734    0.7454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9660   -0.4431   -0.5595 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2870   -0.4680   -0.5469 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1277    0.2694   -1.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9665    1.1133   -0.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7445    1.0319    0.5176 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9309    1.0689    1.2654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9744   -0.2314    0.7673 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8453   -1.2897    1.1033 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3247   -1.9861   -0.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6049   -1.9481   -1.0304 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2289   -0.9022   -0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449   -0.3550   -0.6810 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0279    2.3843   -0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0312    2.4018    1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5601   -1.4807    1.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2197    0.2937    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4128    0.3408   -1.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5982   -1.6249   -0.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0968    0.1833   -2.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7383    1.7417   -1.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1107    1.9077    0.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7129    0.6703    2.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2450   -0.0337    1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7347   -1.0568    0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5425   -2.6847   -0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0520   -2.6725   -1.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1683   -0.8311   -1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  7 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
 19  6  2  0
 15 10  1  0
  1 21  1  0
  3 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  6
 11 27  1  0
 12 28  1  0
 13 29  1  1
 14 30  1  0
 15 31  1  1
 16 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      26.935 -26.339   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.467 -26.179   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.772 -25.757   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.639 -24.030   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.266 -25.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.309 -24.933   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.787 -24.672   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.121 -26.467   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.453 -23.902   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.788 -25.697   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.121 -28.007   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.454 -28.007   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      17.120 -28.777   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      24.803 -24.612   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      20.108 -24.191   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      18.454 -26.467   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      19.788 -28.777   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      30.194 -24.046   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      27.292 -22.371   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      22.455 -28.777   0.000  0.00  0.00           O+0
CONECT    1    6    2                                                       
CONECT    2    1    7                                                       
CONECT    3    5   14                                                       
CONECT    4    5   15                                                       
CONECT    5    3    4    8                                                  
CONECT    6    1   14    9                                                  
CONECT    7    2   18    9                                                  
CONECT    8    5   10   11                                                  
CONECT    9    6    7   19                                                  
CONECT   10    8   16   15                                                  
CONECT   11    8   20   17                                                  
CONECT   12   13   16   17                                                  
CONECT   13   12                                                            
CONECT   14    3    6                                                       
CONECT   15    4   10                                                       
CONECT   16   10   12                                                       
CONECT   17   11   12                                                       
CONECT   18    7                                                            
CONECT   19    9                                                            
CONECT   20   11                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0001495
HETATM    1  N1  UNL     1       5.812   1.416  -0.407  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.696   0.823  -0.103  1.00  0.00           C  
HETATM    3  N2  UNL     1       3.801   1.498   0.676  1.00  0.00           N  
HETATM    4  C2  UNL     1       2.585   0.979   0.884  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.749   1.590   1.627  1.00  0.00           O  
HETATM    6  C3  UNL     1       2.286  -0.229   0.300  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.155  -0.904   0.161  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.238  -0.573   0.745  1.00  0.00           C  
HETATM    9  N3  UNL     1      -0.966  -0.443  -0.559  1.00  0.00           N  
HETATM   10  C6  UNL     1      -2.287  -0.468  -0.547  1.00  0.00           C  
HETATM   11  C7  UNL     1      -3.128   0.269  -1.532  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.967   1.113  -0.919  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.745   1.032   0.518  1.00  0.00           C  
HETATM   14  O2  UNL     1      -4.931   1.069   1.265  1.00  0.00           O  
HETATM   15  C10 UNL     1      -2.974  -0.231   0.767  1.00  0.00           C  
HETATM   16  O3  UNL     1      -3.845  -1.290   1.103  1.00  0.00           O  
HETATM   17  C11 UNL     1       1.325  -1.986  -0.659  1.00  0.00           C  
HETATM   18  N4  UNL     1       2.605  -1.948  -1.030  1.00  0.00           N  
HETATM   19  C12 UNL     1       3.229  -0.902  -0.487  1.00  0.00           C  
HETATM   20  N5  UNL     1       4.445  -0.355  -0.681  1.00  0.00           N  
HETATM   21  H1  UNL     1       6.028   2.384  -0.063  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.031   2.402   1.121  1.00  0.00           H  
HETATM   23  H3  UNL     1      -0.560  -1.481   1.282  1.00  0.00           H  
HETATM   24  H4  UNL     1      -0.220   0.294   1.305  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.413   0.341  -1.073  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.598  -1.625  -0.777  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.097   0.183  -2.612  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.738   1.742  -1.427  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.111   1.908   0.845  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.713   0.670   2.147  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.245  -0.034   1.609  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.735  -1.057   0.681  1.00  0.00           H  
HETATM   33  H13 UNL     1       0.543  -2.685  -0.925  1.00  0.00           H  
HETATM   34  H14 UNL     1       3.052  -2.673  -1.645  1.00  0.00           H  
HETATM   35  H15 UNL     1       5.168  -0.831  -1.260  1.00  0.00           H  
CONECT    1    2    2   21
CONECT    2    3   20
CONECT    3    4   22
CONECT    4    5    5    6
CONECT    6    7   19   19
CONECT    7    8   17   17
CONECT    8    9   23   24
CONECT    9   10   25
CONECT   10   11   15   26
CONECT   11   12   12   27
CONECT   12   13   28
CONECT   13   14   15   29
CONECT   14   30
CONECT   15   16   31
CONECT   16   32
CONECT   17   18   33
CONECT   18   19   34
CONECT   19   20
CONECT   20   35
END

HMDB0001495
     RDKit          3D
Queuine
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.8116    1.4162   -0.4075 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6955    0.8232   -0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8012    1.4979    0.6765 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5853    0.9793    0.8837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7487    1.5901    1.6273 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2858   -0.2286    0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1554   -0.9036    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2375   -0.5734    0.7454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9660   -0.4431   -0.5595 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2870   -0.4680   -0.5469 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1277    0.2694   -1.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9665    1.1133   -0.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7445    1.0319    0.5176 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9309    1.0689    1.2654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9744   -0.2314    0.7673 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8453   -1.2897    1.1033 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3247   -1.9861   -0.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6049   -1.9481   -1.0304 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2289   -0.9022   -0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449   -0.3550   -0.6810 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0279    2.3843   -0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0312    2.4018    1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5601   -1.4807    1.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2197    0.2937    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4128    0.3408   -1.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5982   -1.6249   -0.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0968    0.1833   -2.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7383    1.7417   -1.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1107    1.9077    0.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7129    0.6703    2.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2450   -0.0337    1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7347   -1.0568    0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5425   -2.6847   -0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0520   -2.6725   -1.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1683   -0.8311   -1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  7 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
 19  6  2  0
 15 10  1  0
  1 21  1  0
  3 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  6
 11 27  1  0
 12 28  1  0
 13 29  1  1
 14 30  1  0
 15 31  1  1
 16 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
M  END

Synonyms

Value	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
7-(3,4-trans-4,5-cis-Dihydroxy-1-cyclopenten-3-ylaminomethyl)-7-deazaguanine	HMDB
Base Q	HMDB

Molecular Formula

C₁₂H₁₅N₅O₃

Average Mass

277.2792

Monoisotopic Mass

277.117489371

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

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

CAS Registry Number

72496-59-4

SMILES

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

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

Chemical Taxonomy

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05mk-5090000000-652d0769b52b975c5157	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0pkc-9008300000-f8b2fbd8eff39e3fc559	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-0490000000-fb52b5c6a2d47b051994	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0930000000-fbf4852f9df58f0e7c7a	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-2900000000-e9fb13544e19e8acbdc5	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0290000000-d43c7510712f48a509a9	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002e-5690000000-c52e490ff589e882ed09	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0007-6900000000-80c4828f9526f8918043	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-0490000000-237adb25ec0428e0dd22	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03fr-0980000000-51b408b7c28c2878bc58	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-0910000000-0bc9779e624e8314aab5	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0970000000-89efef47c25a5bb1e162	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01r2-0890000000-06643dd86a98e7fb7a9e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-3900000000-062fe840765b80e24461	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Amniotic Fluid
Feces
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192464	Queuine tRNA-ribosyltransferase	Unknown	Q9BXR0	Homo sapiens
MMDBp0195886	Queuine tRNA-ribosyltransferase subunit QTRTD1	Enzyme	Q9H974	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified						HMDB
Human Amniotic fluid	Detected and Quantified	0.105	uM	Not Specified	Female	Normal	HMDB	7063869
Human Placenta	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0001495

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022654

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C01449

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Queuine

METLIN ID

6279

PubChem Compound

53477731

PDB ID

Not Available

ChEBI ID

17433

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Baranowski W, Tomaszewski J, Keith G: Unusual deficiency of the modified purine base queuine in transfer ribonucleic acid from the human placenta as tested by enzymatic assay. Am J Obstet Gynecol. 1993 Sep;169(3):581-2. doi: 10.1016/0002-9378(93)90626-t. [PubMed:8372867 ]
Marks T, Farkas WR: Effects of a diet deficient in tyrosine and queuine on germfree mice. Biochem Biophys Res Commun. 1997 Jan 13;230(2):233-7. doi: 10.1006/bbrc.1996.5768. [PubMed:9016755 ]

Showing metabocard for Queuine (MMDBc0029663)

MOL for #<Metabolite:0x00007feca5577b98>

3D MOL for #<Metabolite:0x00007feca5577b98>

3D SDF for #<Metabolite:0x00007feca5577b98>

3D-SDF for #<Metabolite:0x00007feca5577b98>

PDB for #<Metabolite:0x00007feca5577b98>

3D PDB for #<Metabolite:0x00007feca5577b98>

SMILES for #<Metabolite:0x00007feca5577b98>

INCHI for #<Metabolite:0x00007feca5577b98>

Structure for #<Metabolite:0x00007feca5577b98>

3D Structure for #<Metabolite:0x00007feca5577b98>