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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:19:30 UTC

HMDB ID

HMDB0001495

Secondary Accession Numbers

HMDB01495

Metabolite Identification

Common 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 ).

Structure

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

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    6.2151    0.7119   -0.2707 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9632    0.5838   -0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1784    1.6749   -0.0188 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8590    1.5338    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0810    2.5011    0.2291 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3521    0.2547    0.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0891   -0.2385    0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1867    0.5470    0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2840   -0.2979    0.7057 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2392   -0.4892   -0.3056 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8797    0.6490   -0.9673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8970    1.1804   -0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0068    0.3613    0.9828 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3112    0.3409    1.4885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5142   -0.9969    0.5174 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3485   -1.5107   -0.4342 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1731   -1.6303    0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363   -1.9798    0.3298 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1654   -0.8591    0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4764   -0.6855    0.0222 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8962   -0.1124   -0.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5945    2.6536   -0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2653    1.1702   -0.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1130    1.2862    1.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877   -0.5366    1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0115   -1.3072   -1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5749    1.0605   -1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5414    2.0246   -0.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2993    0.7943    1.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5777    1.3053    1.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1780   -1.6607    1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9541   -1.5112   -1.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3210   -2.3030    0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7587   -2.9978    0.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1110   -1.5170   -0.0322 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>
HMDB0001495

> <DATABASE_NAME>
hmdb

> <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

$$$$

https://cactus.nci.nih.gov/chemical/structure/O%5BC@@H%5D1C=C%5BC@@H%5D(NCC2=...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:34})
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.3693   -0.8189   -1.3651 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1089   -0.1881   -1.1289 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5543   -0.0884   -2.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3097    1.1657   -0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4802    1.3443    0.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878    0.1392    0.6897 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5149   -0.1194    1.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2530    0.4000    0.1345 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3913    1.0611    1.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9663    1.3119    0.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4214    2.4738    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7089    2.3008   -0.4479 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1027    1.0371   -0.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403    0.3504    0.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1682   -1.0623    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3260   -1.6416    1.3841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2889   -1.6885    0.2690 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1715   -1.0254   -0.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9104   -1.7043   -1.3905 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2788    0.3572   -0.5173 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2872   -0.9956   -0.0974 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5570   -1.6372   -0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1435   -1.7588    0.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9372   -0.3427   -1.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0435    1.8904   -0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4375    2.2360    1.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3140    0.9442   -0.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2865    0.4210    1.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8387    2.0102    1.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628    3.3971   -0.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2512    2.9927   -0.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4677   -2.6059    0.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8382   -2.6710   -1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1201    0.8169   -0.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6032   -2.4814    0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 24  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  2 21  1  0  0  0  0
  4  5  2  0  0  0  0
  4 25  1  0  0  0  0
  5  6  1  0  0  0  0
  5 26  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  6 21  1  0  0  0  0
  8  9  1  0  0  0  0
  8 27  1  0  0  0  0
  9 10  1  0  0  0  0
  9 28  1  0  0  0  0
  9 29  1  0  0  0  0
 10 11  2  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 30  1  0  0  0  0
 12 13  1  0  0  0  0
 12 31  1  0  0  0  0
 13 14  2  0  0  0  0
 13 20  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 32  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 19 33  1  0  0  0  0
 20 34  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 35  1  0  0  0  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    https://cactus.nci.nih.gov/chemical/structure/O%5BC@@H%5D1C=C%5BC@@H%5D(NCC2=... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  O   UNL     1       5.369  -0.819  -1.365  1.00  0.00           O  
HETATM    2  C   UNL     1       4.109  -0.188  -1.129  1.00  0.00           C  
HETATM    3  H   UNL     1       3.554  -0.088  -2.062  1.00  0.00           H  
HETATM    4  C   UNL     1       4.310   1.166  -0.489  1.00  0.00           C  
HETATM    5  C   UNL     1       3.480   1.344   0.503  1.00  0.00           C  
HETATM    6  C   UNL     1       2.588   0.139   0.690  1.00  0.00           C  
HETATM    7  H   UNL     1       2.515  -0.119   1.746  1.00  0.00           H  
HETATM    8  N   UNL     1       1.253   0.400   0.135  1.00  0.00           N  
HETATM    9  C   UNL     1       0.391   1.061   1.124  1.00  0.00           C  
HETATM   10  C   UNL     1      -0.966   1.312   0.519  1.00  0.00           C  
HETATM   11  C   UNL     1      -1.421   2.474   0.008  1.00  0.00           C  
HETATM   12  N   UNL     1      -2.709   2.301  -0.448  1.00  0.00           N  
HETATM   13  C   UNL     1      -3.103   1.037  -0.243  1.00  0.00           C  
HETATM   14  C   UNL     1      -2.040   0.350   0.366  1.00  0.00           C  
HETATM   15  C   UNL     1      -2.168  -1.062   0.723  1.00  0.00           C  
HETATM   16  O   UNL     1      -1.326  -1.642   1.384  1.00  0.00           O  
HETATM   17  N   UNL     1      -3.289  -1.688   0.269  1.00  0.00           N  
HETATM   18  C   UNL     1      -4.171  -1.025  -0.558  1.00  0.00           C  
HETATM   19  N   UNL     1      -4.910  -1.704  -1.391  1.00  0.00           N  
HETATM   20  N   UNL     1      -4.279   0.357  -0.517  1.00  0.00           N  
HETATM   21  C   UNL     1       3.287  -0.996  -0.097  1.00  0.00           C  
HETATM   22  H   UNL     1       2.557  -1.637  -0.591  1.00  0.00           H  
HETATM   23  O   UNL     1       4.144  -1.759   0.755  1.00  0.00           O  
HETATM   24  H   UNL     1       5.937  -0.343  -1.986  1.00  0.00           H  
HETATM   25  H   UNL     1       5.043   1.890  -0.809  1.00  0.00           H  
HETATM   26  H   UNL     1       3.438   2.236   1.111  1.00  0.00           H  
HETATM   27  H   UNL     1       1.314   0.944  -0.713  1.00  0.00           H  
HETATM   28  H   UNL     1       0.286   0.421   2.000  1.00  0.00           H  
HETATM   29  H   UNL     1       0.839   2.010   1.419  1.00  0.00           H  
HETATM   30  H   UNL     1      -0.863   3.397  -0.036  1.00  0.00           H  
HETATM   31  H   UNL     1      -3.251   2.993  -0.858  1.00  0.00           H  
HETATM   32  H   UNL     1      -3.468  -2.606   0.529  1.00  0.00           H  
HETATM   33  H   UNL     1      -4.838  -2.671  -1.426  1.00  0.00           H  
HETATM   34  H   UNL     1      -5.120   0.817  -0.665  1.00  0.00           H  
HETATM   35  H   UNL     1       4.603  -2.481   0.305  1.00  0.00           H  
CONECT    1    2   24                                                 
CONECT    2    1    3    4   21                                       
CONECT    3    2                                                      
CONECT    4    2    5    5   25                                       
CONECT    5    4    4    6   26                                       
CONECT    6    5    7    8   21                                       
CONECT    7    6                                                      
CONECT    8    6    9   27                                            
CONECT    9    8   10   28   29                                       
CONECT   10    9   11   11   14                                       
CONECT   11   10   10   12   30                                       
CONECT   12   11   13   31                                            
CONECT   13   12   14   14   20                                       
CONECT   14   13   13   10   15                                       
CONECT   15   14   16   16   17                                       
CONECT   16   15   15                                                 
CONECT   17   15   18   32                                            
CONECT   18   17   19   19   20                                       
CONECT   19   18   18   33                                            
CONECT   20   18   13   34                                            
CONECT   21    6   22    2   23                                       
CONECT   22   21                                                      
CONECT   23   21   35                                                 
CONECT   24    1                                                      
CONECT   25    4                                                      
CONECT   26    5                                                      
CONECT   27    8                                                      
CONECT   28    9                                                      
CONECT   29    9                                                      
CONECT   30   11                                                      
CONECT   31   12                                                      
CONECT   32   17                                                      
CONECT   33   19                                                      
CONECT   34   20                                                      
CONECT   35   23                                                      
MASTER        0    0    0    0    0    0    0    0   35    0   35    0
END

https://cactus.nci.nih.gov/chemical/structure/O%5BC@@H%5D1C=C%5BC@@H%5D(NCC2=...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:34})
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.3693   -0.8189   -1.3651 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1089   -0.1881   -1.1289 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5543   -0.0884   -2.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3097    1.1657   -0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4802    1.3443    0.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878    0.1392    0.6897 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5149   -0.1194    1.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2530    0.4000    0.1345 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3913    1.0611    1.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9663    1.3119    0.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4214    2.4738    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7089    2.3008   -0.4479 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1027    1.0371   -0.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403    0.3504    0.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1682   -1.0623    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3260   -1.6416    1.3841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2889   -1.6885    0.2690 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1715   -1.0254   -0.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9104   -1.7043   -1.3905 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2788    0.3572   -0.5173 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2872   -0.9956   -0.0974 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5570   -1.6372   -0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1435   -1.7588    0.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9372   -0.3427   -1.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0435    1.8904   -0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4375    2.2360    1.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3140    0.9442   -0.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2865    0.4210    1.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8387    2.0102    1.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628    3.3971   -0.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2512    2.9927   -0.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4677   -2.6059    0.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8382   -2.6710   -1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1201    0.8169   -0.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6032   -2.4814    0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 24  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  2 21  1  0  0  0  0
  4  5  2  0  0  0  0
  4 25  1  0  0  0  0
  5  6  1  0  0  0  0
  5 26  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  6 21  1  0  0  0  0
  8  9  1  0  0  0  0
  8 27  1  0  0  0  0
  9 10  1  0  0  0  0
  9 28  1  0  0  0  0
  9 29  1  0  0  0  0
 10 11  2  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 30  1  0  0  0  0
 12 13  1  0  0  0  0
 12 31  1  0  0  0  0
 13 14  2  0  0  0  0
 13 20  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 32  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 19 33  1  0  0  0  0
 20 34  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 35  1  0  0  0  0
M  END
$$$$

View in JSmol View Stereo Labels

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

Chemical Formula

C₁₂H₁₅N₅O₃

Average Molecular Weight

277.2792

Monoisotopic Molecular Weight

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

Ontology

Disposition

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Tissue and substructures:

Placenta

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Molecular 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

Predicted Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference
DarkChem	[M+H]+	Predicted	Not Available	163.516	31661259
DarkChem	[M-H]-	Predicted	Not Available	160.785	31661259
AllCCS	[M+H]+	Predicted	Not Available	165.102	32859911
AllCCS	[M-H]-	Predicted	Not Available	163.715	32859911

Retention Indices

Underivatized

Not Available

Derivatized

Derivative	Value	Reference
Queuine,1TMS,#1	2889.9683	https://arxiv.org/abs/1905.12712
Queuine,1TMS,#2	2896.334	https://arxiv.org/abs/1905.12712
Queuine,1TMS,#3	2885.325	https://arxiv.org/abs/1905.12712
Queuine,1TMS,#4	2840.4036	https://arxiv.org/abs/1905.12712
Queuine,1TMS,#5	2857.681	https://arxiv.org/abs/1905.12712
Queuine,1TMS,#6	2822.393	https://arxiv.org/abs/1905.12712
Queuine,1TMS,#7	2819.782	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#1	2854.523	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#2	2842.324	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#3	2804.189	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#4	2794.8916	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#5	2789.164	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#6	2852.6255	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#7	2855.3616	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#8	2812.4102	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#9	2811.8735	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#10	2793.4766	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#11	2869.895	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#12	2814.5867	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#13	2802.0596	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#14	2788.3818	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#15	2853.3857	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#16	2830.8645	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#17	2779.4504	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#18	2794.7954	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#19	2816.15	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#20	2836.4993	https://arxiv.org/abs/1905.12712
Queuine,2TMS,#21	2808.266	https://arxiv.org/abs/1905.12712
Queuine,1TBDMS,#1	3105.2231	https://arxiv.org/abs/1905.12712
Queuine,1TBDMS,#2	3112.1707	https://arxiv.org/abs/1905.12712
Queuine,1TBDMS,#3	3115.8062	https://arxiv.org/abs/1905.12712
Queuine,1TBDMS,#4	3073.705	https://arxiv.org/abs/1905.12712
Queuine,1TBDMS,#5	3082.5896	https://arxiv.org/abs/1905.12712
Queuine,1TBDMS,#6	3083.8596	https://arxiv.org/abs/1905.12712
Queuine,1TBDMS,#7	3019.465	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#1	3257.8513	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#2	3232.4897	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#3	3222.5918	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#4	3197.7332	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#5	3187.9863	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#6	3265.2778	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#7	3240.3633	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#8	3235.9941	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#9	3219.2524	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#10	3192.387	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#11	3282.495	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#12	3262.5051	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#13	3219.459	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#14	3197.4685	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#15	3269.6382	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#16	3312.8916	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#17	3223.551	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#18	3262.356	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#19	3265.7437	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#20	3295.319	https://arxiv.org/abs/1905.12712
Queuine,2TBDMS,#21	3240.6807	https://arxiv.org/abs/1905.12712

Spectra

GC-MS

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

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
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	2021-09-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03fr-0980000000-51b408b7c28c2878bc58	2021-09-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-0910000000-0bc9779e624e8314aab5	2021-09-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0970000000-89efef47c25a5bb1e162	2021-09-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01r2-0890000000-06643dd86a98e7fb7a9e	2021-09-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-3900000000-062fe840765b80e24461	2021-09-09	View Spectrum

NMR

Spectrum Type	Description	Deposition Date	View
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 (predicted from logP)

Biospecimen Locations

Amniotic Fluid

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Amniotic Fluid	Detected and Quantified	0.105 uM	Not Specified	Female	Normal	7063869	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

VMH ID

M02820

MarkerDB ID

Not Available

References

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

Material Safety Data Sheet (MSDS)

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. [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. [PubMed:9016755 ]

Enzymes

Enzyme Details

1. Queuine tRNA-ribosyltransferase

General function:: Involved in queuine tRNA-ribosyltransferase activity
Specific function:: Interacts with QTRTD1 to form an active queuine tRNA-ribosyltransferase. This enzyme exchanges queuine for the guanine at the wobble position of tRNAs with GU(N) anticodons (tRNA-Asp, -Asn, -His and -Tyr), thereby forming the hypermodified nucleoside queuosine (Q) (7-(((4,5-cis-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanosine) (By similarity).
Gene Name:: QTRT1
Uniprot ID:: Q9BXR0
Molecular weight:: 44047.3

Reactions

Guanine(34) in tRNA + Queuine → queuosine(34) in tRNA + Guanine	details
tRNA guanine + Queuine → tRNA queuine + Guanine	details

Enzyme Details

2. Queuine tRNA-ribosyltransferase subunit QTRTD1

General function:: Involved in queuine tRNA-ribosyltransferase activity
Specific function:: Interacts with QTRT1 to form an active queuine tRNA-ribosyltransferase. This enzyme exchanges queuine for the guanine at the wobble position of tRNAs with GU(N) anticodons (tRNA-Asp, -Asn, -His and -Tyr), thereby forming the hypermodified nucleoside queuosine (Q) (7-(((4,5-cis-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanosine) (By similarity).
Gene Name:: QTRTD1
Uniprot ID:: Q9H974
Molecular weight:: 48203.07

Reactions

Guanine(34) in tRNA + Queuine → queuosine(34) in tRNA + Guanine	details
tRNA guanine + Queuine → tRNA queuine + Guanine	details

Showing metabocard for Queuine (HMDB0001495)

MOL for HMDB0001495 (Queuine)

3D MOL for HMDB0001495 (Queuine)

3D SDF for HMDB0001495 (Queuine)

3D-SDF for HMDB0001495 (Queuine)

PDB for HMDB0001495 (Queuine)

3D PDB for HMDB0001495 (Queuine)

SMILES for HMDB0001495 (Queuine)

INCHI for HMDB0001495 (Queuine)

Structure for HMDB0001495 (Queuine)

3D Structure for HMDB0001495 (Queuine)

Collision Cross Sections

Retention Indices

Underivatized

Derivatized

GC-MS

LC-MS/MS

NMR

Enzymes

Reactions

Reactions