Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:25:45 UTC

Update Date

2022-03-07 02:55:38 UTC

HMDB ID

HMDB0038145

Secondary Accession Numbers

HMDB38145

Metabolite Identification

Common Name

Junosine

Description

Junosine belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety. Junosine has been detected, but not quantified in, citrus. This could make junosine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Junosine.

Structure

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

HMDB0038145
     RDKit          3D
Junosine
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.1701    1.9036    0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5298    0.5723   -0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9584   -0.5093    0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5921    0.3802   -0.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.9071   -1.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4539   -0.8653   -0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6885   -1.9668   -1.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -3.1094   -1.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6915   -2.0129   -0.9018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3304   -0.9132   -0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602    0.2211   -0.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8161    0.2587   -0.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6235    1.3205   -0.0792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1757    1.3204    0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5531    2.3647    0.7023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5378    1.2685    0.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1617    2.3776    1.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5247    2.3785    1.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2385    1.2555    1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6525    0.1062    0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4373   -1.0017    0.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3050    0.1412    0.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6558   -0.9407   -0.1437 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4846   -2.0806   -0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2352    2.3609   -0.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1905    1.8230    0.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5644    2.5816    0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1497   -0.6264    1.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1515   -1.4569    0.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9002   -0.2341    1.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3084    1.2020   -1.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3986   -1.7652   -0.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9989   -1.1301   -2.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2808   -3.0879   -1.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1850   -2.9317   -1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5076    2.1926    0.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5611    3.2367    1.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9170    3.2899    1.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2946    1.2434    1.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4258   -0.9887    0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9060   -2.5936    0.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2559   -1.8326   -1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797   -2.8447   -0.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 11 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  1  0
 12  6  1  0
 22 16  1  0
 23 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 13 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 24 41  1  0
 24 42  1  0
 24 43  1  0
M  END


  Mrv0541 05061310152D          

 24 26  0  0  0  0            999 V2000
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  5  1  0  0  0  0
 13  9  2  0  0  0  0
 14  6  2  0  0  0  0
 15  9  1  0  0  0  0
 15 11  2  0  0  0  0
 16 13  1  0  0  0  0
 17 12  2  0  0  0  0
 17 14  1  0  0  0  0
 18 11  1  0  0  0  0
 18 16  2  0  0  0  0
 19 12  1  0  0  0  0
 19 16  1  0  0  0  0
 20  3  1  0  0  0  0
 20 13  1  0  0  0  0
 20 17  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 23 18  1  0  0  0  0
 24 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038145

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2=CC(O)=C(CC=C(C)C)C(O)=C2C(=O)C2=C1C(O)=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H19NO4/c1-10(2)7-8-11-15(22)9-13-16(18(11)23)19(24)12-5-4-6-14(21)17(12)20(13)3/h4-7,9,21-23H,8H2,1-3H3

> <INCHI_KEY>
YDKCXKMKJZNVHQ-UHFFFAOYSA-N

> <FORMULA>
C19H19NO4

> <MOLECULAR_WEIGHT>
325.3585

> <EXACT_MASS>
325.131408101

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
35.22582715855279

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,5-trihydroxy-10-methyl-2-(3-methylbut-2-en-1-yl)-9,10-dihydroacridin-9-one

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
4.590825912666667

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.189440101092872

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.878529642509557

> <JCHEM_PKA_STRONGEST_BASIC>
-3.015438616746258

> <JCHEM_POLAR_SURFACE_AREA>
81

> <JCHEM_REFRACTIVITY>
94.14389999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,5-trihydroxy-10-methyl-2-(3-methylbut-2-en-1-yl)acridin-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038145
     RDKit          3D
Junosine
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.1701    1.9036    0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5298    0.5723   -0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9584   -0.5093    0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5921    0.3802   -0.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.9071   -1.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4539   -0.8653   -0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6885   -1.9668   -1.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -3.1094   -1.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6915   -2.0129   -0.9018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3304   -0.9132   -0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602    0.2211   -0.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8161    0.2587   -0.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6235    1.3205   -0.0792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1757    1.3204    0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5531    2.3647    0.7023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5378    1.2685    0.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1617    2.3776    1.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5247    2.3785    1.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2385    1.2555    1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6525    0.1062    0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4373   -1.0017    0.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3050    0.1412    0.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6558   -0.9407   -0.1437 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4846   -2.0806   -0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2352    2.3609   -0.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1905    1.8230    0.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5644    2.5816    0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1497   -0.6264    1.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1515   -1.4569    0.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9002   -0.2341    1.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3084    1.2020   -1.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3986   -1.7652   -0.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9989   -1.1301   -2.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2808   -3.0879   -1.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1850   -2.9317   -1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5076    2.1926    0.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5611    3.2367    1.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9170    3.2899    1.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2946    1.2434    1.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4258   -0.9887    0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9060   -2.5936    0.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2559   -1.8326   -1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797   -2.8447   -0.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 11 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  1  0
 12  6  1  0
 22 16  1  0
 23 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 13 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 24 41  1  0
 24 42  1  0
 24 43  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   20                                                            
CONECT    4    5    6                                                       
CONECT    5    4   12                                                       
CONECT    6    4   14                                                       
CONECT    7    8   10                                                       
CONECT    8    7   11                                                       
CONECT    9   13   15                                                       
CONECT   10    1    2    7                                                  
CONECT   11    8   15   18                                                  
CONECT   12    5   17   19                                                  
CONECT   13    9   16   20                                                  
CONECT   14    6   17   21                                                  
CONECT   15    9   11   22                                                  
CONECT   16   13   18   19                                                  
CONECT   17   12   14   20                                                  
CONECT   18   11   16   23                                                  
CONECT   19   12   16   24                                                  
CONECT   20    3   13   17                                                  
CONECT   21   14                                                            
CONECT   22   15                                                            
CONECT   23   18                                                            
CONECT   24   19                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0038145
HETATM    1  C1  UNL     1       5.170   1.904   0.123  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.530   0.572  -0.020  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.958  -0.509   0.883  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.592   0.380  -0.944  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.922  -0.907  -1.136  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.454  -0.865  -0.862  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.688  -1.967  -1.133  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.293  -3.109  -1.667  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.691  -2.013  -0.902  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.330  -0.913  -0.379  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.560   0.221  -0.097  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.816   0.259  -0.330  1.00  0.00           C  
HETATM   13  O2  UNL     1       1.623   1.320  -0.079  1.00  0.00           O  
HETATM   14  C12 UNL     1      -1.176   1.320   0.428  1.00  0.00           C  
HETATM   15  O3  UNL     1      -0.553   2.365   0.702  1.00  0.00           O  
HETATM   16  C13 UNL     1      -2.538   1.268   0.661  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.162   2.378   1.199  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.525   2.378   1.460  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.238   1.255   1.174  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.653   0.106   0.628  1.00  0.00           C  
HETATM   21  O4  UNL     1      -5.437  -1.002   0.362  1.00  0.00           O  
HETATM   22  C18 UNL     1      -3.305   0.141   0.382  1.00  0.00           C  
HETATM   23  N1  UNL     1      -2.656  -0.941  -0.144  1.00  0.00           N  
HETATM   24  C19 UNL     1      -3.485  -2.081  -0.440  1.00  0.00           C  
HETATM   25  H1  UNL     1       5.235   2.361  -0.884  1.00  0.00           H  
HETATM   26  H2  UNL     1       6.191   1.823   0.538  1.00  0.00           H  
HETATM   27  H3  UNL     1       4.564   2.582   0.765  1.00  0.00           H  
HETATM   28  H4  UNL     1       4.150  -0.626   1.656  1.00  0.00           H  
HETATM   29  H5  UNL     1       5.151  -1.457   0.363  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.900  -0.234   1.417  1.00  0.00           H  
HETATM   31  H7  UNL     1       3.308   1.202  -1.602  1.00  0.00           H  
HETATM   32  H8  UNL     1       3.399  -1.765  -0.616  1.00  0.00           H  
HETATM   33  H9  UNL     1       2.999  -1.130  -2.244  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.281  -3.088  -1.835  1.00  0.00           H  
HETATM   35  H11 UNL     1      -1.185  -2.932  -1.148  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.508   2.193   0.265  1.00  0.00           H  
HETATM   37  H13 UNL     1      -2.561   3.237   1.407  1.00  0.00           H  
HETATM   38  H14 UNL     1      -4.917   3.290   1.879  1.00  0.00           H  
HETATM   39  H15 UNL     1      -6.295   1.243   1.374  1.00  0.00           H  
HETATM   40  H16 UNL     1      -6.426  -0.989   0.557  1.00  0.00           H  
HETATM   41  H17 UNL     1      -3.906  -2.594   0.438  1.00  0.00           H  
HETATM   42  H18 UNL     1      -4.256  -1.833  -1.240  1.00  0.00           H  
HETATM   43  H19 UNL     1      -2.880  -2.845  -0.958  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4    4
CONECT    3   28   29   30
CONECT    4    5   31
CONECT    5    6   32   33
CONECT    6    7    7   12
CONECT    7    8    9
CONECT    8   34
CONECT    9   10   10   35
CONECT   10   11   23
CONECT   11   12   12   14
CONECT   12   13
CONECT   13   36
CONECT   14   15   15   16
CONECT   16   17   17   22
CONECT   17   18   37
CONECT   18   19   19   38
CONECT   19   20   39
CONECT   20   21   22   22
CONECT   21   40
CONECT   22   23
CONECT   23   24
CONECT   24   41   42   43
END

HMDB0038145
     RDKit          3D
Junosine
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.1701    1.9036    0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5298    0.5723   -0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9584   -0.5093    0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5921    0.3802   -0.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.9071   -1.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4539   -0.8653   -0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6885   -1.9668   -1.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -3.1094   -1.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6915   -2.0129   -0.9018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3304   -0.9132   -0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602    0.2211   -0.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8161    0.2587   -0.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6235    1.3205   -0.0792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1757    1.3204    0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5531    2.3647    0.7023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5378    1.2685    0.6610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1617    2.3776    1.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5247    2.3785    1.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2385    1.2555    1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6525    0.1062    0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4373   -1.0017    0.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3050    0.1412    0.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6558   -0.9407   -0.1437 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4846   -2.0806   -0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2352    2.3609   -0.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1905    1.8230    0.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5644    2.5816    0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1497   -0.6264    1.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1515   -1.4569    0.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9002   -0.2341    1.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3084    1.2020   -1.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3986   -1.7652   -0.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9989   -1.1301   -2.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2808   -3.0879   -1.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1850   -2.9317   -1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5076    2.1926    0.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5611    3.2367    1.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9170    3.2899    1.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2946    1.2434    1.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4258   -0.9887    0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9060   -2.5936    0.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2559   -1.8326   -1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797   -2.8447   -0.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 11 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  1  0
 12  6  1  0
 22 16  1  0
 23 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 13 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 24 41  1  0
 24 42  1  0
 24 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3,5-Trihydroxy-10-methyl-2-prenylacridone	HMDB

Chemical Formula

C₁₉H₁₉NO₄

Average Molecular Weight

325.3585

Monoisotopic Molecular Weight

325.131408101

IUPAC Name

1,3,5-trihydroxy-10-methyl-2-(3-methylbut-2-en-1-yl)-9,10-dihydroacridin-9-one

Traditional Name

1,3,5-trihydroxy-10-methyl-2-(3-methylbut-2-en-1-yl)acridin-9-one

CAS Registry Number

103956-34-9

SMILES

CN1C2=CC(O)=C(CC=C(C)C)C(O)=C2C(=O)C2=C1C(O)=CC=C2

InChI Identifier

InChI=1S/C19H19NO4/c1-10(2)7-8-11-15(22)9-13-16(18(11)23)19(24)12-5-4-6-14(21)17(12)20(13)3/h4-7,9,21-23H,8H2,1-3H3

InChI Key

YDKCXKMKJZNVHQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridones

Alternative Parents

Substituents

Acridone
Dihydroquinolone
8-hydroxyquinoline
Dihydroquinoline
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Vinylogous acid
Polyol
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0038145)

Cellular substructure

Membrane (HMDB: HMDB0038145)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038145)

Source

Exogenous

Food

Food (HMDB: HMDB0038145)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0038145)

Not Available

Nutrient (HMDB: HMDB0038145)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	210 - 213 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.6 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.074 g/L	ALOGPS
logP	3.07	ALOGPS
logP	4.59	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.88	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	81 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.14 m³·mol⁻¹	ChemAxon
Polarizability	35.23 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	176.489	30932474
DeepCCS	[M-H]-	174.131	30932474
DeepCCS	[M-2H]-	207.672	30932474
DeepCCS	[M+Na]+	183.025	30932474
AllCCS	[M+H]+	176.8	32859911
AllCCS	[M+H-H2O]+	173.4	32859911
AllCCS	[M+NH4]+	179.9	32859911
AllCCS	[M+Na]+	180.8	32859911
AllCCS	[M-H]-	179.4	32859911
AllCCS	[M+Na-2H]-	178.8	32859911
AllCCS	[M+HCOO]-	178.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Junosine	CN1C2=CC(O)=C(CC=C(C)C)C(O)=C2C(=O)C2=C1C(O)=CC=C2	3894.4	Standard polar	33892256
Junosine	CN1C2=CC(O)=C(CC=C(C)C)C(O)=C2C(=O)C2=C1C(O)=CC=C2	2574.5	Standard non polar	33892256
Junosine	CN1C2=CC(O)=C(CC=C(C)C)C(O)=C2C(=O)C2=C1C(O)=CC=C2	3193.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Junosine,1TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C2C(=C1O)C(=O)C1=CC=CC(O)=C1N2C	3127.8	Semi standard non polar	33892256
Junosine,1TMS,isomer #2	CC(C)=CCC1=C(O)C=C2C(=C1O[Si](C)(C)C)C(=O)C1=CC=CC(O)=C1N2C	3101.8	Semi standard non polar	33892256
Junosine,1TMS,isomer #3	CC(C)=CCC1=C(O)C=C2C(=C1O)C(=O)C1=CC=CC(O[Si](C)(C)C)=C1N2C	3142.9	Semi standard non polar	33892256
Junosine,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C2C(=C1O[Si](C)(C)C)C(=O)C1=CC=CC(O)=C1N2C	3029.3	Semi standard non polar	33892256
Junosine,2TMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C)C=C2C(=C1O)C(=O)C1=CC=CC(O[Si](C)(C)C)=C1N2C	3029.3	Semi standard non polar	33892256
Junosine,2TMS,isomer #3	CC(C)=CCC1=C(O)C=C2C(=C1O[Si](C)(C)C)C(=O)C1=CC=CC(O[Si](C)(C)C)=C1N2C	3024.3	Semi standard non polar	33892256
Junosine,3TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C2C(=C1O[Si](C)(C)C)C(=O)C1=CC=CC(O[Si](C)(C)C)=C1N2C	3024.4	Semi standard non polar	33892256
Junosine,1TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2C(=C1O)C(=O)C1=CC=CC(O)=C1N2C	3367.5	Semi standard non polar	33892256
Junosine,1TBDMS,isomer #2	CC(C)=CCC1=C(O)C=C2C(=C1O[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CC(O)=C1N2C	3351.1	Semi standard non polar	33892256
Junosine,1TBDMS,isomer #3	CC(C)=CCC1=C(O)C=C2C(=C1O)C(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1N2C	3368.9	Semi standard non polar	33892256
Junosine,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2C(=C1O[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CC(O)=C1N2C	3505.7	Semi standard non polar	33892256
Junosine,2TBDMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2C(=C1O)C(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1N2C	3512.6	Semi standard non polar	33892256
Junosine,2TBDMS,isomer #3	CC(C)=CCC1=C(O)C=C2C(=C1O[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1N2C	3496.0	Semi standard non polar	33892256
Junosine,3TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2C(=C1O[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1N2C	3677.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Junosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-1093000000-96dc7771ab29bd2b5be7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Junosine GC-MS (3 TMS) - 70eV, Positive	splash10-004i-2000490000-9c6a71468632be613119	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Junosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosine 10V, Positive-QTOF	splash10-004i-0029000000-c8984270a5f10afdc4b6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosine 20V, Positive-QTOF	splash10-05xr-4097000000-136ea1534bcce5d71bf9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosine 40V, Positive-QTOF	splash10-016r-5090000000-2ea329ec9c120cab4bc3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosine 10V, Negative-QTOF	splash10-00di-0009000000-3452d7da818acb1b0deb	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosine 20V, Negative-QTOF	splash10-00di-0029000000-c2400ef84561c39760dd	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosine 40V, Negative-QTOF	splash10-0a4l-2191000000-8c60718664e544fc9596	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosine 10V, Negative-QTOF	splash10-00di-0009000000-fd8a579508e412fbe114	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosine 20V, Negative-QTOF	splash10-00di-0029000000-119677c90612ef88f4fb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosine 40V, Negative-QTOF	splash10-0w2c-1290000000-882dface08f57c4b6cac	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosine 10V, Positive-QTOF	splash10-00b9-0089000000-d2cfa3f4a6f33fb7cbe7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosine 20V, Positive-QTOF	splash10-00di-0090000000-2c468a9f9844ac8d11ee	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosine 40V, Positive-QTOF	splash10-014l-0190000000-c277756dac4fc0aa1d5d	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB017373

KNApSAcK ID

C00024263

Chemspider ID

30777236

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15286413

PDB ID

Not Available

ChEBI ID

175152

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1866031

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Junosine (HMDB0038145)

MOL for HMDB0038145 (Junosine)

3D MOL for HMDB0038145 (Junosine)

3D SDF for HMDB0038145 (Junosine)

3D-SDF for HMDB0038145 (Junosine)

PDB for HMDB0038145 (Junosine)

3D PDB for HMDB0038145 (Junosine)

SMILES for HMDB0038145 (Junosine)

INCHI for HMDB0038145 (Junosine)

Structure for HMDB0038145 (Junosine)

3D Structure for HMDB0038145 (Junosine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra