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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:32:54 UTC

Update Date

2022-03-07 02:52:18 UTC

HMDB ID

HMDB0029827

Secondary Accession Numbers

HMDB29827

Metabolite Identification

Common Name

Junosidine

Description

Junosidine is a member of the class of compounds known as acridones. Acridones are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety. Junosidine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Junosidine is an alkaloid that has been found in the root bark of Citrus junos (yuzu).

Structure

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

HMDB0029827
     RDKit          3D
Junosidine
 44 47  0  0  0  0  0  0  0  0999 V2000
    5.1316   -2.8363    0.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8853   -2.1860    0.3505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8551   -0.8359    0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0632   -0.1415   -0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0683    1.2047   -0.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8872    1.9024   -0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6914    1.2376   -0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5098    1.9827   -0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6055    3.2012   -0.6377 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301    1.3136   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8645    1.9809   -0.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9837    3.3239   -0.5722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0866    1.3278   -0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0425   -0.0058    0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8354   -0.7188    0.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3426   -0.0490    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5083   -0.7640    0.1428 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5448   -2.1822    0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6893   -0.1157   -0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2326   -0.7137    0.3024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4971   -0.1076    0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2776   -0.2783    1.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2999   -0.7473   -0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4837    1.3404   -0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3650    2.0034   -0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7223   -2.3308    1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7162   -2.7067   -0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0209   -3.9220    0.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9769   -0.7137   -0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0051    1.7389   -0.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870    2.9778   -0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3077    3.9844   -0.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8911   -1.7570    0.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5403   -2.6468    0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9946   -2.4557    1.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015   -2.7544   -0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3357   -0.4754    1.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8740   -1.0689    2.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2767    0.6763    2.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6896   -0.6381   -1.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2660   -0.1841   -0.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5437   -1.7905   -0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4656    1.8575   -0.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3585    3.0728   -0.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 14 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  2  0
 19  3  1  0
 19  7  2  0
 16 10  1  0
 25 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
 12 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 22 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 23 41  1  0
 23 42  1  0
 24 43  1  0
 25 44  1  0
M  END


  Mrv1652309272007252D          

 25 28  0  0  0  0            999 V2000
 9998.9567 9998.0932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.529810001.4058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.678210001.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.956710001.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3823 9998.0932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.331710000.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.801610000.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.381810000.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3817 9998.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.529910000.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.815410000.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8153 9999.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5298 9998.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.956110000.5743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.241610000.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2416 9999.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9561 9998.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6706 9999.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.670610000.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.807610000.5743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.093110000.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0931 9999.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8076 9998.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5221 9999.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.522110000.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 10  2  1  0  0  0  0
  9  5  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 20 21  1  0  0  0  0
 20 25  1  0  0  0  0
 25  7  1  0  0  0  0
 25  6  1  0  0  0  0
 21  8  2  0  0  0  0
  9 22  2  0  0  0  0
 14  4  1  0  0  0  0
  1 17  2  0  0  0  0
  8 19  1  0  0  0  0
 18  9  1  0  0  0  0
 15 10  2  0  0  0  0
 13 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029827

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2N(C)C3=C(C(O)=C4C=CC(C)(C)OC4=C3)C(=O)C2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H19NO4/c1-20(2)9-8-11-15(25-20)10-13-16(18(11)22)19(23)12-6-5-7-14(24-4)17(12)21(13)3/h5-10,22H,1-4H3

> <INCHI_KEY>
AUWXWUDANKEVNS-UHFFFAOYSA-N

> <FORMULA>
C20H19NO4

> <MOLECULAR_WEIGHT>
337.3692

> <EXACT_MASS>
337.131408101

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
36.44602726982549

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-10-methoxy-2,2,11-trimethyl-6,11-dihydro-2H-1-oxa-11-azatetracen-6-one

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
4.212341692999999

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.695617464133832

> <JCHEM_PKA_STRONGEST_BASIC>
-4.589741933676475

> <JCHEM_POLAR_SURFACE_AREA>
59.0

> <JCHEM_REFRACTIVITY>
96.79589999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-10-methoxy-2,2,11-trimethyl-1-oxa-11-azatetracen-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029827
     RDKit          3D
Junosidine
 44 47  0  0  0  0  0  0  0  0999 V2000
    5.1316   -2.8363    0.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8853   -2.1860    0.3505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8551   -0.8359    0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0632   -0.1415   -0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0683    1.2047   -0.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8872    1.9024   -0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6914    1.2376   -0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5098    1.9827   -0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6055    3.2012   -0.6377 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301    1.3136   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8645    1.9809   -0.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9837    3.3239   -0.5722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0866    1.3278   -0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0425   -0.0058    0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8354   -0.7188    0.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3426   -0.0490    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5083   -0.7640    0.1428 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5448   -2.1822    0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6893   -0.1157   -0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2326   -0.7137    0.3024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4971   -0.1076    0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2776   -0.2783    1.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2999   -0.7473   -0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4837    1.3404   -0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3650    2.0034   -0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7223   -2.3308    1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7162   -2.7067   -0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0209   -3.9220    0.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9769   -0.7137   -0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0051    1.7389   -0.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870    2.9778   -0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3077    3.9844   -0.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8911   -1.7570    0.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5403   -2.6468    0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9946   -2.4557    1.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015   -2.7544   -0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3357   -0.4754    1.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8740   -1.0689    2.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2767    0.6763    2.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6896   -0.6381   -1.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2660   -0.1841   -0.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5437   -1.7905   -0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4656    1.8575   -0.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3585    3.0728   -0.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 14 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  2  0
 19  3  1  0
 19  7  2  0
 16 10  1  0
 25 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
 12 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 22 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 23 41  1  0
 23 42  1  0
 24 43  1  0
 25 44  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8664.7198663.107   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8662.0568669.291   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8660.4668670.207   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8664.7198669.291   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8667.3808663.107   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8672.8868666.708   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8671.8968668.425   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8667.3798667.738   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8667.3798664.658   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.0568667.738   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8660.7228666.968   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8660.7228665.429   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.0568664.658   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0    8664.7188667.739   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0    8663.3848666.969   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.3848665.429   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.7188664.659   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8666.0528665.429   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.0528666.969   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0    8670.0418667.739   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0    8668.7078666.969   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.7078665.429   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8670.0418664.659   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8671.3758665.429   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8671.3758666.969   0.000  0.00  0.00           C+0
CONECT    1   17                                                            
CONECT    2    3   10                                                       
CONECT    3    2                                                            
CONECT    4   14                                                            
CONECT    5    9                                                            
CONECT    6   25                                                            
CONECT    7   25                                                            
CONECT    8   21   19                                                       
CONECT    9    5   22   18                                                  
CONECT   10   11    2   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   16                                                       
CONECT   14   15   19    4                                                  
CONECT   15   16   14   10                                                  
CONECT   16   15   17   13                                                  
CONECT   17   16   18    1                                                  
CONECT   18   17   19    9                                                  
CONECT   19   18   14    8                                                  
CONECT   20   21   25                                                       
CONECT   21   22   20    8                                                  
CONECT   22   21   23    9                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20    7    6                                             
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0029827
HETATM    1  C1  UNL     1       5.132  -2.836   0.442  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.885  -2.186   0.351  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.855  -0.836   0.085  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.063  -0.141  -0.087  1.00  0.00           C  
HETATM    5  C4  UNL     1       5.068   1.205  -0.351  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.887   1.902  -0.454  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.691   1.238  -0.288  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.510   1.983  -0.395  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.605   3.201  -0.638  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.330   1.314  -0.225  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.864   1.981  -0.313  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.984   3.324  -0.572  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.087   1.328  -0.140  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.043  -0.006   0.120  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.835  -0.719   0.216  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.343  -0.049   0.042  1.00  0.00           C  
HETATM   17  N1  UNL     1       1.508  -0.764   0.143  1.00  0.00           N  
HETATM   18  C14 UNL     1       1.545  -2.182   0.403  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.689  -0.116  -0.022  1.00  0.00           C  
HETATM   20  O4  UNL     1      -3.233  -0.714   0.302  1.00  0.00           O  
HETATM   21  C16 UNL     1      -4.497  -0.108   0.229  1.00  0.00           C  
HETATM   22  C17 UNL     1      -5.278  -0.278   1.521  1.00  0.00           C  
HETATM   23  C18 UNL     1      -5.300  -0.747  -0.916  1.00  0.00           C  
HETATM   24  C19 UNL     1      -4.484   1.340  -0.056  1.00  0.00           C  
HETATM   25  C20 UNL     1      -3.365   2.003  -0.227  1.00  0.00           C  
HETATM   26  H1  UNL     1       5.722  -2.331   1.235  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.716  -2.707  -0.502  1.00  0.00           H  
HETATM   28  H3  UNL     1       5.021  -3.922   0.617  1.00  0.00           H  
HETATM   29  H4  UNL     1       5.977  -0.714  -0.001  1.00  0.00           H  
HETATM   30  H5  UNL     1       6.005   1.739  -0.484  1.00  0.00           H  
HETATM   31  H6  UNL     1       3.887   2.978  -0.665  1.00  0.00           H  
HETATM   32  H7  UNL     1      -0.308   3.984  -0.727  1.00  0.00           H  
HETATM   33  H8  UNL     1      -0.891  -1.757   0.427  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.540  -2.647   0.436  1.00  0.00           H  
HETATM   35  H10 UNL     1       1.995  -2.456   1.381  1.00  0.00           H  
HETATM   36  H11 UNL     1       2.002  -2.754  -0.471  1.00  0.00           H  
HETATM   37  H12 UNL     1      -6.336  -0.475   1.254  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.874  -1.069   2.164  1.00  0.00           H  
HETATM   39  H14 UNL     1      -5.277   0.676   2.122  1.00  0.00           H  
HETATM   40  H15 UNL     1      -4.690  -0.638  -1.825  1.00  0.00           H  
HETATM   41  H16 UNL     1      -6.266  -0.184  -0.977  1.00  0.00           H  
HETATM   42  H17 UNL     1      -5.544  -1.791  -0.663  1.00  0.00           H  
HETATM   43  H18 UNL     1      -5.466   1.858  -0.122  1.00  0.00           H  
HETATM   44  H19 UNL     1      -3.358   3.073  -0.437  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   29
CONECT    5    6    6   30
CONECT    6    7   31
CONECT    7    8   19   19
CONECT    8    9    9   10
CONECT   10   11   11   16
CONECT   11   12   13
CONECT   12   32
CONECT   13   14   14   25
CONECT   14   15   20
CONECT   15   16   16   33
CONECT   16   17
CONECT   17   18   19
CONECT   18   34   35   36
CONECT   20   21
CONECT   21   22   23   24
CONECT   22   37   38   39
CONECT   23   40   41   42
CONECT   24   25   25   43
CONECT   25   44
END

HMDB0029827
     RDKit          3D
Junosidine
 44 47  0  0  0  0  0  0  0  0999 V2000
    5.1316   -2.8363    0.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8853   -2.1860    0.3505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8551   -0.8359    0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0632   -0.1415   -0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0683    1.2047   -0.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8872    1.9024   -0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6914    1.2376   -0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5098    1.9827   -0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6055    3.2012   -0.6377 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301    1.3136   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8645    1.9809   -0.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9837    3.3239   -0.5722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0866    1.3278   -0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0425   -0.0058    0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8354   -0.7188    0.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3426   -0.0490    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5083   -0.7640    0.1428 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5448   -2.1822    0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6893   -0.1157   -0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2326   -0.7137    0.3024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4971   -0.1076    0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2776   -0.2783    1.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2999   -0.7473   -0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4837    1.3404   -0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3650    2.0034   -0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7223   -2.3308    1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7162   -2.7067   -0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0209   -3.9220    0.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9769   -0.7137   -0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0051    1.7389   -0.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870    2.9778   -0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3077    3.9844   -0.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8911   -1.7570    0.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5403   -2.6468    0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9946   -2.4557    1.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015   -2.7544   -0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3357   -0.4754    1.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8740   -1.0689    2.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2767    0.6763    2.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6896   -0.6381   -1.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2660   -0.1841   -0.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5437   -1.7905   -0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4656    1.8575   -0.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3585    3.0728   -0.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 14 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  2  0
 19  3  1  0
 19  7  2  0
 16 10  1  0
 25 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
 12 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 22 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 23 41  1  0
 23 42  1  0
 24 43  1  0
 25 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,11-Dihydro-5-hydroxy-10-methoxy-2,2,11-trimethyl-6H-pyrano[3,2-b]acridin-6-one, 9ci	HMDB

Chemical Formula

C₂₀H₁₉NO₄

Average Molecular Weight

337.3692

Monoisotopic Molecular Weight

337.131408101

IUPAC Name

5-hydroxy-10-methoxy-2,2,11-trimethyl-6,11-dihydro-2H-1-oxa-11-azatetracen-6-one

Traditional Name

5-hydroxy-10-methoxy-2,2,11-trimethyl-1-oxa-11-azatetracen-6-one

CAS Registry Number

110883-39-1

SMILES

COC1=C2N(C)C3=C(C(O)=C4C=CC(C)(C)OC4=C3)C(=O)C2=CC=C1

InChI Identifier

InChI=1S/C20H19NO4/c1-20(2)9-8-11-15(25-20)10-13-16(18(11)22)19(23)12-6-5-7-14(24-4)17(12)21(13)3/h5-10,22H,1-4H3

InChI Key

AUWXWUDANKEVNS-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
Chromenopyridine
2,2-dimethyl-1-benzopyran
Dihydroquinolone
Benzopyran
Dihydroquinoline
1-benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Vinylogous acid
Oxacycle
Ether
Azacycle
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029827)
Cell membrane (HMDB: HMDB0029827)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029827)

Source

Endogenous

Endogenous (HMDB: HMDB0029827)

Plant

Plant (HMDB: HMDB0029827)

Exogenous

Food

Food (HMDB: HMDB0029827)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Exogenous (HMDB: HMDB0029827)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	188 - 189 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.26 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	0.15 g/L	ALOGPS
logP	3.64	ALOGPS
logP	4.21	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	96.8 m³·mol⁻¹	ChemAxon
Polarizability	36.45 Å³	ChemAxon
Number of Rings	4	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
DarkChem	[M+H]+	177.31	31661259
DarkChem	[M-H]-	179.376	31661259
DeepCCS	[M+H]+	187.121	30932474
DeepCCS	[M-H]-	184.763	30932474
DeepCCS	[M-2H]-	218.598	30932474
DeepCCS	[M+Na]+	193.826	30932474
AllCCS	[M+H]+	178.9	32859911
AllCCS	[M+H-H2O]+	175.5	32859911
AllCCS	[M+NH4]+	182.0	32859911
AllCCS	[M+Na]+	182.9	32859911
AllCCS	[M-H]-	185.7	32859911
AllCCS	[M+Na-2H]-	185.0	32859911
AllCCS	[M+HCOO]-	184.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.01 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0689 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.17 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2478.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	222.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	161.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	170.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	91.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	493.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	509.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	130.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	933.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	385.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	960.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	332.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	357.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	301.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	308.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Junosidine	COC1=C2N(C)C3=C(C(O)=C4C=CC(C)(C)OC4=C3)C(=O)C2=CC=C1	3836.2	Standard polar	33892256
Junosidine	COC1=C2N(C)C3=C(C(O)=C4C=CC(C)(C)OC4=C3)C(=O)C2=CC=C1	2795.1	Standard non polar	33892256
Junosidine	COC1=C2N(C)C3=C(C(O)=C4C=CC(C)(C)OC4=C3)C(=O)C2=CC=C1	3225.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Junosidine,1TMS,isomer #1	COC1=CC=CC2=C1N(C)C1=CC3=C(C=CC(C)(C)O3)C(O[Si](C)(C)C)=C1C2=O	3099.6	Semi standard non polar	33892256
Junosidine,1TBDMS,isomer #1	COC1=CC=CC2=C1N(C)C1=CC3=C(C=CC(C)(C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	3265.3	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 - Junosidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-0398000000-3c3bcb80f1c56d17a48a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Junosidine GC-MS (1 TMS) - 70eV, Positive	splash10-0076-2309000000-dff359af08c4f68adad0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Junosidine 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 - Junosidine 10V, Positive-QTOF	splash10-000i-0009000000-2c671cf08f3b57803e8f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosidine 20V, Positive-QTOF	splash10-000i-1049000000-ab2783a781d97e9ef8bc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosidine 40V, Positive-QTOF	splash10-0gbd-4090000000-0f4524e0ba280ce7eace	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosidine 10V, Negative-QTOF	splash10-000i-0009000000-c75feaf8a50830d59bb9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosidine 20V, Negative-QTOF	splash10-000i-0019000000-90b655a01cc13ef81a7a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosidine 40V, Negative-QTOF	splash10-0udi-0090000000-cc38342ab6abc20a5c8d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosidine 10V, Positive-QTOF	splash10-000i-0009000000-195152c9499dc2b0f3dd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosidine 20V, Positive-QTOF	splash10-000i-0009000000-ead8640ecca32d9c4844	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosidine 40V, Positive-QTOF	splash10-05ar-0392000000-6766aa3fd524e4d5073c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosidine 10V, Negative-QTOF	splash10-000i-0009000000-e425d548b88b81358192	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosidine 20V, Negative-QTOF	splash10-000i-0009000000-ce9daf74b97523428005	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Junosidine 40V, Negative-QTOF	splash10-0006-0092000000-df927ad89fa7c7237783	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

FDB001039

KNApSAcK ID

C00052330

Chemspider ID

9834814

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11660079

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1811581

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 Junosidine (HMDB0029827)

MOL for HMDB0029827 (Junosidine)

3D MOL for HMDB0029827 (Junosidine)

3D SDF for HMDB0029827 (Junosidine)

3D-SDF for HMDB0029827 (Junosidine)

PDB for HMDB0029827 (Junosidine)

3D PDB for HMDB0029827 (Junosidine)

SMILES for HMDB0029827 (Junosidine)

INCHI for HMDB0029827 (Junosidine)

Structure for HMDB0029827 (Junosidine)

3D Structure for HMDB0029827 (Junosidine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra