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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:46:35 UTC

Update Date

2022-03-07 02:53:10 UTC

HMDB ID

HMDB0031930

Secondary Accession Numbers

HMDB31930

Metabolite Identification

Common Name

Benzosimuline

Description

Benzosimuline belongs to the class of organic compounds known as pyranoquinolines. These are polycyclic compounds containing a pyran ring fused to a quinoline moiety. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine. Based on a literature review very few articles have been published on Benzosimuline.

Structure

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

HMDB0031930
     RDKit          3D
Benzosimuline
 42 45  0  0  0  0  0  0  0  0999 V2000
    4.0079    3.1448   -0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2637    1.8602    0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0032    0.7076    0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3153   -0.4768    0.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9211   -0.5615    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2291    0.6305    0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8853    1.8299   -0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2340    0.5385   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8337   -0.7083    0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2207   -0.7782   -0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8033   -2.0201    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1641   -2.1296   -0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9391   -0.9842   -0.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3198    0.2428   -0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9525    0.3730   -0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3409    1.5609   -0.3388 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1566    2.7330   -0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9715    1.6711   -0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4741    2.7986   -0.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1149   -1.8368    0.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2612   -1.8852    0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7766   -2.7950   -0.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5656   -2.5336    1.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3495    3.9221    0.3695 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9648    3.1162    0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1587    3.4372   -1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822    0.7196    0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373   -1.4360    0.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125    2.7692   -0.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1866   -2.9045    0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6073   -3.1162    0.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0140   -1.0844   -0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9278    1.1245   -0.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5992    3.6766   -0.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265    2.7457    0.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7103    2.7178   -1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9615   -3.4590   -1.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6120   -3.4157   -0.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1485   -2.2324   -1.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0830   -3.5186    1.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0265   -1.9031    2.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316   -2.5407    1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  9 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
  7  2  1  0
 18  8  1  0
 21  5  1  0
 15 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  7 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 17 34  1  0
 17 35  1  0
 17 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
M  END


  Mrv0541 05061306142D          

 23 26  0  0  0  0            999 V2000
    5.5753    1.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1229    4.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1207    4.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    3.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    3.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    3.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    2.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    3.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    2.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    2.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    3.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149    4.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    1.6402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449    1.1725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    3.9789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  2  0  0  0  0
 12  1  1  0  0  0  0
 12  9  1  0  0  0  0
 12 11  2  0  0  0  0
 13  7  2  0  0  0  0
 14 11  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  2  0  0  0  0
 16  8  2  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 13  1  0  0  0  0
 18 17  2  0  0  0  0
 19 17  1  0  0  0  0
 20  2  1  0  0  0  0
 20  3  1  0  0  0  0
 20 15  1  0  0  0  0
 21  4  1  0  0  0  0
 21 16  1  0  0  0  0
 21 19  1  0  0  0  0
 22 19  2  0  0  0  0
 23 18  1  0  0  0  0
 23 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031930

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(=O)C2=C(OC(C)(C)C3=C2C=C(C)C=C3)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H19NO2/c1-12-9-10-15-14(11-12)17-18(23-20(15,2)3)13-7-5-6-8-16(13)21(4)19(17)22/h5-11H,1-4H3

> <INCHI_KEY>
OSBHLKXCNYMURI-UHFFFAOYSA-N

> <FORMULA>
C20H19NO2

> <MOLECULAR_WEIGHT>
305.3704

> <EXACT_MASS>
305.141578857

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.47727104064775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8,13,17,17-tetramethyl-18-oxa-8-azatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

> <ALOGPS_LOGP>
3.88

> <JCHEM_LOGP>
3.4503770796666675

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3520519218308453

> <JCHEM_POLAR_SURFACE_AREA>
29.540000000000003

> <JCHEM_REFRACTIVITY>
92.14349999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.51e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8,13,17,17-tetramethyl-18-oxa-8-azatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0031930
     RDKit          3D
Benzosimuline
 42 45  0  0  0  0  0  0  0  0999 V2000
    4.0079    3.1448   -0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2637    1.8602    0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0032    0.7076    0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3153   -0.4768    0.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9211   -0.5615    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2291    0.6305    0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8853    1.8299   -0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2340    0.5385   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8337   -0.7083    0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2207   -0.7782   -0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8033   -2.0201    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1641   -2.1296   -0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9391   -0.9842   -0.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3198    0.2428   -0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9525    0.3730   -0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3409    1.5609   -0.3388 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1566    2.7330   -0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9715    1.6711   -0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4741    2.7986   -0.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1149   -1.8368    0.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2612   -1.8852    0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7766   -2.7950   -0.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5656   -2.5336    1.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3495    3.9221    0.3695 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9648    3.1162    0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1587    3.4372   -1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822    0.7196    0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373   -1.4360    0.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125    2.7692   -0.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1866   -2.9045    0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6073   -3.1162    0.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0140   -1.0844   -0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9278    1.1245   -0.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5992    3.6766   -0.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265    2.7457    0.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7103    2.7178   -1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9615   -3.4590   -1.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6120   -3.4157   -0.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1485   -2.2324   -1.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0830   -3.5186    1.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0265   -1.9031    2.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316   -2.5407    1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  9 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
  7  2  1  0
 18  8  1  0
 21  5  1  0
 15 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  7 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 17 34  1  0
 17 35  1  0
 17 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
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      10.407   3.062   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.696   8.509   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.825   9.157   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.846   1.607   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.326   6.554   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.179   5.099   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.838   6.845   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.830   3.935   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.903   5.681   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.895   6.845   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.887   3.935   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.399   4.226   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.846   5.681   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.879   5.099   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.383   6.554   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.342   4.226   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.366   4.808   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.358   5.972   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.862   3.353   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.374   7.718   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       3.350   3.062   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       5.870   2.189   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.862   7.427   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   20                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5   13                                                       
CONECT    8    6   16                                                       
CONECT    9   10   12                                                       
CONECT   10    9   15                                                       
CONECT   11   12   14                                                       
CONECT   12    1    9   11                                                  
CONECT   13    7   16   18                                                  
CONECT   14   11   15   17                                                  
CONECT   15   10   14   20                                                  
CONECT   16    8   13   21                                                  
CONECT   17   14   18   19                                                  
CONECT   18   13   17   23                                                  
CONECT   19   17   21   22                                                  
CONECT   20    2    3   15   23                                             
CONECT   21    4   16   19                                                  
CONECT   22   19                                                            
CONECT   23   18   20                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0031930
HETATM    1  C1  UNL     1       4.008   3.145  -0.083  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.264   1.860   0.010  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.003   0.708   0.190  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.315  -0.477   0.276  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.921  -0.561   0.190  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.229   0.631   0.009  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.885   1.830  -0.080  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.234   0.539  -0.080  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.834  -0.708   0.019  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.221  -0.778  -0.068  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.803  -2.020   0.031  1.00  0.00           C  
HETATM   12  C12 UNL     1      -4.164  -2.130  -0.049  1.00  0.00           C  
HETATM   13  C13 UNL     1      -4.939  -0.984  -0.231  1.00  0.00           C  
HETATM   14  C14 UNL     1      -4.320   0.243  -0.326  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.952   0.373  -0.247  1.00  0.00           C  
HETATM   16  N1  UNL     1      -2.341   1.561  -0.339  1.00  0.00           N  
HETATM   17  C16 UNL     1      -3.157   2.733  -0.526  1.00  0.00           C  
HETATM   18  C17 UNL     1      -0.971   1.671  -0.258  1.00  0.00           C  
HETATM   19  O1  UNL     1      -0.474   2.799  -0.350  1.00  0.00           O  
HETATM   20  O2  UNL     1      -0.115  -1.837   0.194  1.00  0.00           O  
HETATM   21  C18 UNL     1       1.261  -1.885   0.294  1.00  0.00           C  
HETATM   22  C19 UNL     1       1.777  -2.795  -0.814  1.00  0.00           C  
HETATM   23  C20 UNL     1       1.566  -2.534   1.645  1.00  0.00           C  
HETATM   24  H1  UNL     1       3.349   3.922   0.370  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.965   3.116   0.472  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.159   3.437  -1.152  1.00  0.00           H  
HETATM   27  H4  UNL     1       5.082   0.720   0.262  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.837  -1.436   0.419  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.413   2.769  -0.218  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.187  -2.904   0.173  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.607  -3.116   0.031  1.00  0.00           H  
HETATM   32  H9  UNL     1      -6.014  -1.084  -0.293  1.00  0.00           H  
HETATM   33  H10 UNL     1      -4.928   1.124  -0.466  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.599   3.677  -0.442  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.927   2.746   0.274  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.710   2.718  -1.485  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.961  -3.459  -1.165  1.00  0.00           H  
HETATM   38  H15 UNL     1       2.612  -3.416  -0.418  1.00  0.00           H  
HETATM   39  H16 UNL     1       2.148  -2.232  -1.671  1.00  0.00           H  
HETATM   40  H17 UNL     1       1.083  -3.519   1.638  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.027  -1.903   2.398  1.00  0.00           H  
HETATM   42  H19 UNL     1       2.632  -2.541   1.868  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    7
CONECT    3    4   27
CONECT    4    5    5   28
CONECT    5    6   21
CONECT    6    7    7    8
CONECT    7   29
CONECT    8    9    9   18
CONECT    9   10   20
CONECT   10   11   11   15
CONECT   11   12   30
CONECT   12   13   13   31
CONECT   13   14   32
CONECT   14   15   15   33
CONECT   15   16
CONECT   16   17   18
CONECT   17   34   35   36
CONECT   18   19   19
CONECT   20   21
CONECT   21   22   23
CONECT   22   37   38   39
CONECT   23   40   41   42
END

HMDB0031930
     RDKit          3D
Benzosimuline
 42 45  0  0  0  0  0  0  0  0999 V2000
    4.0079    3.1448   -0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2637    1.8602    0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0032    0.7076    0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3153   -0.4768    0.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9211   -0.5615    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2291    0.6305    0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8853    1.8299   -0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2340    0.5385   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8337   -0.7083    0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2207   -0.7782   -0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8033   -2.0201    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1641   -2.1296   -0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9391   -0.9842   -0.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3198    0.2428   -0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9525    0.3730   -0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3409    1.5609   -0.3388 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1566    2.7330   -0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9715    1.6711   -0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4741    2.7986   -0.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1149   -1.8368    0.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2612   -1.8852    0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7766   -2.7950   -0.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5656   -2.5336    1.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3495    3.9221    0.3695 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9648    3.1162    0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1587    3.4372   -1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822    0.7196    0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373   -1.4360    0.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125    2.7692   -0.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1866   -2.9045    0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6073   -3.1162    0.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0140   -1.0844   -0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9278    1.1245   -0.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5992    3.6766   -0.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265    2.7457    0.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7103    2.7178   -1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9615   -3.4590   -1.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6120   -3.4157   -0.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1485   -2.2324   -1.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0830   -3.5186    1.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0265   -1.9031    2.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316   -2.5407    1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  9 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
  7  2  1  0
 18  8  1  0
 21  5  1  0
 15 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  7 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 17 34  1  0
 17 35  1  0
 17 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
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₁₉NO₂

Average Molecular Weight

305.3704

Monoisotopic Molecular Weight

305.141578857

IUPAC Name

8,13,17,17-tetramethyl-18-oxa-8-azatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

Traditional Name

8,13,17,17-tetramethyl-18-oxa-8-azatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

CAS Registry Number

198336-58-2

SMILES

CN1C(=O)C2=C(OC(C)(C)C3=C2C=C(C)C=C3)C2=CC=CC=C12

InChI Identifier

InChI=1S/C20H19NO2/c1-12-9-10-15-14(11-12)17-18(23-20(15,2)3)13-7-5-6-8-16(13)21(4)19(17)22/h5-11H,1-4H3

InChI Key

OSBHLKXCNYMURI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoquinolines. These are polycyclic compounds containing a pyran ring fused to a quinoline moiety. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Pyranoquinolines

Alternative Parents

Substituents

Pyranoquinoline
Dihydroquinolone
Benzopyran
Dihydroquinoline
Pyranopyridine
2-benzopyran
Alkyl aryl ether
Pyridinone
Pyran
Benzenoid
Pyridine
Heteroaromatic compound
Vinylogous ester
Lactam
Oxacycle
Ether
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
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

Cellular substructure

Membrane (HMDB: HMDB0031930)
Cell membrane (HMDB: HMDB0031930)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031930)

Source

Endogenous

Endogenous (HMDB: HMDB0031930)

Plant

Plant (HMDB: HMDB0031930)

Exogenous

Food

Food (HMDB: HMDB0031930)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0031930)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.055 g/L	ALOGPS
logP	3.88	ALOGPS
logP	3.45	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	92.14 m³·mol⁻¹	ChemAxon
Polarizability	34.48 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	169.971	31661259
DarkChem	[M-H]-	168.261	31661259
DeepCCS	[M-2H]-	208.187	30932474
DeepCCS	[M+Na]+	183.414	30932474
AllCCS	[M+H]+	169.9	32859911
AllCCS	[M+H-H2O]+	166.3	32859911
AllCCS	[M+NH4]+	173.2	32859911
AllCCS	[M+Na]+	174.2	32859911
AllCCS	[M-H]-	179.5	32859911
AllCCS	[M+Na-2H]-	178.6	32859911
AllCCS	[M+HCOO]-	177.6	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.	8.25 minutes	32390414
Predicted by Siyang on May 30, 2022	16.9353 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.53 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2228.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	481.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	215.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	244.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	250.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	744.2 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	705.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	97.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1403.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	681.4 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	1693.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	465.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	427.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	358.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	375.9 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	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzosimuline	CN1C(=O)C2=C(OC(C)(C)C3=C2C=C(C)C=C3)C2=CC=CC=C12	3565.5	Standard polar	33892256
Benzosimuline	CN1C(=O)C2=C(OC(C)(C)C3=C2C=C(C)C=C3)C2=CC=CC=C12	2578.2	Standard non polar	33892256
Benzosimuline	CN1C(=O)C2=C(OC(C)(C)C3=C2C=C(C)C=C3)C2=CC=CC=C12	2777.7	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 - Benzosimuline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-1392000000-d3b40697281cd741ef26	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzosimuline 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 - Benzosimuline 10V, Positive-QTOF	splash10-0a4i-0009000000-6d859e66fae6e08d3a7b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzosimuline 20V, Positive-QTOF	splash10-0a4i-0029000000-711241de4b6f673f9e88	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzosimuline 40V, Positive-QTOF	splash10-0uxr-1090000000-35bf8c08aa1f941c5dc9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzosimuline 10V, Negative-QTOF	splash10-0udi-0009000000-1635b3b1c251b9efcecb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzosimuline 20V, Negative-QTOF	splash10-0udi-0009000000-596ccfee61b69117d40f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzosimuline 40V, Negative-QTOF	splash10-000i-0091000000-79c2f338ba59bd9d501f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzosimuline 10V, Negative-QTOF	splash10-0udi-0009000000-248fe7254ed5315b6281	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzosimuline 20V, Negative-QTOF	splash10-0udi-0009000000-248fe7254ed5315b6281	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzosimuline 40V, Negative-QTOF	splash10-000i-0091000000-5b216006d2a241f1adab	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzosimuline 10V, Positive-QTOF	splash10-0a4i-0009000000-1b45b769d99640fbb13d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzosimuline 20V, Positive-QTOF	splash10-0a4i-0049000000-93c2118244f3d42185a7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzosimuline 40V, Positive-QTOF	splash10-02i6-0290000000-f49f6dd12ef9f1d4828d	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

FDB008618

KNApSAcK ID

C00026405

Chemspider ID

4479559

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321951

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 Benzosimuline (HMDB0031930)

MOL for HMDB0031930 (Benzosimuline)

3D MOL for HMDB0031930 (Benzosimuline)

3D SDF for HMDB0031930 (Benzosimuline)

3D-SDF for HMDB0031930 (Benzosimuline)

PDB for HMDB0031930 (Benzosimuline)

3D PDB for HMDB0031930 (Benzosimuline)

SMILES for HMDB0031930 (Benzosimuline)

INCHI for HMDB0031930 (Benzosimuline)

Structure for HMDB0031930 (Benzosimuline)

3D Structure for HMDB0031930 (Benzosimuline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra