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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:53:47 UTC

Update Date

2022-03-07 02:56:34 UTC

HMDB ID

HMDB0040368

Secondary Accession Numbers

HMDB40368

Metabolite Identification

Common Name

Zanthosimuline

Description

Zanthosimuline 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. Zanthosimuline has been detected, but not quantified in, fruits and herbs and spices. This could make zanthosimuline a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Zanthosimuline.

Structure

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

HMDB0040368
     RDKit          3D
Zanthosimuline
 46 48  0  0  0  0  0  0  0  0999 V2000
    4.2072    0.0535    0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2257   -1.0417    0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9665   -2.0953    1.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5964   -1.1057   -0.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8532   -0.0886   -1.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080    0.6136   -2.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8426    1.3884   -1.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6999    2.4522   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1410    2.2122   -2.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4197    2.1056   -1.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9479    1.1819   -0.9813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1059    0.3906   -0.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6006   -0.4883    0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7711   -1.2794    1.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2311   -2.1637    2.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6154   -2.2514    2.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4448   -1.4618    1.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9647   -0.5663    0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109    0.1890    0.1613 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2176    0.0478    0.3938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3039    1.0379   -0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0957    1.7577   -1.4456 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2360    0.5352   -0.4467 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7060    1.0229    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7165   -0.1655    1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0048    0.0986    0.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658   -2.9105    1.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9358   -2.5409    1.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4180   -1.6495    2.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8981   -1.9346   -0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5690    0.6722   -1.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4210   -0.6365   -2.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1063    1.2863   -3.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0266   -0.1358   -2.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2235    3.4360   -0.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6730    2.4709   -1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7214    2.2422    0.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777    2.9167   -2.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1070    2.7155   -2.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2874   -1.1795    1.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6035   -2.7926    3.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0140   -2.9364    3.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5095   -1.5481    2.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4085    0.2229    1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6293   -0.9183    0.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7441    0.8406   -0.1746 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  1  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
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
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 19 21  1  0
 21 22  2  0
 12 23  1  0
 23  7  1  0
 21 11  1  0
 18 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  8 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END


  Mrv0541 05061311472D          

 23 25  0  0  0  0            999 V2000
   -1.2467   -2.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1652   -1.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1877    0.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012   -0.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7580   -1.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2692    0.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3900   -1.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.0789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  8  2  0  0  0  0
 15  9  2  0  0  0  0
 16 11  1  0  0  0  0
 17 10  2  0  0  0  0
 17 15  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  2  0  0  0  0
 19 16  1  0  0  0  0
 20  3  1  0  0  0  0
 20 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21  4  1  0  0  0  0
 21 17  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>
HMDB0040368

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO2/c1-14(2)8-7-12-20(3)13-11-16-18(23-20)15-9-5-6-10-17(15)21(4)19(16)22/h5-6,8-11,13H,7,12H2,1-4H3

> <INCHI_KEY>
VMCDFWKTDCXEJZ-UHFFFAOYSA-N

> <FORMULA>
C20H23NO2

> <MOLECULAR_WEIGHT>
309.4021

> <EXACT_MASS>
309.172878985

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
35.52806701240676

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-dimethyl-2-(4-methylpent-3-en-1-yl)-2H,5H,6H-pyrano[3,2-c]quinolin-5-one

> <ALOGPS_LOGP>
4.63

> <JCHEM_LOGP>
3.415880673333333

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9438734912848054

> <JCHEM_POLAR_SURFACE_AREA>
29.540000000000003

> <JCHEM_REFRACTIVITY>
96.01029999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-dimethyl-2-(4-methylpent-3-en-1-yl)pyrano[3,2-c]quinolin-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0040368
     RDKit          3D
Zanthosimuline
 46 48  0  0  0  0  0  0  0  0999 V2000
    4.2072    0.0535    0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2257   -1.0417    0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9665   -2.0953    1.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5964   -1.1057   -0.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8532   -0.0886   -1.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080    0.6136   -2.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8426    1.3884   -1.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6999    2.4522   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1410    2.2122   -2.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4197    2.1056   -1.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9479    1.1819   -0.9813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1059    0.3906   -0.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6006   -0.4883    0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7711   -1.2794    1.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2311   -2.1637    2.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6154   -2.2514    2.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4448   -1.4618    1.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9647   -0.5663    0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109    0.1890    0.1613 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2176    0.0478    0.3938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3039    1.0379   -0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0957    1.7577   -1.4456 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2360    0.5352   -0.4467 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7060    1.0229    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7165   -0.1655    1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0048    0.0986    0.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658   -2.9105    1.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9358   -2.5409    1.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4180   -1.6495    2.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8981   -1.9346   -0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5690    0.6722   -1.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4210   -0.6365   -2.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1063    1.2863   -3.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0266   -0.1358   -2.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2235    3.4360   -0.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6730    2.4709   -1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7214    2.2422    0.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777    2.9167   -2.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1070    2.7155   -2.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2874   -1.1795    1.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6035   -2.7926    3.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0140   -2.9364    3.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5095   -1.5481    2.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4085    0.2229    1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6293   -0.9183    0.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7441    0.8406   -0.1746 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  1  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
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 12 23  1  0
 23  7  1  0
 21 11  1  0
 18 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  8 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  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      -2.327  -4.783   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.042  -2.740   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.217   1.220   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.850   7.081   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.390   1.746   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.160   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.682  -0.760   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.415  -2.277   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.850   1.746   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.390   4.414   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.770   4.414   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.503   0.230   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.540   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.595  -3.267   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.770   4.414   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.850   4.414   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.540   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.540   5.747   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.770   1.746   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       3.080   5.747   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       0.770   7.081   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.770   1.746   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    8   12                                                       
CONECT    8    7   14                                                       
CONECT    9    5   15                                                       
CONECT   10    6   17                                                       
CONECT   11   13   16                                                       
CONECT   12    7   20                                                       
CONECT   13   11   20                                                       
CONECT   14    1    2    8                                                  
CONECT   15    9   17   18                                                  
CONECT   16   11   18   19                                                  
CONECT   17   10   15   21                                                  
CONECT   18   15   16   23                                                  
CONECT   19   16   21   22                                                  
CONECT   20    3   12   13   23                                             
CONECT   21    4   17   19                                                  
CONECT   22   19                                                            
CONECT   23   18   20                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0040368
HETATM    1  C1  UNL     1       4.207   0.054   0.779  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.226  -1.042   0.468  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.966  -2.095   1.486  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.596  -1.106  -0.698  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.853  -0.089  -1.724  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.708   0.614  -2.315  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.843   1.388  -1.363  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.700   2.452  -0.648  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.141   2.212  -2.157  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.420   2.106  -1.969  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.948   1.182  -0.981  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.106   0.391  -0.214  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.601  -0.488   0.727  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.771  -1.279   1.498  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.231  -2.164   2.444  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.615  -2.251   2.620  1.00  0.00           C  
HETATM   17  C17 UNL     1      -3.445  -1.462   1.851  1.00  0.00           C  
HETATM   18  C18 UNL     1      -2.965  -0.566   0.891  1.00  0.00           C  
HETATM   19  N1  UNL     1      -3.811   0.189   0.161  1.00  0.00           N  
HETATM   20  C19 UNL     1      -5.218   0.048   0.394  1.00  0.00           C  
HETATM   21  C20 UNL     1      -3.304   1.038  -0.749  1.00  0.00           C  
HETATM   22  O1  UNL     1      -4.096   1.758  -1.446  1.00  0.00           O  
HETATM   23  O2  UNL     1       0.236   0.535  -0.447  1.00  0.00           O  
HETATM   24  H1  UNL     1       3.706   1.023   0.868  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.717  -0.166   1.750  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.005   0.099   0.021  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.366  -2.910   1.047  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.936  -2.541   1.790  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.418  -1.650   2.331  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.898  -1.935  -0.843  1.00  0.00           H  
HETATM   31  H8  UNL     1       3.569   0.672  -1.293  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.421  -0.636  -2.546  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.106   1.286  -3.130  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.027  -0.136  -2.805  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.223   3.436  -0.756  1.00  0.00           H  
HETATM   36  H13 UNL     1       2.673   2.471  -1.130  1.00  0.00           H  
HETATM   37  H14 UNL     1       1.721   2.242   0.443  1.00  0.00           H  
HETATM   38  H15 UNL     1       0.278   2.917  -2.912  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.107   2.716  -2.559  1.00  0.00           H  
HETATM   40  H17 UNL     1       0.287  -1.180   1.333  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.604  -2.793   3.059  1.00  0.00           H  
HETATM   42  H19 UNL     1      -3.014  -2.936   3.355  1.00  0.00           H  
HETATM   43  H20 UNL     1      -4.510  -1.548   2.005  1.00  0.00           H  
HETATM   44  H21 UNL     1      -5.409   0.223   1.483  1.00  0.00           H  
HETATM   45  H22 UNL     1      -5.629  -0.918   0.055  1.00  0.00           H  
HETATM   46  H23 UNL     1      -5.744   0.841  -0.175  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4    4
CONECT    3   27   28   29
CONECT    4    5   30
CONECT    5    6   31   32
CONECT    6    7   33   34
CONECT    7    8    9   23
CONECT    8   35   36   37
CONECT    9   10   10   38
CONECT   10   11   39
CONECT   11   12   12   21
CONECT   12   13   23
CONECT   13   14   14   18
CONECT   14   15   40
CONECT   15   16   16   41
CONECT   16   17   42
CONECT   17   18   18   43
CONECT   18   19
CONECT   19   20   21
CONECT   20   44   45   46
CONECT   21   22   22
END

HMDB0040368
     RDKit          3D
Zanthosimuline
 46 48  0  0  0  0  0  0  0  0999 V2000
    4.2072    0.0535    0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2257   -1.0417    0.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9665   -2.0953    1.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5964   -1.1057   -0.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8532   -0.0886   -1.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080    0.6136   -2.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8426    1.3884   -1.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6999    2.4522   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1410    2.2122   -2.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4197    2.1056   -1.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9479    1.1819   -0.9813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1059    0.3906   -0.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6006   -0.4883    0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7711   -1.2794    1.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2311   -2.1637    2.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6154   -2.2514    2.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4448   -1.4618    1.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9647   -0.5663    0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109    0.1890    0.1613 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2176    0.0478    0.3938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3039    1.0379   -0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0957    1.7577   -1.4456 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2360    0.5352   -0.4467 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7060    1.0229    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7165   -0.1655    1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0048    0.0986    0.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3658   -2.9105    1.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9358   -2.5409    1.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4180   -1.6495    2.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8981   -1.9346   -0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5690    0.6722   -1.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4210   -0.6365   -2.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1063    1.2863   -3.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0266   -0.1358   -2.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2235    3.4360   -0.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6730    2.4709   -1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7214    2.2422    0.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777    2.9167   -2.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1070    2.7155   -2.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2874   -1.1795    1.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6035   -2.7926    3.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0140   -2.9364    3.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5095   -1.5481    2.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4085    0.2229    1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6293   -0.9183    0.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7441    0.8406   -0.1746 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  1  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
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 12 23  1  0
 23  7  1  0
 21 11  1  0
 18 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  8 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₃NO₂

Average Molecular Weight

309.4021

Monoisotopic Molecular Weight

309.172878985

IUPAC Name

2,6-dimethyl-2-(4-methylpent-3-en-1-yl)-2H,5H,6H-pyrano[3,2-c]quinolin-5-one

Traditional Name

2,6-dimethyl-2-(4-methylpent-3-en-1-yl)pyrano[3,2-c]quinolin-5-one

CAS Registry Number

155416-20-9

SMILES

CN1C(=O)C2=C(OC(C)(CCC=C(C)C)C=C2)C2=CC=CC=C12

InChI Identifier

InChI=1S/C20H23NO2/c1-14(2)8-7-12-20(3)13-11-16-18(23-20)15-9-5-6-10-17(15)21(4)19(16)22/h5-6,8-11,13H,7,12H2,1-4H3

InChI Key

VMCDFWKTDCXEJZ-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
Dihydroquinoline
Pyranopyridine
Alkyl aryl ether
Pyridinone
Pyran
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous ester
Lactam
Oxacycle
Ether
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen 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: HMDB0040368)

Cellular substructure

Membrane (HMDB: HMDB0040368)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040368)

Source

Exogenous

Food

Food (HMDB: HMDB0040368)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0040368)

Not Available

Nutrient (HMDB: HMDB0040368)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	127 - 128 °C	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	0.013 g/L	ALOGPS
logP	4.63	ALOGPS
logP	3.42	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-0.94	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	3	ChemAxon
Refractivity	96.01 m³·mol⁻¹	ChemAxon
Polarizability	35.53 Å³	ChemAxon
Number of Rings	3	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]+	176.47	31661259
DarkChem	[M-H]-	174.707	31661259
DeepCCS	[M-2H]-	205.973	30932474
DeepCCS	[M+Na]+	181.2	30932474
AllCCS	[M+H]+	174.9	32859911
AllCCS	[M+H-H2O]+	171.4	32859911
AllCCS	[M+NH4]+	178.2	32859911
AllCCS	[M+Na]+	179.1	32859911
AllCCS	[M-H]-	180.6	32859911
AllCCS	[M+Na-2H]-	180.2	32859911
AllCCS	[M+HCOO]-	179.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zanthosimuline	CN1C(=O)C2=C(OC(C)(CCC=C(C)C)C=C2)C2=CC=CC=C12	3335.2	Standard polar	33892256
Zanthosimuline	CN1C(=O)C2=C(OC(C)(CCC=C(C)C)C=C2)C2=CC=CC=C12	2481.0	Standard non polar	33892256
Zanthosimuline	CN1C(=O)C2=C(OC(C)(CCC=C(C)C)C=C2)C2=CC=CC=C12	2627.0	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 - Zanthosimuline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9780000000-dc6a438ca915ff19530e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zanthosimuline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zanthosimuline 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 - Zanthosimuline 10V, Positive-QTOF	splash10-03di-1229000000-e516c8cf7d204d83cce6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthosimuline 20V, Positive-QTOF	splash10-000i-4941000000-2e434a1de107b0ce0b9f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthosimuline 40V, Positive-QTOF	splash10-0aor-9800000000-1f42ac1a8a7c203cb95d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthosimuline 10V, Negative-QTOF	splash10-0a4i-0009000000-ad6fc423baec2e13904e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthosimuline 20V, Negative-QTOF	splash10-0a4i-1049000000-15860db92bf6477b9637	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthosimuline 40V, Negative-QTOF	splash10-0a59-1910000000-1c8f0f9ba2358123330e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthosimuline 10V, Negative-QTOF	splash10-0a4i-0009000000-ef9ecbcc77a6beed41c8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthosimuline 20V, Negative-QTOF	splash10-0a4i-0049000000-6ec6d7743c7e24b0ecb2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthosimuline 40V, Negative-QTOF	splash10-004i-0190000000-efe03727758e71a3e798	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthosimuline 10V, Positive-QTOF	splash10-03di-0098000000-fd95ca089dba79cf0a4f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthosimuline 20V, Positive-QTOF	splash10-0hmo-0091000000-bc263f41c22a6d2f07a0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthosimuline 40V, Positive-QTOF	splash10-0fba-2590000000-6b10824cc7a282e16771	2021-09-22	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

FDB020098

KNApSAcK ID

C00052091

Chemspider ID

4474739

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5315426

PDB ID

Not Available

ChEBI ID

174221

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 Zanthosimuline (HMDB0040368)

MOL for HMDB0040368 (Zanthosimuline)

3D MOL for HMDB0040368 (Zanthosimuline)

3D SDF for HMDB0040368 (Zanthosimuline)

3D-SDF for HMDB0040368 (Zanthosimuline)

PDB for HMDB0040368 (Zanthosimuline)

3D PDB for HMDB0040368 (Zanthosimuline)

SMILES for HMDB0040368 (Zanthosimuline)

INCHI for HMDB0040368 (Zanthosimuline)

Structure for HMDB0040368 (Zanthosimuline)

3D Structure for HMDB0040368 (Zanthosimuline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra