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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:04:13 UTC

Update Date

2022-03-07 02:53:40 UTC

HMDB ID

HMDB0033354

Secondary Accession Numbers

HMDB33354

Metabolite Identification

Common Name

Cassythicine

Description

Cassythicine belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Cassythicine is a very strong basic compound (based on its pKa). Outside of the human body, cassythicine has been detected, but not quantified in, a few different foods, such as herbs and spices, sweet bay, and tea. This could make cassythicine a potential biomarker for the consumption of these foods.

Structure

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

HMDB0033354
     RDKit          3D
Cassythicine
 43 47  0  0  0  0  0  0  0  0999 V2000
    4.9454    0.4999   -0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5769   -0.7572   -0.4178 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2931   -1.0762   -0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3321   -0.0620   -0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0490   -0.3496    0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6717   -1.5833    0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6643   -2.5748    0.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9597   -2.3236    0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9603   -3.3023    0.5411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6642   -2.0002    1.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7027   -0.9444    1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2970    0.3566    0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2615    1.3307    0.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0263    2.5810    0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7370    2.8935   -0.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2556    1.9399   -0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0250    0.6547    0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4087    2.5531   -0.7452 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2034    3.9397   -0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2146    4.0904   -0.8585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6217    0.9533    0.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9970   -0.4466    0.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9524   -1.4025    0.5893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8343   -1.9863   -0.6949 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0194    0.5745   -1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6066    1.3384   -0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4251    0.6444   -1.8854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6315    0.8972   -0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4066   -3.5509    1.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7508   -4.2147    0.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5107   -2.3464    2.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9204   -2.8896    0.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897   -0.7262    2.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7684    3.3567   -0.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6401    4.4492    0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6048    4.4029   -1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7660    1.1302    2.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3385    1.6291    0.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7497   -0.7882    1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5608   -0.4815   -0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9552   -1.6092   -1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7249   -1.7143   -1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7868   -3.0857   -0.7180 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  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 13 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 23 11  1  0
 17  5  1  0
 17 12  1  0
 20 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 14 34  1  0
 19 35  1  0
 19 36  1  0
 21 37  1  0
 21 38  1  0
 22 39  1  0
 22 40  1  0
 24 41  1  0
 24 42  1  0
 24 43  1  0
M  END


  Mrv0541 05061307042D          

 24 28  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3149    2.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 11  6  2  0  0  0  0
 12  8  2  0  0  0  0
 12 11  1  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  2  0  0  0  0
 16  7  1  0  0  0  0
 17 10  1  0  0  0  0
 17 13  1  0  0  0  0
 18 12  1  0  0  0  0
 18 17  2  0  0  0  0
 19 16  2  0  0  0  0
 19 18  1  0  0  0  0
 20  1  1  0  0  0  0
 20  4  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  1  0  0  0  0
 22  2  1  0  0  0  0
 22 15  1  0  0  0  0
 23  9  1  0  0  0  0
 23 16  1  0  0  0  0
 24  9  1  0  0  0  0
 24 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033354

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C2CC3N(C)CCC4=CC5=C(OCO5)C(C2=C1)=C34

> <INCHI_IDENTIFIER>
InChI=1S/C19H19NO4/c1-20-4-3-10-7-16-19(24-9-23-16)18-12-8-15(22-2)14(21)6-11(12)5-13(20)17(10)18/h6-8,13,21H,3-5,9H2,1-2H3

> <INCHI_KEY>
MPWZJVCAMFAIGV-UHFFFAOYSA-N

> <FORMULA>
C19H19NO4

> <MOLECULAR_WEIGHT>
325.3585

> <EXACT_MASS>
325.131408101

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
34.98067502130791

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-16-ol

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.863408908

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.700392791151108

> <JCHEM_PKA_STRONGEST_BASIC>
7.068612886622441

> <JCHEM_POLAR_SURFACE_AREA>
51.16000000000001

> <JCHEM_REFRACTIVITY>
90.23729999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.59e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-16-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033354
     RDKit          3D
Cassythicine
 43 47  0  0  0  0  0  0  0  0999 V2000
    4.9454    0.4999   -0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5769   -0.7572   -0.4178 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2931   -1.0762   -0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3321   -0.0620   -0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0490   -0.3496    0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6717   -1.5833    0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6643   -2.5748    0.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9597   -2.3236    0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9603   -3.3023    0.5411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6642   -2.0002    1.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7027   -0.9444    1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2970    0.3566    0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2615    1.3307    0.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0263    2.5810    0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7370    2.8935   -0.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2556    1.9399   -0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0250    0.6547    0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4087    2.5531   -0.7452 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2034    3.9397   -0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2146    4.0904   -0.8585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6217    0.9533    0.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9970   -0.4466    0.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9524   -1.4025    0.5893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8343   -1.9863   -0.6949 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0194    0.5745   -1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6066    1.3384   -0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4251    0.6444   -1.8854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6315    0.8972   -0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4066   -3.5509    1.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7508   -4.2147    0.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5107   -2.3464    2.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9204   -2.8896    0.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897   -0.7262    2.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7684    3.3567   -0.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6401    4.4492    0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6048    4.4029   -1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7660    1.1302    2.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3385    1.6291    0.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7497   -0.7882    1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5608   -0.4815   -0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9552   -1.6092   -1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7249   -1.7143   -1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7868   -3.0857   -0.7180 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  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 13 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 23 11  1  0
 17  5  1  0
 17 12  1  0
 20 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 14 34  1  0
 19 35  1  0
 19 36  1  0
 21 37  1  0
 21 38  1  0
 22 39  1  0
 22 40  1  0
 24 41  1  0
 24 42  1  0
 24 43  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.853   3.977   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.321   3.816   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.479   2.570   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   22                                                            
CONECT    3    4   10                                                       
CONECT    4    3   20                                                       
CONECT    5   11   13                                                       
CONECT    6   11   14                                                       
CONECT    7   10   16                                                       
CONECT    8   12   15                                                       
CONECT    9   23   24                                                       
CONECT   10    3    7   17                                                  
CONECT   11    5    6   12                                                  
CONECT   12    8   11   18                                                  
CONECT   13    5   17   20                                                  
CONECT   14    6   15   21                                                  
CONECT   15    8   14   22                                                  
CONECT   16    7   19   23                                                  
CONECT   17   10   13   18                                                  
CONECT   18   12   17   19                                                  
CONECT   19   16   18   24                                                  
CONECT   20    1    4   13                                                  
CONECT   21   14                                                            
CONECT   22    2   15                                                       
CONECT   23    9   16                                                       
CONECT   24    9   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0033354
HETATM    1  C1  UNL     1       4.945   0.500  -0.906  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.577  -0.757  -0.418  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.293  -1.076  -0.014  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.332  -0.062  -0.112  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.049  -0.350   0.282  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.672  -1.583   0.764  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.664  -2.575   0.848  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.960  -2.324   0.463  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.960  -3.302   0.541  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.664  -2.000   1.203  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.703  -0.944   1.163  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.297   0.357   0.628  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.262   1.331   0.541  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.026   2.581   0.073  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.737   2.893  -0.340  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.256   1.940  -0.266  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.025   0.655   0.223  1.00  0.00           C  
HETATM   18  O3  UNL     1       1.409   2.553  -0.745  1.00  0.00           O  
HETATM   19  C16 UNL     1       1.203   3.940  -0.782  1.00  0.00           C  
HETATM   20  O4  UNL     1      -0.215   4.090  -0.858  1.00  0.00           O  
HETATM   21  C17 UNL     1      -3.622   0.953   0.992  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.997  -0.447   0.600  1.00  0.00           C  
HETATM   23  N1  UNL     1      -2.952  -1.403   0.589  1.00  0.00           N  
HETATM   24  C19 UNL     1      -2.834  -1.986  -0.695  1.00  0.00           C  
HETATM   25  H1  UNL     1       6.019   0.575  -1.113  1.00  0.00           H  
HETATM   26  H2  UNL     1       4.607   1.338  -0.237  1.00  0.00           H  
HETATM   27  H3  UNL     1       4.425   0.644  -1.885  1.00  0.00           H  
HETATM   28  H4  UNL     1       2.631   0.897  -0.489  1.00  0.00           H  
HETATM   29  H5  UNL     1       1.407  -3.551   1.221  1.00  0.00           H  
HETATM   30  H6  UNL     1       3.751  -4.215   0.882  1.00  0.00           H  
HETATM   31  H7  UNL     1      -0.511  -2.346   2.275  1.00  0.00           H  
HETATM   32  H8  UNL     1      -0.920  -2.890   0.568  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.990  -0.726   2.249  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.768   3.357  -0.003  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.640   4.449   0.078  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.605   4.403  -1.716  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.766   1.130   2.078  1.00  0.00           H  
HETATM   38  H14 UNL     1      -4.339   1.629   0.480  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.750  -0.788   1.372  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.561  -0.482  -0.357  1.00  0.00           H  
HETATM   41  H17 UNL     1      -1.955  -1.609  -1.260  1.00  0.00           H  
HETATM   42  H18 UNL     1      -3.725  -1.714  -1.333  1.00  0.00           H  
HETATM   43  H19 UNL     1      -2.787  -3.086  -0.718  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   28
CONECT    5    6    6   17
CONECT    6    7   10
CONECT    7    8    8   29
CONECT    8    9
CONECT    9   30
CONECT   10   11   31   32
CONECT   11   12   23   33
CONECT   12   13   13   17
CONECT   13   14   21
CONECT   14   15   15   34
CONECT   15   16   20
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20   35   36
CONECT   21   22   37   38
CONECT   22   23   39   40
CONECT   23   24
CONECT   24   41   42   43
END

HMDB0033354
     RDKit          3D
Cassythicine
 43 47  0  0  0  0  0  0  0  0999 V2000
    4.9454    0.4999   -0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5769   -0.7572   -0.4178 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2931   -1.0762   -0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3321   -0.0620   -0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0490   -0.3496    0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6717   -1.5833    0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6643   -2.5748    0.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9597   -2.3236    0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9603   -3.3023    0.5411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6642   -2.0002    1.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7027   -0.9444    1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2970    0.3566    0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2615    1.3307    0.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0263    2.5810    0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7370    2.8935   -0.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2556    1.9399   -0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0250    0.6547    0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4087    2.5531   -0.7452 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2034    3.9397   -0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2146    4.0904   -0.8585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6217    0.9533    0.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9970   -0.4466    0.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9524   -1.4025    0.5893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8343   -1.9863   -0.6949 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0194    0.5745   -1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6066    1.3384   -0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4251    0.6444   -1.8854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6315    0.8972   -0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4066   -3.5509    1.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7508   -4.2147    0.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5107   -2.3464    2.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9204   -2.8896    0.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897   -0.7262    2.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7684    3.3567   -0.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6401    4.4492    0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6048    4.4029   -1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7660    1.1302    2.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3385    1.6291    0.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7497   -0.7882    1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5608   -0.4815   -0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9552   -1.6092   -1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7249   -1.7143   -1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7868   -3.0857   -0.7180 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  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 13 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 23 11  1  0
 17  5  1  0
 17 12  1  0
 20 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 14 34  1  0
 19 35  1  0
 19 36  1  0
 21 37  1  0
 21 38  1  0
 22 39  1  0
 22 40  1  0
 24 41  1  0
 24 42  1  0
 24 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Cassythicine	HMDB
9-Hydroxy-10-methoxy-1,2-methylenedioxyaporphine	HMDB
N-Methylactinodaphnine	HMDB
N-Methyl-actinodaphnine	HMDB

Chemical Formula

C₁₉H₁₉NO₄

Average Molecular Weight

325.3585

Monoisotopic Molecular Weight

325.131408101

IUPAC Name

17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-16-ol

Traditional Name

17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-16-ol

CAS Registry Number

5890-28-8

SMILES

COC1=C(O)C=C2CC3N(C)CCC4=CC5=C(OCO5)C(C2=C1)=C34

InChI Identifier

InChI=1S/C19H19NO4/c1-20-4-3-10-7-16-19(24-9-23-16)18-12-8-15(22-2)14(21)6-11(12)5-13(20)17(10)18/h6-8,13,21H,3-5,9H2,1-2H3

InChI Key

MPWZJVCAMFAIGV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
Naphthalene
Quinoline
Tetrahydroisoquinoline
Benzodioxole
Anisole
Aralkylamine
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Oxacycle
Azacycle
Acetal
Ether
Hydrocarbon derivative
Organic oxygen compound
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Amine
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033354)
Cytoplasm (HMDB: HMDB0033354)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033354)

Source

Exogenous

Food

Food (HMDB: HMDB0033354)

Tea

Herb and spice

Herb

Sweet bay (FooDB: FOOD00097)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033354)

Not Available

Nutrient (HMDB: HMDB0033354)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	210 - 212 °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	0.36 g/L	ALOGPS
logP	2.36	ALOGPS
logP	2.86	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.7	ChemAxon
pKa (Strongest Basic)	7.07	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.16 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	90.24 m³·mol⁻¹	ChemAxon
Polarizability	34.98 Å³	ChemAxon
Number of Rings	5	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]+	174.828	31661259
DarkChem	[M-H]-	174.232	31661259
DeepCCS	[M-2H]-	217.484	30932474
DeepCCS	[M+Na]+	192.711	30932474
AllCCS	[M+H]+	176.6	32859911
AllCCS	[M+H-H2O]+	173.3	32859911
AllCCS	[M+NH4]+	179.6	32859911
AllCCS	[M+Na]+	180.5	32859911
AllCCS	[M-H]-	183.8	32859911
AllCCS	[M+Na-2H]-	183.0	32859911
AllCCS	[M+HCOO]-	182.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cassythicine	COC1=C(O)C=C2CC3N(C)CCC4=CC5=C(OCO5)C(C2=C1)=C34	4215.6	Standard polar	33892256
Cassythicine	COC1=C(O)C=C2CC3N(C)CCC4=CC5=C(OCO5)C(C2=C1)=C34	2678.8	Standard non polar	33892256
Cassythicine	COC1=C(O)C=C2CC3N(C)CCC4=CC5=C(OCO5)C(C2=C1)=C34	3067.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cassythicine,1TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CC1C3=C(C=C4OCOC4=C23)CCN1C	2885.0	Semi standard non polar	33892256
Cassythicine,1TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1C3=C(C=C4OCOC4=C23)CCN1C	3121.1	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 - Cassythicine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-0193000000-b1bd7077267a5ae2859a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cassythicine GC-MS (1 TMS) - 70eV, Positive	splash10-0089-1109000000-d8fa1a1473a18df11575	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cassythicine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cassythicine 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 - Cassythicine 10V, Positive-QTOF	splash10-004i-0029000000-6a8f43699851886567cd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cassythicine 20V, Positive-QTOF	splash10-004j-0097000000-067dc9f6d0bcca850a54	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cassythicine 40V, Positive-QTOF	splash10-00lr-0090000000-cbaa97460e0a17b3855c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cassythicine 10V, Negative-QTOF	splash10-00di-0009000000-7339316ec2025f970b93	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cassythicine 20V, Negative-QTOF	splash10-00di-0029000000-21dde708790249a3a962	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cassythicine 40V, Negative-QTOF	splash10-0pdi-1092000000-0ceb6e7ae4b1a695dfbc	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cassythicine 10V, Positive-QTOF	splash10-004i-0009000000-8258216b4e41e9caadf2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cassythicine 20V, Positive-QTOF	splash10-004i-0019000000-fc549e0a0c8fe9675faa	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cassythicine 40V, Positive-QTOF	splash10-00sj-0092000000-e131a57b405054fbe31f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cassythicine 10V, Negative-QTOF	splash10-00di-0009000000-fd8a579508e412fbe114	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cassythicine 20V, Negative-QTOF	splash10-00di-0019000000-f9435823a721940ceaea	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cassythicine 40V, Negative-QTOF	splash10-00di-0097000000-29fd0bf8c0716a7a5aa1	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4440434

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 Cassythicine (HMDB0033354)

MOL for HMDB0033354 (Cassythicine)

3D MOL for HMDB0033354 (Cassythicine)

3D SDF for HMDB0033354 (Cassythicine)

3D-SDF for HMDB0033354 (Cassythicine)

PDB for HMDB0033354 (Cassythicine)

3D PDB for HMDB0033354 (Cassythicine)

SMILES for HMDB0033354 (Cassythicine)

INCHI for HMDB0033354 (Cassythicine)

Structure for HMDB0033354 (Cassythicine)

3D Structure for HMDB0033354 (Cassythicine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra