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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:04:31 UTC

Update Date

2022-03-07 02:53:41 UTC

HMDB ID

HMDB0033359

Secondary Accession Numbers

HMDB33359

Metabolite Identification

Common Name

Cryptodorine

Description

Cryptodorine, also known as norneolitsine, 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. Cryptodorine is a very strong basic compound (based on its pKa). Outside of the human body, cryptodorine has been detected, but not quantified in, a few different foods, such as herbs and spices, sweet bay, and tea. This could make cryptodorine a potential biomarker for the consumption of these foods.

Structure

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

HMDB0033359
     RDKit          3D
Cryptodorine
 38 43  0  0  0  0  0  0  0  0999 V2000
    2.7038   -1.6642   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3562   -1.2437   -0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069    0.0846   -0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355    1.0249   -0.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3556    0.6034   -0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6909   -0.7203   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -0.8374   -0.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6358    0.4506   -0.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5289    1.3276   -0.4492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768    0.5458   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6815    1.8888   -0.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0146    2.2524   -0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0330    1.3296   -0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6716   -0.0152   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3531   -0.4190   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926   -1.8619   -0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3055   -2.2814   -0.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8656   -2.3458    1.1283 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646   -2.2635    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6996   -1.0838    0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1286    3.6334   -0.2712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8591    4.1749   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0158    3.0867   -0.3359 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8786   -2.7265   -0.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7698    2.0478   -0.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0590    0.6925    0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3815    0.6039   -1.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0824    1.6041   -0.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183   -2.3813   -0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4932   -3.0058   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5103   -2.8584    0.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6266   -1.6810    1.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7846   -2.1875    1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6198   -3.2009    0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9856   -1.4285   -0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6274   -0.6311    0.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6696    4.4847    0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7324    5.0015   -0.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  3 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  1  0
 19 20  1  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
  6  1  1  0
 15 10  1  0
 17  2  1  0
  9  5  1  0
 23 11  1  0
 20 14  1  0
  1 24  1  0
  4 25  1  0
  8 26  1  0
  8 27  1  0
 13 28  1  0
 16 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 22 37  1  0
 22 38  1  0
M  END


  Mrv0541 05061307042D          

 23 28  0  0  0  0            999 V2000
    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
    1.4289    0.8250    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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2708   -0.8250    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
    5.7859   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859   -0.1576    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
  2  1  1  0  0  0  0
  9  1  1  0  0  0  0
  9  4  2  0  0  0  0
 10  3  1  0  0  0  0
 10  5  2  0  0  0  0
 11  6  2  0  0  0  0
 11 10  1  0  0  0  0
 12  3  1  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
 14 13  2  0  0  0  0
 15  4  1  0  0  0  0
 16  9  1  0  0  0  0
 16 12  1  0  0  0  0
 17 11  1  0  0  0  0
 17 16  2  0  0  0  0
 18 15  2  0  0  0  0
 18 17  1  0  0  0  0
 19  2  1  0  0  0  0
 19 12  1  0  0  0  0
 20  7  1  0  0  0  0
 20 13  1  0  0  0  0
 21  7  1  0  0  0  0
 21 14  1  0  0  0  0
 22  8  1  0  0  0  0
 22 15  1  0  0  0  0
 23  8  1  0  0  0  0
 23 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033359

> <DATABASE_NAME>
hmdb

> <SMILES>
C1OC2=C(O1)C=C1C(CC3NCCC4=CC5=C(OCO5)C1=C34)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C18H15NO4/c1-2-19-12-3-10-5-13-14(21-7-20-13)6-11(10)17-16(12)9(1)4-15-18(17)23-8-22-15/h4-6,12,19H,1-3,7-8H2

> <INCHI_KEY>
OMIDMWVBRZAVMK-UHFFFAOYSA-N

> <FORMULA>
C18H15NO4

> <MOLECULAR_WEIGHT>
309.316

> <EXACT_MASS>
309.100107973

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.70709005632242

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7,19,21-tetraoxa-13-azahexacyclo[10.10.1.0²,¹⁰.0⁴,⁸.0¹⁶,²³.0¹⁸,²²]tricosa-1(23),2,4(8),9,16,18(22)-hexaene

> <ALOGPS_LOGP>
1.97

> <JCHEM_LOGP>
2.5648310256666664

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.427788131294523

> <JCHEM_POLAR_SURFACE_AREA>
48.95

> <JCHEM_REFRACTIVITY>
82.2654

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7,19,21-tetraoxa-13-azahexacyclo[10.10.1.0²,¹⁰.0⁴,⁸.0¹⁶,²³.0¹⁸,²²]tricosa-1(23),2,4(8),9,16,18(22)-hexaene

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033359
     RDKit          3D
Cryptodorine
 38 43  0  0  0  0  0  0  0  0999 V2000
    2.7038   -1.6642   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3562   -1.2437   -0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069    0.0846   -0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355    1.0249   -0.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3556    0.6034   -0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6909   -0.7203   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -0.8374   -0.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6358    0.4506   -0.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5289    1.3276   -0.4492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768    0.5458   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6815    1.8888   -0.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0146    2.2524   -0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0330    1.3296   -0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6716   -0.0152   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3531   -0.4190   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926   -1.8619   -0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3055   -2.2814   -0.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8656   -2.3458    1.1283 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646   -2.2635    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6996   -1.0838    0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1286    3.6334   -0.2712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8591    4.1749   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0158    3.0867   -0.3359 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8786   -2.7265   -0.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7698    2.0478   -0.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0590    0.6925    0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3815    0.6039   -1.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0824    1.6041   -0.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183   -2.3813   -0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4932   -3.0058   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5103   -2.8584    0.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6266   -1.6810    1.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7846   -2.1875    1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6198   -3.2009    0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9856   -1.4285   -0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6274   -0.6311    0.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6696    4.4847    0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7324    5.0015   -0.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  3 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  1  0
 19 20  1  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
  6  1  1  0
 15 10  1  0
 17  2  1  0
  9  5  1  0
 23 11  1  0
 20 14  1  0
  1 24  1  0
  4 25  1  0
  8 26  1  0
  8 27  1  0
 13 28  1  0
 16 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 22 37  1  0
 22 38  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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.705  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.853   3.977   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      10.800  -2.786   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.800  -0.294   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.321   3.816   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.479   2.570   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1   19                                                       
CONECT    3   10   12                                                       
CONECT    4    9   15                                                       
CONECT    5   10   13                                                       
CONECT    6   11   14                                                       
CONECT    7   20   21                                                       
CONECT    8   22   23                                                       
CONECT    9    1    4   16                                                  
CONECT   10    3    5   11                                                  
CONECT   11    6   10   17                                                  
CONECT   12    3   16   19                                                  
CONECT   13    5   14   20                                                  
CONECT   14    6   13   21                                                  
CONECT   15    4   18   22                                                  
CONECT   16    9   12   17                                                  
CONECT   17   11   16   18                                                  
CONECT   18   15   17   23                                                  
CONECT   19    2   12                                                       
CONECT   20    7   13                                                       
CONECT   21    7   14                                                       
CONECT   22    8   15                                                       
CONECT   23    8   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   56    0
END

COMPND    HMDB0033359
HETATM    1  C1  UNL     1       2.704  -1.664  -0.171  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.356  -1.244  -0.136  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.007   0.085  -0.207  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.036   1.025  -0.315  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.356   0.603  -0.348  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.691  -0.720  -0.278  1.00  0.00           C  
HETATM    7  O1  UNL     1       5.092  -0.837  -0.335  1.00  0.00           O  
HETATM    8  C7  UNL     1       5.636   0.451  -0.267  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.529   1.328  -0.449  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.377   0.546  -0.185  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.681   1.889  -0.243  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.015   2.252  -0.203  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.033   1.330  -0.109  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.672  -0.015  -0.054  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.353  -0.419  -0.092  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.093  -1.862  -0.038  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.305  -2.281  -0.007  1.00  0.00           C  
HETATM   18  N1  UNL     1      -1.866  -2.346   1.128  1.00  0.00           N  
HETATM   19  C16 UNL     1      -3.265  -2.263   0.864  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.700  -1.084   0.050  1.00  0.00           C  
HETATM   21  O3  UNL     1      -2.129   3.633  -0.271  1.00  0.00           O  
HETATM   22  C18 UNL     1      -0.859   4.175  -0.063  1.00  0.00           C  
HETATM   23  O4  UNL     1      -0.016   3.087  -0.336  1.00  0.00           O  
HETATM   24  H1  UNL     1       2.879  -2.726  -0.110  1.00  0.00           H  
HETATM   25  H2  UNL     1       1.770   2.048  -0.370  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.059   0.692   0.732  1.00  0.00           H  
HETATM   27  H4  UNL     1       6.381   0.604  -1.071  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.082   1.604  -0.077  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.618  -2.381  -0.899  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.493  -3.006  -0.864  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.510  -2.858   0.936  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.627  -1.681   1.898  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.785  -2.188   1.858  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.620  -3.201   0.361  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.986  -1.429  -0.983  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.627  -0.631   0.463  1.00  0.00           H  
HETATM   37  H14 UNL     1      -0.670   4.485   0.984  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.732   5.001  -0.793  1.00  0.00           H  
CONECT    1    2    2    6   24
CONECT    2    3   17
CONECT    3    4    4   10
CONECT    4    5   25
CONECT    5    6    6    9
CONECT    6    7
CONECT    7    8
CONECT    8    9   26   27
CONECT   10   11   11   15
CONECT   11   12   23
CONECT   12   13   13   21
CONECT   13   14   28
CONECT   14   15   15   20
CONECT   15   16
CONECT   16   17   18   29
CONECT   17   30   31
CONECT   18   19   32
CONECT   19   20   33   34
CONECT   20   35   36
CONECT   21   22
CONECT   22   23   37   38
END

HMDB0033359
     RDKit          3D
Cryptodorine
 38 43  0  0  0  0  0  0  0  0999 V2000
    2.7038   -1.6642   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3562   -1.2437   -0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069    0.0846   -0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355    1.0249   -0.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3556    0.6034   -0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6909   -0.7203   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -0.8374   -0.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6358    0.4506   -0.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5289    1.3276   -0.4492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768    0.5458   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6815    1.8888   -0.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0146    2.2524   -0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0330    1.3296   -0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6716   -0.0152   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3531   -0.4190   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926   -1.8619   -0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3055   -2.2814   -0.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8656   -2.3458    1.1283 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646   -2.2635    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6996   -1.0838    0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1286    3.6334   -0.2712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8591    4.1749   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0158    3.0867   -0.3359 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8786   -2.7265   -0.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7698    2.0478   -0.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0590    0.6925    0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3815    0.6039   -1.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0824    1.6041   -0.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183   -2.3813   -0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4932   -3.0058   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5103   -2.8584    0.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6266   -1.6810    1.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7846   -2.1875    1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6198   -3.2009    0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9856   -1.4285   -0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6274   -0.6311    0.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6696    4.4847    0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7324    5.0015   -0.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  3 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  1  0
 19 20  1  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
  6  1  1  0
 15 10  1  0
 17  2  1  0
  9  5  1  0
 23 11  1  0
 20 14  1  0
  1 24  1  0
  4 25  1  0
  8 26  1  0
  8 27  1  0
 13 28  1  0
 16 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 22 37  1  0
 22 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2:9,10-Bismethylenedioxynoraporphine	HMDB
Norneolitsine	HMDB

Chemical Formula

C₁₈H₁₅NO₄

Average Molecular Weight

309.316

Monoisotopic Molecular Weight

309.100107973

IUPAC Name

5,7,19,21-tetraoxa-13-azahexacyclo[10.10.1.0²,¹⁰.0⁴,⁸.0¹⁶,²³.0¹⁸,²²]tricosa-1(23),2,4(8),9,16,18(22)-hexaene

Traditional Name

5,7,19,21-tetraoxa-13-azahexacyclo[10.10.1.0²,¹⁰.0⁴,⁸.0¹⁶,²³.0¹⁸,²²]tricosa-1(23),2,4(8),9,16,18(22)-hexaene

CAS Registry Number

41787-55-7

SMILES

C1OC2=C(O1)C=C1C(CC3NCCC4=CC5=C(OCO5)C1=C34)=C2

InChI Identifier

InChI=1S/C18H15NO4/c1-2-19-12-3-10-5-13-14(21-7-20-13)6-11(10)17-16(12)9(1)4-15-18(17)23-8-22-15/h4-6,12,19H,1-3,7-8H2

InChI Key

OMIDMWVBRZAVMK-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

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033359)
Cytoplasm (HMDB: HMDB0033359)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033359)

Source

Exogenous

Food

Food (HMDB: HMDB0033359)

Tea

Herb and spice

Herb

Sweet bay (FooDB: FOOD00097)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033359)

Not Available

Nutrient (HMDB: HMDB0033359)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	219 - 221 °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	0.14 g/L	ALOGPS
logP	1.97	ALOGPS
logP	2.56	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	9.43	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	48.95 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	82.27 m³·mol⁻¹	ChemAxon
Polarizability	32.71 Å³	ChemAxon
Number of Rings	6	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]+	170.263	31661259
DarkChem	[M-H]-	167.254	31661259
DeepCCS	[M-2H]-	215.607	30932474
DeepCCS	[M+Na]+	190.939	30932474
AllCCS	[M+H]+	171.9	32859911
AllCCS	[M+H-H2O]+	168.4	32859911
AllCCS	[M+NH4]+	175.1	32859911
AllCCS	[M+Na]+	176.0	32859911
AllCCS	[M-H]-	178.4	32859911
AllCCS	[M+Na-2H]-	177.2	32859911
AllCCS	[M+HCOO]-	176.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cryptodorine	C1OC2=C(O1)C=C1C(CC3NCCC4=CC5=C(OCO5)C1=C34)=C2	4267.3	Standard polar	33892256
Cryptodorine	C1OC2=C(O1)C=C1C(CC3NCCC4=CC5=C(OCO5)C1=C34)=C2	2708.0	Standard non polar	33892256
Cryptodorine	C1OC2=C(O1)C=C1C(CC3NCCC4=CC5=C(OCO5)C1=C34)=C2	3044.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cryptodorine,1TMS,isomer #1	C[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC2=C(C=C13)OCO2	2885.7	Semi standard non polar	33892256
Cryptodorine,1TMS,isomer #1	C[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC2=C(C=C13)OCO2	2861.2	Standard non polar	33892256
Cryptodorine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC2=C(C=C13)OCO2	3104.0	Semi standard non polar	33892256
Cryptodorine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC2=C(C=C13)OCO2	3097.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cryptodorine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0096-0090000000-5b494b79b00171587439	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cryptodorine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cryptodorine 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 - Cryptodorine 10V, Negative-QTOF	splash10-0a4i-0019000000-78b89009c65272118911	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptodorine 20V, Negative-QTOF	splash10-0a4i-0069000000-3eb29ebf0fef6374ecaa	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptodorine 40V, Negative-QTOF	splash10-01p6-0190000000-cef99ce841654a344a1f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptodorine 10V, Negative-QTOF	splash10-0a4i-0009000000-032c4ad1d38e89ca2312	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptodorine 20V, Negative-QTOF	splash10-0a4i-0039000000-1c4e174e83b5ed3fd4f0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptodorine 40V, Negative-QTOF	splash10-002f-0091000000-46c4cbe431c35f2f121d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptodorine 10V, Positive-QTOF	splash10-03di-0039000000-8a6efb2179eb428d154b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptodorine 20V, Positive-QTOF	splash10-03di-0095000000-835e4f20b57c086df87e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptodorine 40V, Positive-QTOF	splash10-00m0-0290000000-2d7a350c10b6a1b9825f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptodorine 10V, Positive-QTOF	splash10-03di-0009000000-ca0f623accd9ac4b341d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptodorine 20V, Positive-QTOF	splash10-03di-0009000000-41b6b27220c1b707b284	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptodorine 40V, Positive-QTOF	splash10-03ec-0193000000-a41d4d21118ff411e2a8	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

FDB011387

KNApSAcK ID

Not Available

Chemspider ID

9613142

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11438278

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 Cryptodorine (HMDB0033359)

MOL for HMDB0033359 (Cryptodorine)

3D MOL for HMDB0033359 (Cryptodorine)

3D SDF for HMDB0033359 (Cryptodorine)

3D-SDF for HMDB0033359 (Cryptodorine)

PDB for HMDB0033359 (Cryptodorine)

3D PDB for HMDB0033359 (Cryptodorine)

SMILES for HMDB0033359 (Cryptodorine)

INCHI for HMDB0033359 (Cryptodorine)

Structure for HMDB0033359 (Cryptodorine)

3D Structure for HMDB0033359 (Cryptodorine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra