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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:04:17 UTC

Update Date

2022-03-07 02:53:40 UTC

HMDB ID

HMDB0033355

Secondary Accession Numbers

HMDB33355

Metabolite Identification

Common Name

Dehydroaporheine

Description

Dehydroaporheine, also known as dehydroremerine, 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. Dehydroaporheine is a strong basic compound (based on its pKa). Outside of the human body, dehydroaporheine has been detected, but not quantified in, coffee and coffee products and root vegetables. This could make dehydroaporheine a potential biomarker for the consumption of these foods.

Structure

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

HMDB0033355
     RDKit          3D
Dehydroaporheine
 36 40  0  0  0  0  0  0  0  0999 V2000
    3.8324    1.0275   -0.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7967    0.1074    0.0230 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -1.2480    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2236   -2.2543   -0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8157   -1.8571   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1655   -2.8652   -0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877   -2.5277   -0.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9162   -1.1927   -0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9436   -0.2233   -0.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311   -0.5533   -0.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3936    0.4272    0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0329    1.7401    0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3074    2.0509    0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6530    3.3831    0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9597    3.7769    0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9637    2.8426    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6391    1.4857    0.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3231    1.1169    0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2832   -1.1914   -0.1338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7734   -2.4918   -0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6270   -3.3101   -0.2722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5297    1.8144   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2987    1.4732    0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505    0.4592   -0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0994   -1.2695    1.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060   -1.4026    0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4854   -2.4492   -1.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3231   -3.1904    0.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1997   -3.8740   -0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8043    2.5183    0.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1244    4.1187    0.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1865    4.8512    0.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9894    3.1752    0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4478    0.8136   -0.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1795   -2.6382    0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5303   -2.6436   -0.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  8 19  1  0
 19 20  1  0
 20 21  1  0
 11  2  1  0
 18 13  1  0
 10  5  1  0
 21  7  1  0
 18  9  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
 20 36  1  0
M  END


  Mrv0541 05061307042D          

 21 25  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
    5.0013   -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
    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
    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
    3.1354    2.1307    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
    1.4289    0.0000    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
    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
    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
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
 11  4  2  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 12  9  2  0  0  0  0
 13  5  2  0  0  0  0
 13 11  1  0  0  0  0
 14  8  2  0  0  0  0
 15  9  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 13  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  1  1  0  0  0  0
 19  7  1  0  0  0  0
 19 14  1  0  0  0  0
 20 10  1  0  0  0  0
 20 15  1  0  0  0  0
 21 10  1  0  0  0  0
 21 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033355

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C31

> <INCHI_IDENTIFIER>
InChI=1S/C18H15NO2/c1-19-7-6-12-9-15-18(21-10-20-15)17-13-5-3-2-4-11(13)8-14(19)16(12)17/h2-5,8-9H,6-7,10H2,1H3

> <INCHI_KEY>
YUWBTKIVDAWQHK-UHFFFAOYSA-N

> <FORMULA>
C18H15NO2

> <MOLECULAR_WEIGHT>
277.3172

> <EXACT_MASS>
277.110278729

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.72001265337041

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14,16,18-heptaene

> <ALOGPS_LOGP>
3.80

> <JCHEM_LOGP>
3.7233651619999995

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.672678795837851

> <JCHEM_POLAR_SURFACE_AREA>
21.700000000000003

> <JCHEM_REFRACTIVITY>
82.4635

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14,16,18-heptaene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0033355
     RDKit          3D
Dehydroaporheine
 36 40  0  0  0  0  0  0  0  0999 V2000
    3.8324    1.0275   -0.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7967    0.1074    0.0230 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -1.2480    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2236   -2.2543   -0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8157   -1.8571   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1655   -2.8652   -0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877   -2.5277   -0.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9162   -1.1927   -0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9436   -0.2233   -0.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311   -0.5533   -0.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3936    0.4272    0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0329    1.7401    0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3074    2.0509    0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6530    3.3831    0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9597    3.7769    0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9637    2.8426    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6391    1.4857    0.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3231    1.1169    0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2832   -1.1914   -0.1338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7734   -2.4918   -0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6270   -3.3101   -0.2722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5297    1.8144   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2987    1.4732    0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505    0.4592   -0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0994   -1.2695    1.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060   -1.4026    0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4854   -2.4492   -1.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3231   -3.1904    0.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1997   -3.8740   -0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8043    2.5183    0.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1244    4.1187    0.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1865    4.8512    0.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9894    3.1752    0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4478    0.8136   -0.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1795   -2.6382    0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5303   -2.6436   -0.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  8 19  1  0
 19 20  1  0
 20 21  1  0
 11  2  1  0
 18 13  1  0
 10  5  1  0
 21  7  1  0
 18  9  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
 20 36  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       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.853   3.977   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   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       4.321   3.816   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.479   2.570   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   11                                                       
CONECT    5    3   13                                                       
CONECT    6    7   12                                                       
CONECT    7    6   19                                                       
CONECT    8   11   14                                                       
CONECT    9   12   15                                                       
CONECT   10   20   21                                                       
CONECT   11    4    8   13                                                  
CONECT   12    6    9   16                                                  
CONECT   13    5   11   17                                                  
CONECT   14    8   16   19                                                  
CONECT   15    9   18   20                                                  
CONECT   16   12   14   17                                                  
CONECT   17   13   16   18                                                  
CONECT   18   15   17   21                                                  
CONECT   19    1    7   14                                                  
CONECT   20   10   15                                                       
CONECT   21   10   18                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

COMPND    HMDB0033355
HETATM    1  C1  UNL     1       3.832   1.028  -0.311  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.797   0.107   0.023  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.129  -1.248   0.399  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.224  -2.254  -0.192  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.816  -1.857  -0.148  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.166  -2.865  -0.224  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.488  -2.528  -0.211  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.916  -1.193  -0.123  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.944  -0.223  -0.049  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.431  -0.553  -0.061  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.394   0.427   0.023  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.033   1.740   0.114  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.307   2.051   0.122  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.653   3.383   0.215  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.960   3.777   0.229  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.964   2.843   0.151  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.639   1.486   0.057  1.00  0.00           C  
HETATM   18  C17 UNL     1      -1.323   1.117   0.044  1.00  0.00           C  
HETATM   19  O1  UNL     1      -3.283  -1.191  -0.134  1.00  0.00           O  
HETATM   20  C18 UNL     1      -3.773  -2.492  -0.017  1.00  0.00           C  
HETATM   21  O2  UNL     1      -2.627  -3.310  -0.272  1.00  0.00           O  
HETATM   22  H1  UNL     1       3.530   1.814  -1.025  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.299   1.473   0.614  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.651   0.459  -0.803  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.099  -1.270   1.512  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.206  -1.403   0.124  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.485  -2.449  -1.254  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.323  -3.190   0.400  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.200  -3.874  -0.289  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.804   2.518   0.178  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.124   4.119   0.276  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.186   4.851   0.305  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.989   3.175   0.165  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.448   0.814  -0.001  1.00  0.00           H  
HETATM   35  H14 UNL     1      -4.180  -2.638   0.987  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.530  -2.644  -0.826  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   11
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6    6   10
CONECT    6    7   29
CONECT    7    8    8   21
CONECT    8    9   19
CONECT    9   10   18   18
CONECT   10   11   11
CONECT   11   12
CONECT   12   13   13   30
CONECT   13   14   18
CONECT   14   15   15   31
CONECT   15   16   32
CONECT   16   17   17   33
CONECT   17   18   34
CONECT   19   20
CONECT   20   21   35   36
END

HMDB0033355
     RDKit          3D
Dehydroaporheine
 36 40  0  0  0  0  0  0  0  0999 V2000
    3.8324    1.0275   -0.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7967    0.1074    0.0230 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -1.2480    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2236   -2.2543   -0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8157   -1.8571   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1655   -2.8652   -0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877   -2.5277   -0.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9162   -1.1927   -0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9436   -0.2233   -0.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311   -0.5533   -0.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3936    0.4272    0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0329    1.7401    0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3074    2.0509    0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6530    3.3831    0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9597    3.7769    0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9637    2.8426    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6391    1.4857    0.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3231    1.1169    0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2832   -1.1914   -0.1338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7734   -2.4918   -0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6270   -3.3101   -0.2722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5297    1.8144   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2987    1.4732    0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505    0.4592   -0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0994   -1.2695    1.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060   -1.4026    0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4854   -2.4492   -1.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3231   -3.1904    0.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1997   -3.8740   -0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8043    2.5183    0.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1244    4.1187    0.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1865    4.8512    0.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9894    3.1752    0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4478    0.8136   -0.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1795   -2.6382    0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5303   -2.6436   -0.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  8 19  1  0
 19 20  1  0
 20 21  1  0
 11  2  1  0
 18 13  1  0
 10  5  1  0
 21  7  1  0
 18  9  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
 20 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6a,7-Didehydroaporheine	HMDB
Dehydroremerine	HMDB
Dehydroroemerine	MeSH

Chemical Formula

C₁₈H₁₅NO₂

Average Molecular Weight

277.3172

Monoisotopic Molecular Weight

277.110278729

IUPAC Name

11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14,16,18-heptaene

Traditional Name

11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14,16,18-heptaene

CAS Registry Number

36285-03-7

SMILES

CN1CCC2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C31

InChI Identifier

InChI=1S/C18H15NO2/c1-19-7-6-12-9-15-18(21-10-20-15)17-13-5-3-2-4-11(13)8-14(19)16(12)17/h2-5,8-9H,6-7,10H2,1H3

InChI Key

YUWBTKIVDAWQHK-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
Benzodioxole
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Aralkylamine
Benzenoid
Tertiary amine
Organoheterocyclic compound
Acetal
Azacycle
Oxacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033355)

Cellular substructure

Membrane (HMDB: HMDB0033355)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033355)

Source

Exogenous

Food

Food (HMDB: HMDB0033355)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Endogenous

Plant

Plant (HMDB: HMDB0033355)
Coffea (HMDB: HMDB0033355)

Not Available

Nutrient (HMDB: HMDB0033355)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	88 - 89 °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	0.014 g/L	ALOGPS
logP	3.8	ALOGPS
logP	3.72	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	4.67	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	21.7 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	82.46 m³·mol⁻¹	ChemAxon
Polarizability	30.72 Å³	ChemAxon
Number of Rings	5	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]+	165.092	31661259
DarkChem	[M-H]-	164.933	31661259
DeepCCS	[M-2H]-	191.793	30932474
DeepCCS	[M+Na]+	167.093	30932474
AllCCS	[M+H]+	163.0	32859911
AllCCS	[M+H-H2O]+	159.2	32859911
AllCCS	[M+NH4]+	166.6	32859911
AllCCS	[M+Na]+	167.6	32859911
AllCCS	[M-H]-	171.6	32859911
AllCCS	[M+Na-2H]-	170.3	32859911
AllCCS	[M+HCOO]-	169.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydroaporheine	CN1CCC2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C31	3716.8	Standard polar	33892256
Dehydroaporheine	CN1CCC2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C31	2473.9	Standard non polar	33892256
Dehydroaporheine	CN1CCC2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C31	2914.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroaporheine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ta-0090000000-d8ed0f562436435092f7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroaporheine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroaporheine 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 - Dehydroaporheine 10V, Positive-QTOF	splash10-004i-0090000000-f3f8c842f82c4a99a8a1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroaporheine 20V, Positive-QTOF	splash10-004j-0090000000-99da6b258c612afb32ec	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroaporheine 40V, Positive-QTOF	splash10-0gba-0090000000-e03e25aea35beeb1a5e4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroaporheine 10V, Negative-QTOF	splash10-004i-0090000000-d0f05bfcbd2ac2dd0206	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroaporheine 20V, Negative-QTOF	splash10-004i-0090000000-edb18a3ee3aa69a914e5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroaporheine 40V, Negative-QTOF	splash10-03di-2090000000-68dcc4313624ba8dc344	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroaporheine 10V, Positive-QTOF	splash10-004i-0090000000-aa2847a431e62b643117	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroaporheine 20V, Positive-QTOF	splash10-004i-0090000000-aa2847a431e62b643117	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroaporheine 40V, Positive-QTOF	splash10-002b-0090000000-c031da6ba3b1a9bb9ac5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroaporheine 10V, Negative-QTOF	splash10-004i-0090000000-9987ea1030550780a9d6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroaporheine 20V, Negative-QTOF	splash10-004i-0090000000-4c83087bdfecf1d24c2e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroaporheine 40V, Negative-QTOF	splash10-0002-0090000000-4faa8a57043035ad7d5e	2021-09-25	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

FDB011383

KNApSAcK ID

C00025845

Chemspider ID

142190

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

161899

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 Dehydroaporheine (HMDB0033355)

MOL for HMDB0033355 (Dehydroaporheine)

3D MOL for HMDB0033355 (Dehydroaporheine)

3D SDF for HMDB0033355 (Dehydroaporheine)

3D-SDF for HMDB0033355 (Dehydroaporheine)

PDB for HMDB0033355 (Dehydroaporheine)

3D PDB for HMDB0033355 (Dehydroaporheine)

SMILES for HMDB0033355 (Dehydroaporheine)

INCHI for HMDB0033355 (Dehydroaporheine)

Structure for HMDB0033355 (Dehydroaporheine)

3D Structure for HMDB0033355 (Dehydroaporheine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra