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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:03:44 UTC

Update Date

2022-03-07 02:55:53 UTC

HMDB ID

HMDB0038723

Secondary Accession Numbers

HMDB38723

Metabolite Identification

Common Name

(S)-Annocherine A

Description

(S)-Annocherine A belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached (S)-Annocherine A has been detected, but not quantified in, fruits. This could make (S)-annocherine a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (S)-Annocherine A.

Structure

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

HMDB0038723
     RDKit          3D
(S)-Annocherine A
 37 39  0  0  0  0  0  0  0  0999 V2000
    5.3021    1.3263    0.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0706    1.4522    1.0369 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9582    0.6496    0.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0085   -0.3271   -0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9290   -1.1088   -0.5637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0361   -2.0719   -1.5400 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9287   -2.8336   -1.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2415   -2.6478   -1.1472 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3707   -1.7155   -0.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358   -1.5199    0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4954   -2.6348    0.3731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4103   -0.3327    0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6656   -0.1866    0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4659    0.8878    0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0473    1.8789   -0.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8881    2.9278   -0.7694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7962    1.7285   -1.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9731    0.6427   -0.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156   -0.9275    0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6369    0.0391    1.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7568    0.8136    1.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6304    1.7651    2.3567 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1336    1.1358   -0.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8951    0.5269    0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8190    2.3250    0.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9172   -0.4940   -0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9857   -2.1891   -2.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0383   -3.5876   -2.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4736   -1.4726    1.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7139   -2.6837   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0320   -0.9313    1.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4421    0.9851    0.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8055    3.0173   -0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4299    2.4810   -1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110    0.5607   -1.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2920    0.1810    1.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4278    2.3399    2.5843 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
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  9 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 19  5  1  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
 22 37  1  0
M  END

  Mrv0541 02241211412D          

 22 24  0  0  0  0            999 V2000
   -0.7135    1.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7135    0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006    0.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7134    0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7134    1.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006    2.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4276    0.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1404    0.8256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1404    1.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4276    2.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4276   -0.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7121   -0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034   -0.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7175   -0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7175   -1.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034   -2.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7121   -1.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4330   -2.0641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4276    2.0641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    1.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    0.4128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432   -0.8256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1 19  1  0  0  0  0
  2  3  1  0  0  0  0
  2 21  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  7  8  2  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 12  1  0  0  0  0
 11 22  1  0  0  0  0
 12 13  2  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 17  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038723

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C2C(C=CN=C2C(O)C2=CC=C(O)C=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H15NO4/c1-22-15-8-11-6-7-18-16(13(11)9-14(15)20)17(21)10-2-4-12(19)5-3-10/h2-9,17,19-21H,1H3

> <INCHI_KEY>
XWZBLZPLPZOXQV-UHFFFAOYSA-N

> <FORMULA>
C17H15NO4

> <MOLECULAR_WEIGHT>
297.3053

> <EXACT_MASS>
297.100107973

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
30.53779540197036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[hydroxy(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
2.2307997646666666

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.628716007756628

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.960342515734698

> <JCHEM_PKA_STRONGEST_BASIC>
5.463015523426112

> <JCHEM_POLAR_SURFACE_AREA>
82.81000000000002

> <JCHEM_REFRACTIVITY>
81.4279

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[hydroxy(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038723
     RDKit          3D
(S)-Annocherine A
 37 39  0  0  0  0  0  0  0  0999 V2000
    5.3021    1.3263    0.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0706    1.4522    1.0369 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9582    0.6496    0.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0085   -0.3271   -0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9290   -1.1088   -0.5637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0361   -2.0719   -1.5400 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9287   -2.8336   -1.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2415   -2.6478   -1.1472 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3707   -1.7155   -0.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358   -1.5199    0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4954   -2.6348    0.3731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4103   -0.3327    0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6656   -0.1866    0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4659    0.8878    0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0473    1.8789   -0.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8881    2.9278   -0.7694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7962    1.7285   -1.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9731    0.6427   -0.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156   -0.9275    0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6369    0.0391    1.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7568    0.8136    1.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6304    1.7651    2.3567 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1336    1.1358   -0.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8951    0.5269    0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8190    2.3250    0.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9172   -0.4940   -0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9857   -2.1891   -2.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0383   -3.5876   -2.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4736   -1.4726    1.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7139   -2.6837   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0320   -0.9313    1.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4421    0.9851    0.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8055    3.0173   -0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4299    2.4810   -1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110    0.5607   -1.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2920    0.1810    1.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4278    2.3399    2.5843 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
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  9 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 19  5  1  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
 22 37  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.332   3.082   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.332   1.541   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.001   0.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.332   1.541   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.332   3.082   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.001   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.665   0.771   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.995   1.541   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.995   3.082   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.665   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.665  -0.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.329  -1.541   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.006  -0.773   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.339  -1.541   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.339  -3.082   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.006  -3.853   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.329  -3.082   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.675  -3.853   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.665   3.853   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.001   3.082   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.667   0.771   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001  -1.541   0.000  0.00  0.00           O+0
CONECT    1    2    6   19                                                  
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    5    9                                                       
CONECT   11    7   12   22                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   12   16                                                       
CONECT   18   15                                                            
CONECT   19    1   20                                                       
CONECT   20   19                                                            
CONECT   21    2                                                            
CONECT   22   11                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0038723
HETATM    1  C1  UNL     1       5.302   1.326   0.402  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.071   1.452   1.037  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.958   0.650   0.719  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.009  -0.327  -0.252  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.929  -1.109  -0.564  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.036  -2.072  -1.540  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.929  -2.834  -1.815  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.241  -2.648  -1.147  1.00  0.00           N  
HETATM    9  C7  UNL     1      -0.371  -1.716  -0.192  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.636  -1.520   0.514  1.00  0.00           C  
HETATM   11  O2  UNL     1      -2.495  -2.635   0.373  1.00  0.00           O  
HETATM   12  C9  UNL     1      -2.410  -0.333   0.130  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.666  -0.187   0.682  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.466   0.888   0.377  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.047   1.879  -0.503  1.00  0.00           C  
HETATM   16  O3  UNL     1      -4.888   2.928  -0.769  1.00  0.00           O  
HETATM   17  C13 UNL     1      -2.796   1.728  -1.050  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.973   0.643  -0.749  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.716  -0.927   0.118  1.00  0.00           C  
HETATM   20  C16 UNL     1       0.637   0.039   1.091  1.00  0.00           C  
HETATM   21  C17 UNL     1       1.757   0.814   1.378  1.00  0.00           C  
HETATM   22  O4  UNL     1       1.630   1.765   2.357  1.00  0.00           O  
HETATM   23  H1  UNL     1       5.134   1.136  -0.680  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.895   0.527   0.893  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.819   2.325   0.499  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.917  -0.494  -0.792  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.986  -2.189  -2.050  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.038  -3.588  -2.590  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.474  -1.473   1.637  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.714  -2.684  -0.601  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.032  -0.931   1.370  1.00  0.00           H  
HETATM   32  H10 UNL     1      -5.442   0.985   0.817  1.00  0.00           H  
HETATM   33  H11 UNL     1      -5.806   3.017  -0.354  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.430   2.481  -1.743  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.011   0.561  -1.199  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.292   0.181   1.615  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.428   2.340   2.584  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   26
CONECT    5    6    6   19
CONECT    6    7   27
CONECT    7    8    8   28
CONECT    8    9
CONECT    9   10   19   19
CONECT   10   11   12   29
CONECT   11   30
CONECT   12   13   13   18
CONECT   13   14   31
CONECT   14   15   15   32
CONECT   15   16   17
CONECT   16   33
CONECT   17   18   18   34
CONECT   18   35
CONECT   19   20
CONECT   20   21   21   36
CONECT   21   22
CONECT   22   37
END

HMDB0038723
     RDKit          3D
(S)-Annocherine A
 37 39  0  0  0  0  0  0  0  0999 V2000
    5.3021    1.3263    0.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0706    1.4522    1.0369 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9582    0.6496    0.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0085   -0.3271   -0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9290   -1.1088   -0.5637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0361   -2.0719   -1.5400 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9287   -2.8336   -1.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2415   -2.6478   -1.1472 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3707   -1.7155   -0.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358   -1.5199    0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4954   -2.6348    0.3731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4103   -0.3327    0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6656   -0.1866    0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4659    0.8878    0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0473    1.8789   -0.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8881    2.9278   -0.7694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7962    1.7285   -1.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9731    0.6427   -0.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156   -0.9275    0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6369    0.0391    1.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7568    0.8136    1.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6304    1.7651    2.3567 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1336    1.1358   -0.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8951    0.5269    0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8190    2.3250    0.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9172   -0.4940   -0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9857   -2.1891   -2.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0383   -3.5876   -2.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4736   -1.4726    1.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7139   -2.6837   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0320   -0.9313    1.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4421    0.9851    0.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8055    3.0173   -0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4299    2.4810   -1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110    0.5607   -1.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2920    0.1810    1.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4278    2.3399    2.5843 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
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  9 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 19  5  1  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
 22 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₁₅NO₄

Average Molecular Weight

297.3053

Monoisotopic Molecular Weight

297.100107973

IUPAC Name

1-[hydroxy(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol

Traditional Name

1-[hydroxy(4-hydroxyphenyl)methyl]-6-methoxyisoquinolin-7-ol

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2C(C=CN=C2C(O)C2=CC=C(O)C=C2)=C1

InChI Identifier

InChI=1S/C17H15NO4/c1-22-15-8-11-6-7-18-16(13(11)9-14(15)20)17(21)10-2-4-12(19)5-3-10/h2-9,17,19-21H,1H3

InChI Key

XWZBLZPLPZOXQV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Benzylisoquinolines

Direct Parent

Benzylisoquinolines

Alternative Parents

Substituents

Benzylisoquinoline
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Pyridine
Benzenoid
Heteroaromatic compound
Secondary alcohol
Ether
Azacycle
Aromatic alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038723)
Cytoplasm (HMDB: HMDB0038723)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038723)

Source

Exogenous

Exogenous (HMDB: HMDB0038723)

Food

Food (HMDB: HMDB0038723)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0038723)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038723)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	156 - 158 °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	0.24 g/L	ALOGPS
logP	2.1	ALOGPS
logP	2.23	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	8.96	ChemAxon
pKa (Strongest Basic)	5.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	82.81 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.43 m³·mol⁻¹	ChemAxon
Polarizability	30.54 Å³	ChemAxon
Number of Rings	3	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]+	168.326	31661259
DarkChem	[M-H]-	171.558	31661259
DeepCCS	[M+H]+	173.491	30932474
DeepCCS	[M-H]-	171.134	30932474
DeepCCS	[M-2H]-	204.442	30932474
DeepCCS	[M+Na]+	179.669	30932474
AllCCS	[M+H]+	170.9	32859911
AllCCS	[M+H-H2O]+	167.3	32859911
AllCCS	[M+NH4]+	174.2	32859911
AllCCS	[M+Na]+	175.2	32859911
AllCCS	[M-H]-	172.3	32859911
AllCCS	[M+Na-2H]-	171.8	32859911
AllCCS	[M+HCOO]-	171.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-Annocherine A	COC1=C(O)C=C2C(C=CN=C2C(O)C2=CC=C(O)C=C2)=C1	4511.1	Standard polar	33892256
(S)-Annocherine A	COC1=C(O)C=C2C(C=CN=C2C(O)C2=CC=C(O)C=C2)=C1	2803.7	Standard non polar	33892256
(S)-Annocherine A	COC1=C(O)C=C2C(C=CN=C2C(O)C2=CC=C(O)C=C2)=C1	2978.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-Annocherine A,1TMS,isomer #1	COC1=CC2=CC=NC(C(O)C3=CC=C(O)C=C3)=C2C=C1O[Si](C)(C)C	2889.9	Semi standard non polar	33892256
(S)-Annocherine A,1TMS,isomer #2	COC1=CC2=CC=NC(C(O[Si](C)(C)C)C3=CC=C(O)C=C3)=C2C=C1O	2845.0	Semi standard non polar	33892256
(S)-Annocherine A,1TMS,isomer #3	COC1=CC2=CC=NC(C(O)C3=CC=C(O[Si](C)(C)C)C=C3)=C2C=C1O	2781.0	Semi standard non polar	33892256
(S)-Annocherine A,2TMS,isomer #1	COC1=CC2=CC=NC(C(O[Si](C)(C)C)C3=CC=C(O)C=C3)=C2C=C1O[Si](C)(C)C	2765.6	Semi standard non polar	33892256
(S)-Annocherine A,2TMS,isomer #2	COC1=CC2=CC=NC(C(O)C3=CC=C(O[Si](C)(C)C)C=C3)=C2C=C1O[Si](C)(C)C	2726.1	Semi standard non polar	33892256
(S)-Annocherine A,2TMS,isomer #3	COC1=CC2=CC=NC(C(O[Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C3)=C2C=C1O	2690.5	Semi standard non polar	33892256
(S)-Annocherine A,3TMS,isomer #1	COC1=CC2=CC=NC(C(O[Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C3)=C2C=C1O[Si](C)(C)C	2694.8	Semi standard non polar	33892256
(S)-Annocherine A,1TBDMS,isomer #1	COC1=CC2=CC=NC(C(O)C3=CC=C(O)C=C3)=C2C=C1O[Si](C)(C)C(C)(C)C	3173.7	Semi standard non polar	33892256
(S)-Annocherine A,1TBDMS,isomer #2	COC1=CC2=CC=NC(C(O[Si](C)(C)C(C)(C)C)C3=CC=C(O)C=C3)=C2C=C1O	3117.5	Semi standard non polar	33892256
(S)-Annocherine A,1TBDMS,isomer #3	COC1=CC2=CC=NC(C(O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C2C=C1O	3053.6	Semi standard non polar	33892256
(S)-Annocherine A,2TBDMS,isomer #1	COC1=CC2=CC=NC(C(O[Si](C)(C)C(C)(C)C)C3=CC=C(O)C=C3)=C2C=C1O[Si](C)(C)C(C)(C)C	3296.9	Semi standard non polar	33892256
(S)-Annocherine A,2TBDMS,isomer #2	COC1=CC2=CC=NC(C(O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C2C=C1O[Si](C)(C)C(C)(C)C	3251.7	Semi standard non polar	33892256
(S)-Annocherine A,2TBDMS,isomer #3	COC1=CC2=CC=NC(C(O[Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C2C=C1O	3250.1	Semi standard non polar	33892256
(S)-Annocherine A,3TBDMS,isomer #1	COC1=CC2=CC=NC(C(O[Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=C2C=C1O[Si](C)(C)C(C)(C)C	3438.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Annocherine A GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1890000000-769aa225de0451ffd894	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Annocherine A GC-MS (3 TMS) - 70eV, Positive	splash10-0002-4131900000-489e0dd2b4369da7144b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Annocherine A 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 - (S)-Annocherine A 10V, Positive-QTOF	splash10-0002-0190000000-c376ec102384cfa9ee22	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Annocherine A 20V, Positive-QTOF	splash10-00di-0930000000-d0530acd9434a934389f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Annocherine A 40V, Positive-QTOF	splash10-00dl-9410000000-bd5cc73bcaf4c1f1177c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Annocherine A 10V, Negative-QTOF	splash10-0002-0090000000-329be6e8b2d0a053a340	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Annocherine A 20V, Negative-QTOF	splash10-0002-2090000000-75e3e4d26cdf88d515f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Annocherine A 40V, Negative-QTOF	splash10-0a4l-3940000000-36c50a53923f3afde9e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Annocherine A 10V, Negative-QTOF	splash10-002b-0090000000-79d61e288cbbd8b779f1	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Annocherine A 20V, Negative-QTOF	splash10-0c0v-1690000000-a422dc09e6358b9010ec	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Annocherine A 40V, Negative-QTOF	splash10-0f6x-6980000000-afe8314cb3adf8418598	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Annocherine A 10V, Positive-QTOF	splash10-000t-0090000000-2f0cc89acf3eca59d80f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Annocherine A 20V, Positive-QTOF	splash10-001i-0090000000-55c4546122bfa987591d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Annocherine A 40V, Positive-QTOF	splash10-0a4i-2930000000-95225cdfe4074b38c3ce	2021-09-25	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

FDB019811

KNApSAcK ID

Not Available

Chemspider ID

20057386

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22297560

PDB ID

Not Available

ChEBI ID

169192

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 (S)-Annocherine A (HMDB0038723)

MOL for HMDB0038723 ((S)-Annocherine A)

3D MOL for HMDB0038723 ((S)-Annocherine A)

3D SDF for HMDB0038723 ((S)-Annocherine A)

3D-SDF for HMDB0038723 ((S)-Annocherine A)

PDB for HMDB0038723 ((S)-Annocherine A)

3D PDB for HMDB0038723 ((S)-Annocherine A)

SMILES for HMDB0038723 ((S)-Annocherine A)

INCHI for HMDB0038723 ((S)-Annocherine A)

Structure for HMDB0038723 ((S)-Annocherine A)

3D Structure for HMDB0038723 ((S)-Annocherine A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra