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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 01:18:21 UTC

Update Date

2021-09-24 01:18:21 UTC

HMDB ID

HMDB0303359

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Coclaurine

Description

Coclaurine, also known as (r,s)-coclaurine or machiline, is a member of the class of compounds known as benzylisoquinolines. Benzylisoquinolines are organic compounds containing an isoquinoline to which a benzyl group is attached. Coclaurine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Coclaurine can be found in custard apple and soursop, which makes coclaurine a potential biomarker for the consumption of these food products. Coclaurine is a nicotinic acetylcholine receptor antagonist which has been isolated from a variety of plant sources including Nelumbo nucifera, Sarcopetalum harveyanum, Ocotea duckei, and others. It belongs to the class of tetrahydroisoquinoline alkaloids. Dimerization of coclaurine leads to the biscoclaurine alkaloids such as cepharanthine .

Structure

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

HMDB0303359
     RDKit          3D
Coclaurine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -6.0582   -0.0453    0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1720    0.6500   -0.5729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7855    0.5982   -0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1961   -0.1276    0.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7920   -0.1564    0.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9790    0.5342   -0.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5846    1.2739   -1.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9591    1.2958   -1.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5421    2.0370   -2.2704 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4899    0.5081    0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1581   -0.2931   -1.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6326   -0.2862   -0.8620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128   -1.2274   -0.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6847   -1.1697    0.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4211   -0.1848   -0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8116   -0.1344   -0.4207 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7738    0.7728   -1.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167    0.7125   -1.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8448    0.0991    1.3523 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2266   -1.1336    1.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2462   -0.9602    1.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6977   -1.0184    0.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9916   -0.2152   -0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3809    0.5443    1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8069   -0.6946    1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9176    1.8155   -1.7762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5425    2.0606   -2.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9078    1.5556   -0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8094   -1.3446   -1.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9679    0.1695   -2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7707   -2.0267    0.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1839   -1.9298    0.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2486    0.3555    0.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3546    1.5641   -1.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9120    1.4759   -2.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9038    0.8127    2.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5412   -2.0136    1.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5933   -1.3089    2.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6074   -0.5757    2.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7066   -1.9890    1.7700 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
 15 17  1  0
 17 18  2  0
 10 19  1  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 18 12  1  0
 21  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 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
 19 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
M  END

  Mrv0541 02241218522D          

 21 23  0  0  0  0            999 V2000
   -1.7734    1.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309    2.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709    1.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4534    0.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133    0.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734    0.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5159    0.4541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3716    2.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    1.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    0.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4534    0.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3716   -0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2883   -0.8659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8559    2.0208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5159    1.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5159    0.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8559    0.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8559   -0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -0.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -1.6909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8559   -2.1034    0.0000 C   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
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
 10 11  1  0  0  0  0
 10 17  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 19  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303359

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1O)C(CC1=CC=C(O)C=C1)NCC2

> <INCHI_IDENTIFIER>
InChI=1S/C17H19NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-5,9-10,15,18-20H,6-8H2,1H3

> <INCHI_KEY>
LVVKXRQZSRUVPY-UHFFFAOYSA-N

> <FORMULA>
C17H19NO3

> <MOLECULAR_WEIGHT>
285.3377

> <EXACT_MASS>
285.136493479

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.313315221840032

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol

> <ALOGPS_LOGP>
2.20

> <JCHEM_LOGP>
2.5109961516827504

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.510331536726953

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.916751037094782

> <JCHEM_PKA_STRONGEST_BASIC>
8.91020233984593

> <JCHEM_POLAR_SURFACE_AREA>
61.72

> <JCHEM_REFRACTIVITY>
82.07840000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(RS)-coclaurine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303359
     RDKit          3D
Coclaurine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -6.0582   -0.0453    0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1720    0.6500   -0.5729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7855    0.5982   -0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1961   -0.1276    0.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7920   -0.1564    0.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9790    0.5342   -0.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5846    1.2739   -1.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9591    1.2958   -1.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5421    2.0370   -2.2704 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4899    0.5081    0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1581   -0.2931   -1.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6326   -0.2862   -0.8620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128   -1.2274   -0.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6847   -1.1697    0.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4211   -0.1848   -0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8116   -0.1344   -0.4207 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7738    0.7728   -1.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167    0.7125   -1.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8448    0.0991    1.3523 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2266   -1.1336    1.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2462   -0.9602    1.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6977   -1.0184    0.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9916   -0.2152   -0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3809    0.5443    1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8069   -0.6946    1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9176    1.8155   -1.7762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5425    2.0606   -2.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9078    1.5556   -0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8094   -1.3446   -1.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9679    0.1695   -2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7707   -2.0267    0.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1839   -1.9298    0.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2486    0.3555    0.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3546    1.5641   -1.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9120    1.4759   -2.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9038    0.8127    2.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5412   -2.0136    1.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5933   -1.3089    2.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6074   -0.5757    2.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7066   -1.9890    1.7700 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
 15 17  1  0
 17 18  2  0
 10 19  1  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 18 12  1  0
 21  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 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
 19 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  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      -3.310   3.156   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.924   3.926   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.692   3.156   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.846   1.616   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.078   0.848   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.310   1.616   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.696   0.848   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.694   3.926   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.078   3.002   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.078   1.462   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.846   0.694   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.694  -0.846   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.538  -1.616   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       3.464   3.772   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.696   3.002   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.696   1.462   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.464   0.694   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.464  -0.846   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.078  -1.616   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.078  -3.156   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.464  -3.926   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6                                                            
CONECT    8    3    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12                                                            
CONECT   14    9   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   10   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19   12   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0303359
HETATM    1  C1  UNL     1      -6.058  -0.045   0.273  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.172   0.650  -0.573  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.785   0.598  -0.397  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.196  -0.128   0.602  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.792  -0.156   0.749  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.979   0.534  -0.096  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.585   1.274  -1.116  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.959   1.296  -1.251  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.542   2.037  -2.270  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.490   0.508   0.047  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.158  -0.293  -1.049  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.633  -0.286  -0.862  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.313  -1.227  -0.130  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.685  -1.170   0.010  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.421  -0.185  -0.568  1.00  0.00           C  
HETATM   16  O3  UNL     1       6.812  -0.134  -0.421  1.00  0.00           O  
HETATM   17  C14 UNL     1       4.774   0.773  -1.307  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.417   0.713  -1.443  1.00  0.00           C  
HETATM   19  N1  UNL     1       0.845   0.099   1.352  1.00  0.00           N  
HETATM   20  C16 UNL     1       0.227  -1.134   1.778  1.00  0.00           C  
HETATM   21  C17 UNL     1      -1.246  -0.960   1.852  1.00  0.00           C  
HETATM   22  H1  UNL     1      -5.698  -1.018   0.605  1.00  0.00           H  
HETATM   23  H2  UNL     1      -6.992  -0.215  -0.328  1.00  0.00           H  
HETATM   24  H3  UNL     1      -6.381   0.544   1.153  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.807  -0.695   1.301  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.918   1.815  -1.776  1.00  0.00           H  
HETATM   27  H6  UNL     1      -4.543   2.061  -2.379  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.908   1.556  -0.076  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.809  -1.345  -1.086  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.968   0.170  -2.040  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.771  -2.027   0.346  1.00  0.00           H  
HETATM   32  H11 UNL     1       5.184  -1.930   0.595  1.00  0.00           H  
HETATM   33  H12 UNL     1       7.249   0.356   0.323  1.00  0.00           H  
HETATM   34  H13 UNL     1       5.355   1.564  -1.772  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.912   1.476  -2.031  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.904   0.813   2.077  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.541  -2.014   1.210  1.00  0.00           H  
HETATM   38  H17 UNL     1       0.593  -1.309   2.833  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.607  -0.576   2.828  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.707  -1.989   1.770  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   25
CONECT    5    6    6   21
CONECT    6    7   10
CONECT    7    8    8   26
CONECT    8    9
CONECT    9   27
CONECT   10   11   19   28
CONECT   11   12   29   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   36
CONECT   20   21   37   38
CONECT   21   39   40
END

HMDB0303359
     RDKit          3D
Coclaurine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -6.0582   -0.0453    0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1720    0.6500   -0.5729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7855    0.5982   -0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1961   -0.1276    0.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7920   -0.1564    0.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9790    0.5342   -0.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5846    1.2739   -1.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9591    1.2958   -1.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5421    2.0370   -2.2704 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4899    0.5081    0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1581   -0.2931   -1.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6326   -0.2862   -0.8620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128   -1.2274   -0.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6847   -1.1697    0.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4211   -0.1848   -0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8116   -0.1344   -0.4207 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7738    0.7728   -1.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167    0.7125   -1.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8448    0.0991    1.3523 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2266   -1.1336    1.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2462   -0.9602    1.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6977   -1.0184    0.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9916   -0.2152   -0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3809    0.5443    1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8069   -0.6946    1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9176    1.8155   -1.7762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5425    2.0606   -2.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9078    1.5556   -0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8094   -1.3446   -1.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9679    0.1695   -2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7707   -2.0267    0.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1839   -1.9298    0.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2486    0.3555    0.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3546    1.5641   -1.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9120    1.4759   -2.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9038    0.8127    2.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5412   -2.0136    1.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5933   -1.3089    2.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6074   -0.5757    2.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7066   -1.9890    1.7700 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
 15 17  1  0
 17 18  2  0
 10 19  1  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 18 12  1  0
 21  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 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
 19 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(R,S)-Coclaurine	ChEBI
6-Methoxy-7-hydroxy-1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline	ChEBI
Coclaurine	ChEBI
DL-Coclaurine	Kegg
Machiline	Kegg

Chemical Formula

C₁₇H₁₉NO₃

Average Molecular Weight

285.3377

Monoisotopic Molecular Weight

285.136493479

IUPAC Name

1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol

Traditional Name

(RS)-coclaurine

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1O)C(CC1=CC=C(O)C=C1)NCC2

InChI Identifier

InChI=1S/C17H19NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-5,9-10,15,18-20H,6-8H2,1H3

InChI Key

LVVKXRQZSRUVPY-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
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Benzenoid
Monocyclic benzene moiety
Secondary amine
Ether
Secondary aliphatic amine
Azacycle
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

coclaurine (CHEBI:18417 )

Ontology

Not Available

Exogenous (HMDB: HMDB0303359)

Food

Fruit

Tropical fruit

Custard apple (FooDB: FOOD00014)
Soursop (FooDB: FOOD00478)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0303359)
Antioxidant (HMDB: HMDB0303359)

Biological role

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
logP	2.2	ALOGPS
logP	2.51	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.92	ChemAxon
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	61.72 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.08 m³·mol⁻¹	ChemAxon
Polarizability	31.31 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
AllCCS	[M+H]+	169.6	32859911
AllCCS	[M+H-H2O]+	165.991	32859911
AllCCS	[M+Na]+	173.914	32859911
AllCCS	[M+NH4]+	172.95	32859911
AllCCS	[M-H]-	173.084	32859911
AllCCS	[M+Na-2H]-	172.786	32859911
AllCCS	[M+HCOO]-	172.594	32859911
DeepCCS	[M+H]+	165.415	30932474
DeepCCS	[M-H]-	163.057	30932474
DeepCCS	[M-2H]-	195.943	30932474
DeepCCS	[M+Na]+	171.508	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Coclaurine,3TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)C(CC1=CC=C(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)CC2	2746.9	Semi standard non polar	33892256
Coclaurine,3TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)C(CC1=CC=C(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)CC2	2721.3	Standard non polar	33892256
Coclaurine,3TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)C(CC1=CC=C(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)CC2	3048.7	Standard polar	33892256
Coclaurine,3TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)CC2	3450.8	Semi standard non polar	33892256
Coclaurine,3TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)CC2	3371.6	Standard non polar	33892256
Coclaurine,3TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)CC2	3346.0	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coclaurine 10V, Positive-QTOF	splash10-000i-0190000000-c51f7399519ef56e73ba	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coclaurine 20V, Positive-QTOF	splash10-0699-0950000000-4a1f90323b9937adb67b	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coclaurine 40V, Positive-QTOF	splash10-056r-3900000000-60e9e4b45ae16bb78dc0	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coclaurine 10V, Negative-QTOF	splash10-001i-0090000000-4d22fc04b303cacd4270	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coclaurine 20V, Negative-QTOF	splash10-001i-0090000000-4279946a636b9df45307	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coclaurine 40V, Negative-QTOF	splash10-03dj-0930000000-40765f612e0f0de506c9	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coclaurine 10V, Positive-QTOF	splash10-000i-0090000000-12d6d7cf9e71a6a9ec09	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coclaurine 20V, Positive-QTOF	splash10-014r-0290000000-39a70d9490efac07fddf	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coclaurine 40V, Positive-QTOF	splash10-052f-5890000000-ef66b814d4e0abf637f1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coclaurine 10V, Negative-QTOF	splash10-001i-0090000000-793f02ff50658d83401d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coclaurine 20V, Negative-QTOF	splash10-001i-0090000000-03a1e9c6f6233f4aefc6	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coclaurine 40V, Negative-QTOF	splash10-03k9-0910000000-2ed17eca31b57752c4b6	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

18417

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

Not Available

Showing metabocard for Coclaurine (HMDB0303359)

MOL for HMDB0303359 (Coclaurine)

3D MOL for HMDB0303359 (Coclaurine)

3D SDF for HMDB0303359 (Coclaurine)

3D-SDF for HMDB0303359 (Coclaurine)

PDB for HMDB0303359 (Coclaurine)

3D PDB for HMDB0303359 (Coclaurine)

SMILES for HMDB0303359 (Coclaurine)

INCHI for HMDB0303359 (Coclaurine)

Structure for HMDB0303359 (Coclaurine)

3D Structure for HMDB0303359 (Coclaurine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra