Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 00:53:22 UTC

Update Date

2022-03-07 03:17:43 UTC

HMDB ID

HMDB0060319

Secondary Accession Numbers

HMDB60319

Metabolite Identification

Common Name

(S)-N-Methylcoclaurine

Description

(S)-N-Methylcoclaurine 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)-N-Methylcoclaurine is a very strong basic compound (based on its pKa) (S)-N-Methylcoclaurine exists in all living organisms, ranging from bacteria to humans. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Structure

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

HMDB0060319
     RDKit          3D
(S)-N-Methylcoclaurine
 43 45  0  0  0  0  0  0  0  0999 V2000
   -5.8479    1.4023    0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1638    0.5553   -0.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7852    0.4422   -0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0904    1.1605    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398    1.0295    0.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0811    0.1799   -0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7530   -0.5326   -1.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1239   -0.3973   -1.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8907   -1.0833   -2.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3924    0.1346   -0.1675 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0909   -0.7504   -1.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5434   -0.7086   -0.8534 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3744    0.2267   -1.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7255    0.2648   -1.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3079   -0.6148   -0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6637   -0.6255   -0.0300 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -1.5559    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1389   -1.5903    0.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6273   -0.2008    1.2203 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0072   -1.4605    1.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1980    0.8662    2.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8682    1.7386    1.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3652    2.4210    0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8906    1.5823    0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8480    1.0296    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5801    1.8227    1.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2171   -1.1805   -1.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4107   -1.6961   -2.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7596    1.1706   -0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7525   -1.8054   -1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8962   -0.3913   -2.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8823    0.9176   -2.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3273    1.0047   -1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3362    0.0094   -0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9551   -2.2588    0.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5512   -2.3396    0.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698   -2.0242    2.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8816   -1.2780    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3308   -2.0386    0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2079    0.3725    3.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0748    1.4561    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3622    2.5530    0.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4405    2.1926    2.3541 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
 19 21  1  0
 21 22  1  0
  8  3  1  0
 18 12  1  0
 22  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  1
 11 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
M  END


  Mrv0541 05161317532D          

 22 24  0  0  0  0            999 V2000
    0.0000   -1.6500    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   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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
    3.5724   -3.7125    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
    1.4289   -1.6500    0.0000 C   0  0  1  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
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  1  0  0  0  0
 12  3  2  0  0  0  0
 12  4  1  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  2  0  0  0  0
 14  5  2  0  0  0  0
 14  6  1  0  0  0  0
 15 11  2  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  6  0  0  0
 16 15  1  0  0  0  0
 17 11  1  0  0  0  0
 18 10  1  0  0  0  0
 18 17  2  0  0  0  0
 19  1  1  0  0  0  0
 19  8  1  0  0  0  0
 19 16  1  0  0  0  0
 20 14  1  0  0  0  0
 21 17  1  0  0  0  0
 22  2  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060319

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C2[C@H](CC3=CC=C(O)C=C3)N(C)CCC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H21NO3/c1-19-8-7-13-10-18(22-2)17(21)11-15(13)16(19)9-12-3-5-14(20)6-4-12/h3-6,10-11,16,20-21H,7-9H2,1-2H3/t16-/m0/s1

> <INCHI_KEY>
BOKVLBSSPUTWLV-INIZCTEOSA-N

> <FORMULA>
C18H21NO3

> <MOLECULAR_WEIGHT>
299.3642

> <EXACT_MASS>
299.152143543

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.249873541988606

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
3.1348029627290432

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.478747372643047

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.87366736995705

> <JCHEM_PKA_STRONGEST_BASIC>
8.196163455842322

> <JCHEM_POLAR_SURFACE_AREA>
52.93000000000001

> <JCHEM_REFRACTIVITY>
87.3731

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-N-methylcoclaurine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060319
     RDKit          3D
(S)-N-Methylcoclaurine
 43 45  0  0  0  0  0  0  0  0999 V2000
   -5.8479    1.4023    0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1638    0.5553   -0.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7852    0.4422   -0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0904    1.1605    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398    1.0295    0.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0811    0.1799   -0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7530   -0.5326   -1.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1239   -0.3973   -1.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8907   -1.0833   -2.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3924    0.1346   -0.1675 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0909   -0.7504   -1.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5434   -0.7086   -0.8534 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3744    0.2267   -1.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7255    0.2648   -1.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3079   -0.6148   -0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6637   -0.6255   -0.0300 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -1.5559    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1389   -1.5903    0.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6273   -0.2008    1.2203 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0072   -1.4605    1.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1980    0.8662    2.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8682    1.7386    1.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3652    2.4210    0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8906    1.5823    0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8480    1.0296    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5801    1.8227    1.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2171   -1.1805   -1.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4107   -1.6961   -2.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7596    1.1706   -0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7525   -1.8054   -1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8962   -0.3913   -2.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8823    0.9176   -2.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3273    1.0047   -1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3362    0.0094   -0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9551   -2.2588    0.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5512   -2.3396    0.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698   -2.0242    2.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8816   -1.2780    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3308   -2.0386    0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2079    0.3725    3.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0748    1.4561    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3622    2.5530    0.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4405    2.1926    2.3541 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
 19 21  1  0
 21 22  1  0
  8  3  1  0
 18 12  1  0
 22  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  1
 11 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
M  END

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -6.930   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       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   22                                                            
CONECT    3    5   12                                                       
CONECT    4    6   12                                                       
CONECT    5    3   14                                                       
CONECT    6    4   14                                                       
CONECT    7    8   13                                                       
CONECT    8    7   19                                                       
CONECT    9   12   16                                                       
CONECT   10   13   18                                                       
CONECT   11   15   17                                                       
CONECT   12    3    4    9                                                  
CONECT   13    7   10   15                                                  
CONECT   14    5    6   20                                                  
CONECT   15   11   13   16                                                  
CONECT   16    9   15   19                                                  
CONECT   17   11   18   21                                                  
CONECT   18   10   17   22                                                  
CONECT   19    1    8   16                                                  
CONECT   20   14                                                            
CONECT   21   17                                                            
CONECT   22    2   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0060319
HETATM    1  C1  UNL     1      -5.848   1.402   0.340  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.164   0.555  -0.549  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.785   0.442  -0.465  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.090   1.161   0.490  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.740   1.030   0.549  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.081   0.180  -0.348  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.753  -0.533  -1.293  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.124  -0.397  -1.350  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.891  -1.083  -2.279  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.392   0.135  -0.168  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.091  -0.750  -1.135  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.543  -0.709  -0.853  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.374   0.227  -1.460  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.726   0.265  -1.199  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.308  -0.615  -0.333  1.00  0.00           C  
HETATM   16  O3  UNL     1       6.664  -0.626  -0.030  1.00  0.00           O  
HETATM   17  C14 UNL     1       4.504  -1.556   0.284  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.139  -1.590   0.017  1.00  0.00           C  
HETATM   19  N1  UNL     1       0.627  -0.201   1.220  1.00  0.00           N  
HETATM   20  C16 UNL     1       0.007  -1.461   1.585  1.00  0.00           C  
HETATM   21  C17 UNL     1       0.198   0.866   2.085  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.868   1.739   1.520  1.00  0.00           C  
HETATM   23  H1  UNL     1      -5.365   2.421   0.393  1.00  0.00           H  
HETATM   24  H2  UNL     1      -6.891   1.582   0.047  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.848   1.030   1.378  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.580   1.823   1.193  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.217  -1.180  -1.972  1.00  0.00           H  
HETATM   28  H6  UNL     1      -3.411  -1.696  -2.925  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.760   1.171  -0.319  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.753  -1.805  -1.104  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.896  -0.391  -2.160  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.882   0.918  -2.147  1.00  0.00           H  
HETATM   33  H11 UNL     1       5.327   1.005  -1.691  1.00  0.00           H  
HETATM   34  H12 UNL     1       7.336   0.009  -0.418  1.00  0.00           H  
HETATM   35  H13 UNL     1       4.955  -2.259   0.973  1.00  0.00           H  
HETATM   36  H14 UNL     1       2.551  -2.340   0.519  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.770  -2.024   2.177  1.00  0.00           H  
HETATM   38  H16 UNL     1      -0.882  -1.278   2.217  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.331  -2.039   0.702  1.00  0.00           H  
HETATM   40  H18 UNL     1      -0.208   0.372   3.014  1.00  0.00           H  
HETATM   41  H19 UNL     1       1.075   1.456   2.386  1.00  0.00           H  
HETATM   42  H20 UNL     1      -0.362   2.553   0.938  1.00  0.00           H  
HETATM   43  H21 UNL     1      -1.441   2.193   2.354  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   26
CONECT    5    6    6   22
CONECT    6    7   10
CONECT    7    8    8   27
CONECT    8    9
CONECT    9   28
CONECT   10   11   19   29
CONECT   11   12   30   31
CONECT   12   13   13   18
CONECT   13   14   32
CONECT   14   15   15   33
CONECT   15   16   17
CONECT   16   34
CONECT   17   18   18   35
CONECT   18   36
CONECT   19   20   21
CONECT   20   37   38   39
CONECT   21   22   40   41
CONECT   22   42   43
END

HMDB0060319
     RDKit          3D
(S)-N-Methylcoclaurine
 43 45  0  0  0  0  0  0  0  0999 V2000
   -5.8479    1.4023    0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1638    0.5553   -0.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7852    0.4422   -0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0904    1.1605    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398    1.0295    0.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0811    0.1799   -0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7530   -0.5326   -1.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1239   -0.3973   -1.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8907   -1.0833   -2.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3924    0.1346   -0.1675 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0909   -0.7504   -1.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5434   -0.7086   -0.8534 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3744    0.2267   -1.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7255    0.2648   -1.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3079   -0.6148   -0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6637   -0.6255   -0.0300 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -1.5559    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1389   -1.5903    0.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6273   -0.2008    1.2203 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0072   -1.4605    1.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1980    0.8662    2.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8682    1.7386    1.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3652    2.4210    0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8906    1.5823    0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8480    1.0296    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5801    1.8227    1.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2171   -1.1805   -1.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4107   -1.6961   -2.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7596    1.1706   -0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7525   -1.8054   -1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8962   -0.3913   -2.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8823    0.9176   -2.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3273    1.0047   -1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3362    0.0094   -0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9551   -2.2588    0.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5512   -2.3396    0.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698   -2.0242    2.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8816   -1.2780    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3308   -2.0386    0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2079    0.3725    3.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0748    1.4561    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3622    2.5530    0.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4405    2.1926    2.3541 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
 19 21  1  0
 21 22  1  0
  8  3  1  0
 18 12  1  0
 22  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  1
 11 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(S)-1,2,3,4-Tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinol	ChEBI

Chemical Formula

C₁₈H₂₁NO₃

Average Molecular Weight

299.3642

Monoisotopic Molecular Weight

299.152143543

IUPAC Name

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

Traditional Name

(S)-N-methylcoclaurine

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2[C@H](CC3=CC=C(O)C=C3)N(C)CCC2=C1

InChI Identifier

InChI=1S/C18H21NO3/c1-19-8-7-13-10-18(22-2)17(21)11-15(13)16(19)9-12-3-5-14(20)6-4-12/h3-6,10-11,16,20-21H,7-9H2,1-2H3/t16-/m0/s1

InChI Key

BOKVLBSSPUTWLV-INIZCTEOSA-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
Monocyclic benzene moiety
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Azacycle
Ether
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

N-methylcoclaurine (CHEBI:17041 )
Isoquinoline alkaloids (C05176 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0060319)

Source

Exogenous

Exogenous (HMDB: HMDB0060319)

Process

Not Available

Role

Not Available

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
Water Solubility	0.29 g/L	ALOGPS
logP	2.69	ALOGPS
logP	3.13	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	8.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.93 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	87.37 m³·mol⁻¹	ChemAxon
Polarizability	33.25 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]+	171.152	31661259
DarkChem	[M-H]-	173.265	31661259
DeepCCS	[M+H]+	180.365	30932474
DeepCCS	[M-H]-	178.007	30932474
DeepCCS	[M-2H]-	211.923	30932474
DeepCCS	[M+Na]+	187.149	30932474
AllCCS	[M+H]+	173.5	32859911
AllCCS	[M+H-H2O]+	170.0	32859911
AllCCS	[M+NH4]+	176.8	32859911
AllCCS	[M+Na]+	177.7	32859911
AllCCS	[M-H]-	177.7	32859911
AllCCS	[M+Na-2H]-	177.5	32859911
AllCCS	[M+HCOO]-	177.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.51 minutes	32390414
Predicted by Siyang on May 30, 2022	10.4508 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.25 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	965.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	207.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	152.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	159.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	96.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	427.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	371.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	571.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	762.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	316.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1098.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	208.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	287.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	471.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	366.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	12.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-N-Methylcoclaurine	COC1=C(O)C=C2[C@H](CC3=CC=C(O)C=C3)N(C)CCC2=C1	4034.1	Standard polar	33892256
(S)-N-Methylcoclaurine	COC1=C(O)C=C2[C@H](CC3=CC=C(O)C=C3)N(C)CCC2=C1	2642.7	Standard non polar	33892256
(S)-N-Methylcoclaurine	COC1=C(O)C=C2[C@H](CC3=CC=C(O)C=C3)N(C)CCC2=C1	2714.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-N-Methylcoclaurine,1TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)[C@H](CC1=CC=C(O)C=C1)N(C)CC2	2630.9	Semi standard non polar	33892256
(S)-N-Methylcoclaurine,1TMS,isomer #2	COC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O[Si](C)(C)C)C=C1)N(C)CC2	2623.2	Semi standard non polar	33892256
(S)-N-Methylcoclaurine,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)[C@H](CC1=CC=C(O[Si](C)(C)C)C=C1)N(C)CC2	2608.9	Semi standard non polar	33892256
(S)-N-Methylcoclaurine,1TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=C(O)C=C1)N(C)CC2	2894.8	Semi standard non polar	33892256
(S)-N-Methylcoclaurine,1TBDMS,isomer #2	COC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N(C)CC2	2885.0	Semi standard non polar	33892256
(S)-N-Methylcoclaurine,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N(C)CC2	3070.2	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)-N-Methylcoclaurine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-0900000000-086f09f17db300a59724	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-N-Methylcoclaurine GC-MS (2 TMS) - 70eV, Positive	splash10-01t9-1490200000-98a8949aca2ab2217916	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-N-Methylcoclaurine 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)-N-Methylcoclaurine 10V, Positive-QTOF	splash10-0udi-0019000000-c0d82165ca1fb9b38f35	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 20V, Positive-QTOF	splash10-0l06-0942000000-baf99463c63a33e3ae7b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 40V, Positive-QTOF	splash10-05r0-4920000000-116ece8d4676b862dbb5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 10V, Negative-QTOF	splash10-0002-0090000000-c6fad313f45df56a5396	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 20V, Negative-QTOF	splash10-0002-0090000000-bf4c2bfd38d87099b5c6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 40V, Negative-QTOF	splash10-0h00-1690000000-4cf29ba63cf2e71c858c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 10V, Positive-QTOF	splash10-0udi-0009000000-1d8c7ea64ca3af7aef5e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 20V, Positive-QTOF	splash10-1000-0494000000-c1be3351bd3522398f96	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 40V, Positive-QTOF	splash10-006y-4950000000-a6e2e5d2269bf93939e8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 10V, Negative-QTOF	splash10-0002-0090000000-cf6f68fb1a2e8ad8e416	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 20V, Negative-QTOF	splash10-0002-0090000000-3677eb70c67fa707ba17	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 40V, Negative-QTOF	splash10-004i-1690000000-049aecb2081c4545a6d4	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

Not Available

KNApSAcK ID

C00025268

Chemspider ID

Not Available

KEGG Compound ID

C05176

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440584

PDB ID

Not Available

ChEBI ID

17041

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

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Tyrosinase

General function:: Involved in oxidoreductase activity
Specific function:: This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:: TYR
Uniprot ID:: P14679
Molecular weight:: 60392.69

Reactions

(S)-N-Methylcoclaurine + Oxygen + Reduced acceptor → (S)-3-Hydroxy-N-methylcoclaurine + Water + Acceptor	details

Showing metabocard for (S)-N-Methylcoclaurine (HMDB0060319)

MOL for HMDB0060319 ((S)-N-Methylcoclaurine)

3D MOL for HMDB0060319 ((S)-N-Methylcoclaurine)

3D SDF for HMDB0060319 ((S)-N-Methylcoclaurine)

3D-SDF for HMDB0060319 ((S)-N-Methylcoclaurine)

PDB for HMDB0060319 ((S)-N-Methylcoclaurine)

3D PDB for HMDB0060319 ((S)-N-Methylcoclaurine)

SMILES for HMDB0060319 ((S)-N-Methylcoclaurine)

INCHI for HMDB0060319 ((S)-N-Methylcoclaurine)

Structure for HMDB0060319 ((S)-N-Methylcoclaurine)

3D Structure for HMDB0060319 ((S)-N-Methylcoclaurine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions