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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:45 UTC

Update Date

2022-03-07 02:53:36 UTC

HMDB ID

HMDB0033103

Secondary Accession Numbers

HMDB33103

Metabolite Identification

Common Name

(R)-Higenamine

Description

(R)-Higenamine, also known as norcoclaurine, belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached (R)-Higenamine is a sweet, fruity, and milky tasting compound (R)-Higenamine has been detected, but not quantified in, custard apples (Annona reticulata) and opium poppies (Papaver somniferum). This could make (R)-higenamine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (R)-Higenamine.

Structure

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

HMDB0033103
     RDKit          3D
(R)-Higenamine
 37 39  0  0  0  0  0  0  0  0999 V2000
    6.2689   -0.0862   -0.7713 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9096   -0.1776   -0.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1795   -1.2749   -0.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8274   -1.3862   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1697   -0.4023    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7325   -0.4870    0.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1474    0.1292   -0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1151    1.5039   -0.7797 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6036    2.3836    0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0774    2.1979    0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4636    0.7725    0.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719    0.3871    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1404   -0.9369    0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4492   -1.3266    0.7449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1872   -1.8938    0.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5457   -3.2177    0.1544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8921   -1.5497   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5465   -0.1943   -0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125    0.6926    0.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2604    0.8057    0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9890   -0.4520   -0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6551   -2.0618   -1.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2306   -2.2431   -0.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4781   -1.5659    0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4884    0.0037    1.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0695   -0.4159   -1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1309    1.8177   -1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3516    3.4278   -0.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2012    2.2554    1.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5441    2.7482   -0.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5246    2.6645    0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4886    1.1507    0.6237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1447   -0.6481    0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4893   -3.4849    0.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1477   -2.3082   -0.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4712    1.4956    1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8284    1.6773    0.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 18  7  1  0
 18 11  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
M  END


  Mrv0541 02241214502D          

 20 22  0  0  0  0            999 V2000
   -1.7712    1.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0299    1.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3701    1.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4527    0.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    0.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7712    0.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136    0.2478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3711    1.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1124    1.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1124    0.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4527    0.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3711   -0.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2875   -1.0706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8548    1.8130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5136    1.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5136    0.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8548    0.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8548   -0.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1124   -1.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1124   -1.8956    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
  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
M  END
> <DATABASE_ID>
HMDB0033103

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(CC2NCCC3=C2C=C(O)C(O)=C3)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO3/c18-12-3-1-10(2-4-12)7-14-13-9-16(20)15(19)8-11(13)5-6-17-14/h1-4,8-9,14,17-20H,5-7H2

> <INCHI_KEY>
WZRCQWQRFZITDX-UHFFFAOYSA-N

> <FORMULA>
C16H17NO3

> <MOLECULAR_WEIGHT>
271.3111

> <EXACT_MASS>
271.120843415

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.245963941760756

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
2.2310176765251515

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.338482144787472

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.745574891365035

> <JCHEM_PKA_STRONGEST_BASIC>
9.547144490623493

> <JCHEM_POLAR_SURFACE_AREA>
72.72

> <JCHEM_REFRACTIVITY>
77.5961

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
higenamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033103
     RDKit          3D
(R)-Higenamine
 37 39  0  0  0  0  0  0  0  0999 V2000
    6.2689   -0.0862   -0.7713 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9096   -0.1776   -0.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1795   -1.2749   -0.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8274   -1.3862   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1697   -0.4023    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7325   -0.4870    0.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1474    0.1292   -0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1151    1.5039   -0.7797 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6036    2.3836    0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0774    2.1979    0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4636    0.7725    0.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719    0.3871    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1404   -0.9369    0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4492   -1.3266    0.7449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1872   -1.8938    0.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5457   -3.2177    0.1544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8921   -1.5497   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5465   -0.1943   -0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125    0.6926    0.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2604    0.8057    0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9890   -0.4520   -0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6551   -2.0618   -1.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2306   -2.2431   -0.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4781   -1.5659    0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4884    0.0037    1.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0695   -0.4159   -1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1309    1.8177   -1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3516    3.4278   -0.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2012    2.2554    1.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5441    2.7482   -0.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5246    2.6645    0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4886    1.1507    0.6237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1447   -0.6481    0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4893   -3.4849    0.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1477   -2.3082   -0.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4712    1.4956    1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8284    1.6773    0.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 18  7  1  0
 18 11  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 20 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      -3.306   2.768   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.922   3.538   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.691   2.768   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.845   1.230   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.077   0.463   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.306   1.230   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.692   0.463   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.693   3.538   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.076   2.615   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.076   1.075   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.845   0.308   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.693  -1.230   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.537  -1.998   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       3.462   3.384   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.692   2.615   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.692   1.075   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.462   0.308   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.462  -1.230   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.076  -1.998   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.076  -3.538   0.000  0.00  0.00           O+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                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0033103
HETATM    1  O1  UNL     1       6.269  -0.086  -0.771  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.910  -0.178  -0.452  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.179  -1.275  -0.848  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.827  -1.386  -0.541  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.170  -0.402   0.170  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.733  -0.487   0.514  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.147   0.129  -0.551  1.00  0.00           C  
HETATM    8  N1  UNL     1       0.115   1.504  -0.780  1.00  0.00           N  
HETATM    9  C7  UNL     1      -0.604   2.384   0.121  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.077   2.198   0.051  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.464   0.773   0.080  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.772   0.387   0.399  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.140  -0.937   0.426  1.00  0.00           C  
HETATM   14  O2  UNL     1      -5.449  -1.327   0.745  1.00  0.00           O  
HETATM   15  C12 UNL     1      -3.187  -1.894   0.130  1.00  0.00           C  
HETATM   16  O3  UNL     1      -3.546  -3.218   0.154  1.00  0.00           O  
HETATM   17  C13 UNL     1      -1.892  -1.550  -0.188  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.546  -0.194  -0.207  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.912   0.693   0.561  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.260   0.806   0.257  1.00  0.00           C  
HETATM   21  H1  UNL     1       6.989  -0.452  -0.153  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.655  -2.062  -1.403  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.231  -2.243  -0.844  1.00  0.00           H  
HETATM   24  H4  UNL     1       0.478  -1.566   0.563  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.488   0.004   1.469  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.069  -0.416  -1.518  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.131   1.818  -1.753  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.352   3.428  -0.196  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.201   2.255   1.139  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.544   2.748  -0.791  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.525   2.664   0.977  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.489   1.151   0.624  1.00  0.00           H  
HETATM   33  H13 UNL     1      -6.145  -0.648   0.960  1.00  0.00           H  
HETATM   34  H14 UNL     1      -4.489  -3.485   0.385  1.00  0.00           H  
HETATM   35  H15 UNL     1      -1.148  -2.308  -0.420  1.00  0.00           H  
HETATM   36  H16 UNL     1       2.471   1.496   1.116  1.00  0.00           H  
HETATM   37  H17 UNL     1       4.828   1.677   0.575  1.00  0.00           H  
CONECT    1    2   21
CONECT    2    3    3   20
CONECT    3    4   22
CONECT    4    5    5   23
CONECT    5    6   19
CONECT    6    7   24   25
CONECT    7    8   18   26
CONECT    8    9   27
CONECT    9   10   28   29
CONECT   10   11   30   31
CONECT   11   12   12   18
CONECT   12   13   32
CONECT   13   14   15   15
CONECT   14   33
CONECT   15   16   17
CONECT   16   34
CONECT   17   18   18   35
CONECT   19   20   20   36
CONECT   20   37
END

HMDB0033103
     RDKit          3D
(R)-Higenamine
 37 39  0  0  0  0  0  0  0  0999 V2000
    6.2689   -0.0862   -0.7713 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9096   -0.1776   -0.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1795   -1.2749   -0.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8274   -1.3862   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1697   -0.4023    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7325   -0.4870    0.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1474    0.1292   -0.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1151    1.5039   -0.7797 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6036    2.3836    0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0774    2.1979    0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4636    0.7725    0.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719    0.3871    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1404   -0.9369    0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4492   -1.3266    0.7449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1872   -1.8938    0.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5457   -3.2177    0.1544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8921   -1.5497   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5465   -0.1943   -0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125    0.6926    0.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2604    0.8057    0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9890   -0.4520   -0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6551   -2.0618   -1.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2306   -2.2431   -0.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4781   -1.5659    0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4884    0.0037    1.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0695   -0.4159   -1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1309    1.8177   -1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3516    3.4278   -0.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2012    2.2554    1.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5441    2.7482   -0.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5246    2.6645    0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4886    1.1507    0.6237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1447   -0.6481    0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4893   -3.4849    0.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1477   -2.3082   -0.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4712    1.4956    1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8284    1.6773    0.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 18  7  1  0
 18 11  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-1,2,3,4-Tetrahydro-1-((4-hydroxyphenyl)methyl)-6,7-isoquinolinediol	ChEBI
(+-)-Demethylcoclaurine	ChEBI
(+-)-Norcoclaurine	ChEBI
(+-)-O-Demethylcoclaurine	ChEBI
(R,S)-Norcoclaurine	ChEBI
6,7-Dihydroxy-1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline	ChEBI
Higenamine	ChEBI
Norcoclaurine	ChEBI
(+)-Demethylcoclaurine	HMDB
(R)-Norcoclaurine	HMDB
Higenamine hydrobromide, (+-)-isomer	MeSH, HMDB
Higenamine oxalate (1:1), (+-)-isomer	MeSH, HMDB
Higenamine, tartrate (1:1), R-(r,r)-(+-)-isomer	MeSH, HMDB
1-(P-Hydroxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline	MeSH, HMDB
O-Demethylcoclaurine	MeSH, HMDB
Higenamine hydrochloride, (S)-isomer	MeSH, HMDB
1(S)-Norcoclaurine	MeSH, HMDB

Chemical Formula

C₁₆H₁₇NO₃

Average Molecular Weight

271.3111

Monoisotopic Molecular Weight

271.120843415

IUPAC Name

1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol

Traditional Name

higenamine

CAS Registry Number

106032-53-5

SMILES

OC1=CC=C(CC2NCCC3=C2C=C(O)C(O)=C3)C=C1

InChI Identifier

InChI=1S/C16H17NO3/c18-12-3-1-10(2-4-12)7-14-13-9-16(20)15(19)8-11(13)5-6-17-14/h1-4,8-9,14,17-20H,5-7H2

InChI Key

WZRCQWQRFZITDX-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
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Secondary aliphatic amine
Secondary amine
Azacycle
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

norcoclaurine (CHEBI:18418 )

Ontology

Opium poppy (FooDB: FOOD00438)

Fruit

Tropical fruit

Custard apple (FooDB: FOOD00014)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	242 - 244 °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	1.73	ALOGPS
logP	2.23	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	8.75	ChemAxon
pKa (Strongest Basic)	9.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	72.72 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.6 m³·mol⁻¹	ChemAxon
Polarizability	29.25 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]+	165.442	31661259
DarkChem	[M-H]-	163.894	31661259
DeepCCS	[M+H]+	166.501	30932474
DeepCCS	[M-H]-	164.143	30932474
DeepCCS	[M-2H]-	197.029	30932474
DeepCCS	[M+Na]+	172.594	30932474
AllCCS	[M+H]+	165.5	32859911
AllCCS	[M+H-H2O]+	161.7	32859911
AllCCS	[M+NH4]+	168.9	32859911
AllCCS	[M+Na]+	169.9	32859911
AllCCS	[M-H]-	168.1	32859911
AllCCS	[M+Na-2H]-	167.8	32859911
AllCCS	[M+HCOO]-	167.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Higenamine	OC1=CC=C(CC2NCCC3=C2C=C(O)C(O)=C3)C=C1	3436.2	Standard polar	33892256
(R)-Higenamine	OC1=CC=C(CC2NCCC3=C2C=C(O)C(O)=C3)C=C1	2823.3	Standard non polar	33892256
(R)-Higenamine	OC1=CC=C(CC2NCCC3=C2C=C(O)C(O)=C3)C=C1	3001.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-Higenamine,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CC2NCCC3=CC(O)=C(O)C=C32)C=C1	2813.5	Semi standard non polar	33892256
(R)-Higenamine,1TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C=C1O)CCNC2CC1=CC=C(O)C=C1	2813.9	Semi standard non polar	33892256
(R)-Higenamine,1TMS,isomer #3	C[Si](C)(C)OC1=CC2=C(C=C1O)C(CC1=CC=C(O)C=C1)NCC2	2811.7	Semi standard non polar	33892256
(R)-Higenamine,1TMS,isomer #4	C[Si](C)(C)N1CCC2=CC(O)=C(O)C=C2C1CC1=CC=C(O)C=C1	2901.9	Semi standard non polar	33892256
(R)-Higenamine,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CC2NCCC3=CC(O[Si](C)(C)C)=C(O)C=C32)C=C1	2713.2	Semi standard non polar	33892256
(R)-Higenamine,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CC2NCCC3=CC(O)=C(O[Si](C)(C)C)C=C32)C=C1	2715.3	Semi standard non polar	33892256
(R)-Higenamine,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(CC2C3=CC(O)=C(O)C=C3CCN2[Si](C)(C)C)C=C1	2796.5	Semi standard non polar	33892256
(R)-Higenamine,2TMS,isomer #4	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)C(CC1=CC=C(O)C=C1)NCC2	2775.7	Semi standard non polar	33892256
(R)-Higenamine,2TMS,isomer #5	C[Si](C)(C)OC1=CC2=C(C=C1O)CCN([Si](C)(C)C)C2CC1=CC=C(O)C=C1	2773.2	Semi standard non polar	33892256
(R)-Higenamine,2TMS,isomer #6	C[Si](C)(C)OC1=CC2=C(C=C1O)C(CC1=CC=C(O)C=C1)N([Si](C)(C)C)CC2	2788.0	Semi standard non polar	33892256
(R)-Higenamine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CC2NCCC3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C32)C=C1	2775.2	Semi standard non polar	33892256
(R)-Higenamine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CC2C3=CC(O)=C(O[Si](C)(C)C)C=C3CCN2[Si](C)(C)C)C=C1	2759.1	Semi standard non polar	33892256
(R)-Higenamine,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C(CC2C3=CC(O[Si](C)(C)C)=C(O)C=C3CCN2[Si](C)(C)C)C=C1	2748.7	Semi standard non polar	33892256
(R)-Higenamine,3TMS,isomer #4	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)C(CC1=CC=C(O)C=C1)N([Si](C)(C)C)CC2	2751.3	Semi standard non polar	33892256
(R)-Higenamine,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CC2C3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C3CCN2[Si](C)(C)C)C=C1	2809.5	Semi standard non polar	33892256
(R)-Higenamine,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CC2C3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C3CCN2[Si](C)(C)C)C=C1	2729.7	Standard non polar	33892256
(R)-Higenamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CC2NCCC3=CC(O)=C(O)C=C32)C=C1	3097.6	Semi standard non polar	33892256
(R)-Higenamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CCNC2CC1=CC=C(O)C=C1	3098.8	Semi standard non polar	33892256
(R)-Higenamine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)C(CC1=CC=C(O)C=C1)NCC2	3102.0	Semi standard non polar	33892256
(R)-Higenamine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1CCC2=CC(O)=C(O)C=C2C1CC1=CC=C(O)C=C1	3173.1	Semi standard non polar	33892256
(R)-Higenamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CC2NCCC3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C32)C=C1	3243.7	Semi standard non polar	33892256
(R)-Higenamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CC2NCCC3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C32)C=C1	3246.5	Semi standard non polar	33892256
(R)-Higenamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(CC2C3=CC(O)=C(O)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C1	3318.5	Semi standard non polar	33892256
(R)-Higenamine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(CC1=CC=C(O)C=C1)NCC2	3276.6	Semi standard non polar	33892256
(R)-Higenamine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CCN([Si](C)(C)C(C)(C)C)C2CC1=CC=C(O)C=C1	3304.4	Semi standard non polar	33892256
(R)-Higenamine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)C(CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)CC2	3307.3	Semi standard non polar	33892256
(R)-Higenamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CC2NCCC3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C32)C=C1	3470.0	Semi standard non polar	33892256
(R)-Higenamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CC2C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C1	3495.0	Semi standard non polar	33892256
(R)-Higenamine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(CC2C3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C1	3498.3	Semi standard non polar	33892256
(R)-Higenamine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)CC2	3482.3	Semi standard non polar	33892256
(R)-Higenamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CC2C3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C1	3724.0	Semi standard non polar	33892256
(R)-Higenamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CC2C3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C1	3527.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Higenamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-0900000000-6b4e08f9ac4d21085fe1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Higenamine GC-MS (3 TMS) - 70eV, Positive	splash10-0ab9-0009600000-9b9f36994fbe2bc44955	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Higenamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Higenamine 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 - (R)-Higenamine 10V, Positive-QTOF	splash10-00di-0190000000-96f0438a3c8200e429fa	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Higenamine 20V, Positive-QTOF	splash10-074r-0950000000-0a5c9c204527cfedca3e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Higenamine 40V, Positive-QTOF	splash10-0a6r-3900000000-d9dc7703828981b3c07c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Higenamine 10V, Negative-QTOF	splash10-00di-0090000000-22dffcee90bf3f5ca3cc	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Higenamine 20V, Negative-QTOF	splash10-00di-0190000000-0fea9c480c329f5a864d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Higenamine 40V, Negative-QTOF	splash10-03di-1910000000-1d1e1af6c74b76f1bc5b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Higenamine 10V, Positive-QTOF	splash10-00di-0090000000-0ce88f6c7aacd22857e8	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Higenamine 20V, Positive-QTOF	splash10-00di-0290000000-4d665e8a013041d3e4c6	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Higenamine 40V, Positive-QTOF	splash10-0f76-4790000000-ad87407e83862f690589	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Higenamine 10V, Negative-QTOF	splash10-00di-0090000000-19dbfadd3d4c17868278	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Higenamine 20V, Negative-QTOF	splash10-00di-0190000000-89e3c768495d58f4e18c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Higenamine 40V, Negative-QTOF	splash10-008d-1920000000-910f9db17a9a05be6045	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

DB12779

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

114840

PDB ID

Not Available

ChEBI ID

18418

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 (R)-Higenamine (HMDB0033103)

MOL for HMDB0033103 ((R)-Higenamine)

3D MOL for HMDB0033103 ((R)-Higenamine)

3D SDF for HMDB0033103 ((R)-Higenamine)

3D-SDF for HMDB0033103 ((R)-Higenamine)

PDB for HMDB0033103 ((R)-Higenamine)

3D PDB for HMDB0033103 ((R)-Higenamine)

SMILES for HMDB0033103 ((R)-Higenamine)

INCHI for HMDB0033103 ((R)-Higenamine)

Structure for HMDB0033103 ((R)-Higenamine)

3D Structure for HMDB0033103 ((R)-Higenamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra