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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:03:50 UTC

Update Date

2022-03-07 02:55:53 UTC

HMDB ID

HMDB0038725

Secondary Accession Numbers

HMDB38725

Metabolite Identification

Common Name

(R)-Juziphine

Description

(R)-Juziphine 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)-Juziphine has been detected, but not quantified in, fruits. This could make (R)-juziphine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (R)-Juziphine.

Structure

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

HMDB0038725
     RDKit          3D
(R)-Juziphine
 43 45  0  0  0  0  0  0  0  0999 V2000
   -3.8742    3.4719   -0.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7292    2.7181   -0.9128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4861    1.4647   -0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4050    0.8976    0.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1085   -0.3601    0.9658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9634   -0.9992    0.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0053   -0.4021   -0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2843    0.8217   -0.7280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4180    1.4543   -1.5885 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1905   -1.1876   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4486   -0.7187   -1.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2757    0.2269   -0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667    1.5096   -0.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2142    2.4242    0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8022    2.0084    1.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5528    2.9263    2.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6322    0.7003    1.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8870   -0.1736    0.9535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1411   -2.5252   -0.9571 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9954   -3.4094   -1.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -3.1228   -0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6104   -2.3759    1.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0405    4.2823   -1.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9385    3.8326    0.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7531    2.7749   -0.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2980    1.4367    0.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8596   -0.8091    1.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6070    2.3611   -1.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -1.5112    0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2749   -0.2227   -2.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1603   -1.5482   -1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0696    1.9394   -1.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3462    3.4641   -0.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5586    3.0242    1.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1181    0.4048    2.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7437   -1.1994    1.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6392   -4.4854   -1.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7322   -3.2105   -0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4548   -3.2747   -2.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8740   -4.1381    0.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -3.2336   -0.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5239   -2.9112    1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8291   -2.3253    1.8273 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
  7 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  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  9 28  1  0
 10 29  1  0
 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 05061310362D          

 22 24  0  0  0  0            999 V2000
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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    3.3000    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    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
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
 10  9  1  0  0  0  0
 12  3  2  0  0  0  0
 12  4  1  0  0  0  0
 12 11  1  0  0  0  0
 13  5  1  0  0  0  0
 13  9  1  0  0  0  0
 14  6  2  0  0  0  0
 14  7  1  0  0  0  0
 15 11  1  0  0  0  0
 16  8  1  0  0  0  0
 17 13  2  0  0  0  0
 17 15  1  0  0  0  0
 18 16  2  0  0  0  0
 18 17  1  0  0  0  0
 19  1  1  0  0  0  0
 19 10  1  0  0  0  0
 19 15  1  0  0  0  0
 20 14  1  0  0  0  0
 21 18  1  0  0  0  0
 22  2  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038725

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C2=C(CCN(C)C2CC2=CC=C(O)C=C2)C=C1

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

> <INCHI_KEY>
QRKWLDOOAQAGAE-UHFFFAOYSA-N

> <FORMULA>
C18H21NO3

> <MOLECULAR_WEIGHT>
299.3642

> <EXACT_MASS>
299.152143543

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.77719288563671

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(4-hydroxyphenyl)methyl]-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-8-ol

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
1.89205327058791

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.056345639742618

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.269703308579916

> <JCHEM_PKA_STRONGEST_BASIC>
12.36091578747669

> <JCHEM_POLAR_SURFACE_AREA>
52.93000000000001

> <JCHEM_REFRACTIVITY>
87.37310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(4-hydroxyphenyl)methyl]-7-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-8-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038725
     RDKit          3D
(R)-Juziphine
 43 45  0  0  0  0  0  0  0  0999 V2000
   -3.8742    3.4719   -0.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7292    2.7181   -0.9128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4861    1.4647   -0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4050    0.8976    0.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1085   -0.3601    0.9658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9634   -0.9992    0.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0053   -0.4021   -0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2843    0.8217   -0.7280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4180    1.4543   -1.5885 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1905   -1.1876   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4486   -0.7187   -1.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2757    0.2269   -0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667    1.5096   -0.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2142    2.4242    0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8022    2.0084    1.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5528    2.9263    2.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6322    0.7003    1.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8870   -0.1736    0.9535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1411   -2.5252   -0.9571 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9954   -3.4094   -1.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -3.1228   -0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6104   -2.3759    1.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0405    4.2823   -1.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9385    3.8326    0.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7531    2.7749   -0.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2980    1.4367    0.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8596   -0.8091    1.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6070    2.3611   -1.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -1.5112    0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2749   -0.2227   -2.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1603   -1.5482   -1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0696    1.9394   -1.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3462    3.4641   -0.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5586    3.0242    1.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1181    0.4048    2.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7437   -1.1994    1.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6392   -4.4854   -1.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7322   -3.2105   -0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4548   -3.2747   -2.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8740   -4.1381    0.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -3.2336   -0.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5239   -2.9112    1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8291   -2.3253    1.8273 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
  7 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  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  9 28  1  0
 10 29  1  0
 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                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       4.001   3.850   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       8.002   9.240   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   22                                                            
CONECT    3    6   12                                                       
CONECT    4    7   12                                                       
CONECT    5    8   13                                                       
CONECT    6    3   14                                                       
CONECT    7    4   14                                                       
CONECT    8    5   16                                                       
CONECT    9   10   13                                                       
CONECT   10    9   19                                                       
CONECT   11   12   15                                                       
CONECT   12    3    4   11                                                  
CONECT   13    5    9   17                                                  
CONECT   14    6    7   20                                                  
CONECT   15   11   17   19                                                  
CONECT   16    8   18   22                                                  
CONECT   17   13   15   18                                                  
CONECT   18   16   17   21                                                  
CONECT   19    1   10   15                                                  
CONECT   20   14                                                            
CONECT   21   18                                                            
CONECT   22    2   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0038725
HETATM    1  C1  UNL     1      -3.874   3.472  -0.655  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.729   2.718  -0.913  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.486   1.465  -0.378  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.405   0.898   0.462  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.108  -0.360   0.966  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.963  -0.999   0.646  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.005  -0.402  -0.226  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.284   0.822  -0.728  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.418   1.454  -1.588  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.191  -1.188  -0.487  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.449  -0.719  -1.000  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.276   0.227  -0.241  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.467   1.510  -0.605  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.214   2.424   0.125  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.802   2.008   1.292  1.00  0.00           C  
HETATM   16  O3  UNL     1       4.553   2.926   2.025  1.00  0.00           O  
HETATM   17  C14 UNL     1       3.632   0.700   1.699  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.887  -0.174   0.953  1.00  0.00           C  
HETATM   19  N1  UNL     1      -0.141  -2.525  -0.957  1.00  0.00           N  
HETATM   20  C16 UNL     1       0.995  -3.409  -1.042  1.00  0.00           C  
HETATM   21  C17 UNL     1      -1.187  -3.123  -0.161  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.610  -2.376   1.062  1.00  0.00           C  
HETATM   23  H1  UNL     1      -4.040   4.282  -1.366  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.938   3.833   0.401  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.753   2.775  -0.777  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.298   1.437   0.691  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.860  -0.809   1.642  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.607   2.361  -1.980  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.454  -1.511   0.676  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.275  -0.223  -2.025  1.00  0.00           H  
HETATM   31  H9  UNL     1       2.160  -1.548  -1.297  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.070   1.939  -1.542  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.346   3.464  -0.204  1.00  0.00           H  
HETATM   34  H12 UNL     1       5.559   3.024   1.838  1.00  0.00           H  
HETATM   35  H13 UNL     1       4.118   0.405   2.637  1.00  0.00           H  
HETATM   36  H14 UNL     1       2.744  -1.199   1.257  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.639  -4.485  -1.017  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.732  -3.211  -0.272  1.00  0.00           H  
HETATM   39  H17 UNL     1       1.455  -3.275  -2.038  1.00  0.00           H  
HETATM   40  H18 UNL     1      -0.874  -4.138   0.147  1.00  0.00           H  
HETATM   41  H19 UNL     1      -2.080  -3.234  -0.828  1.00  0.00           H  
HETATM   42  H20 UNL     1      -2.524  -2.911   1.457  1.00  0.00           H  
HETATM   43  H21 UNL     1      -0.829  -2.325   1.827  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   27
CONECT    6    7   22
CONECT    7    8    8   10
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

HMDB0038725
     RDKit          3D
(R)-Juziphine
 43 45  0  0  0  0  0  0  0  0999 V2000
   -3.8742    3.4719   -0.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7292    2.7181   -0.9128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4861    1.4647   -0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4050    0.8976    0.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1085   -0.3601    0.9658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9634   -0.9992    0.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0053   -0.4021   -0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2843    0.8217   -0.7280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4180    1.4543   -1.5885 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1905   -1.1876   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4486   -0.7187   -1.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2757    0.2269   -0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667    1.5096   -0.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2142    2.4242    0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8022    2.0084    1.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5528    2.9263    2.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6322    0.7003    1.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8870   -0.1736    0.9535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1411   -2.5252   -0.9571 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9954   -3.4094   -1.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -3.1228   -0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6104   -2.3759    1.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0405    4.2823   -1.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9385    3.8326    0.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7531    2.7749   -0.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2980    1.4367    0.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8596   -0.8091    1.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6070    2.3611   -1.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -1.5112    0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2749   -0.2227   -2.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1603   -1.5482   -1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0696    1.9394   -1.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3462    3.4641   -0.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5586    3.0242    1.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1181    0.4048    2.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7437   -1.1994    1.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6392   -4.4854   -1.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7322   -3.2105   -0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4548   -3.2747   -2.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8740   -4.1381    0.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -3.2336   -0.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5239   -2.9112    1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8291   -2.3253    1.8273 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
  7 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  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  9 28  1  0
 10 29  1  0
 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
(+)-Juziphine	HMDB
Juziphine	HMDB
Yuziphine	HMDB

Chemical Formula

C₁₈H₂₁NO₃

Average Molecular Weight

299.3642

Monoisotopic Molecular Weight

299.152143543

IUPAC Name

1-[(4-hydroxyphenyl)methyl]-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-8-ol

Traditional Name

1-[(4-hydroxyphenyl)methyl]-7-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-8-ol

CAS Registry Number

64091-05-0

SMILES

COC1=C(O)C2=C(CCN(C)C2CC2=CC=C(O)C=C2)C=C1

InChI Identifier

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

InChI Key

QRKWLDOOAQAGAE-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
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Aralkylamine
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Ether
Azacycle
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0038725)
Cell membrane (HMDB: HMDB0038725)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038725)

Source

Exogenous

Exogenous (HMDB: HMDB0038725)

Food

Food (HMDB: HMDB0038725)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0038725)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038725)

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	1454 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.33 g/L	ALOGPS
logP	2.65	ALOGPS
logP	1.89	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.27	ChemAxon
pKa (Strongest Basic)	12.36	ChemAxon
Physiological Charge	0	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	32.78 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]+	171.226	31661259
DarkChem	[M-H]-	170.777	31661259
DeepCCS	[M+H]+	174.662	30932474
DeepCCS	[M-H]-	172.304	30932474
DeepCCS	[M-2H]-	205.549	30932474
DeepCCS	[M+Na]+	180.775	30932474
AllCCS	[M+H]+	172.8	32859911
AllCCS	[M+H-H2O]+	169.3	32859911
AllCCS	[M+NH4]+	176.1	32859911
AllCCS	[M+Na]+	177.1	32859911
AllCCS	[M-H]-	177.5	32859911
AllCCS	[M+Na-2H]-	177.2	32859911
AllCCS	[M+HCOO]-	177.0	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.	3.63 minutes	32390414
Predicted by Siyang on May 30, 2022	10.607 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.3 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	31.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1046.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	213.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	158.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	110.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	459.9 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	414.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	550.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	806.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	332.1 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	1151.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	219.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	303.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	438.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	360.6 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	12.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Juziphine	COC1=C(O)C2=C(CCN(C)C2CC2=CC=C(O)C=C2)C=C1	3819.0	Standard polar	33892256
(R)-Juziphine	COC1=C(O)C2=C(CCN(C)C2CC2=CC=C(O)C=C2)C=C1	2591.4	Standard non polar	33892256
(R)-Juziphine	COC1=C(O)C2=C(CCN(C)C2CC2=CC=C(O)C=C2)C=C1	2699.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-Juziphine,1TMS,isomer #1	COC1=CC=C2CCN(C)C(CC3=CC=C(O)C=C3)C2=C1O[Si](C)(C)C	2614.7	Semi standard non polar	33892256
(R)-Juziphine,1TMS,isomer #2	COC1=CC=C2CCN(C)C(CC3=CC=C(O[Si](C)(C)C)C=C3)C2=C1O	2533.7	Semi standard non polar	33892256
(R)-Juziphine,2TMS,isomer #1	COC1=CC=C2CCN(C)C(CC3=CC=C(O[Si](C)(C)C)C=C3)C2=C1O[Si](C)(C)C	2549.5	Semi standard non polar	33892256
(R)-Juziphine,1TBDMS,isomer #1	COC1=CC=C2CCN(C)C(CC3=CC=C(O)C=C3)C2=C1O[Si](C)(C)C(C)(C)C	2872.2	Semi standard non polar	33892256
(R)-Juziphine,1TBDMS,isomer #2	COC1=CC=C2CCN(C)C(CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C2=C1O	2796.6	Semi standard non polar	33892256
(R)-Juziphine,2TBDMS,isomer #1	COC1=CC=C2CCN(C)C(CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C2=C1O[Si](C)(C)C(C)(C)C	3010.6	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 - (R)-Juziphine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-0900000000-2d8c725c8ce2c1cd4d13	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Juziphine GC-MS (2 TMS) - 70eV, Positive	splash10-0201-5390300000-314cc1edc0a53d5c2fde	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Juziphine 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)-Juziphine 10V, Positive-QTOF	splash10-0udi-0129000000-51cf4e91fdd62d2e0ff8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Juziphine 20V, Positive-QTOF	splash10-0gi3-0921000000-c9faa0d32a1dab0e36ec	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Juziphine 40V, Positive-QTOF	splash10-0690-4900000000-d5293c67c3a9341d176c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Juziphine 10V, Negative-QTOF	splash10-0002-0090000000-3fba0f9fe6f906e51a6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Juziphine 20V, Negative-QTOF	splash10-0002-0090000000-dfe47c64124d663e4b4e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Juziphine 40V, Negative-QTOF	splash10-004i-1970000000-643c5506b5d97aa1e4ce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Juziphine 10V, Positive-QTOF	splash10-0udi-0009000000-d2a7655cdd6ad3624955	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Juziphine 20V, Positive-QTOF	splash10-0udi-0947000000-ac5070413cef715b7aa2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Juziphine 40V, Positive-QTOF	splash10-0m4x-3920000000-136a326a093e635104f3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Juziphine 10V, Negative-QTOF	splash10-0002-0090000000-cf6f68fb1a2e8ad8e416	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Juziphine 20V, Negative-QTOF	splash10-0002-0090000000-6bcee3d3660d35c7df49	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Juziphine 40V, Negative-QTOF	splash10-0fml-0490000000-e40be6dee122f93650d7	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB018133

KNApSAcK ID

C00025924

Chemspider ID

35014647

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14526072

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1870791

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)-Juziphine (HMDB0038725)

MOL for HMDB0038725 ((R)-Juziphine)

3D MOL for HMDB0038725 ((R)-Juziphine)

3D SDF for HMDB0038725 ((R)-Juziphine)

3D-SDF for HMDB0038725 ((R)-Juziphine)

PDB for HMDB0038725 ((R)-Juziphine)

3D PDB for HMDB0038725 ((R)-Juziphine)

SMILES for HMDB0038725 ((R)-Juziphine)

INCHI for HMDB0038725 ((R)-Juziphine)

Structure for HMDB0038725 ((R)-Juziphine)

3D Structure for HMDB0038725 ((R)-Juziphine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra