Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:03:48 UTC

Update Date

2022-03-07 02:53:40 UTC

HMDB ID

HMDB0033347

Secondary Accession Numbers

HMDB33347

Metabolite Identification

Common Name

Lotusine

Description

Lotusine belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. Lotusine has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make lotusine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Lotusine.

Structure

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

HMDB0033347
     RDKit          3D
Lotusine
 47 49  0  0  0  0  0  0  0  0999 V2000
   -1.3950    3.8633    2.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3426    3.3691    1.1609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2748    2.0835    0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2869    1.1943    0.9878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2689   -0.0657    0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377   -0.4254   -0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2617    0.4689   -0.8112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2632    1.7247   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841    2.6222   -0.6247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3158   -1.8122   -1.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5167   -2.7452   -0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1888   -2.2243    0.0815 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.4689   -2.1697   -1.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190   -3.1859    0.8939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2216   -0.9911    0.8330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1191   -0.4885    1.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9906    0.1885    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9736    1.5096   -0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8822    2.1263   -0.8695 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8657    1.3882   -1.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7803    1.9955   -2.3453 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9171    0.0380   -1.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0163   -0.5347   -0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2985    3.0700    2.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4149    4.0295    1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7627    4.7572    2.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5707    1.5641    1.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0093    0.1371   -1.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2541    3.5356   -0.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3481   -2.1604   -1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8816   -1.7391   -2.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0978   -2.8925    0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4862   -3.7227   -0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4172   -2.7837   -1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1571   -2.7469   -1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5534   -1.1835   -1.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0713   -4.2175    0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5968   -3.2334    0.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4174   -2.9677    1.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6106   -1.3804    1.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0134    0.1166    2.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6669   -1.4077    1.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2632    2.1581    0.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8433    3.1840   -1.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5592    2.0583   -3.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7020   -0.5145   -1.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1125   -1.5901   -0.1969 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  1  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
  8  3  1  0
 23 17  1  0
 15  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 19 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
M  CHG  1  12   1
M  END


  Mrv0541 05061307042D          

 23 25  0  0  0  0            999 V2000
   -0.0980   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323   -2.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    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  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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  3  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    0.0000    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
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  8  1  0  0  0  0
 13  4  2  0  0  0  0
 13  5  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  2  0  0  0  0
 15  6  2  0  0  0  0
 15  7  1  0  0  0  0
 16 12  2  0  0  0  0
 16 14  1  0  0  0  0
 17 10  1  0  0  0  0
 17 16  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 19 18  2  0  0  0  0
 20  1  1  0  0  0  0
 20  2  1  0  0  0  0
 20  9  1  0  0  0  0
 20 17  1  0  0  0  0
 21 15  1  0  0  0  0
 22 18  1  0  0  0  0
 23  3  1  0  0  0  0
 23 19  1  0  0  0  0
M  CHG  1  20   1
M  END
> <DATABASE_ID>
HMDB0033347

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C2CC[N+](C)(C)C(CC3=CC=C(O)C=C3)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H23NO3/c1-20(2)9-8-14-11-18(22)19(23-3)12-16(14)17(20)10-13-4-6-15(21)7-5-13/h4-7,11-12,17H,8-10H2,1-3H3,(H-,21,22)/p+1

> <INCHI_KEY>
ZKTMLINFIQCERN-UHFFFAOYSA-O

> <FORMULA>
C19H24NO3

> <MOLECULAR_WEIGHT>
314.3988

> <EXACT_MASS>
314.175618639

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.437128776758456

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.80

> <JCHEM_LOGP>
-0.8997060438050789

> <ALOGPS_LOGS>
-5.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.059867437665552

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.34976195524079

> <JCHEM_PKA_STRONGEST_BASIC>
-4.891829385662694

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
103.2867

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-1-[(4-hydroxyphenyl)methyl]-7-methoxy-2,2-dimethyl-3,4-dihydro-1H-isoquinolin-2-ium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033347
     RDKit          3D
Lotusine
 47 49  0  0  0  0  0  0  0  0999 V2000
   -1.3950    3.8633    2.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3426    3.3691    1.1609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2748    2.0835    0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2869    1.1943    0.9878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2689   -0.0657    0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377   -0.4254   -0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2617    0.4689   -0.8112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2632    1.7247   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841    2.6222   -0.6247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3158   -1.8122   -1.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5167   -2.7452   -0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1888   -2.2243    0.0815 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.4689   -2.1697   -1.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190   -3.1859    0.8939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2216   -0.9911    0.8330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1191   -0.4885    1.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9906    0.1885    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9736    1.5096   -0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8822    2.1263   -0.8695 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8657    1.3882   -1.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7803    1.9955   -2.3453 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9171    0.0380   -1.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0163   -0.5347   -0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2985    3.0700    2.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4149    4.0295    1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7627    4.7572    2.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5707    1.5641    1.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0093    0.1371   -1.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2541    3.5356   -0.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3481   -2.1604   -1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8816   -1.7391   -2.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0978   -2.8925    0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4862   -3.7227   -0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4172   -2.7837   -1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1571   -2.7469   -1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5534   -1.1835   -1.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0713   -4.2175    0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5968   -3.2334    0.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4174   -2.9677    1.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6106   -1.3804    1.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0134    0.1166    2.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6669   -1.4077    1.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2632    2.1581    0.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8433    3.1840   -1.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5592    2.0583   -3.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7020   -0.5145   -1.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1125   -1.5901   -0.1969 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  1  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
  8  3  1  0
 23 17  1  0
 15  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 19 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
M  CHG  1  12   1
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      -0.183  -2.043   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.807  -3.757   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   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  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+1
HETATM   21  O   UNK     0       8.002  -7.700   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
HETATM   23  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   20                                                            
CONECT    3   23                                                            
CONECT    4    6   13                                                       
CONECT    5    7   13                                                       
CONECT    6    4   15                                                       
CONECT    7    5   15                                                       
CONECT    8    9   14                                                       
CONECT    9    8   20                                                       
CONECT   10   13   17                                                       
CONECT   11   14   18                                                       
CONECT   12   16   19                                                       
CONECT   13    4    5   10                                                  
CONECT   14    8   11   16                                                  
CONECT   15    6    7   21                                                  
CONECT   16   12   14   17                                                  
CONECT   17   10   16   20                                                  
CONECT   18   11   19   22                                                  
CONECT   19   12   18   23                                                  
CONECT   20    1    2    9   17                                             
CONECT   21   15                                                            
CONECT   22   18                                                            
CONECT   23    3   19                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0033347
HETATM    1  C1  UNL     1      -1.395   3.863   2.090  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.343   3.369   1.161  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.275   2.083   0.642  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.287   1.194   0.988  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.269  -0.066   0.442  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.238  -0.425  -0.440  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.262   0.469  -0.811  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.263   1.725  -0.257  1.00  0.00           C  
HETATM    9  O2  UNL     1      -4.284   2.622  -0.625  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.316  -1.812  -1.048  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.517  -2.745  -0.175  1.00  0.00           C  
HETATM   12  N1  UNL     1      -0.189  -2.224   0.081  1.00  0.00           N1+
HETATM   13  C10 UNL     1       0.469  -2.170  -1.195  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.519  -3.186   0.894  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.222  -0.991   0.833  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.119  -0.489   1.159  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.991   0.189   0.268  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.974   1.510  -0.012  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.882   2.126  -0.869  1.00  0.00           C  
HETATM   20  C17 UNL     1       3.866   1.388  -1.485  1.00  0.00           C  
HETATM   21  O3  UNL     1       4.780   1.996  -2.345  1.00  0.00           O  
HETATM   22  C18 UNL     1       3.917   0.038  -1.224  1.00  0.00           C  
HETATM   23  C19 UNL     1       3.016  -0.535  -0.382  1.00  0.00           C  
HETATM   24  H1  UNL     1      -1.299   3.070   2.875  1.00  0.00           H  
HETATM   25  H2  UNL     1      -0.415   4.030   1.638  1.00  0.00           H  
HETATM   26  H3  UNL     1      -1.763   4.757   2.608  1.00  0.00           H  
HETATM   27  H4  UNL     1      -0.571   1.564   1.709  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.009   0.137  -1.517  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.254   3.536  -0.198  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.348  -2.160  -1.129  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.882  -1.739  -2.056  1.00  0.00           H  
HETATM   32  H9  UNL     1      -2.098  -2.892   0.754  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.486  -3.723  -0.686  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.417  -2.784  -1.212  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.157  -2.747  -1.959  1.00  0.00           H  
HETATM   36  H13 UNL     1       0.553  -1.184  -1.638  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.071  -4.217   0.787  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.597  -3.233   0.678  1.00  0.00           H  
HETATM   39  H16 UNL     1       0.417  -2.968   1.995  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.611  -1.380   1.853  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.013   0.117   2.138  1.00  0.00           H  
HETATM   42  H19 UNL     1       1.667  -1.408   1.586  1.00  0.00           H  
HETATM   43  H20 UNL     1       1.263   2.158   0.424  1.00  0.00           H  
HETATM   44  H21 UNL     1       2.843   3.184  -1.074  1.00  0.00           H  
HETATM   45  H22 UNL     1       4.559   2.058  -3.344  1.00  0.00           H  
HETATM   46  H23 UNL     1       4.702  -0.515  -1.723  1.00  0.00           H  
HETATM   47  H24 UNL     1       3.112  -1.590  -0.197  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   27
CONECT    5    6    6   15
CONECT    6    7   10
CONECT    7    8    8   28
CONECT    8    9
CONECT    9   29
CONECT   10   11   30   31
CONECT   11   12   32   33
CONECT   12   13   14   15
CONECT   13   34   35   36
CONECT   14   37   38   39
CONECT   15   16   40
CONECT   16   17   41   42
CONECT   17   18   18   23
CONECT   18   19   43
CONECT   19   20   20   44
CONECT   20   21   22
CONECT   21   45
CONECT   22   23   23   46
CONECT   23   47
END

HMDB0033347
     RDKit          3D
Lotusine
 47 49  0  0  0  0  0  0  0  0999 V2000
   -1.3950    3.8633    2.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3426    3.3691    1.1609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2748    2.0835    0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2869    1.1943    0.9878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2689   -0.0657    0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377   -0.4254   -0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2617    0.4689   -0.8112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2632    1.7247   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841    2.6222   -0.6247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3158   -1.8122   -1.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5167   -2.7452   -0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1888   -2.2243    0.0815 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.4689   -2.1697   -1.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190   -3.1859    0.8939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2216   -0.9911    0.8330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1191   -0.4885    1.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9906    0.1885    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9736    1.5096   -0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8822    2.1263   -0.8695 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8657    1.3882   -1.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7803    1.9955   -2.3453 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9171    0.0380   -1.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0163   -0.5347   -0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2985    3.0700    2.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4149    4.0295    1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7627    4.7572    2.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5707    1.5641    1.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0093    0.1371   -1.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2541    3.5356   -0.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3481   -2.1604   -1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8816   -1.7391   -2.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0978   -2.8925    0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4862   -3.7227   -0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4172   -2.7837   -1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1571   -2.7469   -1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5534   -1.1835   -1.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0713   -4.2175    0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5968   -3.2334    0.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4174   -2.9677    1.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6106   -1.3804    1.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0134    0.1166    2.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6669   -1.4077    1.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2632    2.1581    0.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8433    3.1840   -1.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5592    2.0583   -3.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7020   -0.5145   -1.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1125   -1.5901   -0.1969 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  1  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
  8  3  1  0
 23 17  1  0
 15  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 19 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
M  CHG  1  12   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-Lotusine	HMDB
(R,S)-Reticuline	HMDB
D-(-)-Lotusine	HMDB

Chemical Formula

C₁₉H₂₄NO₃

Average Molecular Weight

314.3988

Monoisotopic Molecular Weight

314.175618639

IUPAC Name

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

Traditional Name

6-hydroxy-1-[(4-hydroxyphenyl)methyl]-7-methoxy-2,2-dimethyl-3,4-dihydro-1H-isoquinolin-2-ium

CAS Registry Number

6871-67-6

SMILES

COC1=C(O)C=C2CC[N+](C)(C)C(CC3=CC=C(O)C=C3)C2=C1

InChI Identifier

InChI=1S/C19H23NO3/c1-20(2)9-8-14-11-18(22)19(23-3)12-16(14)17(20)10-13-4-6-15(21)7-5-13/h4-7,11-12,17H,8-10H2,1-3H3,(H-,21,22)/p+1

InChI Key

ZKTMLINFIQCERN-UHFFFAOYSA-O

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
Phenol
Alkyl aryl ether
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Tetraalkylammonium salt
Quaternary ammonium salt
Azacycle
Ether
Amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic salt
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033347)
Cytoplasm (HMDB: HMDB0033347)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033347)

Source

Exogenous

Food

Food (HMDB: HMDB0033347)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0033347)

Not Available

Nutrient (HMDB: HMDB0033347)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	213 - 215 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	500.2 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	0.0015 g/L	ALOGPS
logP	0.8	ALOGPS
logP	-0.9	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	7.35	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	103.29 m³·mol⁻¹	ChemAxon
Polarizability	34.44 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	174.208	31661259
DarkChem	[M-H]-	172.423	31661259
DeepCCS	[M+H]+	175.255	30932474
DeepCCS	[M-H]-	172.869	30932474
DeepCCS	[M-2H]-	207.188	30932474
DeepCCS	[M+Na]+	182.416	30932474
AllCCS	[M+H]+	176.6	32859911
AllCCS	[M+H-H2O]+	173.4	32859911
AllCCS	[M+NH4]+	179.6	32859911
AllCCS	[M+Na]+	180.4	32859911
AllCCS	[M-H]-	185.5	32859911
AllCCS	[M+Na-2H]-	186.0	32859911
AllCCS	[M+HCOO]-	186.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lotusine	COC1=C(O)C=C2CC[N+](C)(C)C(CC3=CC=C(O)C=C3)C2=C1	4109.3	Standard polar	33892256
Lotusine	COC1=C(O)C=C2CC[N+](C)(C)C(CC3=CC=C(O)C=C3)C2=C1	2580.9	Standard non polar	33892256
Lotusine	COC1=C(O)C=C2CC[N+](C)(C)C(CC3=CC=C(O)C=C3)C2=C1	2823.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lotusine,1TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CC[N+](C)(C)C2CC1=CC=C(O)C=C1	2765.2	Semi standard non polar	33892256
Lotusine,1TMS,isomer #2	COC1=CC2=C(C=C1O)CC[N+](C)(C)C2CC1=CC=C(O[Si](C)(C)C)C=C1	2758.4	Semi standard non polar	33892256
Lotusine,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)CC[N+](C)(C)C2CC1=CC=C(O[Si](C)(C)C)C=C1	2774.5	Semi standard non polar	33892256
Lotusine,1TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC[N+](C)(C)C2CC1=CC=C(O)C=C1	3015.2	Semi standard non polar	33892256
Lotusine,1TBDMS,isomer #2	COC1=CC2=C(C=C1O)CC[N+](C)(C)C2CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3014.8	Semi standard non polar	33892256
Lotusine,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC[N+](C)(C)C2CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3209.4	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 - Lotusine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0970000000-55c8aa651621361c4f43	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lotusine GC-MS (2 TMS) - 70eV, Positive	splash10-06tf-1390300000-736b93e2d37ec2cdd801	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lotusine 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 - Lotusine 10V, Positive-QTOF	splash10-03di-0119000000-0a8fe1a7f5009a3206c1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lotusine 20V, Positive-QTOF	splash10-0a4i-0951000000-85b9cfbae2f8720c18c2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lotusine 40V, Positive-QTOF	splash10-056r-7900000000-c709a0bb5b22c531fd3f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lotusine 10V, Positive-QTOF	splash10-03di-0049000000-4607b8efe1863232ea28	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lotusine 20V, Positive-QTOF	splash10-0a4i-0491000000-18ff991aa890b08db98e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lotusine 40V, Positive-QTOF	splash10-002f-9720000000-01bdaa63bef2888cdc0e	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

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

78381113

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1835031

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 Lotusine (HMDB0033347)

MOL for HMDB0033347 (Lotusine)

3D MOL for HMDB0033347 (Lotusine)

3D SDF for HMDB0033347 (Lotusine)

3D-SDF for HMDB0033347 (Lotusine)

PDB for HMDB0033347 (Lotusine)

3D PDB for HMDB0033347 (Lotusine)

SMILES for HMDB0033347 (Lotusine)

INCHI for HMDB0033347 (Lotusine)

Structure for HMDB0033347 (Lotusine)

3D Structure for HMDB0033347 (Lotusine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra