NP-MRD: Showing NP-Card for (1s)-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2,2-dimethyl-3,4-dihydro-1h-isoquinolin-2-ium (NP0186633)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 02:33:34 UTC

Updated at

2022-09-04 02:33:34 UTC

NP-MRD ID

NP0186633

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s)-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2,2-dimethyl-3,4-dihydro-1h-isoquinolin-2-ium

Description

(S)-tembetarine belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached (S)-tembetarine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (1s)-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2,2-dimethyl-3,4-dihydro-1h-isoquinolin-2-ium is found in Cymbopetalum brasiliense, Parabaena sagittata, Thalictrum foliolosum, Tinospora cordifolia, Xylopia parviflora, Zanthoxylum chalybeum, Zanthoxylum gilletii, Zanthoxylum martinicense, Zanthoxylum mayu, Zanthoxylum nitidum, Zanthoxylum rhoifolium and Zanthoxylum usambarense. (1s)-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2,2-dimethyl-3,4-dihydro-1h-isoquinolin-2-ium was first documented in 2013 (PMID: 23823874). Based on a literature review very few articles have been published on (S)-tembetarine (PMID: 26944237).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042204332D          

 25 27  0  0  1  0            999 V2000
   -2.1434    2.0625    0.0000 C   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
   -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
    0.7145    2.0625    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
    1.4289    0.0000    0.0000 C   0  0  1  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
    2.8579    0.0000    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
    4.2868   -0.0000    0.0000 O   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
    4.2868   -1.6500    0.0000 O   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
    2.8579   -1.6500    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.1100   -0.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773    0.2871    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
   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  CHG  1  20   1
M  END

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
    7.0539   -1.0527    0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9341   -1.5651   -0.4117 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6732   -1.0483   -0.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755    0.1433    0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9862    0.5957   -0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0108   -0.1256   -0.7516 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6403    0.4250   -0.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2796    0.2480    0.2332 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5909    0.8934   -0.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7737    1.5352   -1.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0130    2.1311   -1.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2332    2.7884   -2.7678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0697    2.0864   -0.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2701    2.6511   -0.9250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4312    2.7347   -0.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8280    1.4185    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6308    0.8421    0.7904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225    0.1146    2.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6985   -1.1866    1.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4518   -1.0173    0.8440 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.6044   -1.2451    1.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3758   -2.1441   -0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4574   -1.3032   -1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7398   -1.7908   -1.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1199   -3.0034   -1.7933 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6452   -1.8089    0.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6890   -0.5495   -0.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7498   -0.2537    0.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0007    0.7229    0.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7074    1.5302    0.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8017    1.5257   -1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2326    0.0498   -1.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1092    0.9368    1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0007    1.6215   -2.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1281    3.2068   -2.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4550    2.0733    0.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2609    2.3290   -0.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7760    3.7653    0.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6622    1.3762    1.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5577    0.6931    2.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2074   -0.1259    2.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4240   -1.7508    0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4927   -1.8206    2.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7320   -0.2766    2.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2876   -2.0030    2.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5658   -1.5209    1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4847   -1.8396   -1.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2578   -2.7901    0.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4921   -2.8101    0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7607   -1.9014   -1.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4070   -3.5047   -2.2992 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  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
  6 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 20  8  1  0
 17  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  1
 10 34  1  0
 12 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 25 51  1  0
M  CHG  1  20   1
M  END


  Mrv1652309042204332D          

 25 27  0  0  1  0            999 V2000
   -2.1434    2.0625    0.0000 C   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
   -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
    0.7145    2.0625    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
    1.4289    0.0000    0.0000 C   0  0  1  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
    2.8579    0.0000    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
    4.2868   -0.0000    0.0000 O   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
    4.2868   -1.6500    0.0000 O   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
    2.8579   -1.6500    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.1100   -0.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773    0.2871    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
   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  CHG  1  20   1
M  END
> <DATABASE_ID>
NP0186633

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C[C@H]2C3=CC(O)=C(OC)C=C3CC[N+]2(C)C)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H25NO4/c1-21(2)8-7-14-11-20(25-4)18(23)12-15(14)16(21)9-13-5-6-19(24-3)17(22)10-13/h5-6,10-12,16H,7-9H2,1-4H3,(H-,22,23)/p+1/t16-/m0/s1

> <INCHI_KEY>
ABSDACFLIMOXJY-INIZCTEOSA-O

> <FORMULA>
C20H26NO4

> <MOLECULAR_WEIGHT>
344.43

> <EXACT_MASS>
344.185634741

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.662066241169406

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-1.0573773094717447

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.182772664267468

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.574044997838799

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5894046747284225

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
109.7499

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+1
HETATM   21  C   UNK     0      -0.205  -0.716   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.518   0.536   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16    9   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    8   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    6   24                                                       
CONECT   24   23    3   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
(+)-Tembetarine	ChEBI
(S)-(+)-Tembetarine	ChEBI
Tembetarine	ChEBI
Tembetarine chloride, (S)-isomer	MeSH

Chemical Formula

C₂₀H₂₆NO₄

Average Mass

344.4300 Da

Monoisotopic Mass

344.18563 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C[C@H]2C3=CC(O)=C(OC)C=C3CC[N+]2(C)C)C=C1O

InChI Identifier

InChI=1S/C20H25NO4/c1-21(2)8-7-14-11-20(25-4)18(23)12-15(14)16(21)9-13-5-6-19(24-3)17(22)10-13/h5-6,10-12,16H,7-9H2,1-4H3,(H-,22,23)/p+1/t16-/m0/s1

InChI Key

ABSDACFLIMOXJY-INIZCTEOSA-O

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cymbopetalum brasiliense	LOTUS Database	35616633
Parabaena sagittata	LOTUS Database	35616633
Thalictrum foliolosum	LOTUS Database	35616633
Tinospora cordifolia	LOTUS Database	35616633
Xylopia parviflora	LOTUS Database	35616633
Zanthoxylum chalybeum	LOTUS Database	35616633
Zanthoxylum gilletii	LOTUS Database	35616633
Zanthoxylum martinicense	LOTUS Database	35616633
Zanthoxylum mayu	LOTUS Database	35616633
Zanthoxylum nitidum	LOTUS Database	35616633
Zanthoxylum rhoifolium	LOTUS Database	35616633
Zanthoxylum usambarense	LOTUS Database	35616633

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
Methoxyphenol
Tetrahydroisoquinoline
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Monocyclic benzene moiety
Benzenoid
Tetraalkylammonium salt
Quaternary ammonium salt
Azacycle
Ether
Organic salt
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Amine
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.1	ChemAxon
pKa (Strongest Acidic)	9.57	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.75 m³·mol⁻¹	ChemAxon
Polarizability	37.66 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00025347

Chemspider ID

146715

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

167718

PDB ID

Not Available

ChEBI ID

134199

Good Scents ID

Not Available

References

General References

Cordeiro KW, Felipe JL, Malange KF, do Prado PR, de Oliveira Figueiredo P, Garcez FR, de Cassia Freitas K, Garcez WS, Toffoli-Kadri MC: Anti-inflammatory and antinociceptive activities of Croton urucurana Baillon bark. J Ethnopharmacol. 2016 May 13;183:128-135. doi: 10.1016/j.jep.2016.02.051. Epub 2016 Mar 2. [PubMed:26944237 ]
Yan R, Wang W, Guo J, Liu H, Zhang J, Yang B: Studies on the alkaloids of the bark of Magnolia officinalis: isolation and on-line analysis by HPLC-ESI-MS(n). Molecules. 2013 Jul 3;18(7):7739-50. doi: 10.3390/molecules18077739. [PubMed:23823874 ]
LOTUS database [Link]

Showing NP-Card for (1s)-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2,2-dimethyl-3,4-dihydro-1h-isoquinolin-2-ium (NP0186633)

MOL for NP0186633 ((1s)-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2,2-dimethyl-3,4-dihydro-1h-isoquinolin-2-ium)

3D MOL for NP0186633 ((1s)-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2,2-dimethyl-3,4-dihydro-1h-isoquinolin-2-ium)

3D SDF for NP0186633 ((1s)-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2,2-dimethyl-3,4-dihydro-1h-isoquinolin-2-ium)

3D-SDF for NP0186633 ((1s)-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2,2-dimethyl-3,4-dihydro-1h-isoquinolin-2-ium)

PDB for NP0186633 ((1s)-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2,2-dimethyl-3,4-dihydro-1h-isoquinolin-2-ium)

3D PDB for NP0186633 ((1s)-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2,2-dimethyl-3,4-dihydro-1h-isoquinolin-2-ium)

SMILES for NP0186633 ((1s)-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2,2-dimethyl-3,4-dihydro-1h-isoquinolin-2-ium)

INCHI for NP0186633 ((1s)-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2,2-dimethyl-3,4-dihydro-1h-isoquinolin-2-ium)

Structure for NP0186633 ((1s)-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2,2-dimethyl-3,4-dihydro-1h-isoquinolin-2-ium)

3D Structure for NP0186633 ((1s)-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2,2-dimethyl-3,4-dihydro-1h-isoquinolin-2-ium)