NP-MRD: Showing NP-Card for (1r,4'r)-3-(4-{[(1r)-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one (NP0225585)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-06 04:20:51 UTC

Updated at

2022-09-06 04:20:52 UTC

NP-MRD ID

NP0225585

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4'r)-3-(4-{[(1r)-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

Description

(1R,4'R)-3-(4-{[(1R)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]Dodecane]-1'(12'),2,5,8',10'-pentaen-4-one belongs to the class of organic compounds known as proaporphines. These are benzylisoquinoline derivatives characterized by the presence of a spirocyclohexane ring that can occur in various oxidation levels, from cyclohexadienone to cyclohexanol. (1r,4'r)-3-(4-{[(1r)-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one is found in Berberis vulgaris. Based on a literature review very few articles have been published on (1R,4'R)-3-(4-{[(1R)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]Dodecane]-1'(12'),2,5,8',10'-pentaen-4-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062206202D          

 46 52  0  0  1  0            999 V2000
   11.2305    0.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8180    0.9175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9930    0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5805    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7555    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3430    0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7555    0.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5805    0.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9930   -0.5114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8180   -0.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5180    0.9175    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1055    0.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2805    0.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8680   -0.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0430   -0.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6305    0.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8055    0.2030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3930    0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5680    0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1555    1.6320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5680    2.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3930    2.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8055    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6305    1.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6706    0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8860    1.2195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8860    2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715    2.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    3.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2291    3.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4006    4.4654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875    5.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8421    3.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6268    3.3613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    4.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6706    2.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5429    2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5429    1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715    0.8070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715   -0.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0430    0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8680    0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1055    1.6320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2805    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5180    2.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3430    2.3464    0.0000 C   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
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  2  0  0  0  0
 20 25  1  1  0  0  0
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  2  0  0  0  0
 27 36  1  0  0  0  0
 20 36  1  0  0  0  0
 28 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 26 39  1  0  0  0  0
 39 40  1  0  0  0  0
 16 41  1  0  0  0  0
 41 42  2  0  0  0  0
 13 42  1  0  0  0  0
 11 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
  5 46  1  0  0  0  0
M  END


  Mrv1652309062206202D          

 46 52  0  0  1  0            999 V2000
   11.2305    0.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8180    0.9175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9930    0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5805    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7555    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3430    0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7555    0.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5805    0.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9930   -0.5114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8180   -0.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5180    0.9175    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1055    0.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2805    0.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8680   -0.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0430   -0.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6305    0.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8055    0.2030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3930    0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5680    0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1555    1.6320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5680    2.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3930    2.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8055    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6305    1.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6706    0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8860    1.2195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8860    2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715    2.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    3.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2291    3.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4006    4.4654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875    5.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8421    3.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6268    3.3613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    4.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6706    2.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5429    2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5429    1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715    0.8070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715   -0.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0430    0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8680    0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1055    1.6320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2805    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5180    2.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3430    2.3464    0.0000 C   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
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  2  0  0  0  0
 20 25  1  1  0  0  0
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  2  0  0  0  0
 27 36  1  0  0  0  0
 20 36  1  0  0  0  0
 28 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 26 39  1  0  0  0  0
 39 40  1  0  0  0  0
 16 41  1  0  0  0  0
 41 42  2  0  0  0  0
 13 42  1  0  0  0  0
 11 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
  5 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225585

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC)[C@@H](CC1=CC=C(OC3=C[C@@]4(C[C@H]5N(C)CCC6=C5C4=C(OC)C(OC)=C6)C=CC3=O)C=C1)N(C)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C38H42N2O6/c1-39-15-12-24-18-31(42-3)32(43-4)20-27(24)28(39)17-23-7-9-26(10-8-23)46-34-22-38(14-11-30(34)41)21-29-35-25(13-16-40(29)2)19-33(44-5)37(45-6)36(35)38/h7-11,14,18-20,22,28-29H,12-13,15-17,21H2,1-6H3/t28-,29-,38+/m1/s1

> <INCHI_KEY>
IAFYZOROUCWFHK-HQILYBJNSA-N

> <FORMULA>
C38H42N2O6

> <MOLECULAR_WEIGHT>
622.762

> <EXACT_MASS>
622.30428708

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
69.74341091495798

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4'R)-3-(4-{[(1R)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

> <JCHEM_LOGP>
5.480927319666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
7.874794283175937

> <JCHEM_POLAR_SURFACE_AREA>
69.7

> <JCHEM_REFRACTIVITY>
182.31379999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4'R)-3-(4-{[(1R)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      20.964   0.379   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      20.194   1.713   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      18.654   1.713   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.884   3.046   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.344   3.046   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.574   1.713   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.344   0.379   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.884   0.379   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      18.654  -0.955   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      20.194  -0.955   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.034   1.713   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.264   0.379   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.724   0.379   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.954  -0.955   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.414  -0.955   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.644   0.379   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.104   0.379   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.334   1.713   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.794   1.713   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.024   3.046   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.794   4.380   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.334   4.380   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.104   3.046   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.644   3.046   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.118   1.800   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.654   2.276   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.654   3.816   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.320   4.586   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.830   6.353   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.294   6.829   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.614   8.335   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.470   9.366   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.439   5.799   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.903   6.274   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.223   7.781   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.118   4.292   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.013   3.816   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.013   2.276   0.000  0.00  0.00           C+0
HETATM   39  N   UNK     0       0.320   1.506   0.000  0.00  0.00           N+0
HETATM   40  C   UNK     0       0.320  -0.034   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.414   1.713   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.954   1.713   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0      13.264   3.046   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      11.724   3.046   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      14.034   4.380   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      15.574   4.380   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   46                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    6   12   43                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   42                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   41                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   25   36                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18   24                                                  
CONECT   24   23                                                            
CONECT   25   20   26                                                       
CONECT   26   25   27   39                                                  
CONECT   27   26   28   36                                                  
CONECT   28   27   29   37                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   27   20                                                  
CONECT   37   28   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   26   40                                                  
CONECT   40   39                                                            
CONECT   41   16   42                                                       
CONECT   42   41   13                                                       
CONECT   43   11   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46                                                       
CONECT   46   45    5                                                       
MASTER        0    0    0    0    0    0    0    0   46    0  104    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₈H₄₂N₂O₆

Average Mass

622.7620 Da

Monoisotopic Mass

622.30429 Da

IUPAC Name

Traditional Name

(1R,4'R)-3-(4-{[(1R)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1OC)[C@@H](CC1=CC=C(OC3=C[C@@]4(C[C@H]5N(C)CCC6=C5C4=C(OC)C(OC)=C6)C=CC3=O)C=C1)N(C)CC2

InChI Identifier

InChI=1S/C38H42N2O6/c1-39-15-12-24-18-31(42-3)32(43-4)20-27(24)28(39)17-23-7-9-26(10-8-23)46-34-22-38(14-11-30(34)41)21-29-35-25(13-16-40(29)2)19-33(44-5)37(45-6)36(35)38/h7-11,14,18-20,22,28-29H,12-13,15-17,21H2,1-6H3/t28-,29-,38+/m1/s1

InChI Key

IAFYZOROUCWFHK-HQILYBJNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Berberis vulgaris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proaporphines. These are benzylisoquinoline derivatives characterized by the presence of a spirocyclohexane ring that can occur in various oxidation levels, from cyclohexadienone to cyclohexanol.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Proaporphines

Sub Class

Not Available

Direct Parent

Proaporphines

Alternative Parents

Substituents

Proaporphine
Benzylisoquinoline
Tetrahydroisoquinoline
Indane
Phenoxy compound
Anisole
Alkyl aryl ether
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Ketone
Tertiary amine
Tertiary aliphatic amine
Cyclic ketone
Azacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
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	5.48	ChemAxon
pKa (Strongest Basic)	7.87	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.7 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	182.31 m³·mol⁻¹	ChemAxon
Polarizability	69.74 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162977106

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4'r)-3-(4-{[(1r)-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one (NP0225585)

MOL for NP0225585 ((1r,4'r)-3-(4-{[(1r)-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)

3D MOL for NP0225585 ((1r,4'r)-3-(4-{[(1r)-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)

3D SDF for NP0225585 ((1r,4'r)-3-(4-{[(1r)-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)

3D-SDF for NP0225585 ((1r,4'r)-3-(4-{[(1r)-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)

PDB for NP0225585 ((1r,4'r)-3-(4-{[(1r)-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)

3D PDB for NP0225585 ((1r,4'r)-3-(4-{[(1r)-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)

SMILES for NP0225585 ((1r,4'r)-3-(4-{[(1r)-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)

INCHI for NP0225585 ((1r,4'r)-3-(4-{[(1r)-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)

Structure for NP0225585 ((1r,4'r)-3-(4-{[(1r)-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)

3D Structure for NP0225585 ((1r,4'r)-3-(4-{[(1r)-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl}phenoxy)-10',11'-dimethoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)