NP-MRD: Showing NP-Card for (1r,2's,4'r,4''s)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0⁴,¹²]dodecane]-1''(11''),8''(12''),9''-trien-11''-ol (NP0291240)

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Record Information

Version

1.0

Created at

2022-09-09 22:15:23 UTC

Updated at

2022-09-09 22:15:23 UTC

NP-MRD ID

NP0291240

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2's,4'r,4''s)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0⁴,¹²]dodecane]-1''(11''),8''(12''),9''-trien-11''-ol

Description

(1R,2'S,4'R,4''S)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0⁴,¹²]Dodecane]-1''(12''),8'',10''-trien-11''-ol belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. (1r,2's,4'r,4''s)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0⁴,¹²]dodecane]-1''(11''),8''(12''),9''-trien-11''-ol is found in Roemeria refracta. Based on a literature review very few articles have been published on (1R,2'S,4'R,4''S)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0⁴,¹²]Dodecane]-1''(12''),8'',10''-trien-11''-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102200152D          

 39 45  0  0  1  0            999 V2000
    7.0621    3.6662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3393    2.8892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8050    2.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9935    2.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4592    1.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6346    1.7568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4021    0.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0832    0.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7365    1.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5480    0.8550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0823    1.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8938    1.3352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1711    0.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0204   -0.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2766   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5956   -0.2144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6584    0.6082    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0613    0.0389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0752    1.0731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4219    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7409    1.0349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9733    1.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4039    2.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9324    3.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7571    3.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1490    4.0044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162    4.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1898    2.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0145    2.5996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7979    1.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3978    2.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302    1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0609    0.8404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933    0.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6723    1.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4638    1.4100    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0609    1.9793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8664    2.7810    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  3 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17  7  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
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 26 27  1  0  0  0  0
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 29 31  2  0  0  0  0
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 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 22 34  1  0  0  0  0
 34 35  1  0  0  0  0
 20 36  1  0  0  0  0
 36 37  1  0  0  0  0
 17 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
M  END

     RDKit          3D

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    4.9410    1.6852    1.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0199    0.8758    0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4820   -0.1680   -0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1241    0.1324   -0.0069 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5467   -0.9521   -0.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3871    2.1606   -0.7525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4022    2.8745   -1.3949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1181    0.8243   -0.4605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3789   -0.1312    1.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9527   -1.5661    1.2712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0479   -1.9686    0.2379 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7615   -3.3637    0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1496   -0.1256    0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0833   -1.0121    0.3533 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8278   -0.8599    1.5466 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8699   -2.0406    2.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7664    3.6247    2.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0455    2.9989    2.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5977    4.2209    1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5971    2.5098    1.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1726   -1.2479   -1.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4023   -1.6878   -2.8454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0642   -2.7864   -1.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
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 13 46  1  0
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 10 45  1  0
M  END


  Mrv1652309102200152D          

 39 45  0  0  1  0            999 V2000
    7.0621    3.6662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3393    2.8892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8050    2.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9935    2.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4592    1.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6346    1.7568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4021    0.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0832    0.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7365    1.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5480    0.8550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0823    1.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8938    1.3352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1711    0.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0204   -0.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5956   -0.2144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0752    1.0731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4219    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7409    1.0349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9733    1.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4039    2.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9324    3.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7571    3.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1490    4.0044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162    4.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1898    2.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0145    2.5996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7979    1.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3978    2.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302    1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0609    0.8404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933    0.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6723    1.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4638    1.4100    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0609    1.9793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8664    2.7810    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  3 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17  7  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 23 31  1  0  0  0  0
 20 31  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 22 34  1  0  0  0  0
 34 35  1  0  0  0  0
 20 36  1  0  0  0  0
 36 37  1  0  0  0  0
 17 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291240

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C[C@]2(C[C@@H]3N(C)CCC4=C3C2=C(O)C(OC)=C4)CC[C@]11NCCC2=C1NC1=CC(OC)=C(OC)C=C21

> <INCHI_IDENTIFIER>
InChI=1S/C31H39N3O5/c1-34-11-7-17-12-24(38-4)28(35)27-26(17)21(34)15-30(27)8-9-31(25(16-30)39-5)29-18(6-10-32-31)19-13-22(36-2)23(37-3)14-20(19)33-29/h12-14,21,25,32-33,35H,6-11,15-16H2,1-5H3/t21-,25-,30+,31-/m0/s1

> <INCHI_KEY>
ZEQJFLRBPFWVDX-QMAOYEQLSA-N

> <FORMULA>
C31H39N3O5

> <MOLECULAR_WEIGHT>
533.669

> <EXACT_MASS>
533.288971368

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
60.69096534974447

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2'S,4'R,4''S)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0^{4,12}]dodecane]-1''(11''),8''(12''),9''-trien-11''-ol

> <JCHEM_LOGP>
3.284347279961306

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
16.489512295066444

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.739952991415986

> <JCHEM_PKA_STRONGEST_BASIC>
8.92074561951489

> <JCHEM_POLAR_SURFACE_AREA>
88.21000000000001

> <JCHEM_REFRACTIVITY>
150.87619999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2'S,4'R,4''S)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0^{4,12}]dodecane]-1''(11''),8''(12''),9''-trien-11''-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      13.183   6.844   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      13.700   5.393   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.703   4.220   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.188   4.497   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.191   3.323   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       8.651   3.279   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       8.217   1.802   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.489   0.932   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.708   1.873   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.223   1.596   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.220   2.769   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      14.735   2.492   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      15.253   1.042   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.371  -0.603   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.983  -1.269   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       6.712  -0.400   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       6.829   1.135   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.714   0.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.237   0.506   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.874   2.003   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.654   1.063   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.383   1.932   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.817   3.409   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.754   4.524   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.741   6.076   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.280   6.120   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.011   7.475   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.204   8.786   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.088   4.809   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.627   4.853   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.356   3.453   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.743   4.161   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.176   2.683   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      -0.114   1.569   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0      -0.547   0.091   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.988   3.066   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.466   2.632   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       7.580   3.695   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       7.217   5.191   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10    3   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    8   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    7   18   37                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   31   36                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   34                                                  
CONECT   23   22   24   31                                                  
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   23   20                                                  
CONECT   32   24   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   22   35                                                  
CONECT   35   34                                                            
CONECT   36   20   37                                                       
CONECT   37   36   17   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₉N₃O₅

Average Mass

533.6690 Da

Monoisotopic Mass

533.28897 Da

IUPAC Name

(1R,2'S,4'R,4''S)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0^{4,12}]dodecane]-1''(11''),8''(12''),9''-trien-11''-ol

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@H]1C[C@]2(C[C@@H]3N(C)CCC4=C3C2=C(O)C(OC)=C4)CC[C@]11NCCC2=C1NC1=CC(OC)=C(OC)C=C21

InChI Identifier

InChI=1S/C31H39N3O5/c1-34-11-7-17-12-24(38-4)28(35)27-26(17)21(34)15-30(27)8-9-31(25(16-30)39-5)29-18(6-10-32-31)19-13-22(36-2)23(37-3)14-20(19)33-29/h12-14,21,25,32-33,35H,6-11,15-16H2,1-5H3/t21-,25-,30+,31-/m0/s1

InChI Key

ZEQJFLRBPFWVDX-QMAOYEQLSA-N

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
Roemeria refracta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harmaline
Harman
Beta-carboline
Pyridoindole
3-alkylindole
Tetrahydroisoquinoline
Indane
Indole
Indole or derivatives
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Pyrrole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Secondary amine
Dialkyl ether
Secondary aliphatic amine
Organoheterocyclic compound
Azacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Amine
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	3.28	ChemAxon
pKa (Strongest Acidic)	10.74	ChemAxon
pKa (Strongest Basic)	8.92	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	88.21 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	150.88 m³·mol⁻¹	ChemAxon
Polarizability	60.69 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

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

163195583

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2's,4'r,4''s)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0⁴,¹²]dodecane]-1''(11''),8''(12''),9''-trien-11''-ol (NP0291240)

MOL for NP0291240 ((1r,2's,4'r,4''s)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0⁴,¹²]dodecane]-1''(11''),8''(12''),9''-trien-11''-ol)

3D MOL for NP0291240 ((1r,2's,4'r,4''s)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0⁴,¹²]dodecane]-1''(11''),8''(12''),9''-trien-11''-ol)

3D SDF for NP0291240 ((1r,2's,4'r,4''s)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0⁴,¹²]dodecane]-1''(11''),8''(12''),9''-trien-11''-ol)

3D-SDF for NP0291240 ((1r,2's,4'r,4''s)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0⁴,¹²]dodecane]-1''(11''),8''(12''),9''-trien-11''-ol)

PDB for NP0291240 ((1r,2's,4'r,4''s)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0⁴,¹²]dodecane]-1''(11''),8''(12''),9''-trien-11''-ol)

3D PDB for NP0291240 ((1r,2's,4'r,4''s)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0⁴,¹²]dodecane]-1''(11''),8''(12''),9''-trien-11''-ol)

SMILES for NP0291240 ((1r,2's,4'r,4''s)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0⁴,¹²]dodecane]-1''(11''),8''(12''),9''-trien-11''-ol)

INCHI for NP0291240 ((1r,2's,4'r,4''s)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0⁴,¹²]dodecane]-1''(11''),8''(12''),9''-trien-11''-ol)

Structure for NP0291240 ((1r,2's,4'r,4''s)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0⁴,¹²]dodecane]-1''(11''),8''(12''),9''-trien-11''-ol)

3D Structure for NP0291240 ((1r,2's,4'r,4''s)-2',6,7,10''-tetramethoxy-5''-methyl-2,3,4,9-tetrahydrodispiro[pyrido[3,4-b]indole-1,1'-cyclohexane-4',2''-[5]azatricyclo[6.3.1.0⁴,¹²]dodecane]-1''(11''),8''(12''),9''-trien-11''-ol)