NP-MRD: Showing NP-Card for (1r,2r,4r,5z,12r,13r,16z)-25-{9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol (NP0185266)

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Record Information

Version

2.0

Created at

2022-09-04 00:37:18 UTC

Updated at

2022-09-04 00:37:18 UTC

NP-MRD ID

NP0185266

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4r,5z,12r,13r,16z)-25-{9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol

Description

Manzamine A 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,2r,4r,5z,12r,13r,16z)-25-{9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol was first documented in 2012 (PMID: 23039372). Based on a literature review a significant number of articles have been published on Manzamine A (PMID: 27144573) (PMID: 23410241) (PMID: 35011662) (PMID: 24967948) (PMID: 25647730) (PMID: 30063132).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042202372D          

 41 48  0  0  1  0            999 V2000
    3.8296    1.7982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6855    0.9859    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9091    1.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2793    0.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5029    1.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3563    1.8228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5799    2.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499    1.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0967    0.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8731    0.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8477   -0.3466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0556   -0.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3030   -1.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1258   -1.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5899   -0.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2313    0.0439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4086    0.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4259   -0.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7961   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3461   -2.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5335   -0.2603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8321    0.1740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  2  1  1  1  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
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  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
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 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
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 16 17  1  0  0  0  0
 12 17  2  0  0  0  0
  9 17  1  0  0  0  0
 18  4  1  1  0  0  0
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  2 29  1  0  0  0  0
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 31 32  1  6  0  0  0
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 33 40  1  1  0  0  0
 41 40  1  6  0  0  0
  2 41  1  0  0  0  0
 31 41  1  0  0  0  0
M  END

     RDKit          3D

 85 92  0  0  0  0  0  0  0  0999 V2000
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    4.3543   -1.7098   -1.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6201    3.8935   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6605    2.5301    0.7622 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8050    1.7027   -0.0223 C   0  0  1  0  0  0  0  0  0  0  0  0
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  2  1  1  1
  2 29  1  0
 29 28  1  0
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 18  4  1  0
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 10  5  1  0
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 41 85  1  6
 30 70  1  0
 30 71  1  0
M  END


  Mrv1652309042202372D          

 41 48  0  0  1  0            999 V2000
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    3.6855    0.9859    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.2793    0.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3563    1.8228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5799    2.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499    1.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0967    0.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8731    0.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3030   -1.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1258   -1.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5899   -0.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2313    0.0439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4086    0.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4259   -0.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7961   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9427   -1.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7191   -1.7036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3461   -2.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1505   -2.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9479   -2.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5557   -1.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8347   -0.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7209   -0.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2404    0.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5033    0.9808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2381   -1.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2023   -0.3589    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5145   -1.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3372   -1.0616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7650   -1.7670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5663   -1.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2717   -1.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4680   -0.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0402   -0.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2389    0.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5335   -0.2603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8321    0.1740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  2  1  1  1  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  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
 12 17  2  0  0  0  0
  9 17  1  0  0  0  0
 18  4  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 33 40  1  1  0  0  0
 41 40  1  6  0  0  0
  2 41  1  0  0  0  0
 31 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0185266

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@]12CC\C=C/CCCCN3CC[C@@H](C(=C1)C1=NC=CC4=C1NC1=C4C=CC=C1)[C@]1(C[C@@H]4\C=C/CCCCN4[C@@H]21)C3

> <INCHI_IDENTIFIER>
InChI=1S/C36H44N4O/c41-36-18-10-4-1-2-5-11-20-39-22-17-30(35(25-39)23-26-13-7-3-6-12-21-40(26)34(35)36)29(24-36)32-33-28(16-19-37-32)27-14-8-9-15-31(27)38-33/h1,4,7-9,13-16,19,24,26,30,34,38,41H,2-3,5-6,10-12,17-18,20-23,25H2/b4-1-,13-7-/t26-,30-,34+,35-,36+/m0/s1

> <INCHI_KEY>
FUCSLKWLLSEMDQ-ARPZDLDPSA-N

> <FORMULA>
C36H44N4O

> <MOLECULAR_WEIGHT>
548.775

> <EXACT_MASS>
548.351512053

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
64.32010499176283

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4R,5Z,12R,13R,16Z)-25-{9H-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1^{2,22}.0^{2,12}.0^{4,11}]heptacosa-5,16,25-trien-13-ol

> <JCHEM_LOGP>
5.804885111333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
13.854511607771329

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.060552927410637

> <JCHEM_PKA_STRONGEST_BASIC>
11.014024080726166

> <JCHEM_POLAR_SURFACE_AREA>
55.39000000000001

> <JCHEM_REFRACTIVITY>
169.57429999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4R,5Z,12R,13R,16Z)-25-{9H-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1^{2,22}.0^{2,12}.0^{4,11}]heptacosa-5,16,25-trien-13-ol

> <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  O   UNK     0       7.149   3.357   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.880   1.840   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.430   2.361   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.255   1.366   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.805   1.887   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.532   3.403   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.082   3.923   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.093   2.929   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.180   1.413   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.630   0.892   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.582  -0.647   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.104  -1.077   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.566  -2.464   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.101  -2.578   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.968  -1.305   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.298   0.082   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.763   0.196   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.528  -0.149   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.353  -1.144   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.626  -2.659   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       5.076  -3.180   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       6.246  -4.181   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.748  -4.523   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.236  -4.129   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.371  -3.087   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.891  -1.638   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.679  -0.113   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.782   1.139   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.406   1.831   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.044  -2.254   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.978  -0.670   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.560  -2.095   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.096  -1.982   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.895  -3.298   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.390  -3.665   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.707  -2.866   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.074  -1.370   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.275  -0.054   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.779   0.313   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0       8.463  -0.486   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0       7.153   0.325   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   29   41                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12    9                                                  
CONECT   18    4   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    2                                                       
CONECT   30   21   31                                                       
CONECT   31   30   18   32   41                                             
CONECT   32   31   33                                                       
CONECT   33   32   34   40                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   33   41                                                  
CONECT   41   40    2   31                                                  
MASTER        0    0    0    0    0    0    0    0   41    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₄₄N₄O

Average Mass

548.7750 Da

Monoisotopic Mass

548.35151 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

O[C@]12CC\C=C/CCCCN3CC[C@@H](C(=C1)C1=NC=CC4=C1NC1=C4C=CC=C1)[C@]1(C[C@@H]4\C=C/CCCCN4[C@@H]21)C3

InChI Identifier

InChI=1S/C36H44N4O/c41-36-18-10-4-1-2-5-11-20-39-22-17-30(35(25-39)23-26-13-7-3-6-12-21-40(26)34(35)36)29(24-36)32-33-28(16-19-37-32)27-14-8-9-15-31(27)38-33/h1,4,7-9,13-16,19,24,26,30,34,38,41H,2-3,5-6,10-12,17-18,20-23,25H2/b4-1-,13-7-/t26-,30-,34+,35-,36+/m0/s1

InChI Key

FUCSLKWLLSEMDQ-ARPZDLDPSA-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

Not Available

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

Harman
Beta-carboline
Pyridoindole
Azaspirodecane
Indole
Indole or derivatives
Piperidine
Pyridine
N-alkylpyrrolidine
Benzenoid
Tertiary alcohol
Pyrrolidine
Pyrrole
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Amine
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00026540

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

102060449

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Indraningrat AA, Smidt H, Sipkema D: Bioprospecting Sponge-Associated Microbes for Antimicrobial Compounds. Mar Drugs. 2016 May 2;14(5). pii: md14050087. doi: 10.3390/md14050087. [PubMed:27144573 ]
Espinoza-Moraga M, Njuguna NM, Mugumbate G, Caballero J, Chibale K: In silico comparison of antimycobacterial natural products with known antituberculosis drugs. J Chem Inf Model. 2013 Mar 25;53(3):649-60. doi: 10.1021/ci300467b. Epub 2013 Feb 22. [PubMed:23410241 ]
Jakubec P, Hawkins A, Felzmann W, Dixon DJ: Total synthesis of manzamine A and related alkaloids. J Am Chem Soc. 2012 Oct 24;134(42):17482-5. doi: 10.1021/ja308826x. Epub 2012 Oct 16. [PubMed:23039372 ]
Maglioni S, Arsalan N, Hamacher A, Afshar S, Schiavi A, Beller M, Ventura N: High-Content C. elegans Screen Identifies Natural Compounds Impacting Mitochondria-Lipid Homeostasis and Promoting Healthspan. Cells. 2021 Dec 29;11(1). pii: cells11010100. doi: 10.3390/cells11010100. [PubMed:35011662 ]
Furusato A, Kato H, Nehira T, Eguchi K, Kawabata T, Fujiwara Y, Losung F, Mangindaan RE, de Voogd NJ, Takeya M, Yokosawa H, Tsukamoto S: Acanthomanzamines A-E with new manzamine frameworks from the marine sponge Acanthostrongylophora ingens. Org Lett. 2014 Aug 1;16(15):3888-91. doi: 10.1021/ol5015569. Epub 2014 Jun 26. [PubMed:24967948 ]
Pathak RB, Dobson BC, Ghosh N, Ageel KA, Alshawish MR, Saruengkhanphasit R, Coldham I: Synthesis of the tricyclic core of manzamine A. Org Biomol Chem. 2015 Mar 21;13(11):3331-40. doi: 10.1039/c4ob02582b. [PubMed:25647730 ]
Simithy J, Fuanta NR, Alturki M, Hobrath JV, Wahba AE, Pina I, Rath J, Hamann MT, DeRuiter J, Goodwin DC, Calderon AI: Slow-Binding Inhibition of Mycobacterium tuberculosis Shikimate Kinase by Manzamine Alkaloids. Biochemistry. 2018 Aug 14;57(32):4923-4933. doi: 10.1021/acs.biochem.8b00231. Epub 2018 Jul 31. [PubMed:30063132 ]
Palem JR, Mudit M, Hsia SV, Sayed KAE: Discovery and preliminary structure-activity relationship of the marine natural product manzamines as herpes simplex virus type-1 inhibitors. Z Naturforsch C J Biosci. 2017 Jan 1;72(1-2):49-54. doi: 10.1515/znc-2016-0080. [PubMed:27447204 ]
Yadav AK, Vashishta V, Joshi N, Taneja P: AR-A 014418 Used against GSK3beta Downregulates Expression of hnRNPA1 and SF2/ASF Splicing Factors. J Oncol. 2014;2014:695325. doi: 10.1155/2014/695325. Epub 2014 Jan 2. [PubMed:24550987 ]
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LOTUS database [Link]

Showing NP-Card for (1r,2r,4r,5z,12r,13r,16z)-25-{9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol (NP0185266)

MOL for NP0185266 ((1r,2r,4r,5z,12r,13r,16z)-25-{9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol)

3D MOL for NP0185266 ((1r,2r,4r,5z,12r,13r,16z)-25-{9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol)

3D SDF for NP0185266 ((1r,2r,4r,5z,12r,13r,16z)-25-{9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol)

3D-SDF for NP0185266 ((1r,2r,4r,5z,12r,13r,16z)-25-{9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol)

PDB for NP0185266 ((1r,2r,4r,5z,12r,13r,16z)-25-{9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol)

3D PDB for NP0185266 ((1r,2r,4r,5z,12r,13r,16z)-25-{9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol)

SMILES for NP0185266 ((1r,2r,4r,5z,12r,13r,16z)-25-{9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol)

INCHI for NP0185266 ((1r,2r,4r,5z,12r,13r,16z)-25-{9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol)

Structure for NP0185266 ((1r,2r,4r,5z,12r,13r,16z)-25-{9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol)

3D Structure for NP0185266 ((1r,2r,4r,5z,12r,13r,16z)-25-{9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol)