NP-MRD: Showing NP-Card for (1r,9r,10s,16s)-16-methyl-5-[(1s,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-4-yl]-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene (NP0296752)

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Record Information

Version

2.0

Created at

2022-09-10 06:31:26 UTC

Updated at

2022-09-10 06:31:26 UTC

NP-MRD ID

NP0296752

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,9r,10s,16s)-16-methyl-5-[(1s,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-4-yl]-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene

Description

Complanadine A belongs to the class of organic compounds known as phenanthrolines. These are aromatic polycyclic compounds containing the phenanthroline skeleton, which is a derivative of phenanthrene, and consists of two pyridine rings non-linearly joined by a benzene ring. (1r,9r,10s,16s)-16-methyl-5-[(1s,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-4-yl]-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene was first documented in 2010 (PMID: 20387896). Based on a literature review a small amount of articles have been published on Complanadine A (PMID: 34570487) (PMID: 33403649) (PMID: 24930830) (PMID: 23635039).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102208312D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309102208312D          

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    1.4693   -4.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6452   -4.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1987   -5.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5869   -5.2234    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3205   -5.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2253   -4.7008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9971   -4.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1305   -5.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4921   -6.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7203   -6.0375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  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  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 21  1  0  0  0  0
 20 22  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 26  1  6  0  0  0
  8 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  2 31  1  0  0  0  0
 30 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 36 35  1  6  0  0  0
  4 36  1  0  0  0  0
 30 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296752

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@@H]2CC3=NC(=CC=C3[C@]3(C1)NCCC[C@@H]23)C1=CN=C2CC3C[C@@H](C)C[C@@]4(NCCC[C@H]34)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H42N4/c1-19-12-22-15-30-26(31(16-19)24(22)5-3-9-34-31)7-8-28(36-30)23-13-27-29(33-18-23)14-21-11-20(2)17-32(27)25(21)6-4-10-35-32/h7-8,13,18-22,24-25,34-35H,3-6,9-12,14-17H2,1-2H3/t19-,20+,21?,22+,24-,25+,31+,32-/m0/s1

> <INCHI_KEY>
CBERWKKQXZDPGS-VZCFZVEPSA-N

> <FORMULA>
C32H42N4

> <MOLECULAR_WEIGHT>
482.716

> <EXACT_MASS>
482.340947368

$$$$

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      -4.470 -12.049   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.171 -12.288   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.230 -13.291   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.764 -13.761   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.606 -13.056   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.076 -11.589   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.614 -11.664   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.447 -10.369   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.986 -10.443   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.819  -9.148   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       7.357  -9.223   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       8.298 -10.226   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.228 -11.887   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.057 -12.048   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.555 -13.392   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.850 -14.225   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.355 -13.899   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.232 -15.165   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.188 -12.604   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.862 -11.099   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.567 -10.266   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.570 -12.234   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.074 -10.776   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.564 -10.476   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.549 -11.634   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       6.044 -13.092   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       2.743  -9.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.204  -8.925   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.371 -10.220   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.096  -9.750   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.465 -10.455   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0      -2.287  -8.775   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      -3.728  -9.319   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.977 -10.839   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.785 -11.814   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.345 -11.270   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   36                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   29                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13   16   22   26                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   12                                                       
CONECT   22   20   15   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   15                                                       
CONECT   27    8   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    6   30                                                  
CONECT   30   29   31   32   36                                             
CONECT   31   30    2                                                       
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35    4   30                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₂N₄

Average Mass

482.7160 Da

Monoisotopic Mass

482.34095 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@@H]2CC3=NC(=CC=C3[C@]3(C1)NCCC[C@@H]23)C1=CN=C2CC3C[C@@H](C)C[C@@]4(NCCC[C@H]34)C2=C1

InChI Identifier

InChI=1S/C32H42N4/c1-19-12-22-15-30-26(31(16-19)24(22)5-3-9-34-31)7-8-28(36-30)23-13-27-29(33-18-23)14-21-11-20(2)17-32(27)25(21)6-4-10-35-32/h7-8,13,18-22,24-25,34-35H,3-6,9-12,14-17H2,1-2H3/t19-,20+,21?,22+,24-,25+,31+,32-/m0/s1

InChI Key

CBERWKKQXZDPGS-VZCFZVEPSA-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 phenanthrolines. These are aromatic polycyclic compounds containing the phenanthroline skeleton, which is a derivative of phenanthrene, and consists of two pyridine rings non-linearly joined by a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Phenanthrolines

Sub Class

Not Available

Direct Parent

Phenanthrolines

Alternative Parents

Substituents

1,7-phenanthroline
Bipyridine
Quinolidine
Aralkylamine
Pyridine
Piperidine
Heteroaromatic compound
Azacycle
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00028083

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

102008674

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ma D, Martin BS, Gallagher KS, Saito T, Dai M: One-Carbon Insertion and Polarity Inversion Enabled a Pyrrole Strategy to the Total Syntheses of Pyridine-Containing Lycopodium Alkaloids: Complanadine A and Lycodine. J Am Chem Soc. 2021 Oct 13;143(40):16383-16387. doi: 10.1021/jacs.1c08626. Epub 2021 Sep 27. [PubMed:34570487 ]
Hirasawa Y, Agawa-Kakimoto M, Zaima K, Uchiyama N, Goda Y, Morita H: Complanadine F, a novel dimeric alkaloid from Lycopodium complanatum. J Nat Med. 2021 Mar;75(2):403-407. doi: 10.1007/s11418-020-01476-9. Epub 2021 Jan 6. [PubMed:33403649 ]
Johnson T, Siegel D: Complanadine A, a selective agonist for the Mas-related G protein-coupled receptor X2. Bioorg Med Chem Lett. 2014 Aug 1;24(15):3512-5. doi: 10.1016/j.bmcl.2014.05.060. Epub 2014 May 27. [PubMed:24930830 ]
Yuan C, Chang CT, Siegel D: Syntheses of (+)-complanadine A and lycodine derivatives by regioselective [2 + 2 + 2] cycloadditions. J Org Chem. 2013 Jun 7;78(11):5647-68. doi: 10.1021/jo400695c. Epub 2013 May 23. [PubMed:23635039 ]
Yuan C, Chang CT, Axelrod A, Siegel D: Synthesis of (+)-complanadine A, an inducer of neurotrophic factor excretion. J Am Chem Soc. 2010 May 5;132(17):5924-5. doi: 10.1021/ja101956x. [PubMed:20387896 ]
LOTUS database [Link]

Showing NP-Card for (1r,9r,10s,16s)-16-methyl-5-[(1s,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-4-yl]-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene (NP0296752)

MOL for NP0296752 ((1r,9r,10s,16s)-16-methyl-5-[(1s,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-4-yl]-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)

3D MOL for NP0296752 ((1r,9r,10s,16s)-16-methyl-5-[(1s,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-4-yl]-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)

3D SDF for NP0296752 ((1r,9r,10s,16s)-16-methyl-5-[(1s,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-4-yl]-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)

3D-SDF for NP0296752 ((1r,9r,10s,16s)-16-methyl-5-[(1s,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-4-yl]-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)

PDB for NP0296752 ((1r,9r,10s,16s)-16-methyl-5-[(1s,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-4-yl]-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)

3D PDB for NP0296752 ((1r,9r,10s,16s)-16-methyl-5-[(1s,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-4-yl]-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)

SMILES for NP0296752 ((1r,9r,10s,16s)-16-methyl-5-[(1s,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-4-yl]-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)

INCHI for NP0296752 ((1r,9r,10s,16s)-16-methyl-5-[(1s,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-4-yl]-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)

Structure for NP0296752 ((1r,9r,10s,16s)-16-methyl-5-[(1s,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-4-yl]-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)

3D Structure for NP0296752 ((1r,9r,10s,16s)-16-methyl-5-[(1s,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-4-yl]-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)