NP-MRD: Showing NP-Card for (1r,9r,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene (NP0156185)

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Record Information

Version

2.0

Created at

2022-09-02 13:21:29 UTC

Updated at

2022-09-02 13:21:30 UTC

NP-MRD ID

NP0156185

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(1R,9R,10R,16R)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]Heptadeca-2(7),3,5-triene 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,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene is found in Lycopodiastrum casuarinoides and Palhinhaea cernua. Based on a literature review very few articles have been published on (1R,9R,10R,16R)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]Heptadeca-2(7),3,5-triene.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
    3.3937    0.0537    0.8540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3377   -0.7773    0.2872 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1294   -0.6261   -1.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7050   -0.5913   -1.3282 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4135   -0.6799   -2.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5068   -1.0775   -1.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6078   -1.6954   -1.5384 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5621   -2.0840   -0.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3944   -1.8317    0.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2624   -1.1890    1.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3102   -0.8088    0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1195   -0.0857    0.7515 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0620   -0.9320    1.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4475    0.9227    1.7001 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1036    2.2709    1.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6526    2.7236    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5494    1.6184   -1.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3630    0.6215   -0.4902 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4007   -0.3036    0.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3881    1.1213    0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4353   -0.2069    1.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7714   -1.8346    0.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5697    0.3960   -1.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7185   -1.3239   -1.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5738   -1.6230   -0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7384    0.1912   -2.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3287   -1.5212   -2.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4608   -2.5873   -0.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1451   -2.1346    1.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1609   -1.0142    2.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3673   -0.6424    2.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7080   -1.9776    1.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4444    0.8385    1.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9777    2.4800    1.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5882    2.9293    2.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6876    3.1123    0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0351    3.6093   -0.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0522    2.0582   -1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5521    1.3690   -1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217    1.2323   -0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  1
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13  2  1  0
 18  4  1  0
 11  6  1  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  3 24  1  0
  4 25  1  1
  5 26  1  0
  5 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  1
M  END


  Mrv1652309022215212D          

 18 21  0  0  1  0            999 V2000
   -1.0983   -0.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4836   -0.0832    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1014   -0.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8870   -0.9617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6206   -0.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8723    0.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6964    0.1616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1429    0.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7653    1.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9413    1.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4948    0.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7091    1.1868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0244    0.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0708    1.7093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7010    1.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8344    0.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1960    0.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5758    0.3726    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
  4 18  1  0  0  0  0
 12 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0156185

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H22N2/c1-11-8-12-9-15-14(5-2-6-17-15)16(10-11)13(12)4-3-7-18-16/h2,5-6,11-13,18H,3-4,7-10H2,1H3/t11-,12-,13-,16-/m1/s1

> <INCHI_KEY>
JJPMUZRSJKMFRK-BRXULGCHSA-N

> <FORMULA>
C16H22N2

> <MOLECULAR_WEIGHT>
242.366

> <EXACT_MASS>
242.178298716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
53.35459995053725

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9R,10R,16R)-16-methyl-6,14-diazatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2,4,6-triene

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
2.4260510483333326

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.423943242541469

> <JCHEM_POLAR_SURFACE_AREA>
24.92

> <JCHEM_REFRACTIVITY>
72.70530000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9R,10R,16R)-16-methyl-6,14-diazatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2,4,6-triene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.050  -0.083   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.903  -0.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.189  -1.325   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.656  -1.795   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.025  -1.090   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.495   0.376   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       5.033   0.302   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.867   1.597   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.162   2.966   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.624   3.040   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.790   1.745   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.324   2.215   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.046   1.511   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.132   3.191   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -1.309   2.647   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.557   1.127   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.366   0.151   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.075   0.696   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13   14   18                                             
CONECT   13   12    2                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    4   12                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₂N₂

Average Mass

242.3660 Da

Monoisotopic Mass

242.17830 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

InChI Identifier

InChI=1S/C16H22N2/c1-11-8-12-9-15-14(5-2-6-17-15)16(10-11)13(12)4-3-7-18-16/h2,5-6,11-13,18H,3-4,7-10H2,1H3/t11-,12-,13-,16-/m1/s1

InChI Key

JJPMUZRSJKMFRK-BRXULGCHSA-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
Lycopodiastrum casuarinoides	LOTUS Database	35616633
Palhinhaea cernua	LOTUS Database	35616633

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
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
logP	2.73	ALOGPS
logS	-4	ALOGPS

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

13183620

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442483

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,9r,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene (NP0156185)

MOL for NP0156185 ((1r,9r,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)

3D MOL for NP0156185 ((1r,9r,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)

3D SDF for NP0156185 ((1r,9r,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)

3D-SDF for NP0156185 ((1r,9r,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)

PDB for NP0156185 ((1r,9r,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)

3D PDB for NP0156185 ((1r,9r,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)

SMILES for NP0156185 ((1r,9r,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)

INCHI for NP0156185 ((1r,9r,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)

Structure for NP0156185 ((1r,9r,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)

3D Structure for NP0156185 ((1r,9r,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene)