NP-MRD: Showing NP-Card for (1s,9r)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one (NP0187238)

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Record Information

Version

2.0

Created at

2022-09-04 03:20:06 UTC

Updated at

2022-09-04 03:20:06 UTC

NP-MRD ID

NP0187238

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,9r)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one

Description

(1S,9R)-11-Methyl-7,11-diazatricyclo[7.3.1.02,7]Trideca-2,4-dien-6-one belongs to the class of organic compounds known as cytisine and derivatives. These are lupin alkaloids with a structure based on the cytisine skeleton, which is a tetracyclic ketone containing fused pyridine and piperidine rings that form pyrido[1,2a][1,5]diazocin-8-one. (1s,9r)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one is found in Baptisia australis, Bolusanthus speciosus, Caulophyllum thalictroides, Euchresta japonica, Genista lydia, Gymnospermium albertii, Hovea linearis, Maackia tashiroi, Ormosia emarginata, Pericopsis angolensis, Sophora macrocarpa, Sophora secundiflora, Sophora tomentosa and Thermopsis lanceolata. Based on a literature review very few articles have been published on (1S,9R)-11-Methyl-7,11-diazatricyclo[7.3.1.02,7]Trideca-2,4-dien-6-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
    3.0975   -0.8385    0.9445 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2434   -0.0996    0.0595 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3780   -1.0233   -0.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2714   -0.2900   -1.3669 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5774    1.1856   -1.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6486    1.7417   -0.0832 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4780    0.8581    0.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7876    1.8061    0.4227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4708    0.5463    0.2009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013   -0.4179   -0.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7116   -1.5989   -0.7737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8947   -1.7837   -0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3799   -0.8000    0.7265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6321    0.3603    0.8542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1181    1.2450    1.6349 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2004   -0.3974    1.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1242   -0.8780    0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7517   -1.8892    1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9973   -1.8260   -0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0130   -1.4885   -1.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1297   -0.6747   -2.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3197    1.6519   -1.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4936    1.4008   -2.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0675    2.7542   -0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1768    1.4866    1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8170    0.3487    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7603    2.0234    1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3122    2.5907   -0.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3297   -2.3704   -1.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4548   -2.7012   -0.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2925   -0.9222    1.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  4 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14  9  1  0
  9  8  1  0
  3  2  1  0
  9 10  1  0
  8  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  7 25  1  0
  7 26  1  0
  6 24  1  6
  5 22  1  0
  5 23  1  0
  4 21  1  6
  3 19  1  0
  3 20  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
  8 27  1  0
  8 28  1  0
M  END


  Mrv1652309042205202D          

 15 17  0  0  1  0            999 V2000
    6.2238    0.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4376    0.5941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9058    1.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0838    1.2947    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6672    0.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7370   -0.7598    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3677   -0.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9149   -0.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3831   -0.0591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4531    0.7629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7761    1.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0293    0.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9593    0.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6362   -0.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5663   -1.2316    0.0000 O   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  1  1  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0187238

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C[C@H]2C[C@@H](C1)C1=CC=CC(=O)N1C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N2O/c1-13-6-9-5-10(8-13)11-3-2-4-12(15)14(11)7-9/h2-4,9-10H,5-8H2,1H3/t9-,10+/m1/s1

> <INCHI_KEY>
CULUKMPMGVXCEI-ZJUUUORDSA-N

> <FORMULA>
C12H16N2O

> <MOLECULAR_WEIGHT>
204.273

> <EXACT_MASS>
204.126263143

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
22.270378834202077

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9R)-11-methyl-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-6-one

> <JCHEM_LOGP>
0.1031943303333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.67612416642175

> <JCHEM_POLAR_SURFACE_AREA>
23.55

> <JCHEM_REFRACTIVITY>
62.223

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9R)-11-methyl-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-6-one

> <JCHEM_VEBER_RULE>
1

$$$$

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  C   UNK     0      11.618   1.576   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      10.150   1.109   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       9.158   2.286   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.623   2.417   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.712   0.652   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.842  -1.418   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.020  -0.426   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.308  -1.288   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       6.315  -0.110   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       6.446   1.424   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.182   2.304   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.788   1.650   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.657   0.116   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.921  -0.764   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.790  -2.299   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₆N₂O

Average Mass

204.2730 Da

Monoisotopic Mass

204.12626 Da

IUPAC Name

(1S,9R)-11-methyl-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-6-one

Traditional Name

(1S,9R)-11-methyl-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-6-one

CAS Registry Number

Not Available

SMILES

CN1C[C@H]2C[C@@H](C1)C1=CC=CC(=O)N1C2

InChI Identifier

InChI=1S/C12H16N2O/c1-13-6-9-5-10(8-13)11-3-2-4-12(15)14(11)7-9/h2-4,9-10H,5-8H2,1H3/t9-,10+/m1/s1

InChI Key

CULUKMPMGVXCEI-ZJUUUORDSA-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
Baptisia australis	LOTUS Database	35616633
Bolusanthus speciosus	LOTUS Database	35616633
Caulophyllum thalictroides	LOTUS Database	35616633
Euchresta japonica	LOTUS Database	35616633
Genista lydia	LOTUS Database	35616633
Gymnospermium albertii	LOTUS Database	35616633
Hovea linearis	LOTUS Database	35616633
Maackia tashiroi	LOTUS Database	35616633
Ormosia emarginata	LOTUS Database	35616633
Pericopsis angolensis	LOTUS Database	35616633
Sophora macrocarpa	LOTUS Database	35616633
Sophora secundiflora	LOTUS Database	35616633
Sophora tomentosa	LOTUS Database	35616633
Thermopsis lanceolata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cytisine and derivatives. These are lupin alkaloids with a structure based on the cytisine skeleton, which is a tetracyclic ketone containing fused pyridine and piperidine rings that form pyrido[1,2a][1,5]diazocin-8-one.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Cytisine and derivatives

Direct Parent

Cytisine and derivatives

Alternative Parents

Substituents

Cytisine
Pyridinone
Aralkylamine
Piperidine
Pyridine
Heteroaromatic compound
Lactam
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
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
logP	0.1	ChemAxon
pKa (Strongest Basic)	8.68	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	62.22 m³·mol⁻¹	ChemAxon
Polarizability	22.27 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

1278189

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,9r)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one (NP0187238)

MOL for NP0187238 ((1s,9r)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

3D MOL for NP0187238 ((1s,9r)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

3D SDF for NP0187238 ((1s,9r)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

3D-SDF for NP0187238 ((1s,9r)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

PDB for NP0187238 ((1s,9r)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

3D PDB for NP0187238 ((1s,9r)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

SMILES for NP0187238 ((1s,9r)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

INCHI for NP0187238 ((1s,9r)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

Structure for NP0187238 ((1s,9r)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

3D Structure for NP0187238 ((1s,9r)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)