NP-MRD: Showing NP-Card for (1s,9s)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one (NP0198303)

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Record Information

Version

2.0

Created at

2022-09-04 16:43:55 UTC

Updated at

2022-09-04 16:43:55 UTC

NP-MRD ID

NP0198303

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Caulophylline, also known as N-methylcytisine, 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,9s)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one is found in Ulex europaeus. (1s,9s)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one was first documented in 2005 (PMID: 15686946). Based on a literature review a small amount of articles have been published on Caulophylline (PMID: 25880244) (PMID: 21596111) (PMID: 17703777).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
    3.4977    0.4973   -0.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2837    0.3085   -0.7234 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8866   -1.1104   -0.9562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5512   -1.0913   -0.4767 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7393   -0.5727    0.9506 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2672    0.8713    0.6926 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2032    1.2097   -0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1406    0.5489    0.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0838    1.5350    0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4355    1.3218    0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8359    0.1047   -0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8868   -0.8797   -0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2783   -1.9849   -0.8026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6091   -0.6326   -0.1101 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6771   -1.7853   -0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507   -0.4821   -0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4802    1.0145    0.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1740    1.1168   -0.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1203   -1.4134   -1.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5690   -1.6857   -0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1903   -0.3135   -1.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7581   -0.5947    1.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874   -0.9842    1.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3778    1.4916    1.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7637    2.1282   -0.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7016    1.6171   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8275    2.5202    0.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1665    2.1085    0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8777   -0.0639   -0.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8299   -2.5025    0.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0534   -2.2972   -1.3050 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  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
  7  2  1  0
 14  8  1  0
 15  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  6
  5 22  1  0
  5 23  1  0
  6 24  1  1
  7 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 15 30  1  0
 15 31  1  0
M  END


  Mrv1652309042218432D          

 15 17  0  0  1  0            999 V2000
    5.7229    1.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9367    1.4403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8667    2.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2360    2.7942    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1662    1.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5828    0.7397    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4049    0.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9521    1.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2752    0.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5283    1.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4584    1.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1353    2.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0654    3.2659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8822    2.0935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4140    2.7242    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  1  1  0  0  0
  6  5  1  6  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  2  0  0  0  0
  9 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
 12 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
  4 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0198303

> <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-/m0/s1

> <INCHI_KEY>
CULUKMPMGVXCEI-UWVGGRQHSA-N

> <FORMULA>
C12H16N2O

> <MOLECULAR_WEIGHT>
204.273

> <EXACT_MASS>
204.126263143

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
38.07949289321978

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9S)-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>
23.550000000000004

> <JCHEM_REFRACTIVITY>
62.223000000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9S)-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      10.683   2.222   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       9.215   2.689   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       9.085   4.223   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.907   5.216   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.777   3.146   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.688   1.381   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.222   1.511   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.511   2.373   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.247   1.493   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.853   2.147   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.722   3.682   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.986   4.562   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.855   6.096   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       5.380   3.908   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       6.373   5.085   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    8   15                                                  
CONECT   15   14    4                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Value	Source
N-Methylcytisine	Kegg

Chemical Formula

C₁₂H₁₆N₂O

Average Mass

204.2730 Da

Monoisotopic Mass

204.12626 Da

IUPAC Name

Not Available

Traditional Name

Not Available

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-/m0/s1

InChI Key

CULUKMPMGVXCEI-UWVGGRQHSA-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
Ulex europaeus	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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002216

Chemspider ID

391250

KEGG Compound ID

C10760

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442947

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ma J, Wang S, Huang X, Geng P, Wen C, Zhou Y, Yu L, Wang X: Validated UPLC-MS/MS method for determination of hordenine in rat plasma and its application to pharmacokinetic study. J Pharm Biomed Anal. 2015;111:131-7. doi: 10.1016/j.jpba.2015.03.032. Epub 2015 Apr 3. [PubMed:25880244 ]
Wang XL, Liu BR, Chen CK, Wang JR, Lee SS: Four new fluorenone alkaloids and one new dihydroazafluoranthene alkaloid from Caulophyllum robustum Maxim. Fitoterapia. 2011 Sep;82(6):793-7. doi: 10.1016/j.fitote.2011.04.010. Epub 2011 May 9. [PubMed:21596111 ]
Wang SC, Chen QH, Wei YY, Li HW, He LC: [Analysis of supercritical fluid extracts of Radix caulophylli with gas chromatography-mass spectrometry]. Yao Xue Xue Bao. 2007 May;42(5):525-8. [PubMed:17703777 ]
Fitch RW, Kaneko Y, Klaperski P, Daly JW, Seitz G, Gundisch D: Halogenated and isosteric cytisine derivatives with increased affinity and functional activity at nicotinic acetylcholine receptors. Bioorg Med Chem Lett. 2005 Feb 15;15(4):1221-4. doi: 10.1016/j.bmcl.2004.11.073. [PubMed:15686946 ]
LOTUS database [Link]

Showing NP-Card for (1s,9s)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one (NP0198303)

MOL for NP0198303 ((1s,9s)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

3D MOL for NP0198303 ((1s,9s)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

3D SDF for NP0198303 ((1s,9s)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

3D-SDF for NP0198303 ((1s,9s)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

PDB for NP0198303 ((1s,9s)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

3D PDB for NP0198303 ((1s,9s)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

SMILES for NP0198303 ((1s,9s)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

INCHI for NP0198303 ((1s,9s)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

Structure for NP0198303 ((1s,9s)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

3D Structure for NP0198303 ((1s,9s)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)