NP-MRD: Showing NP-Card for Rhombifoline (NP0140309)

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Record Information

Version

2.0

Created at

2022-06-29 21:22:33 UTC

Updated at

2022-06-29 21:22:33 UTC

NP-MRD ID

NP0140309

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rhombifoline

Description

Rhombifoline 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. Rhombifoline is found in Anagyris foetida, Anarthrophyllum desideratum, Baptisia australis, Castilleja miniata, Clathrotropis brachypetala, Dermatophyllum secundiflorum, Dicraeopetalum stipulare, Genista canariensis, Genista cinerascens, Genista lobelii, Genista tinctoria, Gonocytisus pterocladus, Lamprolobium fruticosum, Lamprolobium grandiflorum, Lupinus angustifolius, Lupinus flavoculatus, Maackia amurensis, Maackia hupehensis, Maackia tashiroi, Petteria ramentacea, Plagiocarpus axillaris, Platycelyphium voense, Retama monosperma, Retama raetam, Sophora chrysophylla, Spartium junceum, Teline maderensis, Thermopsis chinensis and Thermopsis rhombifolia. Rhombifoline was first documented in 2002 (PMID: 12453529). Based on a literature review a small amount of articles have been published on Rhombifoline (PMID: 16876210) (PMID: 16042152).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    4.6846   -1.3233    0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8065   -0.1519    0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6141    0.5831   -0.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3541   -0.1521   -0.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1609    0.4789   -0.6512 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7499    1.6811   -0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6380    1.6227    0.5674 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6277    0.3844    1.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6557   -0.7917    0.4507 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1459   -0.5071   -0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0778   -0.7871    0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7846   -1.9480    0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1117   -1.9259   -0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6458   -0.7249   -0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8491    0.4174   -0.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3945    1.5045   -1.1692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5608    0.3974   -0.3802 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7633    1.6134   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320   -1.7995    0.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658   -1.8645    1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8101    0.2482   -0.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6182    1.5706    0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7355    0.8477   -1.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3908   -1.1621   -0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396   -0.3433    0.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8360    2.5806   -0.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4437    1.8770    0.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6839    2.4911    1.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2040    0.3457    2.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5660    0.4240    2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3730   -1.7309    0.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4697   -0.2630   -1.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6556   -1.4762   -1.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3185   -2.8839    0.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6704   -2.8502   -0.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6913   -0.7044   -1.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4838    2.4234   -0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4816    1.8990   -1.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 10  5  1  0
 17 11  1  0
 18  7  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  1
  8 29  1  0
  8 30  1  0
  9 31  1  1
 10 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 18 37  1  0
 18 38  1  0
M  END


  Mrv1652306292223222D          

 18 20  0  0  1  0            999 V2000
    7.7283    2.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1187    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3325    1.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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  2  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  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  9 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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140309

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C=CCCN1C[C@@H]2C[C@H](C1)C1=CC=CC(=O)N1C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H20N2O/c1-2-3-7-16-9-12-8-13(11-16)14-5-4-6-15(18)17(14)10-12/h2,4-6,12-13H,1,3,7-11H2/t12-,13+/m0/s1

> <INCHI_KEY>
ZVTFRRVBMAUIQW-QWHCGFSZSA-N

> <FORMULA>
C15H20N2O

> <MOLECULAR_WEIGHT>
244.338

> <EXACT_MASS>
244.157563272

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.424887566818843

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9S)-11-(but-3-en-1-yl)-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-6-one

> <ALOGPS_LOGP>
2.77

> <JCHEM_LOGP>
1.1231053586666657

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.29744942362708

> <JCHEM_POLAR_SURFACE_AREA>
23.550000000000004

> <JCHEM_REFRACTIVITY>
76.1407

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9S)-11-(but-3-en-1-yl)-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-6-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      14.426   3.831   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.288   2.793   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.821   3.260   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.683   2.222   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       9.215   2.689   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.085   4.223   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.907   5.216   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.777   3.146   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.688   1.381   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.222   1.511   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.511   2.373   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.247   1.493   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.853   2.147   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.722   3.682   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.986   4.562   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.855   6.096   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       5.380   3.908   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       6.373   5.085   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11   18                                                  
CONECT   18   17    7                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀N₂O

Average Mass

244.3380 Da

Monoisotopic Mass

244.15756 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C=CCCN1C[C@@H]2C[C@H](C1)C1=CC=CC(=O)N1C2

InChI Identifier

InChI=1S/C15H20N2O/c1-2-3-7-16-9-12-8-13(11-16)14-5-4-6-15(18)17(14)10-12/h2,4-6,12-13H,1,3,7-11H2/t12-,13+/m0/s1

InChI Key

ZVTFRRVBMAUIQW-QWHCGFSZSA-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
Anagyris foetida	LOTUS Database	35616633
Anarthrophyllum desideratum	LOTUS Database	35616633
Baptisia australis	LOTUS Database	35616633
Castilleja miniata	LOTUS Database	35616633
Clathrotropis brachypetala	LOTUS Database	35616633
Dermatophyllum secundiflorum	LOTUS Database	35616633
Dicraeopetalum stipulare	LOTUS Database	35616633
Genista canariensis	LOTUS Database	35616633
Genista cinerascens	LOTUS Database	35616633
Genista lobelii	LOTUS Database	35616633
Genista tinctoria	LOTUS Database	35616633
Gonocytisus pterocladus	LOTUS Database	35616633
Lamprolobium fruticosum	LOTUS Database	35616633
Lamprolobium grandiflorum	LOTUS Database	35616633
Lupinus angustifolius	LOTUS Database	35616633
Lupinus flavoculatus	LOTUS Database	35616633
Maackia amurensis	LOTUS Database	35616633
Maackia hupehensis	LOTUS Database	35616633
Maackia tashiroi	LOTUS Database	35616633
Petteria ramentacea	LOTUS Database	35616633
Plagiocarpus axillaris	LOTUS Database	35616633
Platycelyphium voense	LOTUS Database	35616633
Retama monosperma	LOTUS Database	35616633
Retama raetam	LOTUS Database	35616633
Sophora chrysophylla	LOTUS Database	35616633
Spartium junceum	LOTUS Database	35616633
Teline maderensis	LOTUS Database	35616633
Thermopsis chinensis	LOTUS Database	35616633
Thermopsis rhombifolia	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

C00002234

Chemspider ID

83767

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92795

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Maximo P, Lourenco A, Tei A, Wink M: Chemotaxonomy of Portuguese Ulex: quinolizidine alkaloids as taxonomical markers. Phytochemistry. 2006 Sep;67(17):1943-9. doi: 10.1016/j.phytochem.2006.05.037. Epub 2006 Jul 28. [PubMed:16876210 ]
Martins A, Wink M, Tei A, Brum-Bousquet M, Tillequin F, Rauter AP: A phytochemical study of the quinolizidine alkaloids from Genista tenera by gas chromatography-mass spectrometry. Phytochem Anal. 2005 Jul-Aug;16(4):264-6. doi: 10.1002/pca.832. [PubMed:16042152 ]
Sagen AL, Gertsch J, Becker R, Heilmann J, Sticher O: Quinolizidine alkaloids from the curare adjuvant Clathrotropis glaucophylla. Phytochemistry. 2002 Dec;61(8):975-8. doi: 10.1016/s0031-9422(02)00394-1. [PubMed:12453529 ]

Showing NP-Card for Rhombifoline (NP0140309)

MOL for NP0140309 (Rhombifoline)

3D MOL for NP0140309 (Rhombifoline)

3D SDF for NP0140309 (Rhombifoline)

3D-SDF for NP0140309 (Rhombifoline)

PDB for NP0140309 (Rhombifoline)

3D PDB for NP0140309 (Rhombifoline)

SMILES for NP0140309 (Rhombifoline)

INCHI for NP0140309 (Rhombifoline)

Structure for NP0140309 (Rhombifoline)

3D Structure for NP0140309 (Rhombifoline)