NP-MRD: Showing NP-Card for (6e)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-7h-cyclopenta[c]pyridin-5-one (NP0156133)

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Record Information

Version

2.0

Created at

2022-09-02 13:18:12 UTC

Updated at

2022-09-02 13:18:12 UTC

NP-MRD ID

NP0156133

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6e)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-7h-cyclopenta[c]pyridin-5-one

Description

Beatrine B belongs to the class of organic compounds known as aryl ketones. These are organic aromatic compounds that contain a ketone group substituted at one C-atom with an aryl group. They have the generic structure RC(=O)R', where R = aryl group and R'=organyl group. (6e)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-7h-cyclopenta[c]pyridin-5-one is found in Harpagophytum zeyheri. (6e)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-7h-cyclopenta[c]pyridin-5-one was first documented in 1999 (PMID: 10075743). Based on a literature review very few articles have been published on Beatrine B.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -5.2997    0.7988   -0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9627    0.1398   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5498   -1.0186   -0.7173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2207   -1.1852   -0.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8964   -0.1368    0.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6616    0.1815    1.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5291    0.1226    0.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7684    0.5075    1.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9630    0.7034    2.5856 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7763    0.6268    0.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1001    1.0896    0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8432    1.2498   -0.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2653    0.9500   -1.9413 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0195    0.5084   -2.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2469    0.3351   -0.9081 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8970   -0.2564   -0.6893 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0854   -1.7844   -0.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979    0.6252    0.5814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9164    0.3308   -0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8615    0.7373    0.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1778    1.8810   -0.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1218   -1.6590   -1.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6394   -2.0343   -0.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191    0.4971    2.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5219    1.3179    1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8666    1.6039   -0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5444    0.2641   -2.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1787    0.0454   -1.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6430   -2.1944   -1.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6122   -2.2363    0.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1639   -2.0106   -0.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 18  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 18  5  1  0
 15 10  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
 16 28  1  6
  6 24  1  0
  4 23  1  0
  3 22  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
M  END


  Mrv1652309022215182D          

 18 20  0  0  0  0            999 V2000
   -0.7750   -3.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612   -2.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757   -2.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4042   -1.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481   -2.1661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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
  8 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
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 18  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0156133

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1\C(=C/C2=CC=C(C)O2)C(=O)C2=CC=NC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H13NO2/c1-9-3-4-11(18-9)7-13-10(2)14-8-16-6-5-12(14)15(13)17/h3-8,10H,1-2H3/b13-7+

> <INCHI_KEY>
FMELDHMCOAMSPH-NTUHNPAUSA-N

> <FORMULA>
C15H13NO2

> <MOLECULAR_WEIGHT>
239.274

> <EXACT_MASS>
239.094628663

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.043104431510148

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6E)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-5H,6H,7H-cyclopenta[c]pyridin-5-one

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.2201572563333336

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.980496232884099

> <JCHEM_POLAR_SURFACE_AREA>
43.1

> <JCHEM_REFRACTIVITY>
69.80440000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6E)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-7H-cyclopenta[c]pyridin-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

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      -1.447  -6.605   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.608  -5.074   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.941  -4.304   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.621  -2.797   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.650   1.408   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       6.258  -2.073   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.463  -4.043   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15    7   17                                                  
CONECT   17   16                                                            
CONECT   18    5    2                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₃NO₂

Average Mass

239.2740 Da

Monoisotopic Mass

239.09463 Da

IUPAC Name

(6E)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-5H,6H,7H-cyclopenta[c]pyridin-5-one

Traditional Name

(6E)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-7H-cyclopenta[c]pyridin-5-one

CAS Registry Number

Not Available

SMILES

CC1\C(=C/C2=CC=C(C)O2)C(=O)C2=CC=NC=C12

InChI Identifier

InChI=1S/C15H13NO2/c1-9-3-4-11(18-9)7-13-10(2)14-8-16-6-5-12(14)15(13)17/h3-8,10H,1-2H3/b13-7+

InChI Key

FMELDHMCOAMSPH-NTUHNPAUSA-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
Harpagophytum zeyheri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl ketones. These are organic aromatic compounds that contain a ketone group substituted at one C-atom with an aryl group. They have the generic structure RC(=O)R', where R = aryl group and R'=organyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl ketones

Alternative Parents

Substituents

Aryl ketone
Pyridine
Heteroaromatic compound
Furan
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen 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	2.5	ALOGPS
logP	2.22	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	2.98	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.1 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.8 m³·mol⁻¹	ChemAxon
Polarizability	26.04 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

8999199

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10823898

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Baghdikian B, Ollivier E, Faure R, Debrauwer L, Rathelot P, Balansard G: Two new pyridine monoterpene alkaloids by chemical conversion of a commercial extract of harpagophytum procumbens. J Nat Prod. 1999 Feb;62(2):211-3. doi: 10.1021/np980149c. [PubMed:10075743 ]
LOTUS database [Link]

Showing NP-Card for (6e)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-7h-cyclopenta[c]pyridin-5-one (NP0156133)

MOL for NP0156133 ((6e)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-7h-cyclopenta[c]pyridin-5-one)

3D MOL for NP0156133 ((6e)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-7h-cyclopenta[c]pyridin-5-one)

3D SDF for NP0156133 ((6e)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-7h-cyclopenta[c]pyridin-5-one)

3D-SDF for NP0156133 ((6e)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-7h-cyclopenta[c]pyridin-5-one)

PDB for NP0156133 ((6e)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-7h-cyclopenta[c]pyridin-5-one)

3D PDB for NP0156133 ((6e)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-7h-cyclopenta[c]pyridin-5-one)

SMILES for NP0156133 ((6e)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-7h-cyclopenta[c]pyridin-5-one)

INCHI for NP0156133 ((6e)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-7h-cyclopenta[c]pyridin-5-one)

Structure for NP0156133 ((6e)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-7h-cyclopenta[c]pyridin-5-one)

3D Structure for NP0156133 ((6e)-7-methyl-6-[(5-methylfuran-2-yl)methylidene]-7h-cyclopenta[c]pyridin-5-one)