NP-MRD: Showing NP-Card for Cinariolide (NP0061872)

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Record Information

Version

2.0

Created at

2022-04-28 06:34:16 UTC

Updated at

2022-04-28 06:34:17 UTC

NP-MRD ID

NP0061872

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cinariolide

Description

Cinariolide belongs to the class of organic compounds known as vinylogous esters. These are organic compounds containing an ester group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety. Cinariolide is found in Cineraria aspera, Cineraria erodioides, Cineraria parvifolia and Cineraria spp.. Based on a literature review very few articles have been published on Cinariolide.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
    3.8948   -1.6487   -0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3767   -0.4666   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3530    0.6506   -0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0193   -0.0442    0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6931    1.2221   -0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3926    1.8941   -0.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3341    3.1061    0.1402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8704    1.1626   -0.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1360   -0.1305   -0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2683   -1.1969   -0.0405 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0322   -1.0389    0.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3955   -1.8471    1.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4762   -0.5454   -0.8160 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6887   -2.0268   -0.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5666    0.2003   -0.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1461    1.5460    0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0241    2.1087   -0.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9813   -1.8005   -0.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3722   -2.5494    0.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3754    0.2839   -0.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2896    1.4031    0.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0623    1.0092   -1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922    1.8575   -0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3566   -1.8033    1.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227   -2.6024    1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5321   -0.2800   -1.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6606   -2.5259   -1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8850   -2.5013   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7083   -2.2465   -0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8694   -0.4529    0.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4232    0.3226   -0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8206    1.4235    1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9973    2.2677    0.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7282    3.1040   -0.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3423    2.1454   -1.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 11  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
  9 13  1  0
  6  8  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
 13 26  1  6
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 12 24  1  0
 12 25  1  0
  5 23  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  1 18  1  0
  1 19  1  0
M  END


  Mrv1652304282208342D          

 17 18  0  0  1  0            999 V2000
    0.5915   -1.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915   -0.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230    0.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374   -0.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374   -1.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230   -1.6408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1230   -2.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2365    0.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0529    0.9154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408   -0.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3988   -0.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408   -1.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5552   -2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2365   -1.7427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2238   -0.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6363   -0.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6363   -1.5303    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
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  2  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
 12 14  1  0  0  0  0
  1 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0061872

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCCC2=C1OC(=C)C(=CC2=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O2/c1-9(2)13-8-14(16)12-7-5-6-10(3)15(12)17-11(13)4/h8,10H,1,4-7H2,2-3H3/t10-/m0/s1

> <INCHI_KEY>
LIKVZNBOYGRKRL-JTQLQIEISA-N

> <FORMULA>
C15H18O2

> <MOLECULAR_WEIGHT>
230.307

> <EXACT_MASS>
230.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
26.03158021346193

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S)-9-methyl-2-methylidene-3-(prop-1-en-2-yl)-2,5,6,7,8,9-hexahydro-1-benzoxepin-5-one

> <ALOGPS_LOGP>
3.51

> <JCHEM_LOGP>
2.9494585410000003

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.238950041644781

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
71.3484

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9S)-9-methyl-2-methylidene-3-(prop-1-en-2-yl)-6,7,8,9-tetrahydro-1-benzoxepin-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.104  -2.293   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.104  -0.753   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.230   0.017   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.563  -0.753   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.563  -2.293   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.230  -3.063   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.230  -4.603   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.308   0.207   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.965   1.709   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.810  -0.135   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.478  -1.523   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.810  -2.910   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.770  -4.114   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.308  -3.253   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.018  -1.523   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.788  -0.189   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.788  -2.856   0.000  0.00  0.00           C+0
CONECT    1    2    6   14                                                  
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    2    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    1                                                       
CONECT   15   11   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₂

Average Mass

230.3070 Da

Monoisotopic Mass

230.13068 Da

IUPAC Name

(9S)-9-methyl-2-methylidene-3-(prop-1-en-2-yl)-2,5,6,7,8,9-hexahydro-1-benzoxepin-5-one

Traditional Name

(9S)-9-methyl-2-methylidene-3-(prop-1-en-2-yl)-6,7,8,9-tetrahydro-1-benzoxepin-5-one

CAS Registry Number

Not Available

SMILES

C[C@H]1CCCC2=C1OC(=C)C(=CC2=O)C(C)=C

InChI Identifier

InChI=1S/C15H18O2/c1-9(2)13-8-14(16)12-7-5-6-10(3)15(12)17-11(13)4/h8,10H,1,4-7H2,2-3H3/t10-/m0/s1

InChI Key

LIKVZNBOYGRKRL-JTQLQIEISA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cineraria aspera	LOTUS Database	35616633
Cineraria erodioides	LOTUS Database	35616633
Cineraria parvifolia	LOTUS Database	35616633
Cineraria spp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vinylogous esters. These are organic compounds containing an ester group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Vinylogous esters

Sub Class

Not Available

Direct Parent

Vinylogous esters

Alternative Parents

Substituents

Vinylogous ester
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	3.51	ALOGPS
logP	2.95	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.35 m³·mol⁻¹	ChemAxon
Polarizability	26.03 Å³	ChemAxon
Number of Rings	2	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

C00011947

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

101324804

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cinariolide (NP0061872)

MOL for NP0061872 (Cinariolide)

3D MOL for NP0061872 (Cinariolide)

3D SDF for NP0061872 (Cinariolide)

3D-SDF for NP0061872 (Cinariolide)

PDB for NP0061872 (Cinariolide)

3D PDB for NP0061872 (Cinariolide)

SMILES for NP0061872 (Cinariolide)

INCHI for NP0061872 (Cinariolide)

Structure for NP0061872 (Cinariolide)

3D Structure for NP0061872 (Cinariolide)