NP-MRD: Showing NP-Card for swerilactone O (NP0040656)

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Record Information

Version

2.0

Created at

2021-06-20 22:45:36 UTC

Updated at

2021-06-30 00:14:41 UTC

NP-MRD ID

NP0040656

Secondary Accession Numbers

None

Natural Product Identification

Common Name

swerilactone O

Provided By

JEOL Database JEOL Logo

Description

Swerilactone O belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position. swerilactone O is found in Swertia mileensis. swerilactone O was first documented in 2011 (Geng, C.-A., et al.). Based on a literature review very few articles have been published on Swerilactone O.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100453D          

 28 29  0  0  0  0            999 V2000
    4.6940   -1.1224   -0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4223   -0.4221    0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2471   -0.0111    1.4188 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3725   -0.2786   -0.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    0.3953   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570    0.5568   -1.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4406    1.0830   -2.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5746    1.2889   -3.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8917    0.9840   -3.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1949    0.4629   -2.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1745    0.2370   -1.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5764   -0.3012    0.2012 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7817   -1.2042    0.0181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8614   -0.5001   -0.6127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6220    0.1974   -1.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5302    0.6053   -2.4646 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5460   -0.5952    0.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8223   -1.1219   -1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6673   -2.1535    0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5575   -0.7439   -1.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0819    0.8391    0.4783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586    1.3590   -3.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3410    1.7041   -4.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6842    1.1654   -4.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7735   -0.8807    0.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8245    0.5461    0.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5470   -2.0913   -0.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1403   -1.5506    0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0  0  0  0
 10  9  2  0  0  0  0
 11  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
  6  5  1  0  0  0  0
 15 16  2  0  0  0  0
 13 12  1  0  0  0  0
  5  4  2  0  0  0  0
 13 14  1  0  0  0  0
  4  2  1  0  0  0  0
 12 11  1  0  0  0  0
  2  1  1  0  0  0  0
 10 15  1  0  0  0  0
  2  3  2  0  0  0  0
 13 27  1  0  0  0  0
 13 28  1  0  0  0  0
 12 25  1  0  0  0  0
 12 26  1  0  0  0  0
  7 22  1  0  0  0  0
  8 23  1  0  0  0  0
  9 24  1  0  0  0  0
  5 21  1  0  0  0  0
  4 20  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
M  END


  Mrv1652306212100453D          

 28 29  0  0  0  0            999 V2000
    4.6940   -1.1224   -0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4223   -0.4221    0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2471   -0.0111    1.4188 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3725   -0.2786   -0.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    0.3953   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570    0.5568   -1.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4406    1.0830   -2.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5746    1.2889   -3.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8917    0.9840   -3.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1949    0.4629   -2.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1745    0.2370   -1.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5764   -0.3012    0.2012 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7817   -1.2042    0.0181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8614   -0.5001   -0.6127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6220    0.1974   -1.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5302    0.6053   -2.4646 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5460   -0.5952    0.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8223   -1.1219   -1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6673   -2.1535    0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5575   -0.7439   -1.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0819    0.8391    0.4783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586    1.3590   -3.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3410    1.7041   -4.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6842    1.1654   -4.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7735   -0.8807    0.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8245    0.5461    0.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5470   -2.0913   -0.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1403   -1.5506    0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0  0  0  0
 10  9  2  0  0  0  0
 11  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
  6  5  1  0  0  0  0
 15 16  2  0  0  0  0
 13 12  1  0  0  0  0
  5  4  2  0  0  0  0
 13 14  1  0  0  0  0
  4  2  1  0  0  0  0
 12 11  1  0  0  0  0
  2  1  1  0  0  0  0
 10 15  1  0  0  0  0
  2  3  2  0  0  0  0
 13 27  1  0  0  0  0
 13 28  1  0  0  0  0
 12 25  1  0  0  0  0
 12 26  1  0  0  0  0
  7 22  1  0  0  0  0
  8 23  1  0  0  0  0
  9 24  1  0  0  0  0
  5 21  1  0  0  0  0
  4 20  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040656

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\[H])C1=C2C(=C([H])C([H])=C1[H])C(=O)OC([H])([H])C2([H])[H])C(=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O3/c1-9(14)5-6-10-3-2-4-12-11(10)7-8-16-13(12)15/h2-6H,7-8H2,1H3/b6-5+

> <INCHI_KEY>
RINHRISDQZMBAU-AATRIKPKSA-N

> <FORMULA>
C13H12O3

> <MOLECULAR_WEIGHT>
216.236

> <EXACT_MASS>
216.078644246

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.803178512461564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(1E)-3-oxobut-1-en-1-yl]-3,4-dihydro-1H-2-benzopyran-1-one

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
2.3090772529999994

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.687140096555165

> <JCHEM_PKA_STRONGEST_BASIC>
-5.006144094759387

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
61.94590000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(1E)-3-oxobut-1-en-1-yl]-3,4-dihydro-2-benzopyran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       4.694  -1.122  -0.124  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.422  -0.422   0.274  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.247  -0.011   1.419  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.373  -0.279  -0.773  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.245   0.395  -0.503  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.157   0.557  -1.477  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.441   1.083  -2.748  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.575   1.289  -3.683  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.892   0.984  -3.353  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.195   0.463  -2.089  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.175   0.237  -1.146  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.576  -0.301   0.201  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.782  -1.204   0.018  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.861  -0.500  -0.613  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.622   0.197  -1.753  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.530   0.605  -2.465  0.00  0.00           O+0
HETATM   17  H   UNK     0       5.546  -0.595   0.315  0.00  0.00           H+0
HETATM   18  H   UNK     0       4.822  -1.122  -1.210  0.00  0.00           H+0
HETATM   19  H   UNK     0       4.667  -2.154   0.237  0.00  0.00           H+0
HETATM   20  H   UNK     0       2.558  -0.744  -1.733  0.00  0.00           H+0
HETATM   21  H   UNK     0       1.082   0.839   0.478  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.459   1.359  -3.017  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.341   1.704  -4.660  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.684   1.165  -4.077  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.774  -0.881   0.667  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.825   0.546   0.851  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.547  -2.091  -0.583  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.140  -1.551   0.993  0.00  0.00           H+0
CONECT    1    2   17   18   19                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2   20                                                  
CONECT    5    6    4   21                                                  
CONECT    6   11    7    5                                                  
CONECT    7    6    8   22                                                  
CONECT    8    7    9   23                                                  
CONECT    9   10    8   24                                                  
CONECT   10    9   11   15                                                  
CONECT   11    6   10   12                                                  
CONECT   12   13   11   25   26                                             
CONECT   13   12   14   27   28                                             
CONECT   14   15   13                                                       
CONECT   15   14   16   10                                                  
CONECT   16   15                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    4                                                            
CONECT   21    5                                                            
CONECT   22    7                                                            
CONECT   23    8                                                            
CONECT   24    9                                                            
CONECT   25   12                                                            
CONECT   26   12                                                            
CONECT   27   13                                                            
CONECT   28   13                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₂O₃

Average Mass

216.2360 Da

Monoisotopic Mass

216.07864 Da

IUPAC Name

5-[(1E)-3-oxobut-1-en-1-yl]-3,4-dihydro-1H-2-benzopyran-1-one

Traditional Name

5-[(1E)-3-oxobut-1-en-1-yl]-3,4-dihydro-2-benzopyran-1-one

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=C2C(=C([H])C([H])=C1[H])C(=O)OC([H])([H])C2([H])[H])C(=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C13H12O3/c1-9(14)5-6-10-3-2-4-12-11(10)7-8-16-13(12)15/h2-6H,7-8H2,1H3/b6-5+

InChI Key

RINHRISDQZMBAU-AATRIKPKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Swertia leducii	JEOL database	Geng, C.-A., et al, J. Nat. Prod. 74, 1822 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

2-benzopyrans

Direct Parent

2-benzopyrans

Alternative Parents

Substituents

2-benzopyran
Styrene
Benzenoid
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Carboxylic acid ester
Ketone
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

olefinic compound (CHEBI:69299 )

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	1.94	ALOGPS
logP	2.31	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	19.69	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	61.95 m³·mol⁻¹	ChemAxon
Polarizability	22.8 Å³	ChemAxon
Number of Rings	2	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

26610346

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53494395

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Geng, C.-A., et al. (2011). Geng, C.-A., et al, J. Nat. Prod. 74, 1822 (2011). J. Nat. Prod..

Showing NP-Card for swerilactone O (NP0040656)

MOL for NP0040656 (swerilactone O)

3D MOL for NP0040656 (swerilactone O)

3D SDF for NP0040656 (swerilactone O)

3D-SDF for NP0040656 (swerilactone O)

PDB for NP0040656 (swerilactone O)

3D PDB for NP0040656 (swerilactone O)

SMILES for NP0040656 (swerilactone O)

INCHI for NP0040656 (swerilactone O)

Structure for NP0040656 (swerilactone O)

3D Structure for NP0040656 (swerilactone O)