NP-MRD: Showing NP-Card for (4e,7e)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione (NP0199532)

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Record Information

Version

2.0

Created at

2022-09-04 18:11:31 UTC

Updated at

2022-09-04 18:11:31 UTC

NP-MRD ID

NP0199532

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4e,7e)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione

Description

Asteriscunolide D belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. (4e,7e)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione is found in Asteriscus graveolens. (4e,7e)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione was first documented in 2012 (PMID: 22236456). Based on a literature review very few articles have been published on Asteriscunolide D (PMID: 25228021).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.7026   -1.9111   -0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3631   -1.1660    0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4949    0.1557    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8620    1.0988   -0.9581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942    2.3406   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1605    2.1335    0.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1449    1.8593   -0.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1844    1.1793    0.1568 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0776    1.8969    1.3878 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6986    2.1797    1.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0964    2.4213    2.5010 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9709   -0.2766    0.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3268   -0.8915    0.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7717   -0.7988   -1.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8977   -0.7342    1.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0428   -1.7069    1.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1126   -1.8896    0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0290   -2.9053   -0.6218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5420   -1.3509    0.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8679   -2.2084   -1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6002   -2.8045    0.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1552    0.6042    0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1670    0.6353   -1.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016    1.5019   -1.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5057    3.2733   -0.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9239    2.4341    0.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4836    1.9570   -1.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2199    1.4004   -0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3124   -1.9634    0.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3852   -0.7333    1.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0846   -0.3455    0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4248   -1.8302   -1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1086   -0.0690   -1.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7681   -0.7834   -1.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8661   -0.1372    2.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2959   -2.5655    1.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17  2  1  0
 10  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  6
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
M  END


  Mrv1652309042220112D          

 18 19  0  0  0  0            999 V2000
    3.3965   -1.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8933   -1.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0755   -1.1694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7610   -1.9321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9432   -2.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4399   -1.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7476   -0.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709    0.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3240   -0.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3397   -1.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0162   -1.5896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1246    0.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5558    1.3395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6595    1.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8053    0.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7045    0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2078   -0.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255   -0.1888    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  1  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  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0199532

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C/CCC2=CC(OC2=O)C(C)(C)\C=C\C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O3/c1-10-5-4-6-11-9-13(18-14(11)17)15(2,3)8-7-12(10)16/h5,7-9,13H,4,6H2,1-3H3/b8-7+,10-5+

> <INCHI_KEY>
CAHQQYHQUHYOGU-LZIZUESTSA-N

> <FORMULA>
C15H18O3

> <MOLECULAR_WEIGHT>
246.306

> <EXACT_MASS>
246.12559444

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
25.73198279189438

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4E,7E)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione

> <JCHEM_LOGP>
3.585334339666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.932896677031557

> <JCHEM_PKA_STRONGEST_BASIC>
-4.649922733619631

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
71.80489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4E,7E)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

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       6.340  -3.200   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.401  -1.979   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.874  -2.183   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.287  -3.607   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.761  -3.810   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.821  -2.590   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.395  -1.005   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.879   0.445   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.605  -0.546   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.634  -2.086   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.897  -2.967   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.099   1.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.038   2.500   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.098   2.558   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.370   0.515   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.048   0.665   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.988  -0.556   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.514  -0.352   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    2   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₃

Average Mass

246.3060 Da

Monoisotopic Mass

246.12559 Da

IUPAC Name

(4E,7E)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione

Traditional Name

(4E,7E)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione

CAS Registry Number

Not Available

SMILES

C\C1=C/CCC2=CC(OC2=O)C(C)(C)\C=C\C1=O

InChI Identifier

InChI=1S/C15H18O3/c1-10-5-4-6-11-9-13(18-14(11)17)15(2,3)8-7-12(10)16/h5,7-9,13H,4,6H2,1-3H3/b8-7+,10-5+

InChI Key

CAHQQYHQUHYOGU-LZIZUESTSA-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
Asteriscus graveolens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
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	3.59	ChemAxon
pKa (Strongest Acidic)	13.93	ChemAxon
pKa (Strongest Basic)	-4.6	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	0	ChemAxon
Refractivity	71.8 m³·mol⁻¹	ChemAxon
Polarizability	25.73 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

C00012442

Chemspider ID

10312009

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13919623

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Han JC, Li F, Li CC: Collective synthesis of humulanolides using a metathesis cascade reaction. J Am Chem Soc. 2014 Oct 1;136(39):13610-3. doi: 10.1021/ja5084927. Epub 2014 Sep 18. [PubMed:25228021 ]
Trost BM, Burns AC, Bartlett MJ, Tautz T, Weiss AH: Thionium ion initiated medium-sized ring formation: the total synthesis of asteriscunolide D. J Am Chem Soc. 2012 Jan 25;134(3):1474-7. doi: 10.1021/ja210986f. Epub 2012 Jan 10. [PubMed:22236456 ]
LOTUS database [Link]

Showing NP-Card for (4e,7e)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione (NP0199532)

MOL for NP0199532 ((4e,7e)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione)

3D MOL for NP0199532 ((4e,7e)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione)

3D SDF for NP0199532 ((4e,7e)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione)

3D-SDF for NP0199532 ((4e,7e)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione)

PDB for NP0199532 ((4e,7e)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione)

3D PDB for NP0199532 ((4e,7e)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione)

SMILES for NP0199532 ((4e,7e)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione)

INCHI for NP0199532 ((4e,7e)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione)

Structure for NP0199532 ((4e,7e)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione)

3D Structure for NP0199532 ((4e,7e)-5,9,9-trimethyl-11-oxabicyclo[8.2.1]trideca-1(13),4,7-triene-6,12-dione)