NP-MRD: Showing NP-Card for 5,9:6,9-Diepoxy-4-megastigmene (NP0085222)

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Record Information

Version

2.0

Created at

2022-04-29 05:48:17 UTC

Updated at

2022-04-29 05:48:17 UTC

NP-MRD ID

NP0085222

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,9:6,9-Diepoxy-4-megastigmene

Description

5,9:6,9-Diepoxy-4-megastigmene belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. 5,9:6,9-Diepoxy-4-megastigmene is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5,9:6,9-Diepoxy-4-megastigmene has been detected, but not quantified in, alcoholic beverages. 5,9:6,9-Diepoxy-4-megastigmene is found in Cydonia oblonga . This could make 5,9:6,9-Diepoxy-4-megastigmene a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.5428   -1.8000   -0.8145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4126   -0.4466   -0.1466 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0477   -0.5596    1.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2187    0.5331   -0.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1685    1.8947   -0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7339    2.2775   -0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2538    1.3975   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6713    1.8582   -0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4996    0.9322   -0.6022 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1183   -0.3713   -0.4096 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1718   -1.2692   -1.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0368   -0.6207    1.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5394   -0.6571    1.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0257   -0.0599    0.0130 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8571   -0.6615   -0.9286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6259   -1.9328   -1.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9906   -1.8311   -1.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2881   -2.6368   -0.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1650   -0.4903    1.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7877   -1.5350    1.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7706    0.2700    1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2777    0.1970   -0.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8728    0.5944   -1.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6254    1.7949    0.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7556    2.6029   -0.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4745    3.3287   -0.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9941    2.0817    1.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8017    2.8194   -0.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6454   -2.0986   -1.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8438   -0.7124   -1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8201   -1.7108   -0.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5310   -1.5691    1.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4817    0.2104    1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2420   -1.7261    1.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245   -0.1039    2.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 14 13  1  1
 14 15  1  0
 14  7  1  0
  7  8  1  0
  8  9  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  6
  2  3  1  0
 15 10  1  0
  9 10  1  0
  2 14  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
  8 27  1  0
  8 28  1  0
  6 26  1  0
  5 24  1  0
  5 25  1  0
  4 22  1  0
  4 23  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
M  END


  Mrv0541 02241214482D          

 15 17  0  0  0  0            999 V2000
   -2.0030   -0.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0030    0.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818    1.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6407    0.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    1.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8010    1.0413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6824   -1.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2818   -0.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8811   -1.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0798    0.3202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6407   -0.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004   -0.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8010   -0.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1215    0.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0030    0.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085222

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC3(O1)C(CO2)=CCCC3(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O2/c1-11(2)6-4-5-10-9-14-12(3)7-8-13(10,11)15-12/h5H,4,6-9H2,1-3H3

> <INCHI_KEY>
AKKNWGRLXKHQDH-UHFFFAOYSA-N

> <FORMULA>
C13H20O2

> <MOLECULAR_WEIGHT>
208.2967

> <EXACT_MASS>
208.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.70072792226603

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2,9-trimethyl-8,12-dioxatricyclo[7.2.1.0¹,⁶]dodec-5-ene

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
2.569776631999999

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0856394940000405

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
59.9983

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2,9-trimethyl-8,12-dioxatricyclo[7.2.1.0¹,⁶]dodec-5-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.739  -0.149   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.739   1.345   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.393   2.093   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.196   1.345   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.001   2.243   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.495   1.944   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.140  -2.243   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.393  -0.897   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.645  -2.243   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.149   0.598   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.196  -0.149   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.001  -1.196   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.495  -0.747   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.093   0.598   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.739   0.598   0.000  0.00  0.00           C+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5   14                                                       
CONECT    7    8                                                            
CONECT    8    1    7    9   11                                             
CONECT    9    8                                                            
CONECT   10   11   14                                                       
CONECT   11    4    8   10   12                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    6   10   13   15                                             
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Value	Source
2,2,9-Trimethyl-8,12-dioxatricyclo[7.2.1.01,6]dodec-5-ene	HMDB

Chemical Formula

C₁₃H₂₀O₂

Average Mass

208.2967 Da

Monoisotopic Mass

208.14633 Da

IUPAC Name

2,2,9-trimethyl-8,12-dioxatricyclo[7.2.1.0¹,⁶]dodec-5-ene

Traditional Name

2,2,9-trimethyl-8,12-dioxatricyclo[7.2.1.0¹,⁶]dodec-5-ene

CAS Registry Number

Not Available

SMILES

CC12CCC3(O1)C(CO2)=CCCC3(C)C

InChI Identifier

InChI=1S/C13H20O2/c1-11(2)6-4-5-10-9-14-12(3)7-8-13(10,11)15-12/h5H,4,6-9H2,1-3H3

InChI Key

AKKNWGRLXKHQDH-UHFFFAOYSA-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
Cydonia oblonga	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Not Available

Substituents

Not Available

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	3.36	ALOGPS
logP	2.57	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	60 m³·mol⁻¹	ChemAxon
Polarizability	23.7 Å³	ChemAxon
Number of Rings	3	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

HMDB0038529

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017914

KNApSAcK ID

Not Available

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

73817713

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5,9:6,9-Diepoxy-4-megastigmene (NP0085222)

MOL for NP0085222 (5,9:6,9-Diepoxy-4-megastigmene)

3D MOL for NP0085222 (5,9:6,9-Diepoxy-4-megastigmene)

3D SDF for NP0085222 (5,9:6,9-Diepoxy-4-megastigmene)

3D-SDF for NP0085222 (5,9:6,9-Diepoxy-4-megastigmene)

PDB for NP0085222 (5,9:6,9-Diepoxy-4-megastigmene)

3D PDB for NP0085222 (5,9:6,9-Diepoxy-4-megastigmene)

SMILES for NP0085222 (5,9:6,9-Diepoxy-4-megastigmene)

INCHI for NP0085222 (5,9:6,9-Diepoxy-4-megastigmene)

Structure for NP0085222 (5,9:6,9-Diepoxy-4-megastigmene)

3D Structure for NP0085222 (5,9:6,9-Diepoxy-4-megastigmene)