NP-MRD: Showing NP-Card for 4,8,11,11-tetramethyl-9,10-dioxatricyclo[6.3.2.0²,⁷]trideca-2,4,6-triene (NP0189132)

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Record Information

Version

2.0

Created at

2022-09-04 05:34:07 UTC

Updated at

2022-09-04 05:34:07 UTC

NP-MRD ID

NP0189132

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,8,11,11-tetramethyl-9,10-dioxatricyclo[6.3.2.0²,⁷]trideca-2,4,6-triene

Description

10,11-Epidioxycalamene belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane. 10,11-Epidioxycalamene is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 10,11-epidioxycalamene has been detected, but not quantified in, root vegetables. 4,8,11,11-tetramethyl-9,10-dioxatricyclo[6.3.2.0²,⁷]trideca-2,4,6-triene is found in Cyperus rotundus. This could make 10,11-epidioxycalamene a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    3.4180    2.6449    0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4851    1.4916    0.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7598    0.4388    1.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8718   -0.6367    1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7152   -0.6537    0.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4543    0.3946   -0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3002    1.4553   -0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8044    0.3348   -1.1596 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8091   -1.0294   -1.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5151   -2.1650   -0.9230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2907   -1.7390    0.5309 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1637   -2.8996    1.3457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5057   -1.2905    1.0516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3375   -0.8982    0.1125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9850    0.4046   -0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6758    1.1369    1.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0945    1.1277   -0.9475 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2039    3.4507    0.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2794    3.0890   -0.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4737    2.3305    0.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6719    0.4902    1.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0877   -1.4495    1.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    2.2899   -1.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8694    1.0998   -1.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8543   -1.1490   -2.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1536   -1.0298   -2.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3378   -2.7327   -1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3790   -2.8812   -0.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4091   -2.5022    2.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6774   -3.6031    1.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361   -3.3865    0.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6471    1.2544    1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1944    2.1192    0.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0245    0.5558    1.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4353    0.4636   -1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8939    1.4576   -0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6407    2.0162   -1.4372 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  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  7  2  1  0
 15  8  1  0
 11  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  7 23  1  0
  8 24  1  6
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
M  END


  Mrv0541 02241214452D          

 17 19  0  0  0  0            999 V2000
   -1.4824    0.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4824   -0.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7687   -0.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0564   -0.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0564    0.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7687    0.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6573   -0.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3695   -0.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3695    0.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6573    0.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6573    1.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4823    0.8106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4823   -0.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6968    0.0144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6954   -1.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1973   -1.2506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1973   -0.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 17  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 13  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 14  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0189132

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC=C2C(=C1)C1CCC2(C)OOC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O2/c1-10-5-6-13-11(9-10)12-7-8-15(13,4)17-16-14(12,2)3/h5-6,9,12H,7-8H2,1-4H3

> <INCHI_KEY>
ALXPNLYWXCZUCG-UHFFFAOYSA-N

> <FORMULA>
C15H20O2

> <MOLECULAR_WEIGHT>
232.3181

> <EXACT_MASS>
232.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.46150416473576

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,8,11,11-tetramethyl-9,10-dioxatricyclo[6.3.2.0²,⁷]trideca-2,4,6-triene

> <ALOGPS_LOGP>
4.67

> <JCHEM_LOGP>
3.960006084

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.865749997959576

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
67.7636

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.02e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,8,11,11-tetramethyl-9,10-dioxatricyclo[6.3.2.0²,⁷]trideca-2,4,6-triene

> <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      -2.767   0.746   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.767  -0.794   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.435  -1.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.105  -0.794   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.105   0.746   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.435   1.513   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.227  -1.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.556  -0.794   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.556   0.746   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.227   1.513   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.227   3.053   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.767   1.513   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.767  -1.564   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.167   0.027   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.165  -3.053   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.102  -2.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.102  -1.564   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    5    9   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   14                                                       
CONECT   13    7   14   15   16                                             
CONECT   14   12   13                                                       
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17    2                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
10,12-Peroxycalamenene	HMDB

Chemical Formula

C₁₅H₂₀O₂

Average Mass

232.3181 Da

Monoisotopic Mass

232.14633 Da

IUPAC Name

4,8,11,11-tetramethyl-9,10-dioxatricyclo[6.3.2.0²,⁷]trideca-2,4,6-triene

Traditional Name

4,8,11,11-tetramethyl-9,10-dioxatricyclo[6.3.2.0²,⁷]trideca-2,4,6-triene

CAS Registry Number

Not Available

SMILES

CC1=CC=C2C(=C1)C1CCC2(C)OOC1(C)C

InChI Identifier

InChI=1S/C15H20O2/c1-10-5-6-13-11(9-10)12-7-8-15(13,4)17-16-14(12,2)3/h5-6,9,12H,7-8H2,1-4H3

InChI Key

ALXPNLYWXCZUCG-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, 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
Cyperus rotundus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

Alternative Parents

Not Available

Substituents

Not Available

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	4.67	ALOGPS
logP	3.96	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-4.9	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	67.76 m³·mol⁻¹	ChemAxon
Polarizability	26.46 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

HMDB0041062

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020937

KNApSAcK ID

Not Available

Chemspider ID

8574497

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10399059

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,8,11,11-tetramethyl-9,10-dioxatricyclo[6.3.2.0²,⁷]trideca-2,4,6-triene (NP0189132)

MOL for NP0189132 (4,8,11,11-tetramethyl-9,10-dioxatricyclo[6.3.2.0²,⁷]trideca-2,4,6-triene)

3D MOL for NP0189132 (4,8,11,11-tetramethyl-9,10-dioxatricyclo[6.3.2.0²,⁷]trideca-2,4,6-triene)

3D SDF for NP0189132 (4,8,11,11-tetramethyl-9,10-dioxatricyclo[6.3.2.0²,⁷]trideca-2,4,6-triene)

3D-SDF for NP0189132 (4,8,11,11-tetramethyl-9,10-dioxatricyclo[6.3.2.0²,⁷]trideca-2,4,6-triene)

PDB for NP0189132 (4,8,11,11-tetramethyl-9,10-dioxatricyclo[6.3.2.0²,⁷]trideca-2,4,6-triene)

3D PDB for NP0189132 (4,8,11,11-tetramethyl-9,10-dioxatricyclo[6.3.2.0²,⁷]trideca-2,4,6-triene)

SMILES for NP0189132 (4,8,11,11-tetramethyl-9,10-dioxatricyclo[6.3.2.0²,⁷]trideca-2,4,6-triene)

INCHI for NP0189132 (4,8,11,11-tetramethyl-9,10-dioxatricyclo[6.3.2.0²,⁷]trideca-2,4,6-triene)

Structure for NP0189132 (4,8,11,11-tetramethyl-9,10-dioxatricyclo[6.3.2.0²,⁷]trideca-2,4,6-triene)

3D Structure for NP0189132 (4,8,11,11-tetramethyl-9,10-dioxatricyclo[6.3.2.0²,⁷]trideca-2,4,6-triene)