NP-MRD: Showing NP-Card for (3r,5r,7r,8s)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),9,11-trien-11-ol (NP0309076)

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Record Information

Version

2.0

Created at

2022-09-11 03:23:37 UTC

Updated at

2022-09-11 03:23:37 UTC

NP-MRD ID

NP0309076

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,5r,7r,8s)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),9,11-trien-11-ol

Description

(3R,5R,7R,8S)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0⁵,¹³]Trideca-1(13),9,11-trien-11-ol 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. (3r,5r,7r,8s)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),9,11-trien-11-ol is found in Penicillium citrinum. Based on a literature review very few articles have been published on (3R,5R,7R,8S)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0⁵,¹³]Trideca-1(13),9,11-trien-11-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    5.1213   -0.4806    0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8242   -0.2153    1.1374 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0164   -0.0308    0.0153 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9863   -1.1299   -0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9341   -0.6653   -1.0516 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0579   -1.5635   -1.5474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0544   -1.7141   -0.7794 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8317   -2.9590   -1.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9744   -0.4902   -0.7262 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0022   -0.8969    0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969    0.6296   -0.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6828    1.7341    0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1293    1.8859    0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8090    2.7185    0.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3481    3.8314    1.4083 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5591    2.5899    0.7124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1230    1.4847    0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2527    0.4874   -0.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4690    1.2522   -0.0345 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1234   -1.4067    0.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5341    0.3269    0.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8035   -0.6348    1.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6605   -0.1527   -0.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5375   -1.2480    0.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4746   -2.0744   -0.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4829   -0.2219   -1.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7043   -1.8310    0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9270   -3.5784   -0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2690   -3.5494   -1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8130   -2.7094   -1.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3985   -0.3164   -1.7102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7270   -0.6303    1.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0927   -2.0334    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9836   -0.5196    0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2925    3.0228    0.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6629    1.4817    1.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6503    1.6869   -0.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7468    4.5526    1.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2360    3.3673    1.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 19  1  0
 17 18  1  0
 19  3  1  0
 18  5  1  0
 18 11  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  6
  4 24  1  0
  4 25  1  0
  5 26  1  6
  7 27  1  1
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  6
 10 32  1  0
 10 33  1  0
 10 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
M  END


  Mrv1652309112205232D          

 19 21  0  0  1  0            999 V2000
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 18  1  0  0  0  0
  5 18  1  0  0  0  0
 17 19  1  0  0  0  0
  3 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0309076

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C[C@H]2O[C@H](C)[C@@H](C)C3=C(C)C(O)=CC(O1)=C23

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-7-9(3)18-12-6-13(17-4)19-11-5-10(16)8(2)14(7)15(11)12/h5,7,9,12-13,16H,6H2,1-4H3/t7-,9-,12-,13-/m1/s1

> <INCHI_KEY>
CDNXSAOFADQYKT-NHULRPGXSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.321

> <EXACT_MASS>
264.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.515932748731956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,5R,7R,8S)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(13),9,11-trien-11-ol

> <JCHEM_LOGP>
3.160091521333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.71262254993918

> <JCHEM_PKA_STRONGEST_BASIC>
-3.91042947090244

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
71.24449999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,5R,7R,8S)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(13),9,11-trien-11-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   18                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   11    5                                                  
CONECT   19   17    3                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3210 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

(3R,5R,7R,8S)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(13),9,11-trien-11-ol

Traditional Name

(3R,5R,7R,8S)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(13),9,11-trien-11-ol

CAS Registry Number

Not Available

SMILES

CO[C@H]1C[C@H]2O[C@H](C)[C@@H](C)C3=C(C)C(O)=CC(O1)=C23

InChI Identifier

InChI=1S/C15H20O4/c1-7-9(3)18-12-6-13(17-4)19-11-5-10(16)8(2)14(7)15(11)12/h5,7,9,12-13,16H,6H2,1-4H3/t7-,9-,12-,13-/m1/s1

InChI Key

CDNXSAOFADQYKT-NHULRPGXSA-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
Penicillium citrinum	LOTUS Database	35616633

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
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Oxacycle
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

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	3.16	ChemAxon
pKa (Strongest Acidic)	9.71	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.24 m³·mol⁻¹	ChemAxon
Polarizability	28.52 Å³	ChemAxon
Number of Rings	3	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

28185092

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54672227

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,5r,7r,8s)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),9,11-trien-11-ol (NP0309076)

MOL for NP0309076 ((3r,5r,7r,8s)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),9,11-trien-11-ol)

3D MOL for NP0309076 ((3r,5r,7r,8s)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),9,11-trien-11-ol)

3D SDF for NP0309076 ((3r,5r,7r,8s)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),9,11-trien-11-ol)

3D-SDF for NP0309076 ((3r,5r,7r,8s)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),9,11-trien-11-ol)

PDB for NP0309076 ((3r,5r,7r,8s)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),9,11-trien-11-ol)

3D PDB for NP0309076 ((3r,5r,7r,8s)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),9,11-trien-11-ol)

SMILES for NP0309076 ((3r,5r,7r,8s)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),9,11-trien-11-ol)

INCHI for NP0309076 ((3r,5r,7r,8s)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),9,11-trien-11-ol)

Structure for NP0309076 ((3r,5r,7r,8s)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),9,11-trien-11-ol)

3D Structure for NP0309076 ((3r,5r,7r,8s)-3-methoxy-7,8,10-trimethyl-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),9,11-trien-11-ol)