NP-MRD: Showing NP-Card for Cedryl acetate (NP0045131)

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Record Information

Version

2.0

Created at

2022-03-10 18:58:30 UTC

Updated at

2022-03-10 22:19:47 UTC

NP-MRD ID

NP0045131

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cedryl acetate

Description

Cedryl acetate belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiterpenoids with a structure based on the cedrane or the isocedrane skeleton. Isocedrane is a rearranged cedrane arising from the migration of a methyl group from the position 6 to the position 4. Sesquiterpenoides are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Cedryl acetate is the acetylated derivative of cedrol. Cedrol is a tricyclic molecule based on a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety, bearing a tertiary hydroxyl group. Cedryl acetate is a pale-yellow viscous liquid to solid and has a sharp dry woody odor. Cedrol has been reported to show antiseptic, anti-inflammatory, antispasmodic, tonic, astringent, diuretic, sedative, insecticidal, and antifungal activities (PMID 25343299 ). Additionally, cedrol seems to be a potent attractant for female mosquitos during oviposition, which could make cedrol useful in the design of bait traps (PMID: 25885703 ). Cedrol acetate has also been detected as a volatile component in cannabis plant samples (PMID: 26657499 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 47 49  0  0  0  0  0  0  0  0999 V2000
    4.2861    0.6064    1.6124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4843    0.5407    0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9143    1.1640   -0.6453 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3237   -0.1561    0.2387 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962   -0.2806   -0.8649 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2007   -0.9246   -2.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0443    1.0646   -1.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2112    1.5998   -0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1997    0.5461   -0.4668 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8517   -0.6382   -1.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3150   -1.2056   -0.5892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1646   -1.2130    0.8129 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8967   -1.3363    1.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0440   -2.4659    0.9612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9676    0.0236    0.9566 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3096   -0.1261    1.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0778    1.0220    0.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6206    0.8454   -0.5470 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0414    1.9684   -1.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3104    0.2713    1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3644    1.6501    1.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8282   -0.0202    2.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8518   -0.1968   -2.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3818   -1.1676   -2.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6869   -1.8619   -1.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    1.0812   -2.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8409    1.8072   -1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1065    2.0789    0.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5530    2.4456   -1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5676   -0.3265   -2.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6960   -1.3497   -1.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5328   -2.2477   -0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4509   -1.8612    2.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7510   -1.9755    1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2113   -0.3419    2.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4018   -3.3545    0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8742   -2.4743    0.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3955   -2.5237    2.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3815    0.7616    1.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8240   -1.0672    1.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2993    0.0768    2.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1597    0.8566    1.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7435    1.9957    1.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1688   -0.0747   -0.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3509    2.1779   -2.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0355    1.7454   -1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2355    2.8601   -0.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 12  1  0
 12 13  1  1
 12 14  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  6
  8  7  1  0
  7  5  1  0
  5  6  1  0
  5  4  1  1
  4  2  1  0
  2  1  1  0
  2  3  2  0
  9 18  1  0
  9 15  1  0
  5 11  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 18 44  1  6
 17 42  1  0
 17 43  1  0
 16 40  1  0
 16 41  1  0
 15 39  1  1
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 11 32  1  6
 10 30  1  0
 10 31  1  0
  8 28  1  0
  8 29  1  0
  7 26  1  0
  7 27  1  0
  6 23  1  0
  6 24  1  0
  6 25  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
M  END


  Mrv1652303192001443D          

 19 21  0  0  0  0            999 V2000
   -3.3509    1.4408   -1.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9282   -0.3240    0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0233   -0.7982    2.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5609   -2.3184    1.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7690    0.2791   -2.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3230    0.5146    0.7861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2912   -0.2120    1.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7810    1.6778   -0.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6622    1.6810   -0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6469   -0.7026   -1.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8078    0.3931   -0.6149 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6917   -0.4915    0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0185    0.1261    0.9903 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6243   -0.8265   -0.3963 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0360   -0.9082    0.9649 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4782    0.3399   -0.7179 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3369    0.3938   -0.4817 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5226   -1.4727   -0.7312 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6671    0.4403    0.0389 O   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  6  0  0  0
  2 12  1  0  0  0  0
  3 15  1  0  0  0  0
  4 15  1  0  0  0  0
 16  5  1  6  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
 13  7  1  1  0  0  0
  8  9  1  0  0  0  0
  8 16  1  0  0  0  0
 17  9  1  6  0  0  0
 10 14  1  0  0  0  0
 10 17  1  0  0  0  0
 11 17  1  0  0  0  0
 12 18  2  0  0  0  0
 12 19  1  0  0  0  0
 13 15  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045131

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@H]2C(C)(C)[C@H]3C[C@@]12CC[C@@]3(C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H28O2/c1-11-6-7-13-15(3,4)14-10-17(11,13)9-8-16(14,5)19-12(2)18/h11,13-14H,6-10H2,1-5H3/t11-,13+,14-,16-,17+/m1/s1

> <INCHI_KEY>
HQKQRXZEXPXXIG-DTWJZALFSA-N

> <FORMULA>
C17H28O2

> <MOLECULAR_WEIGHT>
264.409

> <EXACT_MASS>
264.208930142

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
31.264983397192026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undecan-8-yl acetate

> <ALOGPS_LOGP>
4.47

> <JCHEM_LOGP>
3.632655852999999

> <ALOGPS_LOGS>
-5.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.01139931451351

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
75.67799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.54e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undecan-8-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0      -3.351   1.441  -1.541  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.928  -0.324   0.850  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.023  -0.798   2.103  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.561  -2.318   1.099  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.769   0.279  -2.205  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.323   0.515   0.786  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.291  -0.212   1.657  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.781   1.678  -0.506  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.662   1.681  -0.835  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.647  -0.703  -1.250  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.808   0.393  -0.615  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.692  -0.492   0.018  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.018   0.126   0.990  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.624  -0.827  -0.396  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.036  -0.908   0.965  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.478   0.340  -0.718  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.337   0.394  -0.482  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.523  -1.473  -0.731  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   0.440   0.039  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5   16                                                            
CONECT    6    7   11                                                       
CONECT    7    6   13                                                       
CONECT    8    9   16                                                       
CONECT    9    8   17                                                       
CONECT   10   14   17                                                       
CONECT   11    1    6   17                                                  
CONECT   12    2   18   19                                                  
CONECT   13    7   15   17                                                  
CONECT   14   10   15   16                                                  
CONECT   15    3    4   13   14                                             
CONECT   16    5    8   14   19                                             
CONECT   17    9   10   11   13                                             
CONECT   18   12                                                            
CONECT   19   12   16                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
Cedryl acetic acid	Generator

Chemical Formula

C₁₇H₂₈O₂

Average Mass

264.4090 Da

Monoisotopic Mass

264.20893 Da

IUPAC Name

(1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undecan-8-yl acetate

Traditional Name

(1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undecan-8-yl acetate

CAS Registry Number

77-54-3

SMILES

C[C@@H]1CC[C@H]2C(C)(C)[C@H]3C[C@@]12CC[C@@]3(C)OC(C)=O

InChI Identifier

InChI=1S/C17H28O2/c1-11-6-7-13-15(3,4)14-10-17(11,13)9-8-16(14,5)19-12(2)18/h11,13-14H,6-10H2,1-5H3/t11-,13+,14-,16-,17+/m1/s1

InChI Key

HQKQRXZEXPXXIG-DTWJZALFSA-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
Artemisia annua	LOTUS Database	35616633
Artemisia annua L.cultivar Jwarharti	Plant	KNApSAcK
Artemisia argyi	LOTUS Database	35616633
Cannabis sativa	NULL	Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Cedrane and isocedrane sesquiterpenoids

Alternative Parents

Substituents

Cedrane sesquiterpenoid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	4.47	ALOGPS
logP	3.63	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.68 m³·mol⁻¹	ChemAxon
Polarizability	31.26 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

13918856

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Cedryl acetate (NP0045131)

MOL for NP0045131 (Cedryl acetate)

3D MOL for NP0045131 (Cedryl acetate)

3D SDF for NP0045131 (Cedryl acetate)

3D-SDF for NP0045131 (Cedryl acetate)

PDB for NP0045131 (Cedryl acetate)

3D PDB for NP0045131 (Cedryl acetate)

SMILES for NP0045131 (Cedryl acetate)

INCHI for NP0045131 (Cedryl acetate)

Structure for NP0045131 (Cedryl acetate)

3D Structure for NP0045131 (Cedryl acetate)