NP-MRD: Showing NP-Card for (+)-sclarene (NP0318596)

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Record Information

Version

2.0

Created at

2022-09-11 19:11:13 UTC

Updated at

2022-09-11 19:11:13 UTC

NP-MRD ID

NP0318596

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-sclarene

Description

Sclarene belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (+)-sclarene is found in Cryptomeria japonica, Halocarpus bidwillii and Lepidothamnus intermedius. (+)-sclarene was first documented in 2000 (PMID: 10793256). Based on a literature review a small amount of articles have been published on sclarene (PMID: 12710734) (PMID: 20397107) (PMID: 21404436).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 52 53  0  0  0  0  0  0  0  0999 V2000
    3.7945    2.3091    1.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8752    1.8494    0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6019    0.4810   -0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7603    0.1969   -1.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1913   -0.5909    0.7620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7763   -0.4470    1.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8681   -0.4918    0.1189 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8029   -1.8615   -0.5372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3090   -2.9558   -0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0388   -1.9261   -1.8260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3421   -1.3200   -1.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2529   -0.0430   -0.8848 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5317    0.7312   -0.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6027    0.0830   -1.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3589    2.1431   -1.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1138    0.9097    0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1315    1.3754    1.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7615    0.8267    1.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6256   -0.3011    0.4679 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0571   -1.5743    1.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0107    3.3603    1.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372    1.7152    2.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1747    2.5857   -0.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5729   -0.8180   -1.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0588    0.9312   -2.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8643   -0.5355    1.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3972   -1.5435    0.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6694    0.5251    1.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5583   -1.2061    2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1958    0.2251   -0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8440   -3.0937    0.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1951   -3.8912   -0.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0962   -2.9622   -2.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6224   -1.3786   -2.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0889   -2.0336   -1.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6647   -1.0404   -2.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5286    0.6011   -1.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8098   -0.9470   -1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5161    0.7277   -1.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2643    0.2244   -2.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118    2.4474   -1.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0109    2.8727   -0.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4898    2.1611   -2.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8738    1.7446    0.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7375    0.0448    0.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5853    1.1805    2.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0485    2.5016    1.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4394    0.4588    2.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0011    1.6078    1.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0496   -2.4495    0.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3378   -1.8492    1.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0895   -1.5606    1.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  1
 19  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  3
  3  2  1  0
  2  1  2  3
  7  8  1  0
  8  9  2  3
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 19  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 20 50  1  0
 20 51  1  0
 20 52  1  0
  7 30  1  6
  6 28  1  0
  6 29  1  0
  5 26  1  0
  5 27  1  0
  4 24  1  0
  4 25  1  0
  2 23  1  0
  1 21  1  0
  1 22  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  6
M  END


  Mrv1652309112221112D          

 20 21  0  0  1  0            999 V2000
    2.8579    0.0000    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8558    0.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3861   -0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0318596

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@]2(C)[C@@H](CCC(=C)C=C)C(=C)CC[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C20H32/c1-7-15(2)9-11-17-16(3)10-12-18-19(4,5)13-8-14-20(17,18)6/h7,17-18H,1-3,8-14H2,4-6H3/t17-,18-,20+/m0/s1

> <INCHI_KEY>
KYLKKZSVPLUGCC-CMKODMSKSA-N

> <FORMULA>
C20H32

> <MOLECULAR_WEIGHT>
272.476

> <EXACT_MASS>
272.25040103

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
34.73649031477957

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aS,5S,8aS)-1,1,4a-trimethyl-6-methylidene-5-(3-methylidenepent-4-en-1-yl)-decahydronaphthalene

> <JCHEM_LOGP>
6.194027287000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
89.25069999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(+)-sclarene

> <JCHEM_VEBER_RULE>
1

$$$$

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   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.670   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.531   1.447   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.521  -0.267   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.004  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337  -1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    7   12   20                                             
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
(+)-Sclarene	ChEBI
Delta(8,17.13,16.14)-Labdatriene	ChEBI
Labda-8(17),13(16),14-triene	ChEBI
Δ(8,17.13,16.14)-labdatriene	Generator

Chemical Formula

C₂₀H₃₂

Average Mass

272.4760 Da

Monoisotopic Mass

272.25040 Da

IUPAC Name

(4aS,5S,8aS)-1,1,4a-trimethyl-6-methylidene-5-(3-methylidenepent-4-en-1-yl)-decahydronaphthalene

Traditional Name

(+)-sclarene

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@]2(C)[C@@H](CCC(=C)C=C)C(=C)CC[C@@H]12

InChI Identifier

InChI=1S/C20H32/c1-7-15(2)9-11-17-16(3)10-12-18-19(4,5)13-8-14-20(17,18)6/h7,17-18H,1-3,8-14H2,4-6H3/t17-,18-,20+/m0/s1

InChI Key

KYLKKZSVPLUGCC-CMKODMSKSA-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
Cryptomeria japonica	LOTUS Database	35616633
Halocarpus bidwillii	LOTUS Database	35616633
Lepidothamnus intermedius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Labdane diterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

diterpene (CHEBI:64281 )

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	6.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	89.25 m³·mol⁻¹	ChemAxon
Polarizability	34.74 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00000893

Chemspider ID

9498211

KEGG Compound ID

Not Available

BioCyc ID

CPD-14025

BiGG ID

Not Available

Wikipedia Link

Sclarene

METLIN ID

Not Available

PubChem Compound

11323257

PDB ID

Not Available

ChEBI ID

64281

Good Scents ID

rw1052881

References

General References

Brophy JJ, Goldsack RJ, Wu MZ, Fookes CJ, Forster PI: The steam volatile oil of Wollemia nobilis and its comparison with other members of the Araucariaceae (Agathis and Araucaria). Biochem Syst Ecol. 2000 Jul 1;28(6):563-578. doi: 10.1016/s0305-1978(99)00090-3. [PubMed:10793256 ]
Mikhaeil BR, Maatooq GT, Badria FA, Amer MM: Chemistry and immunomodulatory activity of frankincense oil. Z Naturforsch C J Biosci. 2003 Mar-Apr;58(3-4):230-8. doi: 10.1515/znc-2003-3-416. [PubMed:12710734 ]
Marongiu B, Piras A, Porcedda S, Falconieri D, Goncalves MJ, Salgueiro L, Maxia A, Lai R: Extraction, separation and isolation of volatiles from Vitex agnus-castus L. (Verbenaceae) wild species of Sardinia, Italy, by supercritical CO2. Nat Prod Res. 2010 Apr;24(6):569-79. doi: 10.1080/14786410902899915. [PubMed:20397107 ]
Gaviria M, Quijano C, Pino J, Madrinan S: Chemical composition and antibacterial activity of the essential oil of Drimys granadensis L.f. leaves from Colombia. Chem Biodivers. 2011 Mar;8(3):532-9. doi: 10.1002/cbdv.201000170. [PubMed:21404436 ]
LOTUS database [Link]

Showing NP-Card for (+)-sclarene (NP0318596)

MOL for NP0318596 ((+)-sclarene)

3D MOL for NP0318596 ((+)-sclarene)

3D SDF for NP0318596 ((+)-sclarene)

3D-SDF for NP0318596 ((+)-sclarene)

PDB for NP0318596 ((+)-sclarene)

3D PDB for NP0318596 ((+)-sclarene)

SMILES for NP0318596 ((+)-sclarene)

INCHI for NP0318596 ((+)-sclarene)

Structure for NP0318596 ((+)-sclarene)

3D Structure for NP0318596 ((+)-sclarene)