NP-MRD: Showing NP-Card for (-)-β-selinene (NP0249914)

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Record Information

Version

2.0

Created at

2022-09-07 12:36:25 UTC

Updated at

2022-09-07 12:36:25 UTC

NP-MRD ID

NP0249914

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-β-selinene

Description

Beta-Helmiscapene, also known as beta-selinene, belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. (-)-β-selinene is found in Cymbopogon martinii, Cyperus rotundus, Hyalosperma glutinosum, Molopospermum peloponnesiacum, Radula perrottetii, Scapania undulata, Senecio squalidus and Valeriana officinalis. (-)-β-selinene was first documented in 2005 (PMID: 15845412). Based on a literature review very few articles have been published on beta-Helmiscapene.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    3.2152    1.0501    1.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0734    0.2133    0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2642   -0.5386   -0.2937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729   -0.0160   -0.4950 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2956   -1.4345   -0.4043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408   -1.5637    0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1166   -0.7248   -0.3716 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2940   -1.2902   -1.7686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3848   -0.9260    0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4573    0.0692    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9830    1.4936    0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5557    1.5215    0.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1405    2.2628    1.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6281    0.6986   -0.3822 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7441    0.8605    0.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1829    1.1780    1.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3884    1.6167    1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9109    0.2026   -0.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8641   -0.9029    0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9689   -1.3594   -0.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8119    0.3128   -1.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0099   -2.0573    0.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013   -1.8704   -1.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0236   -1.3863    1.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3517   -2.6373    0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3873   -1.2641   -2.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6736   -0.7733   -2.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0284   -2.3802   -1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7861   -1.9363    0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1866   -1.0160    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0356   -0.1521   -0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1960    0.0091    0.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0539    1.9215   -0.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5375    2.1791    0.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1160    2.3052    1.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8487    2.8643    2.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6514    1.0220   -1.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    1.9196    0.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099    0.5289    1.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  3
 12 14  1  0
 14 15  1  0
 15  4  1  0
 14  7  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  1 16  1  0
  1 17  1  0
  4 21  1  6
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  6
 15 38  1  0
 15 39  1  0
M  END


  Mrv1652309072214362D          

 15 16  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  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
    3.5724   -0.4125    0.0000 C   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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  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  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 12  1  1  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
  4 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249914

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@H]1CC[C@@]2(C)CCCC(=C)[C@H]2C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h13-14H,1,3,5-10H2,2,4H3/t13-,14+,15+/m0/s1

> <INCHI_KEY>
YOVSPTNQHMDJAG-RRFJBIMHSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.326006317152462

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aR,7S,8aR)-4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-decahydronaphthalene

> <JCHEM_LOGP>
4.577243062000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
66.3799

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,7S,8aR)-4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   14                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7   15                                                  
CONECT   15   14    4                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
b-Helmiscapene	Generator
Β-helmiscapene	Generator
beta-Selinene, (4ar-(4aalpha,7beta,8aalpha))-isomer	MeSH
beta-Selinene, (4as-(4aalpha,7beta,8abeta))-isomer	MeSH
beta-Selinene, ((4aalpha,7alpha,8abeta)-(+-))-isomer	MeSH
beta-Selinene	MeSH

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=C)[C@H]1CC[C@@]2(C)CCCC(=C)[C@H]2C1

InChI Identifier

InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h13-14H,1,3,5-10H2,2,4H3/t13-,14+,15+/m0/s1

InChI Key

YOVSPTNQHMDJAG-RRFJBIMHSA-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
Cymbopogon martinii	LOTUS Database	35616633
Cyperus rotundus	LOTUS Database	35616633
Hyalosperma glutinosum	LOTUS Database	35616633
Molopospermum peloponnesiacum	LOTUS Database	35616633
Radula perrottetii	LOTUS Database	35616633
Scapania undulata	LOTUS Database	35616633
Senecio squalidus	LOTUS Database	35616633
Valeriana officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00012718

Chemspider ID

107562708

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12309814

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tesso H, Konig WA, Asakawa Y: Composition of the essential oil of the liverwort Radula perrottetii of Japanese origin. Phytochemistry. 2005 Apr;66(8):941-9. doi: 10.1016/j.phytochem.2005.03.003. [PubMed:15845412 ]
LOTUS database [Link]

Showing NP-Card for (-)-β-selinene (NP0249914)

MOL for NP0249914 ((-)-β-selinene)

3D MOL for NP0249914 ((-)-β-selinene)

3D SDF for NP0249914 ((-)-β-selinene)

3D-SDF for NP0249914 ((-)-β-selinene)

PDB for NP0249914 ((-)-β-selinene)

3D PDB for NP0249914 ((-)-β-selinene)

SMILES for NP0249914 ((-)-β-selinene)

INCHI for NP0249914 ((-)-β-selinene)

Structure for NP0249914 ((-)-β-selinene)

3D Structure for NP0249914 ((-)-β-selinene)