NP-MRD: Showing NP-Card for (-)-thujopsene (NP0156379)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 13:34:51 UTC

Updated at

2022-09-02 13:34:51 UTC

NP-MRD ID

NP0156379

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-thujopsene

Description

(-)-Thujopsene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (-)-thujopsene is found in Angelica archangelica, Arabidopsis thaliana, Basella alba, Bazzania trilobata, Callitropsis nootkatensis, Centella asiatica, Chamaecyparis lawsoniana, Chamaecyparis obtusa, Chamaecyparis pisifera, Eugenia dysenterica, Frullania falciloba, Juniperus horizontalis, Juniperus recurva, Juniperus rigida, Juniperus thurifera, Lepidozia fauriana, Marsupella emarginata, Microbiota decussata, Perilla frutescens, Persicaria minor, Platycladus orientalis, Rhanterium epapposum, Taxodium distichum, Thujopsis dolabrata, Trocholejeunea sandvicensis and Widdringtonia whytei. Thus, (-)-thujopsene is considered to be an isoprenoid lipid molecule (-)-thujopsene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    3.3703   -0.8996    1.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198   -0.3076    1.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7758    0.9530    1.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4675    1.5494    1.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2390    1.0892   -0.3931 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4764    1.5549   -1.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8921    1.8991   -0.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2601    1.4635   -0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4008   -0.0043   -0.8873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3651   -0.8489   -0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7558   -0.9673    1.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5189   -2.2562   -0.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0545   -0.3785   -0.4024 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9961   -1.3201   -1.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0305   -1.1209    0.4262 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3353   -1.2160    2.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1637   -0.1434    1.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5278   -1.7822    0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5243    1.5372    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5563    2.6570    1.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3550    1.2870    1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2901    1.7411   -2.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8261    2.5500   -0.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3243    0.8839   -1.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421    2.9565   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7872    1.9850   -2.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5383    1.7092    0.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9770    2.0002   -1.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3899   -0.3214   -0.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4354   -0.1439   -1.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8944   -1.0413    1.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3826   -1.8733    1.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4302   -0.1061    1.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5993   -2.5232   -0.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9366   -3.0023   -0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3994   -2.2954   -1.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5779   -2.2834   -1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8203   -0.9814   -1.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6840   -1.9993    1.0530 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  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 13 10  1  1
 13 14  1  0
 14 15  1  0
 15  2  1  0
 13  5  1  0
 15 13  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  6 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 11 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  1
M  END


  Mrv1652303102018462D          

 15 17  0  0  0  0            999 V2000
 9989.3454 9988.3407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.3454 9989.1649    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9989.3454 9989.9944    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9990.0578 9988.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.6317 9988.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.0578 9990.4108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9989.3454 9990.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.6317 9990.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.7690 9989.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.9202 9989.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.7690 9989.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.1634 9991.0416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.1022 9991.0416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.9202 9989.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4822 9990.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  8 12  1  0  0  0  0
  8 13  1  0  0  0  0
 11 15  1  0  0  0  0
 14 10  1  0  0  0  0
 10  5  1  0  0  0  0
  5  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  8  1  0  0  0  0
  8 14  1  0  0  0  0
  3  6  1  0  0  0  0
  6 11  1  0  0  0  0
 11  9  2  0  0  0  0
  9  4  1  0  0  0  0
  4  2  1  0  0  0  0
  3  7  1  1  0  0  0
  6  7  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0156379

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC[C@]2(C)CCCC(C)(C)[C@@]22C[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-11-6-9-14(4)8-5-7-13(2,3)15(14)10-12(11)15/h6,12H,5,7-10H2,1-4H3/t12-,14-,15-/m0/s1

> <INCHI_KEY>
WXQGPFZDVCRBME-QEJZJMRPSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.626552503362497

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1bS,5aS,5bS)-1b,5,5-tetramethyl-H,1H,1bH,2H,3H,4H,5H,5bH-cyclopropa[e]naphthalene

> <ALOGPS_LOGP>
5.99

> <JCHEM_LOGP>
4.11418621

> <ALOGPS_LOGS>
-5.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
65.62089999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.99e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1bS,5aS,5bS)-1b,5,5-tetramethyl-H,1H,2H,3H,4H,5bH-cyclopropa[e]naphthalene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0    8646.7788644.903   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8646.7788646.441   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8646.7788647.990   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8648.1088645.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8645.4468645.666   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8648.1088648.767   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8646.7788649.544   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8645.4468648.767   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8649.4368646.441   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8644.1188646.441   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8649.4368647.990   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8646.4388649.944   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8644.4578649.944   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8644.1188647.990   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8650.7678648.763   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    5    3    4                                             
CONECT    3    2    8    6    7                                             
CONECT    4    9    2                                                       
CONECT    5   10    2                                                       
CONECT    6    3   11    7                                                  
CONECT    7    3    6                                                       
CONECT    8   12   13    3   14                                             
CONECT    9   11    4                                                       
CONECT   10   14    5                                                       
CONECT   11   15    6    9                                                  
CONECT   12    8                                                            
CONECT   13    8                                                            
CONECT   14   10    8                                                       
CONECT   15   11                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Value	Source
(-)-Widdrene	ChEBI
Thujopsene	ChEBI

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(1bS,5aS,5bS)-1b,5,5-tetramethyl-H,1H,1bH,2H,3H,4H,5H,5bH-cyclopropa[e]naphthalene

Traditional Name

(1bS,5aS,5bS)-1b,5,5-tetramethyl-H,1H,2H,3H,4H,5bH-cyclopropa[e]naphthalene

CAS Registry Number

Not Available

SMILES

CC1=CC[C@]2(C)CCCC(C)(C)[C@@]22C[C@@H]12

InChI Identifier

InChI=1S/C15H24/c1-11-6-9-14(4)8-5-7-13(2,3)15(14)10-12(11)15/h6,12H,5,7-10H2,1-4H3/t12-,14-,15-/m0/s1

InChI Key

WXQGPFZDVCRBME-QEJZJMRPSA-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
Angelica archangelica	LOTUS Database	35616633
Arabidopsis thaliana	LOTUS Database	35616633
Basella alba	LOTUS Database	35616633
Bazzania trilobata	LOTUS Database	35616633
Callitropsis nootkatensis	LOTUS Database	35616633
Centella asiatica	LOTUS Database	35616633
Chamaecyparis lawsoniana	LOTUS Database	35616633
Chamaecyparis obtusa	LOTUS Database	35616633
Chamaecyparis pisifera	LOTUS Database	35616633
Eugenia dysenterica	LOTUS Database	35616633
Frullania falciloba	LOTUS Database	35616633
Juniperus horizontalis	LOTUS Database	35616633
Juniperus recurva	LOTUS Database	35616633
Juniperus rigida	LOTUS Database	35616633
Juniperus thurifera	LOTUS Database	35616633
Lepidozia fauriana	LOTUS Database	35616633
Marsupella emarginata	LOTUS Database	35616633
Microbiota decussata	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Persicaria minor	LOTUS Database	35616633
Platycladus orientalis	LOTUS Database	35616633
Rhanterium epapposum	LOTUS Database	35616633
Taxodium distichum	LOTUS Database	35616633
Thujopsis dolabrata	LOTUS Database	35616633
Trocholejeunea sandvicensis	LOTUS Database	35616633
Widdringtonia whytei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Thujopsane sesquiterpenoid
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

thujopsene (CHEBI:9578 )
Thujopsane sesquiterpenoids (C09740 )
Sesquiterpenoids (C15) (C09740 )
Thujopsane sesquiterpenoids (LMPR0103860001 )

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	5.99	ALOGPS
logP	4.11	ChemAxon
logS	-5	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	65.62 m³·mol⁻¹	ChemAxon
Polarizability	25.63 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

C00003194

Chemspider ID

Not Available

KEGG Compound ID

C09740

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442402

PDB ID

Not Available

ChEBI ID

9578

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (-)-thujopsene (NP0156379)

MOL for NP0156379 ((-)-thujopsene)

3D MOL for NP0156379 ((-)-thujopsene)

3D SDF for NP0156379 ((-)-thujopsene)

3D-SDF for NP0156379 ((-)-thujopsene)

PDB for NP0156379 ((-)-thujopsene)

3D PDB for NP0156379 ((-)-thujopsene)

SMILES for NP0156379 ((-)-thujopsene)

INCHI for NP0156379 ((-)-thujopsene)

Structure for NP0156379 ((-)-thujopsene)

3D Structure for NP0156379 ((-)-thujopsene)