NP-MRD: Showing NP-Card for (1r,6s,7s)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene (NP0220893)

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Record Information

Version

2.0

Created at

2022-09-05 22:20:02 UTC

Updated at

2022-09-05 22:20:02 UTC

NP-MRD ID

NP0220893

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,6s,7s)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene

Description

Copaene, also known as alpha-copaene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1r,6s,7s)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene is found in Acorus calamus and Cupressus sempervirens. (1r,6s,7s)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene was first documented in 2022 (PMID: 35886831). Based on a literature review a small amount of articles have been published on Copaene (PMID: 35876169) (PMID: 35873421) (PMID: 35747377) (PMID: 35736037).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -2.8558    2.4130    0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0524    1.2397   -0.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2800    0.7251   -1.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5337   -0.4973   -2.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5786   -0.9167   -0.9634 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2416    0.2808   -0.4642 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3111   -0.1260    0.4828 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7087    0.0652   -0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9594    1.4348   -0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7328   -0.2426    1.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0976   -1.5278    1.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3663   -1.5933    1.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2148   -0.9126    0.4071 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6424   -1.3360    0.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0011    0.6017    0.3847 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0604    2.3339    1.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7953    2.4583   -0.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2784    3.3244   -0.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9771    1.1515   -2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9638   -0.2589   -2.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2640   -1.2668   -2.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0049   -1.7952   -1.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4728    1.0242   -1.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2272    0.5454    1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8544   -0.6735   -0.8556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6741    2.2308    0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0670    1.5434   -0.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5208    1.5868   -1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4934    0.5709    1.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1830   -1.2457    0.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2228   -0.2517    2.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3439   -2.3037    0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7731   -1.6818    1.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4373   -1.0332    2.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7210   -2.6214    1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1560   -0.6389    1.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7483   -2.3414    0.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1849   -1.3197   -0.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767    1.0544    1.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  0
  8  7  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 15  1  0
 15  6  1  0
  6  7  1  0
 15 13  1  0
  6  5  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
  8 25  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
  7 24  1  1
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
  5 22  1  6
  4 20  1  0
  4 21  1  0
  3 19  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
 15 39  1  1
  6 23  1  6
M  END


  Mrv1652309062200202D          

 15 17  0  0  1  0            999 V2000
    0.4333   -1.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9247   -0.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6415   -0.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2097    0.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0090    0.3101    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4476   -0.7151    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3039   -0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7297   -1.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5545   -1.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3306   -2.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6111   -0.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9799    0.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3036   -0.0942    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9179   -0.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7348   -0.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  2 15  1  0  0  0  0
  6 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220893

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1CC[C@]2(C)[C@H]3CC=C(C)C2[C@@H]13

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(15)13(11)12/h5,9,11-14H,6-8H2,1-4H3/t11?,12-,13-,14?,15+/m0/s1

> <INCHI_KEY>
VLXDPFLIRFYIME-PLWLXLEKSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.177315145074893

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,6S,7S)-1,3-dimethyl-8-(propan-2-yl)tricyclo[4.4.0.0^{2,7}]dec-3-ene

> <JCHEM_LOGP>
4.0881301626666655

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
65.7679

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,6S,7S)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0^{2,7}]dec-3-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.809  -2.703   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.726  -1.466   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.197  -0.016   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.258   1.156   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.750   0.579   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.569  -1.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.167  -1.492   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.962  -2.811   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.502  -2.783   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.217  -4.159   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.741  -0.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.562   1.042   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.300  -0.176   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.447  -1.204   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.238  -1.549   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5   14   15                                             
CONECT   14   13                                                            
CONECT   15   13    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Value	Source
alpha-Copaene	MeSH

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(1R,6S,7S)-1,3-dimethyl-8-(propan-2-yl)tricyclo[4.4.0.0^{2,7}]dec-3-ene

Traditional Name

(1R,6S,7S)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0^{2,7}]dec-3-ene

CAS Registry Number

Not Available

SMILES

CC(C)C1CC[C@]2(C)[C@H]3CC=C(C)C2[C@@H]13

InChI Identifier

InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(15)13(11)12/h5,9,11-14H,6-8H2,1-4H3/t11?,12-,13-,14?,15+/m0/s1

InChI Key

VLXDPFLIRFYIME-PLWLXLEKSA-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
Acorus calamus	LOTUS Database	35616633
Cupressus sempervirens	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

Copaane 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

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	4.09	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	65.77 m³·mol⁻¹	ChemAxon
Polarizability	26.18 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

C00003118

Chemspider ID

58829761

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Copaene

METLIN ID

Not Available

PubChem Compound

25245021

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Romero P, Ibarra-Juarez LA, Carrillo D, Guerrero-Analco JA, Kendra PE, Kiel-Martinez AL, Guillen L: Electroantennographic Responses of Wild and Laboratory-Reared Females of Xyleborus affinis Eichhoff and Xyleborus ferrugineus (Fabricius) (Coleoptera: Curculionidae: Scolytinae) to Ethanol and Bark Volatiles of Three Host-Plant Species. Insects. 2022 Jul 21;13(7). pii: insects13070655. doi: 10.3390/insects13070655. [PubMed:35886831 ]
Thinh BB, Khoi NT, Doudkin RV, Thin DB, Ogunwande IA: Chemical composition of essential oil and antioxidant activity of the essential oil and methanol extracts of Knema globularia (Lam.) Warb. from Vietnam. Nat Prod Res. 2022 Jul 24:1-7. doi: 10.1080/14786419.2022.2103698. [PubMed:35876169 ]
Fukalova Fukalova T, Moreno-Peris E, Garcia-Martinez MD, Raigon Jimenez MD: Assessment of the Volatile Profiles and Identification of Differentiating Aromas of Wild Undervalued Plants. Front Nutr. 2022 Jul 8;9:912680. doi: 10.3389/fnut.2022.912680. eCollection 2022. [PubMed:35873421 ]
Wang Z, Zeng Z, Hu Y, Sun H, Tang Y, Liu W: Network Pharmacology and Pharmacological Mechanism of CV-3 in Atrial Fibrillation. Evid Based Complement Alternat Med. 2022 Jun 14;2022:5496299. doi: 10.1155/2022/5496299. eCollection 2022. [PubMed:35747377 ]
Ezediokpu MN, Krause K, Kunert M, Hoffmeister D, Boland W, Kothe E: Ectomycorrhizal Influence on the Dynamics of Sesquiterpene Release by Tricholoma vaccinum. J Fungi (Basel). 2022 May 24;8(6):555. doi: 10.3390/jof8060555. [PubMed:35736037 ]
LOTUS database [Link]

Showing NP-Card for (1r,6s,7s)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene (NP0220893)

MOL for NP0220893 ((1r,6s,7s)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene)

3D MOL for NP0220893 ((1r,6s,7s)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene)

3D SDF for NP0220893 ((1r,6s,7s)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene)

3D-SDF for NP0220893 ((1r,6s,7s)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene)

PDB for NP0220893 ((1r,6s,7s)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene)

3D PDB for NP0220893 ((1r,6s,7s)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene)

SMILES for NP0220893 ((1r,6s,7s)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene)

INCHI for NP0220893 ((1r,6s,7s)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene)

Structure for NP0220893 ((1r,6s,7s)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene)

3D Structure for NP0220893 ((1r,6s,7s)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene)