NP-MRD: Showing NP-Card for beta-Copaene (NP0046534)

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Record Information

Version

2.0

Created at

2022-03-17 20:06:23 UTC

Updated at

2022-03-17 20:06:23 UTC

NP-MRD ID

NP0046534

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-Copaene

Description

Beta-Copaene, also known as β-copaene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. beta-Copaene is found in Ambrosia trifida, Ananas comosus, Cedrus libani , Centaurea atropurpurea, Cistus creticus, Citrus aurantium, Citrus maxima, Citrus retuculata, Citrus unshiu, Copaifera langsdorffii, Curcuma amanda Roxb, Dacrydium nidulum, Dumortiera hirsuta, Dumortiera hirsuta (Sw.) Nees, Humulus lupulus , Larix gmelinii, Larix kaempferi, Larix sibirica, Leptospermum scoparium , Litsea cubeba , Melissa officinalis, Origanum sipyleum, Pelargonium vitifolium, Phagnalon sordidum, Picea koraiensis, Pinus halepensis , Pinus pumila, Piper nigrum , Primula halleri, Salvia absconditiflora, Satureja subspicata , Scapania undulata, Solidago canadensis, Veronica spicata, Xylopia parviflora and Zea mays. beta-Copaene was first documented in 2010 (PMID: 21250484). Beta-Copaene is possibly neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212592D          

 17 19  0  0  0  0            999 V2000
   -3.4179    2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1323    1.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1323    0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4179    0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034    0.9723    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7034    1.7973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9889    2.2098    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9889    0.5598    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2745    0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2745    1.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8468    0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889    3.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034   -0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2745   -0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034    2.6223    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034    0.1473    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  6  1  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 11  2  0  0  0  0
  7 12  1  1  0  0  0
  8 13  1  1  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  4  7  1  0  0  0  0
  6 16  1  1  0  0  0
  5 17  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0046534

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C3C(=C)CC[C@]1([H])[C@]3(C)CC[C@H]2C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(15)13(11)12/h9,11-14H,3,5-8H2,1-2,4H3/t11-,12-,13-,14?,15-/m0/s1

> <INCHI_KEY>
UPVZPMJSRSWJHQ-XIQJJJERSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
35.81289849349238

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,6S,7S,8S)-1-methyl-3-methylidene-8-(propan-2-yl)tricyclo[4.4.0.0²,⁷]decane

> <ALOGPS_LOGP>
3.38

> <JCHEM_LOGP>
4.1460638329999995

> <ALOGPS_LOGS>
-4.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
64.6954

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,6S,7S,8S)-8-isopropyl-1-methyl-3-methylidenetricyclo[4.4.0.0²,⁷]decane

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.380   4.125   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.714   3.355   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.714   1.815   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.380   1.045   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.046   1.815   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.046   3.355   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.713   4.125   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.713   1.045   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.379   1.815   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.379   3.355   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.047   1.045   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.713   5.665   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.713  -0.495   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.046  -1.265   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.379  -1.265   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      -5.046   4.895   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0      -5.046   0.275   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6    8   17                                             
CONECT    6    1    7    5   16                                             
CONECT    7    6   10   12    4                                             
CONECT    8    5    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    7    9                                                       
CONECT   11    3                                                            
CONECT   12    7                                                            
CONECT   13    8   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    6                                                            
CONECT   17    5                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
(1S,6S,7S,8S)-8-Isopropyl-1-methyl-3-methylenetricyclo[4.4.0.0(2,7)]decane	ChEBI
b-Copaene	Generator
Β-copaene	Generator

Chemical Formula

C₁₅H₂₄

Average Mass

204.3511 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(1S,6S,7S,8S)-1-methyl-3-methylidene-8-(propan-2-yl)tricyclo[4.4.0.0²,⁷]decane

Traditional Name

(1S,6S,7S,8S)-8-isopropyl-1-methyl-3-methylidenetricyclo[4.4.0.0²,⁷]decane

CAS Registry Number

Not Available

SMILES

[H][C@@]12C3C(=C)CC[C@]1([H])[C@]3(C)CC[C@H]2C(C)C

InChI Identifier

InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(15)13(11)12/h9,11-14H,3,5-8H2,1-2,4H3/t11-,12-,13-,14?,15-/m0/s1

InChI Key

UPVZPMJSRSWJHQ-XIQJJJERSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ambrosia trifida	Plant	KNApSAcK
Ananas comosus	LOTUS Database	35616633
Cedrus libani	Plant	KNApSAcK
Centaurea atropurpurea	Plant	KNApSAcK
Chamaemelum nobile	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cistus creticus	Plant	KNApSAcK
Citrus aurantium	LOTUS Database	35616633
Citrus maxima	LOTUS Database	35616633
Citrus retuculata	Plant	KNApSAcK
Citrus unshiu	LOTUS Database	35616633
Copaifera langsdorffii	LOTUS Database	35616633
Curcuma amanda Roxb	Plant	KNApSAcK
Dacrydium nidulum	LOTUS Database	35616633
Dumortiera hirsuta	LOTUS Database	35616633
Dumortiera hirsuta (Sw.) Nees	-	KNApSAcK
Humulus lupulus	Plant	KNApSAcK
Illicium verum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Larix gmelini	LOTUS Database	35616633
Larix kaempferi	LOTUS Database	35616633
Larix sibirica	LOTUS Database	35616633
Leptospermum scoparium	Plant	KNApSAcK
Litsea cubeba	Plant	KNApSAcK
Melissa officinalis	LOTUS Database	35616633
Mentha spicata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha x piperita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Origanum sipyleum	LOTUS Database	35616633
Pelargonium vitifolium	LOTUS Database	35616633
Phagnalon sordidum	Plant	KNApSAcK
Picea koraiensis	LOTUS Database	35616633
Pimenta dioica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pinus halepensis	Plant	KNApSAcK
Pinus pumila	LOTUS Database	35616633
Piper nigrum L.	Plant	KNApSAcK
Primula halleri	Plant	KNApSAcK
Psidium guajava	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia absconditiflora	LOTUS Database	35616633
Salvia officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Satureja subspicata	Plant	KNApSAcK
Scapania undulata	LOTUS Database	35616633
Solidago canadensis	LOTUS Database	35616633
Veronica spicata	Plant	KNApSAcK
Xylopia parviflora	Plant	KNApSAcK
Zea mays	LOTUS Database	35616633
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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

bridged compound (CHEBI:64799 )
sesquiterpene (CHEBI:64799 )

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	3.38	ALOGPS
logP	4.15	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	1	ChemAxon
Refractivity	64.7 m³·mol⁻¹	ChemAxon
Polarizability	35.81 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

FDB004831

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C20274

BioCyc ID

CPD-8740

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57339298

PDB ID

Not Available

ChEBI ID

64799

Good Scents ID

Not Available

References

General References

Parra-Garces MI, Caroprese-Araque JF, Arrieta-Prieto D, Stashenko E: [Morphology, anatomy, ontogeny and chemical composition of inflorescences volatile secondary metabolites of Lippia alba (Verbenaceae) at three stages of development]. Rev Biol Trop. 2010 Dec;58(4):1533-48. [PubMed:21250484 ]

Showing NP-Card for beta-Copaene (NP0046534)

MOL for NP0046534 (beta-Copaene)

3D MOL for NP0046534 (beta-Copaene)

3D SDF for NP0046534 (beta-Copaene)

3D-SDF for NP0046534 (beta-Copaene)

PDB for NP0046534 (beta-Copaene)

3D PDB for NP0046534 (beta-Copaene)

SMILES for NP0046534 (beta-Copaene)

INCHI for NP0046534 (beta-Copaene)

Structure for NP0046534 (beta-Copaene)

3D Structure for NP0046534 (beta-Copaene)