NP-MRD: Showing NP-Card for beta-Gurjunene (NP0045814)

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Record Information

Version

2.0

Created at

2022-03-17 19:43:41 UTC

Updated at

2022-03-17 19:43:41 UTC

NP-MRD ID

NP0045814

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-Gurjunene

Description

Beta-Gurjunene, also known as β-gurjunene, belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. beta-Gurjunene is found in Centipeda minima, Cistus albidus, Citrus paradisi, Commiphora gurreh, Curcuma amanda Roxb, Daniellia oliveri, Eucalyptus nova-anglica, Acca sellowiana, Helichrysum odoratissimum, Hypericum androsaemum, Lantana strigocamara, Lantana xenica, Melaleuca alternifolia, Nardostachys jatamansi , Ocimum americanum , Ocimum basilicum , Ocimum gratissimum , Ocimum kilimandscharicim, Ocimum tenuiflorum , Panax ginseng, Persea americana, Pinus halepensis , Primula halleri, Quercus coccifera , Santolina chamaecyparissus, Sideritis tragoriganum, Tanacetum vulgare, Thulinella chrysantha, Thymus broussonetii, Thymus broussonetti, Thymus maroccanus, Thymus praecos, Valeriana jatamansi , Valeriana officinalis and Vitex agnus-castus. Beta-Gurjunene is possibly neutral.

Structure

MOL SDF PDB SMILES InChI

6450812
  Mrv1572001071617122D          

 15 17  0  0  1  0            999 V2000
    3.7157   -0.7019    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3976   -1.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590   -0.3440    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9723   -0.3440    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7888    0.4604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6426    0.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3032    1.1054    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2203   -1.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9327   -1.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1282    1.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2672   -0.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9717    0.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6501   -0.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9452    1.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918   -1.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
  2  9  1  0  0  0  0
  3  6  1  1  0  0  0
  4  5  1  0  0  0  0
  4 11  1  6  0  0  0
  5  7  1  0  0  0  0
  5 12  1  6  0  0  0
  6 10  1  0  0  0  0
  7 10  1  0  0  0  0
  7 14  1  6  0  0  0
 11 13  1  0  0  0  0
 11 15  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045814

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@@H]2[C@H]([C@H]3[C@@H]1CCC3=C)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h9,11-14H,2,5-8H2,1,3-4H3/t9-,11-,12-,13-,14-/m1/s1

> <INCHI_KEY>
IRCZVRWQUNZGSH-DKTYCGPESA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.047096646221537

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1aR,4R,4aR,7aR,7bR)-1,1,4-trimethyl-7-methylidene-decahydro-1H-cyclopropa[e]azulene

> <ALOGPS_LOGP>
3.75

> <JCHEM_LOGP>
4.1460638329999995

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
64.69539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1aR,4R,4aR,7aR,7bR)-1,1,4-trimethyl-7-methylidene-octahydro-1aH-cyclopropa[e]azulene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 6450812                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       6.936  -1.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.209  -2.179   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.323  -0.642   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.548  -0.642   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.206   0.859   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.666   0.859   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.166   2.063   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.745  -2.294   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.341  -3.451   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.706   2.063   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.232  -1.424   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.681   0.993   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080  -0.416   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.498   3.451   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.091  -2.958   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    3    8    9                                             
CONECT    3    1    2    6                                                  
CONECT    4    1    5   11                                                  
CONECT    5    4    7   12                                                  
CONECT    6    3   10                                                       
CONECT    7    5   10   14                                                  
CONECT    8    2                                                            
CONECT    9    2                                                            
CONECT   10    6    7                                                       
CONECT   11    4   13   15                                                  
CONECT   12    5   13                                                       
CONECT   13   11   12                                                       
CONECT   14    7                                                            
CONECT   15   11                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Value	Source
b-Gurjunene	Generator
Β-gurjunene	Generator

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(1aR,4R,4aR,7aR,7bR)-1,1,4-trimethyl-7-methylidene-decahydro-1H-cyclopropa[e]azulene

Traditional Name

(1aR,4R,4aR,7aR,7bR)-1,1,4-trimethyl-7-methylidene-octahydro-1aH-cyclopropa[e]azulene

CAS Registry Number

73464-47-8

SMILES

C[C@@H]1CC[C@@H]2[C@H]([C@H]3[C@@H]1CCC3=C)C2(C)C

InChI Identifier

InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h9,11-14H,2,5-8H2,1,3-4H3/t9-,11-,12-,13-,14-/m1/s1

InChI Key

IRCZVRWQUNZGSH-DKTYCGPESA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Centipeda minima	LOTUS Database	35616633
Cistus albidus	Plant	KNApSAcK
Citrus paradisi	LOTUS Database	35616633
Commiphora gurreh	LOTUS Database	35616633
Curcuma amanda Roxb	Plant	KNApSAcK
Daniellia oliveri	LOTUS Database	35616633
Eucalyptus nova-anglica	LOTUS Database	35616633
Feijoa sellowiana	Plant	KNApSAcK
Helichrysum odoratissimum	LOTUS Database	35616633
Hypericum androsaemum	LOTUS Database	35616633
Lantana strigocamara	LOTUS Database	35616633
Lantana xenica	LOTUS Database	35616633
Melaleuca alternifolia	LOTUS Database	35616633
Nardostachys jatamansi	Plant	KNApSAcK
Ocimum americanum	Plant	KNApSAcK
Ocimum basilicum	Plant	KNApSAcK
Ocimum gratissimum	Plant	KNApSAcK
Ocimum kilimandscharicim	Plant	KNApSAcK
Ocimum tenuiflorum	Plant	KNApSAcK
Panax ginseng	LOTUS Database	35616633
Persea americana	LOTUS Database	35616633
Pinus halepensis	Plant	KNApSAcK
Primula halleri	Plant	KNApSAcK
Quercus coccifera	Plant	KNApSAcK
Salvia rosmarinus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Santolina chamaecyparissus	LOTUS Database	35616633
Satureja montana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sideritis tragoriganum	LOTUS Database	35616633
Tanacetum vulgare	LOTUS Database	35616633
Thulinella chrysantha	LOTUS Database	35616633
Thymus broussonetii	LOTUS Database	35616633
Thymus broussonetti	Plant	KNApSAcK
Thymus maroccanus	Plant	KNApSAcK
Thymus praecos	Plant	KNApSAcK
Valeriana jatamansi	Plant	KNApSAcK
Valeriana officinalis	Plant	KNApSAcK
Vitex agnus-castus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

5,10-cycloaromadendrane sesquiterpenoids

Alternative Parents

Substituents

5,10-cycloaromadendrane sesquiterpenoid
Guaiane 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

sesquiterpenoid (CHEBI:80940 )

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	3.75	ALOGPS
logP	4.15	ChemAxon
logS	-4.9	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	64.7 m³·mol⁻¹	ChemAxon
Polarizability	26.05 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

FDB001866

KNApSAcK ID

C00034456

Chemspider ID

Not Available

KEGG Compound ID

C17120

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6450812

PDB ID

Not Available

ChEBI ID

80940

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for beta-Gurjunene (NP0045814)

MOL for NP0045814 (beta-Gurjunene)

3D MOL for NP0045814 (beta-Gurjunene)

3D SDF for NP0045814 (beta-Gurjunene)

3D-SDF for NP0045814 (beta-Gurjunene)

PDB for NP0045814 (beta-Gurjunene)

3D PDB for NP0045814 (beta-Gurjunene)

SMILES for NP0045814 (beta-Gurjunene)

INCHI for NP0045814 (beta-Gurjunene)

Structure for NP0045814 (beta-Gurjunene)

3D Structure for NP0045814 (beta-Gurjunene)