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Showing NP-Card for (1r,4r)-1,4-dimethyl-7-(propan-2-ylidene)-2,3,4,5,6,8-hexahydro-1h-azulene (NP0176589)

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Record Information
Version2.0
Created at2022-09-03 14:16:49 UTC
Updated at2022-09-03 14:16:49 UTC
NP-MRD IDNP0176589
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,4r)-1,4-dimethyl-7-(propan-2-ylidene)-2,3,4,5,6,8-hexahydro-1h-azulene
DescriptionBeta-Guaiene, also known as β-guaiene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1r,4r)-1,4-dimethyl-7-(propan-2-ylidene)-2,3,4,5,6,8-hexahydro-1h-azulene is found in Cryptomeria japonica, Erigeron philadelphicus, Juniperus excelsa, Panax ginseng, Pinus sylvestris, Pulicaria arabica, Schinus molle and Valeriana officinalis. (1r,4r)-1,4-dimethyl-7-(propan-2-ylidene)-2,3,4,5,6,8-hexahydro-1h-azulene was first documented in 2021 (PMID: 33847097). Based on a literature review a small amount of articles have been published on beta-Guaiene (PMID: 35236800) (PMID: 34930508) (PMID: 33276406) (PMID: 32441157).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0176589 ((1r,4r)-1,4-dimethyl-7-(propan-2-ylidene)-2,3,4,5,6,8-hexahydro-1h-azulene)


  Mrv1652309032216162D          

 15 16  0  0  1  0            999 V2000
    4.3699    3.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713    2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4871    2.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    1.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.1036    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1690   -0.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    1.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    1.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6680    2.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  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  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
M  END
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3D MOL for NP0176589 ((1r,4r)-1,4-dimethyl-7-(propan-2-ylidene)-2,3,4,5,6,8-hexahydro-1h-azulene)

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3D SDF for NP0176589 ((1r,4r)-1,4-dimethyl-7-(propan-2-ylidene)-2,3,4,5,6,8-hexahydro-1h-azulene)

  Mrv1652309032216162D          

 15 16  0  0  1  0            999 V2000
    4.3699    3.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713    2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4871    2.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    1.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.1036    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1690   -0.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    1.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    1.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6680    2.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  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  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0176589

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CCC2=C1CC(CC[C@H]2C)=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h11-12H,5-9H2,1-4H3/t11-,12-/m1/s1

> <INCHI_KEY>
GIBQERSGRNPMEH-VXGBXAGGSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.160038537722787

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4R)-1,4-dimethyl-7-(propan-2-ylidene)-1,2,3,4,5,6,7,8-octahydroazulene

> <JCHEM_LOGP>
4.361032048333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
68.0652

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R)-1,4-dimethyl-7-(propan-2-ylidene)-2,3,4,5,6,8-hexahydro-1H-azulene

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0176589 ((1r,4r)-1,4-dimethyl-7-(propan-2-ylidene)-2,3,4,5,6,8-hexahydro-1h-azulene)
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PDB for NP0176589 ((1r,4r)-1,4-dimethyl-7-(propan-2-ylidene)-2,3,4,5,6,8-hexahydro-1h-azulene)
HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       8.157   5.949   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.720   4.515   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.243   4.286   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.760   3.311   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.428   1.924   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.760   0.536   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258   0.193   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.916  -1.308   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.054   1.154   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.054   2.694   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258   3.654   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590   3.169   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.114   4.634   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.684   1.924   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590   0.678   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    4                                                       
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    9                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

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3D PDB for NP0176589 ((1r,4r)-1,4-dimethyl-7-(propan-2-ylidene)-2,3,4,5,6,8-hexahydro-1h-azulene)
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SMILES for NP0176589 ((1r,4r)-1,4-dimethyl-7-(propan-2-ylidene)-2,3,4,5,6,8-hexahydro-1h-azulene)
C[C@@H]1CCC2=C1CC(CC[C@H]2C)=C(C)C
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INCHI for NP0176589 ((1r,4r)-1,4-dimethyl-7-(propan-2-ylidene)-2,3,4,5,6,8-hexahydro-1h-azulene)
InChI=1S/C15H24/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h11-12H,5-9H2,1-4H3/t11-,12-/m1/s1
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Synonyms
ValueSource
b-GuaieneGenerator
Β-guaieneGenerator
Chemical FormulaC15H24
Average Mass204.3570 Da
Monoisotopic Mass204.18780 Da
IUPAC Name(1R,4R)-1,4-dimethyl-7-(propan-2-ylidene)-1,2,3,4,5,6,7,8-octahydroazulene
Traditional Name(1R,4R)-1,4-dimethyl-7-(propan-2-ylidene)-2,3,4,5,6,8-hexahydro-1H-azulene
CAS Registry NumberNot Available
SMILES
C[C@@H]1CCC2=C1CC(CC[C@H]2C)=C(C)C
InChI Identifier
InChI=1S/C15H24/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h11-12H,5-9H2,1-4H3/t11-,12-/m1/s1
InChI KeyGIBQERSGRNPMEH-VXGBXAGGSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cryptomeria japonicaLOTUS Database
Erigeron philadelphicusLOTUS Database
Juniperus excelsaLOTUS Database
Panax ginsengLOTUS Database
Pinus sylvestrisLOTUS Database
Pulicaria arabicaLOTUS Database
Schinus molleLOTUS Database
Valeriana officinalisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentSesquiterpenoids  
Alternative Parents
Substituents
  • Sesquiterpenoid
    • 

  • Branched unsaturated hydrocarbon
    • 

  • Polycyclic hydrocarbon
    • 

  • Cyclic olefin
    • 

  • Unsaturated aliphatic hydrocarbon
    • 

  • Unsaturated hydrocarbon
    • 

  • Olefin
    • 

  • Hydrocarbon
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.36ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity68.07 m³·mol⁻¹ChemAxon
Polarizability26.16 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00020376  
Chemspider ID64872557  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15560253  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Feng YX, Lu XX, Du YS, Zheng Y, Zeng D, Du SS: Sesquiterpenoid-rich Essential Oils from Two Magnolia Plants: Contact and Repellent Activity to Three Stored-product Insects. J Oleo Sci. 2022;71(3):435-443. doi: 10.5650/jos.ess21241. [PubMed:35236800  ] 
  2. Caselli A, Favaro R, Petacchi R, Angeli S: Infestation of the gall midge Dasineura oleae provides first evidence of induced plant volatiles in olive leaves. Bull Entomol Res. 2022 Aug;112(4):481-493. doi: 10.1017/S0007485321001000. Epub  2021 Dec 21. [PubMed:34930508  ] 
  3. Guz L, Wawrzykowski J, Adaszek L: Anti-babesial potential and chemical composition of essential oil from yarrow Achillea millefolium. Pol J Vet Sci. 2021 Mar;24(1):79-84. doi: 10.24425/pjvs.2021.136795. [PubMed:33847097  ] 
  4. Pavarini DP, Semir J, Lopes JLC, da Silva RR, Lopes NP: Time-Scale Shifting of Volatile Semiochemical Levels in Wild Type Lychnophora ericoides (Brazilian arnica) and Pollinator Records. Planta Med. 2021 Feb;87(1-02):101-112. doi: 10.1055/a-1320-4556. Epub 2020 Dec 4. [PubMed:33276406  ] 
  5. Joshi RK: Volatile constituents of leaf, stem and flower of the traditional shrub Pogostemon plectranthoides Desf. from the Western Ghats, India. Nat Prod Res. 2022 Jan;36(1):411-413. doi: 10.1080/14786419.2020.1768092. Epub  2020 May 22. [PubMed:32441157  ] 
  6. LOTUS database [Link]