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Showing NP-Card for gamma-Himachalene (NP0049044)

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Record Information
Version2.0
Created at2022-03-17 21:06:14 UTC
Updated at2022-03-17 21:06:14 UTC
NP-MRD IDNP0049044
Secondary Accession NumbersNone
Natural Product Identification
Common Namegamma-Himachalene
DescriptionGamma-Himachalene, also known as γ-himachalene or himachal-4,10-diene, belongs to the class of organic compounds known as himachalane and lippifoliane sesquiterpenoids. These are sesquiterpenoids with a structure based on either the himachalane or the lippifoliane skeleton. Thus, gamma-himachalene is considered to be an isoprenoid lipid molecule. Gamma-Himachalene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, gamma-Himachalene has been detected, but not quantified in, a few different foods, such as anises, fats and oils, and herbs and spices. gamma-Himachalene is found in Cedrus libani , Guatteriopsis hispida, Primula halleri, Pterocaulon virgatum , Rhaponticum carthamoides , Scapania undulata and Toona ciliata. This could make gamma-himachalene a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049044 (gamma-Himachalene)

Himachalen-gamma
  Mrv1572001071617122D          
  Mrv0541 01101309102D          
 15 16  0  0  0  0            999 V2000
   -5.7020    2.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4165    1.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4165    0.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7020    0.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9876    0.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9876    1.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1310    2.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3426    0.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5383    0.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1803    1.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5383    1.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3426    2.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1410    2.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8713    2.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5261   -0.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12  6  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  8 15  1  0  0  0  0
M  END
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3D MOL for NP0049044 (gamma-Himachalene)

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3D SDF for NP0049044 (gamma-Himachalene)
Himachalen-gamma
  Mrv1572001071617122D          
  Mrv0541 01101309102D          
 15 16  0  0  0  0            999 V2000
   -5.7020    2.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4165    1.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4165    0.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7020    0.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9876    0.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9876    1.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1310    2.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3426    0.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5383    0.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1803    1.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5383    1.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3426    2.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1410    2.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8713    2.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5261   -0.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12  6  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  8 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049044

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC2C(CC1)C(C)=CCCC2(C)C

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

> <INCHI_KEY>
PUWNTRHCKNHSAT-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.010863236120162

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,5,9-tetramethyl-2,4a,5,6,7,9a-hexahydro-1H-benzo[7]annulene

> <ALOGPS_LOGP>
5.57

> <JCHEM_LOGP>
4.461375721333334

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
68.5249

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.46e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gamma-himachalene

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0049044 (gamma-Himachalene)
Download
PDB for NP0049044 (gamma-Himachalene)
HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Himachalen-gamma                                  
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0     -10.644   3.869   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.977   3.099   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.977   1.559   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.644   0.789   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.310   1.559   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.310   3.099   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -13.311   3.869   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.106   0.599   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.605   0.942   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.937   2.329   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.605   3.717   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.106   4.060   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -7.730   5.553   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.093   5.242   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.449  -0.902   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    5   12                                                  
CONECT    7    2                                                            
CONECT    8    5    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    6   13   14                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    8                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

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3D PDB for NP0049044 (gamma-Himachalene)
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SMILES for NP0049044 (gamma-Himachalene)
CC1=CC2C(CC1)C(C)=CCCC2(C)C
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INCHI for NP0049044 (gamma-Himachalene)
InChI=1S/C15H24/c1-11-7-8-13-12(2)6-5-9-15(3,4)14(13)10-11/h6,10,13-14H,5,7-9H2,1-4H3
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View in JSmol
Synonyms
ValueSource
g-HimachaleneGenerator
Γ-himachaleneGenerator
(1R,6S)-gamma-HimachaleneHMDB
Himachal-4,10-dieneHMDB
Chemical FormulaC15H24
Average Mass204.3570 Da
Monoisotopic Mass204.18780 Da
IUPAC Name3,5,5,9-tetramethyl-2,4a,5,6,7,9a-hexahydro-1H-benzo[7]annulene
Traditional Namegamma-himachalene
CAS Registry Number53111-25-4
SMILES
CC1=CC2C(CC1)C(C)=CCCC2(C)C
InChI Identifier
InChI=1S/C15H24/c1-11-7-8-13-12(2)6-5-9-15(3,4)14(13)10-11/h6,10,13-14H,5,7-9H2,1-4H3
InChI KeyPUWNTRHCKNHSAT-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cedrus libaniPlant
Guatteria hispidaPlant
Pimpinella anisumFooDB
Primula halleriPlant
Pterocaulon virgatumPlant
Rhaponticum carthamoidesPlant
Scapania undulataLOTUS Database
Toona ciliataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as himachalane and lippifoliane sesquiterpenoids. These are sesquiterpenoids with a structure based on either the himachalane or the lippifoliane skeleton.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentHimachalane and lippifoliane sesquiterpenoids  
Alternative Parents
Substituents
  • Himachalane sesquiterpenoid
    • 

  • Branched unsaturated hydrocarbon
    • 

  • Polycyclic hydrocarbon
    • 

  • Cyclic olefin
    • 

  • Unsaturated aliphatic hydrocarbon
    • 

  • Unsaturated hydrocarbon
    • 

  • Olefin
    • 

  • Hydrocarbon
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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
logP5.57ALOGPS
logP4.46ChemAxon
logS-4.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity68.52 m³·mol⁻¹ChemAxon
Polarizability26.01 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038168  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB017399  
KNApSAcK IDC00021310  
Chemspider ID501668  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound577062  
PDB IDNot Available
ChEBI ID49224  
Good Scents IDNot Available
References
General References