NP-MRD: Showing NP-Card for gamma-Humulene (NP0058985)

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Record Information

Version

2.0

Created at

2022-04-28 04:16:45 UTC

Updated at

2022-04-28 04:16:45 UTC

NP-MRD ID

NP0058985

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gamma-Humulene

Description

(1E,6E)-gamma-humulene, also known as (1E,6E)-γ-humulene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, (1E,6E)-gamma-humulene is considered to be an isoprenoid. gamma-Humulene is found in Abies grandis, Abies magnifica, Antiphiona pinnatisecta, Artemisia douglasiana, Artemisia filifolia, Artemisia koidzumii, Artemisia princeps , Artemisia schmidtiana, Callilepis salicifolia, Cinnamomum illicioides, Dittrichia viscosa, Geigeria burkei, Heterotheca grandiflora, Heterotheca subaxillaris, Ichthyothere terminalis, Lasiolaena morii, Othonna arborescens, Othonna coronopifolia, Platycarpha glomerata, Pterocaulon virgatum, Senecio inaequidens, Senecio vulgaris and Silphium integrifolium. Based on a literature review very few articles have been published on (1E,6E)-gamma-humulene.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
    1.4668    2.9872    0.7118 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8452    2.2456   -0.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5117    2.5091   -0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315    1.8625   -0.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9749    0.5467    0.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3241    0.6841    0.9393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3603   -0.3773   -0.9847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0492   -0.0569    1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6013   -1.4573    0.9090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232   -1.7428   -0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6765   -1.9308   -0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0555   -3.4097   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5802   -1.0056    0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5083    0.4471    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7700    1.1979   -0.8097 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5111    2.8387    0.9886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9794    3.7895    1.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6247    3.5550   -1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5354    2.4103   -0.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4842   -0.3321    1.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1217    0.9880    0.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1595    1.3585    1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8919   -0.0453   -1.9597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2699   -1.4399   -0.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4645   -0.1807   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4922   -0.0501    2.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786    0.6162    1.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0065   -1.8259    1.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4715   -2.1599    0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0159   -0.9651   -1.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2144   -2.6703   -0.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3179   -3.9919    0.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0326   -3.5606    0.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1498   -3.6850   -1.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6104   -1.4288    0.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5735    0.8673    0.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1422    0.8279    1.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5290    1.9052   -1.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3675    0.6792   -1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  6 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
M  END


  Mrv1652304282206162D          

 15 15  0  0  0  0            999 V2000
   -0.0244   -0.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2087    0.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0762    0.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5424    1.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3338    1.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3566    0.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9501   -0.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7561   -0.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7171   -1.1349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9151   -1.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3463   -0.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5444   -0.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3113   -1.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9199    1.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    2.2075    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 14  1  0  0  0  0
  4 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0058985

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C/CCC(=C)\C=C\C(C)(C)CCC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h7,10,12H,2,5-6,8-9,11H2,1,3-4H3/b12-10+,13-7+

> <INCHI_KEY>
FNXUOGPQAOCFKU-PVYBRLDNSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.77998934691343

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1E,6E)-1,8,8-trimethyl-5-methylidenecycloundeca-1,6-diene

> <ALOGPS_LOGP>
5.86

> <JCHEM_LOGP>
4.936212775

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
70.476

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.04e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1E,6E)-gamma-humulene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.046  -0.611   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.390   0.866   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.009   1.333   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.879   2.603   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.356   2.168   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.399   0.629   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.507  -0.641   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.011  -0.312   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.072  -2.119   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.575  -2.480   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.513  -1.365   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.016  -1.727   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.581  -3.204   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.717   3.614   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.142   4.121   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   14   15                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    1   13                                                  
CONECT   13   12                                                            
CONECT   14    4                                                            
CONECT   15    4                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
(1E,6E)-1,8,8-Trimethyl-5-methylenecycloundeca-1,6-diene	ChEBI
(1E,6E)-g-Humulene	Generator
(1E,6E)-Γ-humulene	Generator

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(1E,6E)-1,8,8-trimethyl-5-methylidenecycloundeca-1,6-diene

Traditional Name

(1E,6E)-gamma-humulene

CAS Registry Number

Not Available

SMILES

C\C1=C/CCC(=C)\C=C\C(C)(C)CCC1

InChI Identifier

InChI=1S/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h7,10,12H,2,5-6,8-9,11H2,1,3-4H3/b12-10+,13-7+

InChI Key

FNXUOGPQAOCFKU-PVYBRLDNSA-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
Abies grandis	Plant	KNApSAcK
Abies magnifica	LOTUS Database	35616633
Antiphiona pinnatisecta	LOTUS Database	35616633
Artemisia douglasiana	LOTUS Database	35616633
Artemisia filifolia	LOTUS Database	35616633
Artemisia koidzumii	LOTUS Database	35616633
Artemisia princeps	Plant	KNApSAcK
Artemisia schmidtiana	LOTUS Database	35616633
Callilepis salicifolia	LOTUS Database	35616633
Cinnamomum illicioides	Plant	KNApSAcK
Dittrichia viscosa	LOTUS Database	35616633
Geigeria burkei	LOTUS Database	35616633
Heterotheca grandiflora	LOTUS Database	35616633
Heterotheca subaxillaris	LOTUS Database	35616633
Ichthyothere terminalis	LOTUS Database	35616633
Lasiolaena morii	LOTUS Database	35616633
Othonna arborescens	LOTUS Database	35616633
Othonna coronopifolia	Plant	KNApSAcK
Platycarpha glomerata	LOTUS Database	35616633
Pterocaulon virgatum	LOTUS Database	35616633
Senecio inaequidens	LOTUS Database	35616633
Senecio vulgaris	Plant	KNApSAcK
Silphium integrifolium	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

Humulane sesquiterpenoid
Sesquiterpenoid
Branched unsaturated hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

gamma-humulene (CHEBI:49292 )
Humulane sesquiterpenoids (C16829 )
Humulenes (C16829 )
Humulane sesquiterpenoids (LMPR0103110002 )

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	5.86	ALOGPS
logP	4.94	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	0	ChemAxon
Refractivity	70.48 m³·mol⁻¹	ChemAxon
Polarizability	25.78 Å³	ChemAxon
Number of Rings	1	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

Not Available

Chemspider ID

4896122

KEGG Compound ID

C16829

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6365330

PDB ID

Not Available

ChEBI ID

49292

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for gamma-Humulene (NP0058985)

MOL for NP0058985 (gamma-Humulene)

3D MOL for NP0058985 (gamma-Humulene)

3D SDF for NP0058985 (gamma-Humulene)

3D-SDF for NP0058985 (gamma-Humulene)

PDB for NP0058985 (gamma-Humulene)

3D PDB for NP0058985 (gamma-Humulene)

SMILES for NP0058985 (gamma-Humulene)

INCHI for NP0058985 (gamma-Humulene)

Structure for NP0058985 (gamma-Humulene)

3D Structure for NP0058985 (gamma-Humulene)