NP-MRD: Showing NP-Card for beta-Humulene (NP0044889)

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Record Information

Version

2.0

Created at

2022-03-10 18:45:51 UTC

Updated at

2022-03-10 22:18:36 UTC

NP-MRD ID

NP0044889

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-Humulene

Description

Beta-humulene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the cytoplasm (PMID:23746261 ). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Beta-humulene is possibly neutral. Beta-humulene is found in hops (Humulus lupulus) a member of the Cannabaceae family and in Cannabis plants (PMID: 6991645 ). It is also detected in allspice and guava fruit, celery seed, lemon oil and spearmint leaf ( http://Www.Thegoodscentscompany.Com/data/rw1539551.Html#tooccur ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
    0.5359    3.0695   -0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433    2.1589    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7673    1.6810    0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8698    1.6934   -0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4235    0.6237   -0.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9456   -0.7119   -0.2783 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3723   -1.2918    1.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7729   -1.6271   -1.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5304   -1.0401   -0.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3360   -1.5334    0.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271   -1.2586    0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4777   -1.7930    1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2941   -0.4764   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6643    0.9232   -0.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875    1.5714    0.7183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3733    3.5045   -1.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4742    3.3936   -1.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5992    0.8776    1.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9626    2.5613    1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3028    2.6724   -0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2995    0.7524   -1.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5015   -1.3185    1.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0811   -0.8398    1.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0772   -2.3610    1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8087   -1.2946   -1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5958   -2.6566   -0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3305   -1.4965   -2.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1751   -0.1724   -1.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4745   -1.8665   -1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0606   -2.1227    1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5505   -1.7535    1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3105   -1.2619    2.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2365   -2.8839    1.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2705   -1.0069   -0.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7910   -0.4638   -1.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7253    1.5390   -1.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6977    0.9137    0.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3804    2.4205    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6216    0.8745    1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  6  1  0
  6  7  1  1
  6  8  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 15  1  0
 15 14  1  0
 14 13  1  0
 13 11  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 10 30  1  0
  9 28  1  0
  9 29  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  5 21  1  0
  4 20  1  0
  3 18  1  0
  3 19  1  0
  1 16  1  0
  1 17  1  0
 15 38  1  0
 15 39  1  0
 14 36  1  0
 14 37  1  0
 13 34  1  0
 13 35  1  0
M  END


  Mrv1652303202019002D          

 15 15  0  0  0  0            999 V2000
    3.4006   -0.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5989   -0.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7707    2.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8066    1.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815   -1.4765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7095    0.5450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1030   -1.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8681   -0.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2335   -0.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1854    0.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3640    1.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9900    0.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5790   -0.8780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1100   -0.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5424    1.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 11  6  2  0  0  0  0
 12 10  1  0  0  0  0
 13  1  2  0  0  0  0
 13  7  1  0  0  0  0
 13  9  1  0  0  0  0
 14  2  1  0  0  0  0
 14  8  1  0  0  0  0
 14 10  2  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044889

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6,10-11H,1,5,7-9,12H2,2-4H3/b11-6-,14-10-

> <INCHI_KEY>
HAVYZKHVTLAPDZ-PRUKLFJYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.035064463983403

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1Z,5Z)-1,4,4-trimethyl-8-methylidenecycloundeca-1,5-diene

> <ALOGPS_LOGP>
5.97

> <JCHEM_LOGP>
4.936212775

> <ALOGPS_LOGS>
-4.93

> <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>
2.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1Z,5Z)-1,4,4-trimethyl-8-methylidenecycloundeca-1,5-diene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       6.348  -1.779   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.118  -1.438   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.305   4.036   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.506   3.253   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.392  -2.756   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.058   1.017   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.926  -2.897   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.620  -1.258   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.169  -0.241   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.346   0.883   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.413   2.416   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.848   1.223   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.814  -1.639   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.205  -0.650   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.879   2.556   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5    7    8                                                       
CONECT    6    9   11                                                       
CONECT    7    5   13                                                       
CONECT    8    5   14                                                       
CONECT    9    6   13                                                       
CONECT   10   12   14                                                       
CONECT   11    6   15                                                       
CONECT   12   10   15                                                       
CONECT   13    1    7    9                                                  
CONECT   14    2    8   10                                                  
CONECT   15    3    4   11   12                                             
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
b-Humulene	Generator
Β-humulene	Generator
(e,e)-1,4,4-Trimethyl-8-methylene-1,5-cycloundecadiene	HMDB
1,4,4-Trimethyl-8-methylene-(e,e)-1,5-cycloundecadiene	HMDB
1,4,4-Trimethyl-8-methylene-1,5-cycloundecadiene	HMDB

Chemical Formula

C₁₅H₂₄

Average Mass

204.3511 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(1Z,5Z)-1,4,4-trimethyl-8-methylidenecycloundeca-1,5-diene

Traditional Name

(1Z,5Z)-1,4,4-trimethyl-8-methylidenecycloundeca-1,5-diene

CAS Registry Number

116-04-1

SMILES

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

InChI Identifier

InChI=1S/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6,10-11H,1,5,7-9,12H2,2-4H3/b11-6-,14-10-

InChI Key

HAVYZKHVTLAPDZ-PRUKLFJYSA-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
Apium graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cannabis sativa	NULL	Not Available
Citrus limon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lindera aggregata	Plant	KNApSAcK
Mentha spicata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Murraya exotica	Plant	KNApSAcK
Pimenta dioica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pinus sibirica	Plant	KNApSAcK
Psidium guajava	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

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

Not Available

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	5.97	ALOGPS
logP	4.94	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	70.48 m³·mol⁻¹	ChemAxon
Polarizability	26.04 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

HMDB0038214

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017456

KNApSAcK ID

C00012455

Chemspider ID

20120040

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21159064

PDB ID

Not Available

ChEBI ID

49312

Good Scents ID

Not Available

References

General References

Showing NP-Card for beta-Humulene (NP0044889)

MOL for NP0044889 (beta-Humulene)

3D MOL for NP0044889 (beta-Humulene)

3D SDF for NP0044889 (beta-Humulene)

3D-SDF for NP0044889 (beta-Humulene)

PDB for NP0044889 (beta-Humulene)

3D PDB for NP0044889 (beta-Humulene)

SMILES for NP0044889 (beta-Humulene)

INCHI for NP0044889 (beta-Humulene)

Structure for NP0044889 (beta-Humulene)

3D Structure for NP0044889 (beta-Humulene)