MiMeDB: Showing metabocard for Humulene (MMDBc0033657)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:57:45 UTC

Update Date

2022-08-31 22:37:31 UTC

Metabolite ID

MMDBc0033657

Metabolite Identification

Common Name

Humulene

Description

Humulene is one of many sesquiterpenoids that are derived from farnesyl diphosphate (FPP). The biosynthesis begins with the loss of diphosphate from FPP under the action of sesquiterpene synthesis enzymes, generating an allylic cation that is highly susceptible to intramolecular attacks. It is a hop oil constituent/fermentation product.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241223232D          

 15 15  0  0  0  0            999 V2000
    0.0633    0.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6696    1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5424    0.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505    1.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8037    1.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2919    1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8514    0.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4477   -0.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6078   -1.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015   -1.5863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2138   -1.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0324   -0.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2447   -0.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6387    0.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8699    0.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  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
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 12 14  1  0  0  0  0
  8 15  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033657

> <DATABASE_NAME>
MIME

> <SMILES>
C\C1=C/CC(C)(C)\C=C/C\C(C)=C\CC1

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

> <INCHI_KEY>
FAMPSKZZVDUYOS-OWEBEESNSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
25.461649004580067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1Z,4E,8E)-4,8,11,11-tetramethylcycloundeca-1,4,8-triene

> <ALOGPS_LOGP>
6.07

> <JCHEM_LOGP>
4.8782791046666665

> <ALOGPS_LOGS>
-4.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
71.5485

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
humulene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.118   0.959   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.250   2.004   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.879   1.573   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.148   2.928   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.367   3.034   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.278   2.217   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.323   1.085   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.569  -0.258   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.868  -1.917   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.736  -2.961   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.266  -2.503   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.927  -1.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.457  -0.543   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.059   0.043   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.490   0.841   0.000  0.00  0.00           C+0
CONECT    1    2   13                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    1                                                       
CONECT   14   12                                                            
CONECT   15    8                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

Synonyms

Not Available

Molecular Formula

C₁₅H₂₄

Average Mass

204.3511

Monoisotopic Mass

204.187800768

IUPAC Name

(1Z,4E,8E)-4,8,11,11-tetramethylcycloundeca-1,4,8-triene

Traditional Name

humulene

CAS Registry Number

6753-98-6

SMILES

C\C1=C/CC(C)(C)\C=C/C\C(C)=C\CC1

InChI Identifier

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

InChI Key

FAMPSKZZVDUYOS-OWEBEESNSA-N

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

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	6.07	ALOGPS
logP	4.88	ChemAxon
logS	-4.3	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	71.55 m³·mol⁻¹	ChemAxon
Polarizability	25.46 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0920000000-6a79f6794db42ee36f8b	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0290000000-d1375940e9b7ed7922b4	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-2930000000-cdb29a58477970796a70	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kr-4900000000-788e8bfc0021846819ae	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-8ecbabe7146ad2762752	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0390000000-984bd28446d79854bd71	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ri-1900000000-139cbaab33ea7f90de6c	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	4	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Humulene

METLIN ID

Not Available

PubChem Compound

57448905

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Humulene (MMDBc0033657)

MOL for #<Metabolite:0x00007fed15de04e0>

3D MOL for #<Metabolite:0x00007fed15de04e0>

3D SDF for #<Metabolite:0x00007fed15de04e0>

3D-SDF for #<Metabolite:0x00007fed15de04e0>

PDB for #<Metabolite:0x00007fed15de04e0>

3D PDB for #<Metabolite:0x00007fed15de04e0>

SMILES for #<Metabolite:0x00007fed15de04e0>

INCHI for #<Metabolite:0x00007fed15de04e0>

Structure for #<Metabolite:0x00007fed15de04e0>

3D Structure for #<Metabolite:0x00007fed15de04e0>