NP-MRD: Showing NP-Card for alpha-Humulene epoxide I (NP0045001)

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Record Information

Version

2.0

Created at

2022-03-10 18:52:32 UTC

Updated at

2022-03-10 22:18:06 UTC

NP-MRD ID

NP0045001

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-Humulene epoxide I

Description

Alpha-Humulene epoxide I, also known as alpha-humulene oxide I or humulene epoxide I, belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms (one oxygen and two carbon atoms). Alpha-Humulene epoxide I is an extremely weak basic (essentially neutral) compound (based on its pKa). Alpha-Humulene epoxide I is also biochemically classified as a terpenoid. Alpha-Humulene epoxide I is typically found in alcoholic beverages, especially beer. Alpha-Humulene epoxide I is a constituent of hops, cannabis and wild ginger (Zingiber zerumbet) and has a characteristic herbal or ‚Äúhoppy‚Äù fragrance. Alpha-Humulene epoxide I is an oxidation product of humulene. Humulene is a naturally occurring monocyclic sesquiterpene (C15H24), containing an 11-membered ring and consisting of 3 isoprene units containing three nonconjugated C=C double bonds. Humulene is found in the flowering cone of the hops plant, Humulus lupulus, from which it derives its name as well as in the flowers of related plants such as cannabis. The concentration of humulene varies among different varieties of hops and cannabis but can be up to 40% of the essential oil. Multiple epoxides of humulene (such as alpha-humulene epoxide I and alpha-humulene epoxide II) are produced in the brewing process of beer or in the extraction of cannabis oils.¬†

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    3.0817   -2.2604   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427   -0.9692   -0.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0127    0.1313   -0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3152    1.4156   -0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5766    1.6873    0.9543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1727    2.1183    0.7580 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2166    3.0253   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6577    2.1578    1.8513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7469    0.9845    1.1496 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7893    0.7197    0.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1106   -0.7345    0.0238 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3849   -1.0560   -1.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4631   -1.0244    0.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631   -1.6470    0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1780   -1.7702    0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8816   -1.0284   -0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8113   -2.8802   -1.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8722   -2.8386    0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1776   -2.1235   -0.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958    0.0726   -0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6914    1.5363   -1.2342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0904    2.2360   -0.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6256    0.7435    1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0864    2.4531    1.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0451    2.6067   -1.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4388    3.9396   -0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2563    3.3377   -0.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2948    0.1048    1.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5736    1.1201   -0.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7212    1.2505    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0608   -0.2442   -1.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4865   -1.1846   -2.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9826   -2.0134   -1.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8741   -1.9432    0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3217   -1.1971    1.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1224   -0.1675    0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123   -2.2963    1.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8248   -2.5208    0.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4568   -0.0823   -1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8515   -1.6590   -1.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  6
 11 13  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16  2  1  0
  9  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  9 28  1  1
 10 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
M  END


  Mrv1652303192001303D          

 16 17  0  0  0  0            999 V2000
   -3.4129   -2.5724   -0.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7171   -0.4083   -1.7251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3332   -0.9759    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1019    2.4893    1.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0184   -1.3657    0.7511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0855    0.9824    0.3457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2871   -2.0208    0.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8412   -0.2577   -0.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8620   -1.0107   -0.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163    1.6079   -0.7546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1007    1.1741   -0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4782   -1.4971    0.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0645    1.7729   -0.9063 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1909   -0.3437   -0.2522 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0976    2.2307   -0.1202 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7096    3.1014   -0.8151 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2 14  1  0  0  0  0
  3 14  1  0  0  0  0
  4 15  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  2  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  7 12  1  0  0  0  0
  8 12  2  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045001

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C\CC[C@]2(C)O[C@H]2CC(C)(C)\C=C\C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-12-7-5-9-14(2,3)11-13-15(4,16-13)10-6-8-12/h5,8-9,13H,6-7,10-11H2,1-4H3/b9-5+,12-8-/t13-,15-/m0/s1

> <INCHI_KEY>
RKQDKXOBRXTSFS-MQTWWMRFSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.356

> <EXACT_MASS>
220.182715393

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
26.574943075964146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4Z,7E,11S)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene

> <ALOGPS_LOGP>
5.02

> <JCHEM_LOGP>
3.9774975963333326

> <ALOGPS_LOGS>
-4.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.224674113829658

> <JCHEM_POLAR_SURFACE_AREA>
12.53

> <JCHEM_REFRACTIVITY>
70.30900000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4Z,7E,11S)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0      -3.413  -2.572  -0.268  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.717  -0.408  -1.725  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.333  -0.976   0.480  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.102   2.489   1.327  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.018  -1.366   0.751  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.086   0.982   0.346  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.287  -2.021   0.837  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.841  -0.258  -0.023  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.862  -1.011  -0.155  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.316   1.608  -0.755  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.101   1.174  -0.021  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.478  -1.497   0.199  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.065   1.773  -0.906  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.191  -0.344  -0.252  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.098   2.231  -0.120  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.710   3.101  -0.815  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    7    9                                                       
CONECT    6    8   10                                                       
CONECT    7    5   12                                                       
CONECT    8    6   12                                                       
CONECT    9    5   14                                                       
CONECT   10    6   15                                                       
CONECT   11   13   14                                                       
CONECT   12    1    7    8                                                  
CONECT   13   11   15   16                                                  
CONECT   14    2    3    9   11                                             
CONECT   15    4   10   13   16                                             
CONECT   16   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O

Average Mass

220.3560 Da

Monoisotopic Mass

220.18272 Da

IUPAC Name

(1S,4Z,7E,11S)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene

Traditional Name

(1S,4Z,7E,11S)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene

CAS Registry Number

Not Available

SMILES

C\C1=C\CC[C@]2(C)O[C@H]2CC(C)(C)\C=C\C1

InChI Identifier

InChI=1S/C15H24O/c1-12-7-5-9-14(2,3)11-13-15(4,16-13)10-6-8-12/h5,8-9,13H,6-7,10-11H2,1-4H3/b9-5+,12-8-/t13-,15-/m0/s1

InChI Key

RKQDKXOBRXTSFS-MQTWWMRFSA-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
Cannabis sativa	NULL	Not Available
Curcuma xanthorrhiza	Plant	KNApSAcK
Litsea monopetala	Plant	KNApSAcK
Mentha arvensis	Plant	KNApSAcK
Polygonum minus	Plant	KNApSAcK
Psidium guajava	Plant	KNApSAcK
Zingiber zerumbet	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Epoxides

Sub Class

Not Available

Direct Parent

Epoxides

Alternative Parents

Substituents

Oxacycle
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	5.02	ALOGPS
logP	3.98	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.31 m³·mol⁻¹	ChemAxon
Polarizability	26.57 Å³	ChemAxon
Number of Rings	2	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for alpha-Humulene epoxide I (NP0045001)

MOL for NP0045001 (alpha-Humulene epoxide I)

3D MOL for NP0045001 (alpha-Humulene epoxide I)

3D SDF for NP0045001 (alpha-Humulene epoxide I)

3D-SDF for NP0045001 (alpha-Humulene epoxide I)

PDB for NP0045001 (alpha-Humulene epoxide I)

3D PDB for NP0045001 (alpha-Humulene epoxide I)

SMILES for NP0045001 (alpha-Humulene epoxide I)

INCHI for NP0045001 (alpha-Humulene epoxide I)

Structure for NP0045001 (alpha-Humulene epoxide I)

3D Structure for NP0045001 (alpha-Humulene epoxide I)