NP-MRD: Showing NP-Card for (4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene (NP0307604)

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Record Information

Version

2.0

Created at

2022-09-11 00:50:25 UTC

Updated at

2022-09-11 00:50:25 UTC

NP-MRD ID

NP0307604

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene

Description

Humulene epoxide I, also known as alpha-humulene oxide, 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). Humulene epoxide I is an extremely weak basic (essentially neutral) compound (based on its pKa). Humulene epoxide I is a herbal tasting compound. Outside of the human body, Humulene epoxide I has been detected, but not quantified in, several different foods, such as alcoholic beverages, allspices, gingers, herbs and spices, and rosemaries. (4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene is found in Abies sibirica, Aframomum melegueta, Aloysia triphylla, Antidesma laciniatum, Aster scaber, Bothriochloa bladhii, Brillantaisia lamium, Bupleurum acutifolium, Cannabis sativa, Cleonia lusitanica, Eupatorium capillifolium, Humulus lupulus, Juniperus chinensis, Juniperus communis, Laggera alata, Nepeta cataria, Nepeta glomerulosa, Pelargonium quercifolium, Piper gaudichaudianum, Stachys recta and Zingiber ottensii. This could make humulene epoxide I a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    2.9921   -1.8657   -0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461   -1.1482    0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5302    0.0035    0.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8981    0.8775    1.6165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4535    2.2242    1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3920    2.1220   -0.0033 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0850    3.4135   -0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6170    0.9656   -0.7040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4547    1.0507    0.2319 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7212    0.7648   -0.4752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0466   -0.7331   -0.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2826   -1.1394    1.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4504   -0.8338   -0.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1099   -1.6026   -1.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0589   -2.0670   -0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8909   -1.9171    0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0641   -1.5815   -0.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9429   -2.9541   -0.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271   -1.6373   -1.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4974    0.4167    0.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1854    0.3830    2.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7555    1.1502    2.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615    2.7842    1.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3232    2.7214    0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2215    4.2452    0.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7569    3.5899   -1.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9500    3.4939   -1.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3953    0.5616    1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7386    1.0361   -1.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5537    1.3297    0.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8623   -2.1848    1.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9376   -0.4406    1.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3849   -1.3203    1.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3252   -0.7525   -2.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1005   -0.0392   -0.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8889   -1.8229   -0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5228   -1.8750   -2.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5609   -2.7112   -1.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4124   -1.5539    1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2527   -2.9536    0.7424 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  0
 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


  Mrv1652309272007332D          

 16 17  0  0  1  0            999 V2000
    3.9252   -2.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9252   -2.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7099   -3.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7099   -1.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1990   -2.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3444   -3.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3444   -1.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5189   -3.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5189   -1.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9381   -2.8589    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9381   -2.0334    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9646   -0.9940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2146   -2.4411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9965   -3.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2323   -4.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3777   -1.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  6  1  0  0  0  0
  2  4  2  0  0  0  0
  2  7  1  0  0  0  0
  3  5  1  0  0  0  0
  4  5  1  0  0  0  0
  4 12  1  0  0  0  0
  6  8  1  0  0  0  0
  6 14  1  0  0  0  0
  6 15  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 13  1  1  0  0  0
 10 11  1  0  0  0  0
 11 13  1  6  0  0  0
 11 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0307604

> <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-/m1/s1

> <INCHI_KEY>
RKQDKXOBRXTSFS-QZFXXANLSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.3505

> <EXACT_MASS>
220.18271539

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
26.955275126202032

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0       7.327  -5.337   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.327  -3.796   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.792  -5.812   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.792  -3.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.705  -4.557   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.243  -6.421   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.243  -2.692   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.702  -6.421   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.702  -2.692   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.618  -5.337   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.618  -3.796   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.267  -1.855   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.267  -4.557   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.460  -7.353   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.034  -7.943   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.572  -2.654   0.000  0.00  0.00           C+0
CONECT    1    3    6                                                       
CONECT    2    4    7                                                       
CONECT    3    1    5                                                       
CONECT    4    2    5   12                                                  
CONECT    5    3    4                                                       
CONECT    6    1    8   14   15                                             
CONECT    7    2    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   13   11                                                  
CONECT   11    9   10   13   16                                             
CONECT   12    4                                                            
CONECT   13   10   11                                                       
CONECT   14    6                                                            
CONECT   15    6                                                            
CONECT   16   11                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
alpha-Humulene oxide	HMDB
Humulene epoxide	HMDB
Humulene I epoxide	HMDB
Humulene monoxide	HMDB
Humulene oxide	HMDB
Humulene oxide I	HMDB
(1R,4E,7E,11R)-1,5,9,9-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene	PhytoBank
Humulene epoxide I	PhytoBank
Humulen oxide	PhytoBank
alpha-Humulene epoxide I	PhytoBank
α-Humulene epoxide I	PhytoBank
α-Humulene oxide	PhytoBank

Chemical Formula

C₁₅H₂₄O

Average Mass

220.3505 Da

Monoisotopic Mass

220.18272 Da

IUPAC Name

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

Traditional Name

(4Z,7Z)-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-/m1/s1

InChI Key

RKQDKXOBRXTSFS-QZFXXANLSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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 sibirica	LOTUS Database	35616633
Aframomum melegueta	LOTUS Database	35616633
Aloysia triphylla	LOTUS Database	35616633
Antidesma laciniatum	LOTUS Database	35616633
Aster scaber	LOTUS Database	35616633
Bothriochloa bladhii	LOTUS Database	35616633
Brillantaisia lamium	LOTUS Database	35616633
Bupleurum acutifolium	LOTUS Database	35616633
Cannabis sativa	LOTUS Database	35616633
Cleonia lusitanica	LOTUS Database	35616633
Eupatorium capillifolium	LOTUS Database	35616633
Humulus lupulus	LOTUS Database	35616633
Juniperus chinensis	LOTUS Database	35616633
Juniperus communis	LOTUS Database	35616633
Laggera alata	LOTUS Database	35616633
Nepeta cataria	LOTUS Database	35616633
Nepeta glomerulosa	LOTUS Database	35616633
Pelargonium quercifolium	LOTUS Database	35616633
Piper gaudichaudianum	LOTUS Database	35616633
Stachys recta	LOTUS Database	35616633
Zingiber ottensii	LOTUS Database	35616633

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	26.96 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

HMDB0038209

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017451

KNApSAcK ID

C00012443

Chemspider ID

11455314

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22559443

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene (NP0307604)

MOL for NP0307604 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene)

3D MOL for NP0307604 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene)

3D SDF for NP0307604 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene)

3D-SDF for NP0307604 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene)

PDB for NP0307604 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene)

3D PDB for NP0307604 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene)

SMILES for NP0307604 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene)

INCHI for NP0307604 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene)

Structure for NP0307604 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene)

3D Structure for NP0307604 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene)