NP-MRD: Showing NP-Card for Humulene epoxide (NP0333855)

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Record Information

Version

2.0

Created at

2024-09-09 20:57:52 UTC

Updated at

2024-09-09 20:57:52 UTC

NP-MRD ID

NP0333855

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Humulene epoxide

Description

Humulene epoxide is a member of the class of compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms). Humulene epoxide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Humulene epoxide can be found in cloves and sweet basil, which makes humulene epoxide a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05242323302D          

 19 20  0  0  0  0            999 V2000
    6.7867   -0.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4500    2.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6731    1.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5980   -0.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8575    1.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6519   -0.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6297    0.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3727   -0.8943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2959    1.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7639   -0.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2492    0.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9771   -0.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4450    0.7367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4918    1.7094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024   -0.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6408    0.5526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6575    1.4908    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4718   -1.7133    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5385    2.6821    0.0000 H   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 17  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 18  1  0  0  0  0
  8 12  2  0  0  0  0
  9 19  1  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>
NP0333855

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C1=C([H])\C(C)(C)CC2OC2(C)CC\C([H])=C(C)/C1

> <INCHI_IDENTIFIER>
InChI=1/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-

> <INCHI_KEY>
RKQDKXOBRXTSFS-QZFXXANLNA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.356

> <EXACT_MASS>
220.182715393

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
27.00892236418824

> <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

> <JCHEM_LOGP>
3.9774975963333326

> <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

> <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                                 24-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-MAY-23         0                                  
HETATM    1  C   UNK     0      12.668  -0.918   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.307   4.729   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.856   3.381   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.850  -1.145   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.934   2.407   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.684  -0.920   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.509   0.776   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.029  -1.669   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.886   3.535   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.026  -1.225   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.932   1.719   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.157  -0.621   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.431   1.375   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.385   3.191   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.978  -0.097   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.929   1.031   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0      12.427   2.783   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0      10.214  -3.198   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0      10.339   5.007   0.000  0.00  0.00           H+0
CONECT    1   12                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5   17    7    9                                                  
CONECT    6    8   10                                                       
CONECT    7    5   12                                                       
CONECT    8    6   18   12                                                  
CONECT    9    5   19   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                                                       
CONECT   17    5                                                            
CONECT   18    8                                                            
CONECT   19    9                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O

Average Mass

220.3560 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

[H]\C1=C([H])\C(C)(C)CC2OC2(C)CC\C([H])=C(C)/C1

InChI Identifier

InChI=1/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-

InChI Key

RKQDKXOBRXTSFS-QZFXXANLNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as epoxides. These 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	3.98	ChemAxon
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	27.01 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

Fu J, Gao Y, Xing X: Preliminary Study on Phytochemical Constituents and Biological Activities of Essential Oil from Myriactis nepalensis Less. Molecules. 2022 Jul 20;27(14). pii: molecules27144631. doi: 10.3390/molecules27144631. [PubMed:35889501 ]
Raghuvanshi N, Gupta B, Joshi V, Bisht SS, Manikpuri M, Shukla K, Khokhar D, Singh N, Ghosh KK: Influence of essential oil composition on antioxidant and antibacterial activities of three cultivars of Cymbopogon flexuosus: in vitro and in silico study. Chem Biodivers. 2024 Sep 7:e202400966. doi: 10.1002/cbdv.202400966. [PubMed:39243337 ]
Saxena P, Sharma D, Gautam P, Niranjan A, Rastogi S: HPLC-DAD quantification of mangiferin, antioxidant potential and essential oil composition of the leaves of five varieties of Mangifera indica L. of North India. Nat Prod Res. 2024 Jun 4:1-12. doi: 10.1080/14786419.2024.2361476. [PubMed:38832668 ]
Cvetanovic Kljakic A, Ocvirk M, Rutnik K, Kosir IJ, Pavlic B, Maskovic P, Maskovic J, Teslic N, Stupar A, Uba AI, Zengin G: Exploring the composition and potential uses of four hops varieties through different extraction techniques. Food Chem. 2024 Jul 30;447:138910. doi: 10.1016/j.foodchem.2024.138910. Epub 2024 Mar 2. [PubMed:38479143 ]
Kwasnica A, Pachura N, Carbonell-Barrachina AA, Issa-Issa H, Szumny D, Figiel A, Masztalerz K, Klemens M, Szumny A: Effect of Drying Methods on Chemical and Sensory Properties of Cannabis sativa Leaves. Molecules. 2023 Dec 14;28(24):8089. doi: 10.3390/molecules28248089. [PubMed:38138578 ]
Ashmawy NS, Gad HA, El-Nashar HAS: Comparative Study of Essential Oils from Different Organs of Syzygium cumini (Pamposia) Based on GC/MS Chemical Profiling and In Vitro Antiaging Activity. Molecules. 2023 Nov 30;28(23):7861. doi: 10.3390/molecules28237861. [PubMed:38067590 ]
Hussein BA, Karimi I, Yousofvand N: Chemo- and bio-informatics insight into anti-cholinesterase potentials of berries and leaves of Myrtus communis L., Myrtaceae: an in vitro/in silico study. BMC Complement Med Ther. 2023 Nov 21;23(1):421. doi: 10.1186/s12906-023-04241-z. [PubMed:37990185 ]
Maiolini TCS, Nicacio KJ, Rosa W, Miranda DO, Santos MFC, Bueno PCP, Lago JHG, Sartorelli P, Dias DF, Chagas de Paula DA, Soares MG: Potential anti-inflammatory biomarkers from Myrtaceae essential oils revealed by untargeted metabolomics. Nat Prod Res. 2023 Nov 24:1-8. doi: 10.1080/14786419.2023.2283758. [PubMed:38006221 ]
Mohanty S, Ray A, Sahoo C, Sahoo A, Jena S, Panda PC, Nayak S: Volatile profiling coupled with multivariate analysis, antiproliferative and anti-inflammatory activities of rhizome essential oil of four Hedychium species from India. J Ethnopharmacol. 2023 Dec 5;317:116835. doi: 10.1016/j.jep.2023.116835. Epub 2023 Jun 22. [PubMed:37355085 ]
Ghorbani Ranjbary A, Mehrzad J, Talebkhan Garoussi M, Zohdi J: Long Term Oral Administration of Oregano Essence Effectively Relieves Polycystic Ovarian Rats through Endocrine and Inflammatory Balance. Evid Based Complement Alternat Med. 2022 Sep 16;2022:5303583. doi: 10.1155/2022/5303583. eCollection 2022. [PubMed:36159582 ]
Cascaes MM, De Moraes AAB, Cruz JN, Franco CJP, E Silva RC, Nascimento LDD, Ferreira OO, Anjos TOD, de Oliveira MS, Guilhon GMSP, Andrade EHA: Phytochemical Profile, Antioxidant Potential and Toxicity Evaluation of the Essential Oils from Duguetia and Xylopia Species (Annonaceae) from the Brazilian Amazon. Antioxidants (Basel). 2022 Aug 30;11(9):1709. doi: 10.3390/antiox11091709. [PubMed:36139777 ]
Tusha K, Nespor J, Jelinek L, Vodickova H, Kincl T, Dostalek P: Effect of Czech Hop Varieties on Aroma of Dry-Hopped Lager Beer. Foods. 2022 Aug 20;11(16):2520. doi: 10.3390/foods11162520. [PubMed:36010520 ]

Showing NP-Card for Humulene epoxide (NP0333855)

MOL for NP0333855 (Humulene epoxide)

3D MOL for NP0333855 (Humulene epoxide)

3D SDF for NP0333855 (Humulene epoxide)

3D-SDF for NP0333855 (Humulene epoxide)

PDB for NP0333855 (Humulene epoxide)

3D PDB for NP0333855 (Humulene epoxide)

SMILES for NP0333855 (Humulene epoxide)

INCHI for NP0333855 (Humulene epoxide)

Structure for NP0333855 (Humulene epoxide)

3D Structure for NP0333855 (Humulene epoxide)