NP-MRD: Showing NP-Card for (4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one (NP0294714)

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Record Information

Version

2.0

Created at

2022-09-10 03:23:00 UTC

Updated at

2022-09-10 03:23:00 UTC

NP-MRD ID

NP0294714

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one

Description

Zerumbone epoxide belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. (4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one is found in Zingiber ottensii and Zingiber zerumbet. (4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one was first documented in 2014 (PMID: 25126594). Based on a literature review a small amount of articles have been published on Zerumbone epoxide (PMID: 34254812) (PMID: 32302147) (PMID: 32168546) (PMID: 25200721).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.5580    3.5170   -1.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0358    2.4071   -0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971    1.4438   -0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7261    0.2432    0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7904   -1.0235   -0.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0236   -2.1811   -0.0277 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8916   -3.4819   -0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0804   -2.3481   -1.0589 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3026   -2.3481    0.2868 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1660   -1.4445    1.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6730   -0.1739    0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2477   -0.3040    0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5094    0.0899   -0.9546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5360    0.9352    1.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9205    2.0786    1.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2310    2.5589    0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9351    3.4395   -0.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.1838   -2.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9515    4.4297   -1.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5817    3.7448   -1.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8509    1.5179   -1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0551    0.3308    1.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7316    0.2306    0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9010   -1.2598   -0.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6325   -0.6741   -1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5896   -3.3901    0.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2668   -4.3643    0.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3735   -3.4646   -1.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5893   -3.4370    0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5860   -1.1749    1.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0274   -1.9919    1.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4444   -0.5999    1.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6793    0.6785    0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5514   -1.1140   -0.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1381    0.9993   -1.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0611   -0.7271   -1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5628    0.2426   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0191    0.7090    2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0252    2.7229    2.2069 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  1
  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 17  2  0
 16  2  1  0
  9  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  9 29  1  1
 10 30  1  0
 10 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
M  END


  Mrv1652309102205232D          

 17 18  0  0  0  0            999 V2000
    3.6934    0.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8684    0.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4559   -0.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6309   -0.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1460    0.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3614    0.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0258   -0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531    0.7538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3614    1.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1460    1.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6309    2.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8642    2.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7859    2.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4559    2.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8684    1.4683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4559    0.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2809    0.7538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0294714

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C\CCC2(C)OC2CC(C)(C)\C=C/C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-11-6-5-8-15(4)13(17-15)10-14(2,3)9-7-12(11)16/h6-7,9,13H,5,8,10H2,1-4H3/b9-7-,11-6-

> <INCHI_KEY>
UXYYOHOTPOQJPD-BVYZMQRMSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.339

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.484611673578307

> <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-dien-6-one

> <JCHEM_LOGP>
3.6699593813333324

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.007930960006638

> <JCHEM_POLAR_SURFACE_AREA>
29.6

> <JCHEM_REFRACTIVITY>
70.9789

> <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-dien-6-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       6.894   0.074   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.354   0.074   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.584  -1.260   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.044  -1.260   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.139   0.161   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.675   0.637   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.048  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.659   1.407   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.675   2.177   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.139   2.653   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.044   4.075   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.613   4.643   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.334   5.587   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.584   4.075   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.354   2.741   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.584   1.407   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.124   1.407   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    6   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    2   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₂

Average Mass

234.3390 Da

Monoisotopic Mass

234.16198 Da

IUPAC Name

(4Z,7Z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one

Traditional Name

(4Z,7Z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one

CAS Registry Number

Not Available

SMILES

C\C1=C\CCC2(C)OC2CC(C)(C)\C=C/C1=O

InChI Identifier

InChI=1S/C15H22O2/c1-11-6-5-8-15(4)13(17-15)10-14(2,3)9-7-12(11)16/h6-7,9,13H,5,8,10H2,1-4H3/b9-7-,11-6-

InChI Key

UXYYOHOTPOQJPD-BVYZMQRMSA-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
Zingiber ottensii	LOTUS Database	35616633
Zingiber zerumbet	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclic ketones

Alternative Parents

Substituents

Cyclic ketone
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxide
Hydrocarbon derivative
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	3.67	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.98 m³·mol⁻¹	ChemAxon
Polarizability	26.48 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

C00031442

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

90470391

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Biji M, Radhakrishnan KV, Lankalapalli RS: Tandem Photoisomerization and Transannular Cyclizations of Zerumbone Epoxide: A Model for Diversity-Oriented Synthesis Using Abundant Natural Products. Org Lett. 2021 Aug 6;23(15):5871-5875. doi: 10.1021/acs.orglett.1c01997. Epub 2021 Jul 13. [PubMed:34254812 ]
Tan YP, Savchenko AI, Agnew-Francis KA, Boyle GM, Bernhardt PV, Fraser JA, Williams CM: Kalparinol, a Salvialane (Isodaucane) Sesquiterpenoid Derived from Native Australian Dysphania Species That Suggests a Putative Biogenetic Link to Zerumbone. J Nat Prod. 2020 May 22;83(5):1473-1479. doi: 10.1021/acs.jnatprod.9b01039. Epub 2020 Apr 17. [PubMed:32302147 ]
Al-Amin M, Eltayeb NM, Hossain CF, Khairuddean M, Fazalul Rahiman SS, Salhimi SM: Inhibitory Activity of Extract, Fractions, and Compounds from Zingiber montanum Rhizomes on the Migration of Breast Cancer Cells. Planta Med. 2020 Apr;86(6):387-394. doi: 10.1055/a-1129-7026. Epub 2020 Mar 13. [PubMed:32168546 ]
Ajish KR, Antu KA, Riya MP, Preetharani MR, Raghu KG, Dhanya BP, Radhakrishnan KV: Studies on alpha-glucosidase, aldose reductase and glycation inhibitory properties of sesquiterpenes and flavonoids of Zingiber zerumbet Smith. Nat Prod Res. 2015;29(10):947-52. doi: 10.1080/14786419.2014.956741. Epub 2014 Sep 9. [PubMed:25200721 ]
Ahmed Hamdi OA, Syed Abdul Rahman SN, Awang K, Abdul Wahab N, Looi CY, Thomas NF, Abd Malek SN: Cytotoxic constituents from the rhizomes of Curcuma zedoaria. ScientificWorldJournal. 2014;2014:321943. doi: 10.1155/2014/321943. Epub 2014 Jul 13. [PubMed:25126594 ]
LOTUS database [Link]

Showing NP-Card for (4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one (NP0294714)

MOL for NP0294714 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one)

3D MOL for NP0294714 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one)

3D SDF for NP0294714 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one)

3D-SDF for NP0294714 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one)

PDB for NP0294714 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one)

3D PDB for NP0294714 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one)

SMILES for NP0294714 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one)

INCHI for NP0294714 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one)

Structure for NP0294714 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one)

3D Structure for NP0294714 ((4z,7z)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one)