NP-MRD: Showing NP-Card for (6s)-2,2,6-trimethyl-6-[(1s)-4-methylcyclohex-3-en-1-yl]oxan-3-one (NP0281245)

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Record Information

Version

2.0

Created at

2022-09-09 07:28:11 UTC

Updated at

2022-09-09 07:28:11 UTC

NP-MRD ID

NP0281245

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6s)-2,2,6-trimethyl-6-[(1s)-4-methylcyclohex-3-en-1-yl]oxan-3-one

Description

Bisabolone oxide A belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. (6s)-2,2,6-trimethyl-6-[(1s)-4-methylcyclohex-3-en-1-yl]oxan-3-one is found in Matricaria chamomilla. (6s)-2,2,6-trimethyl-6-[(1s)-4-methylcyclohex-3-en-1-yl]oxan-3-one was first documented in 2015 (PMID: 26434140). Based on a literature review a small amount of articles have been published on Bisabolone oxide A (PMID: 35454969) (PMID: 34050388) (PMID: 31177847) (PMID: 30987223).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
    4.9166    0.7136   -0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5385    0.3101   -0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0061   -0.7252   -0.9052 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6340   -1.2003   -0.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6969   -0.0715   -0.3956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5702   -0.5359    0.3393 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1554   -1.1487    1.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2719   -1.5999   -0.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0542   -1.0196   -1.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9476    0.0275   -1.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9112    0.3482   -1.6830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6057    0.5911    0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4740   -0.0002    1.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0309    2.0721    0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2835    0.5858    0.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2638    1.1191    0.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6802    1.0075    0.7189 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4362    1.1522    0.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9346    1.3530   -1.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4902   -0.2155   -0.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6119   -1.2471   -1.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2965   -1.7287   -1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7040   -1.9155    0.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3122    0.2774   -1.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2498   -2.2476    1.6758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7626   -0.7622    2.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9003   -0.9190    1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259   -2.2993   -0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9037   -2.2544    0.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6292   -1.8050   -2.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3440   -0.5674   -2.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5229    0.7556    2.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0629   -0.9104    1.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4550   -0.2221    0.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8492    2.4543    1.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1171    2.0615    0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4722    2.6267   -0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823    2.0609   -0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6539    1.3567    1.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8291    0.4923    1.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1120    2.0300    0.8358 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 16  1  0
 16 17  1  0
  5  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 17  2  1  0
 15  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  6
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
M  END


  Mrv1652309092209282D          

 17 18  0  0  1  0            999 V2000
   -0.3461   -0.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461   -0.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3683   -1.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3683   -2.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461   -2.5015    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3461   -3.3265    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1586   -3.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663   -3.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966   -3.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448   -5.2224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -4.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842   -5.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125   -5.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283   -4.1017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0606   -2.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0606   -1.2640    0.0000 C   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  1  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
  6 15  1  6  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281245

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC[C@H](CC1)[C@]1(C)CCC(=O)C(C)(C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-11-5-7-12(8-6-11)15(4)10-9-13(16)14(2,3)17-15/h5,12H,6-10H2,1-4H3/t12-,15+/m1/s1

> <INCHI_KEY>
MJWZYBQLHJQQJJ-DOMZBBRYSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.355

> <EXACT_MASS>
236.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.104649379972216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6S)-2,2,6-trimethyl-6-[(1S)-4-methylcyclohex-3-en-1-yl]oxan-3-one

> <JCHEM_LOGP>
3.496757980000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.227815209072787

> <JCHEM_PKA_STRONGEST_BASIC>
-4.258332746957605

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
70.20270000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(6S)-2,2,6-trimethyl-6-[(1S)-4-methylcyclohex-3-en-1-yl]oxan-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.646  -0.049   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.646  -1.589   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.688  -2.359   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.688  -3.899   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.646  -4.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.646  -6.209   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.163  -5.942   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.870  -5.942   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.860  -7.122   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -8.569   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.324  -9.749   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.183  -8.836   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.344 -10.283   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.517  -9.606   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.173  -7.657   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.980  -3.899   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.980  -2.359   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7    8   15                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12    6                                                       
CONECT   16    5   17                                                       
CONECT   17   16    2                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₂

Average Mass

236.3550 Da

Monoisotopic Mass

236.17763 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1=CC[C@H](CC1)[C@]1(C)CCC(=O)C(C)(C)O1

InChI Identifier

InChI=1S/C15H24O2/c1-11-5-7-12(8-6-11)15(4)10-9-13(16)14(2,3)17-15/h5,12H,6-10H2,1-4H3/t12-,15+/m1/s1

InChI Key

MJWZYBQLHJQQJJ-DOMZBBRYSA-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
Matricaria chamomilla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

Oxane
Cyclic ketone
Ketone
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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

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

34998996

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91700388

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

El Mihyaoui A, Esteves da Silva JCG, Charfi S, Candela Castillo ME, Lamarti A, Arnao MB: Chamomile (Matricaria chamomilla L.): A Review of Ethnomedicinal Use, Phytochemistry and Pharmacological Uses. Life (Basel). 2022 Mar 25;12(4):479. doi: 10.3390/life12040479. [PubMed:35454969 ]
Slavik B, Roehrer S, Loos HM, Minceva M, Buettner A: Isolation of sesquiterpenoids from Matricaria chamomilla by means of solvent assisted flavor evaporation and centrifugal partition chromatography. Anal Bioanal Chem. 2021 Jul;413(17):4387-4396. doi: 10.1007/s00216-021-03400-w. Epub 2021 May 28. [PubMed:34050388 ]
Xu Q, Zhang L, Yu S, Xia G, Zhu J, Zang H: Chemical composition and biological activities of an essential oil from the aerial parts of Artemisia Gmelinii weber ex Stechm. Nat Prod Res. 2021 Jan;35(2):346-349. doi: 10.1080/14786419.2019.1627349. Epub 2019 Jun 7. [PubMed:31177847 ]
Piri E, Mahmoodi Sourestani M, Khaleghi E, Mottaghipisheh J, Zomborszki ZP, Hohmann J, Csupor D: Chemo-Diversity and Antiradical Potential of Twelve Matricaria chamomilla L. Populations from Iran: Proof of Ecological Effects. Molecules. 2019 Apr 3;24(7):1315. doi: 10.3390/molecules24071315. [PubMed:30987223 ]
Satyal P, Shrestha S, Setzer WN: Composition and Bioactivities of an (E)-beta-Farnesene Chemotype of Chamomile (Matricaria chamomilla) Essential Oil from Nepal. Nat Prod Commun. 2015 Aug;10(8):1453-7. [PubMed:26434140 ]
LOTUS database [Link]

Showing NP-Card for (6s)-2,2,6-trimethyl-6-[(1s)-4-methylcyclohex-3-en-1-yl]oxan-3-one (NP0281245)

MOL for NP0281245 ((6s)-2,2,6-trimethyl-6-[(1s)-4-methylcyclohex-3-en-1-yl]oxan-3-one)

3D MOL for NP0281245 ((6s)-2,2,6-trimethyl-6-[(1s)-4-methylcyclohex-3-en-1-yl]oxan-3-one)

3D SDF for NP0281245 ((6s)-2,2,6-trimethyl-6-[(1s)-4-methylcyclohex-3-en-1-yl]oxan-3-one)

3D-SDF for NP0281245 ((6s)-2,2,6-trimethyl-6-[(1s)-4-methylcyclohex-3-en-1-yl]oxan-3-one)

PDB for NP0281245 ((6s)-2,2,6-trimethyl-6-[(1s)-4-methylcyclohex-3-en-1-yl]oxan-3-one)

3D PDB for NP0281245 ((6s)-2,2,6-trimethyl-6-[(1s)-4-methylcyclohex-3-en-1-yl]oxan-3-one)

SMILES for NP0281245 ((6s)-2,2,6-trimethyl-6-[(1s)-4-methylcyclohex-3-en-1-yl]oxan-3-one)

INCHI for NP0281245 ((6s)-2,2,6-trimethyl-6-[(1s)-4-methylcyclohex-3-en-1-yl]oxan-3-one)

Structure for NP0281245 ((6s)-2,2,6-trimethyl-6-[(1s)-4-methylcyclohex-3-en-1-yl]oxan-3-one)

3D Structure for NP0281245 ((6s)-2,2,6-trimethyl-6-[(1s)-4-methylcyclohex-3-en-1-yl]oxan-3-one)