Showing NP-Card for 3,5,8-Megastigmatrien-7-one (NP0048537)

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Record Information
Version2.0
Created at2022-03-17 20:58:01 UTC
Updated at2022-03-17 20:58:01 UTC
NP-MRD IDNP0048537
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,5,8-Megastigmatrien-7-one
DescriptionBeta-Damascenone, also known as damascenone, belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. Thus, beta-damascenone is considered to be an isoprenoid lipid molecule. Damascenones are a series of closely related chemical compounds that are components of a variety of essential oils. Beta-Damascenone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Beta-Damascenone is a major contributor to the aroma of roses, despite its very low concentration, and is an important fragrance chemical used in perfumery. Beta-Damascenone is a sweet, apple, and apple.Rose tasting compound. Outside of the human body, beta-Damascenone has been detected, but not quantified in, several different foods, such as herbs and spices, cherry tomato, green vegetables, blackberries, and common grapes. This could make beta-damascenone a potential biomarker for the consumption of these foods. 3,5,8-Megastigmatrien-7-one is found in Achillea grandifolia, Agathosma betulina, Artemisia judaica, Aspalathus linearis, Baccharis dracunculifolia, Basella alba, Bellis perennis, Cedronella canariensis, Centaurea armena, Centaurea sessilis, Cirsium palustre, Coffea arabica , Coffea canephora , Dittrichia graveolens , Hamamelis virginiana, Ipomoea pes-caprae, Iris germanica, Malus domestica, Micromeria cristata, Mutisia friesiana, Polygala senega, Rosa damascena , Rosa gallica, Salvia sclarea, Salvia syriaca, Swertia japonica, Tipuana tipu, Tordylium apulum, Vitis vinifera and Vitis labruscana. 3,5,8-Megastigmatrien-7-one was first documented in 2011 (PMID: 21831389). The damascenones belong to a family of chemicals known as rose ketones, which also includes damascones and ionones (PMID: 21417409) (PMID: 21254776) (PMID: 21866982) (PMID: 22324474).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0048537 (3,5,8-Megastigmatrien-7-one)

damascenone
  Mrv1652303102016532D          

 14 14  0  0  0  0            999 V2000
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
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3D MOL for NP0048537 (3,5,8-Megastigmatrien-7-one)

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3D SDF for NP0048537 (3,5,8-Megastigmatrien-7-one)
damascenone
  Mrv1652303102016532D          

 14 14  0  0  0  0            999 V2000
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048537

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\C(=O)C1=C(C)C=CCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+

> <INCHI_KEY>
POIARNZEYGURDG-FNORWQNLSA-N

> <FORMULA>
C13H18O

> <MOLECULAR_WEIGHT>
190.286

> <EXACT_MASS>
190.1357652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
22.606738542802788

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one

> <ALOGPS_LOGP>
4.02

> <JCHEM_LOGP>
3.6816035596666667

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.246642868703947

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
63.01640000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
damascenone

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048537 (3,5,8-Megastigmatrien-7-one)
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PDB for NP0048537 (3,5,8-Megastigmatrien-7-one)
HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: damascenone                                       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.611   3.670   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    6   13   14                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

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3D PDB for NP0048537 (3,5,8-Megastigmatrien-7-one)
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SMILES for NP0048537 (3,5,8-Megastigmatrien-7-one)
C\C=C\C(=O)C1=C(C)C=CCC1(C)C
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INCHI for NP0048537 (3,5,8-Megastigmatrien-7-one)
InChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+
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Synonyms
ValueSource
(2E)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-oneChEBI
(e)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-oneChEBI
(e)-beta-DamascenoneChEBI
beta-(e)-DamascenoneChEBI
DamascenoneChEBI
trans-beta-DamascenoneChEBI
trans-DamascenoneChEBI
(e)-b-DamascenoneGenerator
(e)-Β-damascenoneGenerator
b-(e)-DamascenoneGenerator
Β-(e)-damascenoneGenerator
trans-b-DamascenoneGenerator
trans-Β-damascenoneGenerator
b-DamascenoneGenerator
Β-damascenoneGenerator
1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-oneHMDB
Chemical FormulaC13H18O
Average Mass190.2860 Da
Monoisotopic Mass190.13577 Da
IUPAC Name(2E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
Traditional Namedamascenone
CAS Registry Number23726-93-4
SMILES
C\C=C\C(=O)C1=C(C)C=CCC1(C)C
InChI Identifier
InChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+
InChI KeyPOIARNZEYGURDG-FNORWQNLSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Chemical Taxonomy
Description Belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentEnones  
Alternative Parents
Substituents
  • Enone
    • 

  • Acryloyl-group
    • 

  • Ketone
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.02ALOGPS
logP3.68ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.02 m³·mol⁻¹ChemAxon
Polarizability22.61 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013804  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015480  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDamascenone  
METLIN IDNot Available
PubChem Compound5366074  
PDB IDNot Available
ChEBI ID67251  
Good Scents IDNot Available
References
General References
  1. Jelen HH, Majcher M, Dziadas M, Zawirska-Wojtasiak R, Czaczyk K, Wasowicz E: Volatile compounds responsible for aroma of Jutrzenka liquer wine. J Chromatogr A. 2011 Oct 21;1218(42):7566-73. doi: 10.1016/j.chroma.2011.07.023.  Epub 2011 Jul 20. [PubMed:21831389  ] 
  2. Pino JA, Queris O: Characterization of odor-active compounds in guava wine. J Agric Food Chem. 2011 May 11;59(9):4885-90. doi: 10.1021/jf2011112. Epub 2011 Mar 30. [PubMed:21417409  ] 
  3. Lloyd ND, Capone DL, Ugliano M, Taylor DK, Skouroumounis GK, Sefton MA, Elsey GM: Formation of Damascenone under both commercial and model fermentation conditions. J Agric Food Chem. 2011 Feb 23;59(4):1338-43. doi: 10.1021/jf103741n. Epub 2011 Jan 21. [PubMed:21254776  ] 
  4. Sefton MA, Skouroumounis GK, Elsey GM, Taylor DK: Occurrence, sensory impact, formation, and fate of damascenone in grapes, wines, and other foods and beverages. J Agric Food Chem. 2011 Sep 28;59(18):9717-46. doi: 10.1021/jf201450q. Epub 2011  Aug 26. [PubMed:21866982  ] 
  5. Bowen AJ, Reynolds AG: Odor potency of aroma compounds in Riesling and Vidal blanc table wines and icewines by gas chromatography-olfactometry-mass spectrometry. J Agric Food Chem. 2012 Mar 21;60(11):2874-83. doi: 10.1021/jf203314j. Epub 2012  Mar 9. [PubMed:22324474  ]