NP-MRD: Showing NP-Card for alpha-Damascone (NP0085737)

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Record Information

Version

2.0

Created at

2022-04-29 06:13:00 UTC

Updated at

2022-04-29 06:13:00 UTC

NP-MRD ID

NP0085737

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-Damascone

Description

1-(2,6,6-Trimethylcyclohex-2-en-1-yl)but-2-enone, also known as alpha-damascone or TMCHB, belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. An enone with a trimethylcyclohexenyl substituent at C-1. alpha-Damascone is found in Rhynchosia minima . alpha-Damascone was first documented in 1991 (PMID: 16348390). 1-(2,6,6-Trimethylcyclohex-2-en-1-yl)but-2-enone is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 12581281) (PMID: 15575784) (PMID: 18031884) (PMID: 18031900).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
    4.4403   -0.0610   -0.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9329   -0.1044   -0.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2866   -0.3016    0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511   -0.3510    0.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4263   -0.6129    2.1050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1479   -0.1371   -0.1410 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3932    1.2918   -0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6811    2.1994   -0.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5995    1.8530   -0.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7866    1.0805    0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2770   -0.1050    1.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3905   -0.9336    0.1702 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1484   -1.2631   -1.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9932   -2.2185    0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7603   -1.0585   -0.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7731    0.7658   -1.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8568    0.1532    0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4199    0.0116   -1.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9168   -0.4337    1.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3265   -0.5183   -1.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3083    3.2442   -1.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1629    1.9083   -1.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4568    2.3110   -0.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7018    2.9103   -0.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3324    0.7545   -0.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4450    1.7226    0.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0800   -0.7110    1.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6910    0.3224    1.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2164   -1.4415   -0.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0356   -0.4278   -1.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6858   -2.1571   -1.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0849   -2.3917    0.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2381   -2.2232    1.9334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5222   -3.0777    0.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 12  6  1  0
  2 18  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 19  1  0
  6 20  1  6
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
M  END


  Mrv1572004251600562D          

 16 16  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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    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
   -0.0000    0.0000    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
    0.7145   -0.4125    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
    1.4289   -0.0000    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
    1.4289    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
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8469    2.8324    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  6  1  0  0  0  0
 10  2  1  0  0  0  0
 10  8  2  0  0  0  0
 11  7  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  2  0  0  0  0
 15  5  1  0  0  0  0
 16  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085737

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(C)=C(\[H])C(=O)C1C(C)=CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5,7-8,12H,6,9H2,1-4H3/b7-5+

> <INCHI_KEY>
CRIGTVCBMUKRSL-FNORWQNLSA-N

> <FORMULA>
C13H20O

> <MOLECULAR_WEIGHT>
192.302

> <EXACT_MASS>
192.151415264

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
23.132179916351593

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one

> <ALOGPS_LOGP>
3.96

> <JCHEM_LOGP>
3.8312158590000003

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.98877009448897

> <JCHEM_PKA_STRONGEST_BASIC>
-4.720307204391163

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
62.14050000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-damascone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 25-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-16         0                                  
HETATM    1  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   15  H   UNK     0       6.668   3.850   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       3.448   5.287   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2   10                                                            
CONECT    3   13                                                            
CONECT    4   13                                                            
CONECT    5    1    7   15                                                  
CONECT    6    8    9                                                       
CONECT    7    5   11   16                                                  
CONECT    8    6   10                                                       
CONECT    9    6   13                                                       
CONECT   10    2    8   12                                                  
CONECT   11    7   12   14                                                  
CONECT   12   10   11   13                                                  
CONECT   13    3    4    9   12                                             
CONECT   14   11                                                            
CONECT   15    5                                                            
CONECT   16    7                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-2-butenone	ChEBI
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-trans-2-buten-1-one	ChEBI
4-(2,6,6-Trimethyl-2-cyclohexenyl)-2-buten-4-one	ChEBI
alpha-Damascone	ChEBI
TMCHB	ChEBI
a-Damascone	Generator
Α-damascone	Generator

Chemical Formula

C₁₃H₂₀O

Average Mass

192.3020 Da

Monoisotopic Mass

192.15142 Da

IUPAC Name

(2E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one

Traditional Name

α-damascone

CAS Registry Number

Not Available

SMILES

[H]\C(C)=C(\[H])C(=O)C1C(C)=CCCC1(C)C

InChI Identifier

InChI=1S/C13H20O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5,7-8,12H,6,9H2,1-4H3/b7-5+

InChI Key

CRIGTVCBMUKRSL-FNORWQNLSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Rhynchosia minima	Plant	KNApSAcK

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'.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enones

Alternative Parents

Substituents

Enone
Acryloyl-group
Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

enone (CHEBI:53220 )

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	3.96	ALOGPS
logP	3.83	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	18.99	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.14 m³·mol⁻¹	ChemAxon
Polarizability	23.13 Å³	ChemAxon
Number of Rings	1	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

5366077

PDB ID

Not Available

ChEBI ID

53220

Good Scents ID

Not Available

References

General References

Schoch E, Benda I, Schreier P: Bioconversion of alpha-Damascone by Botrytis cinerea. Appl Environ Microbiol. 1991 Jan;57(1):15-8. doi: 10.1128/aem.57.1.15-18.1991. [PubMed:16348390 ]
Gimenez-Arnau A, Gimenez-Arnau E, Serra-Baldrich E, Lepoittevin JP, Camarasa JG: Principles and methodology for identification of fragrance allergens in consumer products. Contact Dermatitis. 2002 Dec;47(6):345-52. doi: 10.1034/j.1600-0536.2002.470606.x. [PubMed:12581281 ]
Bovolenta M, Castronovo F, Vadala A, Zanoni G, Vidari G: A simple and efficient highly enantioselective synthesis of alpha-ionone and alpha-damascone. J Org Chem. 2004 Dec 10;69(25):8959-62. doi: 10.1021/jo049012j. [PubMed:15575784 ]
Lapczynski A, Lalko J, McGinty D, Bhatia S, Letizia CS, Api AM: Fragrance material review on cis-alpha-damascone. Food Chem Toxicol. 2007;45 Suppl 1:S188-91. doi: 10.1016/j.fct.2007.09.054. Epub 2007 Sep 14. [PubMed:18031884 ]
Lapczynski A, Lalko J, McGinty D, Bhatia S, Letizia CS, Api AM: Fragrance material review on alpha-damascone. Food Chem Toxicol. 2007;45 Suppl 1:S179-87. doi: 10.1016/j.fct.2007.09.044. Epub 2007 Sep 14. [PubMed:18031900 ]

Showing NP-Card for alpha-Damascone (NP0085737)

MOL for NP0085737 (alpha-Damascone)

3D MOL for NP0085737 (alpha-Damascone)

3D SDF for NP0085737 (alpha-Damascone)

3D-SDF for NP0085737 (alpha-Damascone)

PDB for NP0085737 (alpha-Damascone)

3D PDB for NP0085737 (alpha-Damascone)

SMILES for NP0085737 (alpha-Damascone)

INCHI for NP0085737 (alpha-Damascone)

Structure for NP0085737 (alpha-Damascone)

3D Structure for NP0085737 (alpha-Damascone)