Damascenone

Details

• Internal ID: e4889d55-cf64-4bbb-9e56-3abeaeefdcd4
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Alpha,beta-unsaturated ketones > Enones
• IUPAC Name: (E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
• SMILES (Canonical): CC=CC(=O)C1=C(C=CCC1(C)C)C
• SMILES (Isomeric): C/C=C/C(=O)C1=C(C=CCC1(C)C)C
• InChI: 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
• Popularity: 486 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₈O
• Molecular Weight: 190.28 g/mol
• Exact Mass: 190.135765193 g/mol
• Topological Polar Surface Area (TPSA): 17.10 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.43
• H-Bond Acceptor: 1
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• beta-Damascenone
• 23696-85-7
• 23726-93-4
• trans-beta-Damascenone
• trans-damascenone
• .beta.-Damascenone
• 1-(2,6,6-Trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
• 2-BUTEN-1-ONE, 1-(2,6,6-TRIMETHYL-1,3-CYCLOHEXADIEN-1-YL)-
• (E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
• FEMA No. 3420
• (E)-beta-damascenone
• Damascenone (natural)
• (E)-.beta.-Damascenone
• UNII-U66V25TBO0
• U66V25TBO0
• (2E)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one
• (E)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one
• 2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-, (2E)-
• EINECS 245-833-2
• EINECS 245-844-2
• 4-(2,6,6-Trimethylcyclohexa-1,3-dienyl)but-2-en-4-one
• 1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one
• 2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-, (E)-
• 2,6,6-Trimethyl-1-trans-crotonoyl-1,3-cyclohexadiene
• 1-[2,6,6-Trimethyl-1,3-cyclohexadien-1-yl]-2E-buten-1-one
• (2E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
• 2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-, (E)
• DTXSID6041397
• fermentone
• Damascenone, trans-
• damascenone (e-beta)
• beta-(E)-damascenone
• 2,6,6-Trimethyl-1-crotonyl-1,3-cyclohexadiene
• ?-Damascenone, 90%
• trans-.beta.-Damascenone
• .beta.-(E)-Damascenone
• DAMASCENONE,.BETA.-
• SCHEMBL80947
• DISCONTINUED, UNSTABLE"
• trans-2,6,6-Trimethyl-1-crotonylcyclohexa-1,3-diene
• Damascenone, analytical standard
• TRANS-.BETA.-DAMASCENON
• CHEMBL3733030
• CHEBI:67251
• .BETA.-DAMASCENONE [MI]
• DTXCID80196511
• DTXSID90885242
• .BETA.-DAMASCENON, TRANS-
• 1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one; 1-(2,6,6-Trimethyl-1,3-cyclohexadienyl)-2-buten-1-one; 1-Crotonoyl-2,6,6-trimethyl-1,3-cyclohexadiene; 2,6,6-Trimethyl-1-(2-butenoyl)-1,3-cyclohexadiene
• HY-N2543
• Tox21_304001
• LMPR01070304
• MFCD00101024
• s6431
• AKOS015914961
• NCGC00357220-01
• AC-34815
• BS-16271
• CAS-23696-85-7
• CS-0022815
• 1-crotonoyl-2,6,6-trimethylcyclohexa-1,3-diene
• 2,6,6-trimethyl-1-crotonoyl-1,3-cyclohexadiene
• A816852
• Q416126
• (E)-beta-Damascenone 1000 microg/mL in Acetonitrile
• Damascenone, certified reference material, TraceCERT(R)
• 1-(2,6,6-trimethylcyclohexa-1,3-dienyl)-2-buten-1-one
• 4-(2,6,6-Trimethyl cyclohexa-1,3-dienyl)but-2-en-4-one
• (E)-1-(2,6,6-trimethylcyclohexa-1,3-dienyl)but-2-en-1-one
• 2-buten-1-ona, 1-(2,6,6-trimetil-1,3-ciclohexadien-1-il)-
• (e)-1-(2,6,6-trimethyl-1-cyclohexa-1,3-dienyl)but-2-en-1-one
• Damascenone, natural, 1.1-1.3 wt. % (190 proof ethanol), FG
• (2 E)-1-(2,6,6-trimethylcyclohexane-1,3-dien-1-yl)but-2-en-1-one
• 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one, trans-
• 2-buten-1-ona, 1-(2,6,6-trimetil-1,3-ciclohexadien-1-il)-, (2e)-
• 4-(2,6,6-TRIMETHYL CYCLOHEXA-1,3-DIENYL) BUT-2-EN-4-ONE [FHFI]
• 1 - (2,6,6 - trimethyl - 1,3 - cyclohexadien - 1 - yl) - 2 - buten - 1 - one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9939	99.39%
Caco-2	+	0.8789	87.89%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.4840	48.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8769	87.69%
OATP1B3 inhibitior	+	0.8943	89.43%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5231	52.31%
P-glycoprotein inhibitior	-	0.9833	98.33%
P-glycoprotein substrate	-	0.9632	96.32%
CYP3A4 substrate	-	0.5435	54.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8776	87.76%
CYP3A4 inhibition	-	0.8469	84.69%
CYP2C9 inhibition	-	0.7975	79.75%
CYP2C19 inhibition	-	0.7212	72.12%
CYP2D6 inhibition	-	0.9378	93.78%
CYP1A2 inhibition	-	0.7465	74.65%
CYP2C8 inhibition	-	0.9411	94.11%
CYP inhibitory promiscuity	+	0.5121	51.21%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5517	55.17%
Carcinogenicity (trinary)	Non-required	0.4687	46.87%
Eye corrosion	-	0.6377	63.77%
Eye irritation	+	0.7271	72.71%
Skin irritation	+	0.8176	81.76%
Skin corrosion	-	0.9478	94.78%
Ames mutagenesis	-	0.7454	74.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6593	65.93%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	+	0.5229	52.29%
skin sensitisation	+	0.9615	96.15%
Respiratory toxicity	-	0.8778	87.78%
Reproductive toxicity	-	0.6444	64.44%
Mitochondrial toxicity	-	0.9875	98.75%
Nephrotoxicity	+	0.5318	53.18%
Acute Oral Toxicity (c)	III	0.7885	78.85%
Estrogen receptor binding	-	0.9582	95.82%
Androgen receptor binding	-	0.7817	78.17%
Thyroid receptor binding	-	0.8097	80.97%
Glucocorticoid receptor binding	-	0.9342	93.42%
Aromatase binding	-	0.8690	86.90%
PPAR gamma	-	0.9026	90.26%
Honey bee toxicity	-	0.9608	96.08%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9483	94.83%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.89%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.08%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.73%	96.09%
CHEMBL4208	P20618	Proteasome component C5	86.82%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.10%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.23%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.92%	89.00%

Plants that contains it

• Acacia adunca
• Achillea grandifolia
• Actaea cimicifuga
• Actaea dahurica
• Actaea simplex
• Adiantum philippense
• Agathosma betulina
• Akebia quinata
• Akebia trifoliata
• Aldama incana
• Annona cornifolia
• Artemisia judaica
• Artemisia pedemontana subsp. assoana
• Aspalathus linearis
• Astragalus sempervirens
• Baccharis dracunculifolia
• Basella alba
• Bellis perennis
• Calostephane divaricata
• Caragana aurantiaca
• Cedronella canariensis
• Centaurea armena
• Chaenomeles sinensis
• Chamaemelum nobile
• Dumortiera hirsuta
• Echeveria secunda
• Eucalyptus melliodora
• Gnetum latifolium
• Goniothalamus malayanus
• Hamamelis virginiana
• Hedysarum inundatum
• Helichrysum ambiguum
• Humulus lupulus
• Hypericum laricifolium
• Ipomoea digitata
• Ipomoea pes-caprae
• Ixora chinensis
• Lepisorus ussuriensis
• Lysimachia mauritiana
• Malus domestica
• Marrubium anisodon
• Mentha arvensis
• Mentha canadensis
• Mutisia friesiana
• Myristica fragrans
• Naucleopsis ternstroemiiflora
• Ocimum basilicum
• Ocotea pittieri
• Pastinaca sativa
• Peltostigma guatemalense
• Polygala senega
• Premna odorata
• Rauvolfia vomitoria
• Rhodanthe chlorocephala subsp. rosea
• Rosa gallica
• Rumex maritimus
• Salvia sclarea
• Salvia syriaca
• Scutellaria amoena
• Senna alexandrina
• Sideritis amasiaca
• Sideritis dichotoma
• Sideritis hispida
• Solanum laxum
• Swertia franchetiana
• Swertia japonica
• Tordylium apulum
• Uncaria macrophylla
• Vaccinium oxycoccos
• Vitis labrusca
• Vitis vinifera
• Wikstroemia retusa
• Zanthoxylum tetraspermum

Cross-Links

• PubChem: 5366074
• NPASS: NPC37644
• LOTUS: LTS0111465
• wikiData: Q416126