Fenchone

Details

• Internal ID: ade56f38-789a-4ca4-af63-f57778da4deb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Bicyclic monoterpenoids
• IUPAC Name: 1,3,3-trimethylbicyclo[2.2.1]heptan-2-one
• SMILES (Canonical): CC1(C2CCC(C2)(C1=O)C)C
• SMILES (Isomeric): CC1(C2CCC(C2)(C1=O)C)C
• InChI: InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3
• InChI Key: LHXDLQBQYFFVNW-UHFFFAOYSA-N
• Popularity: 174 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23 g/mol
• Exact Mass: 152.120115130 g/mol
• Topological Polar Surface Area (TPSA): 17.10 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.40
• H-Bond Acceptor: 1
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one
• 1195-79-5
• 214-804-6
• CAS-1195-79-5
• dl-fenchone
• EINECS 214-804-6
• Fenchone
• fenchone, (+-)-isomer
• Fenchon
• alpha-Fenchone
• 1,3,3-Trimethyl-2-norbornanone
• 2-Norbornanone, 1,3,3-trimethyl-
• 1,3,3-Trimethylnorcamphor
• 1,3,3-Trimethyl-2-norcamphanone
• Fenchon [German]
• NSC 8896
• D-FENCHONE, 96
• NSC 122687
• Bicyclo[2.2.1]heptan-2-one, 1,3,3-trimethyl-
• CHEBI:4999
• 126-21-6
• DTXSID9025324
• 2-Fenchanone, D-
• d-Fenchone (natural)
• BRN 1861492
• NCGC00166292-01
• 1,3-Trimethylnorcamphor
• AI3-00736
• Bicyclo[2.2.1]heptan-2-one, 1,3,3-trimethyl-, (1S,4R)-
• Bicyclo(2.2.1)heptan-2-one, 1,3,3-trimethyl-
• 1,3-Trimethyl-2-norbornanone
• 1,3-Trimethyl-2-norcamphanone
• 2-Norbornanone,3,3-trimethyl-
• (+-)-Fenchone
• 3,3-Dimethyl-8,9-dinorbornan-2-one
• WLN: L55 A CVTJ B1 D1 D1
• 1,3-Trimethylbicyclo[2.2.1]heptan-2-one
• Bicyclo[2.2.1]heptan-2-one,3,3-trimethyl-
• UNII-4Q6W8568TG
• (1R)-1,3,3-Trimethylbicyclo(2.2.1)heptan-2-one
• (1S)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one
• 1,3,3-Trimethylbicyclo(2.2.1)heptan-2-one, (1S)-
• Bicyclo(2.2.1)heptan-2-one, 1,3,3-trimethyl-, (1S)-
• Bicyclo[2.2.1]heptan-2-one, 1,3,3-trimethyl-, (1S)-
• NSC-8896
• iso-Fenchone
• fenchan-2-one
• NSC-122687
• 1,3,3 - trimethylnorbornan - 2 - one
• 2-07-00-00093 (Beilstein Handbook Reference)
• .ALPHA.-FENCHONE
• (1S)-1,3,3-Trimethylbicyclo(2.2.1)heptan-2-one
• 2-Norbornanone, 1,3,3-trimethyl-, (1R,4S)-()-
• 2,2,4-trimethylbicyclo[2.2.1]heptan-3-one
• 2-Norbornanone, 1,3,3-trimethyl-, (1S,4R)-(-)-
• SCHEMBL57584
• (1S) - 1,3,3 - trimethylbicyclo(2.2.1)heptan - 2 - one
• Bicyclo(2.2.1)heptan-2-one, 1,3,3-trimethyl-, (1S,4R)-
• DTXCID305324
• CHEMBL2268554
• NSC8896
• AMY25685
• Tox21_112396
• BBL018824
• LS-625
• MFCD00248429
• NSC122687
• s5934
• STK802502
• AKOS009158536
• LMPR0102120016
• LS-2759
• VS-06784
• F0163
• F0164
• FT-0604551
• FT-0627597
• 1.3.3-trimethylbicyclo(2.2.1)heptan-2-one
• EN300-54085
• C09859
• 1,3,3-Trimethyl-bicyclo[2.2.1]heptan-2-one
• Bicyclo[2.2.1]heptane-2-one,1,3,3-trimethyl
• A872224
• Q414784
• SR-01000945193
• 3,3 - dimethyl - 8,9 - dinorbornan - 2 - one
• SR-01000945193-1
• Z804948554
• BICYCLO[2.2.1]HEPTAN-2-ONE, 1,3,3,-TRIMETHYL-
• Bicyclo[2.2.1]heptan-2-one, 1,3,3-trimethyl-, (.+/-.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9944	99.44%
Caco-2	+	0.8223	82.23%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Lysosomes	0.4838	48.38%
OATP2B1 inhibitior	-	0.8428	84.28%
OATP1B1 inhibitior	+	0.9479	94.79%
OATP1B3 inhibitior	+	0.9617	96.17%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9414	94.14%
P-glycoprotein inhibitior	-	0.9822	98.22%
P-glycoprotein substrate	-	0.9620	96.20%
CYP3A4 substrate	-	0.5182	51.82%
CYP2C9 substrate	-	0.7907	79.07%
CYP2D6 substrate	-	0.7661	76.61%
CYP3A4 inhibition	-	0.9351	93.51%
CYP2C9 inhibition	-	0.8596	85.96%
CYP2C19 inhibition	-	0.9273	92.73%
CYP2D6 inhibition	-	0.9565	95.65%
CYP1A2 inhibition	-	0.8062	80.62%
CYP2C8 inhibition	-	0.9829	98.29%
CYP inhibitory promiscuity	-	0.9511	95.11%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5905	59.05%
Eye corrosion	-	0.7517	75.17%
Eye irritation	+	0.9479	94.79%
Skin irritation	+	0.8055	80.55%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.9500	95.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7667	76.67%
Micronuclear	-	0.9800	98.00%
Hepatotoxicity	+	0.6302	63.02%
skin sensitisation	+	0.9068	90.68%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.8164	81.64%
Nephrotoxicity	+	0.7185	71.85%
Acute Oral Toxicity (c)	IV	0.6235	62.35%
Estrogen receptor binding	-	0.9049	90.49%
Androgen receptor binding	-	0.8512	85.12%
Thyroid receptor binding	-	0.8518	85.18%
Glucocorticoid receptor binding	-	0.8885	88.85%
Aromatase binding	-	0.8618	86.18%
PPAR gamma	-	0.8562	85.62%
Honey bee toxicity	-	0.9195	91.95%
Biodegradation	+	0.6500	65.00%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	+	0.9417	94.17%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.24%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	87.74%	94.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.57%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.99%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.16%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.06%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.60%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.04%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.57%	100.00%

Plants that contains it

• Abies sibirica
• Achillea abrotanoides
• Ageratum conyzoides
• Aloysia citrodora
• Alpinia breviligulata
• Alpinia zerumbet
• Anethum graveolens
• Artemisia annua
• Artemisia tridentata
• Asarum heterotropoides
• Asarum sieboldii
• Cannabis sativa
• Catha edulis
• Centaurea benedicta
• Centratherum punctatum
• Chaerophyllum macrospermum
• Cinnamomum camphora
• Cinnamomum sieboldii
• Cinnamomum verum
• Cleonia lusitanica
• Curcuma kwangsiensis
• Curcuma phaeocaulis
• Curcuma wenyujin
• Curcuma zedoaria
• Cymbopogon citratus
• Ducrosia ismaelis
• Eucalyptus brassiana
• Eucalyptus bridgesiana
• Eucalyptus jensenii
• Ferula ovina
• Foeniculum vulgare
• Glycyrrhiza glabra
• Hyptis suaveolens
• Hyssopus seravschanicus
• Juniperus communis
• Lavandula angustifolia subsp. angustifolia
• Lavandula stoechas
• Lavandula stoechas subsp. luisieri
• Magnolia biondii
• Magnolia denudata
• Magnolia kobus
• Magnolia salicifolia
• Magnolia sprengeri
• Micromeria juliana
• Ocimum basilicum
• Osbornia octodonta
• Picea abies
• Pimpinella serbica
• Pistacia vera
• Platycladus orientalis
• Plectranthus glabratus
• Prunella vulgaris
• Punica granatum
• Santolina chamaecyparissus
• Sassafras albidum
• Satureja thymbra
• Senna alexandrina
• Sideritis chamaedryfolia
• Sideritis hirsuta
• Sideritis tragoriganum
• Solanum tuberosum
• Stachys aegyptiaca
• Syzygium aromaticum
• Tetradenia riparia
• Thuja occidentalis
• Thuja plicata
• Thymbra capitata
• Thymus pulegioides
• Wurfbainia compacta
• Wurfbainia longiligularis
• Wurfbainia villosa
• Wurfbainia villosa var. xanthioides
• Xylopia sericea
• Zingiber mioga
• Zingiber zerumbet

Cross-Links

• PubChem: 14525
• NPASS: NPC258672
• LOTUS: LTS0126716
• wikiData: Q414784