Menthone

Details

• Internal ID: c1900c2f-9a87-445b-81b6-68b3651985da
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Menthane monoterpenoids
• IUPAC Name: (2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-one
• SMILES (Canonical): CC1CCC(C(=O)C1)C(C)C
• SMILES (Isomeric): C[C@@H]1CC[C@H](C(=O)C1)C(C)C
• InChI: InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s1
• InChI Key: NFLGAXVYCFJBMK-BDAKNGLRSA-N
• Popularity: 499 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25 g/mol
• Exact Mass: 154.135765193 g/mol
• Topological Polar Surface Area (TPSA): 17.10 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.65
• H-Bond Acceptor: 1
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• MENTHONE
• 14073-97-3
• l-MENTHONE
• (2S,5R)-2-isopropyl-5-methylcyclohexanone
• trans-Menthone
• p-Menthone
• Neomenthone
• Menthone racemic
• L-Menthan-3-one
• trans-Menthan-3-one
• 89-80-5
• trans-p-Menthan-3-one
• (1R,4S)-(-)-p-Menthan-3-one
• Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2S,5R)-
• DL-Menthone
• Menthone (natural)
• p-Menthan-3-one, trans-
• FEMA No. 2667
• p-Menthan-3-one racemic
• (dl)-Menthone
• (-)-(2S,5R)-Menthone
• (1R,4S)-p-menthan-3-one
• CCRIS 5747
• (2S,5R)-5-methyl-2-(propan-2-yl)cyclohexanone
• HSDB 1268
• p-Menthan-3-one, dl-
• EINECS 201-941-1
• EINECS 214-049-2
• UNII-9NH5J4V8FN
• (2S,5R)-5-methyl-2-(1-methylethyl)cyclohexanone
• (2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-one
• (2S-trans)-5-methyl-2-(1-methylethyl)cyclohexanone
• Cyclohexanone, 5-methyl-2-(1-methylethyl)-, trans-
• (-)-(1R,4S)-menthone
• UNII-5F709W4OG4
• AI3-11106
• (2S,5R)-5-METHYL-2-(1-METHYLETHYL)-CYCLOHEXANONE
• DTXSID3044384
• CHEBI:15410
• (-)-5-Methyl-2-(1-methylethyl)cyclohexanone
• 5-Methyl-2-(1-methylethyl)cyclohexanone, trans-
• 5F709W4OG4
• Cyclohexan-1-one, 2-isopropyl-5-methyl-, racemic
• EINECS 237-926-1
• (2S,5R)-5-Methyl-2-(Propan-2-Yl)Cyclohexan-1-One
• Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2S-trans)-
• EC 237-926-1
• trans-menthon
• DTXCID1024384
• trans - menthone
• Cyclohexanone, 5-methyl-2-(1-methylethyl)-, trans-(+/-)-
• l-p-Menthan-3-one
• 5-Methyl-2-(1-methylethyl)cyclohexanone
• CAS-14073-97-3
• menthon
• Menthone G
• trans-p-menthone
• 1-menthone
• (-)menthone
• NCGC00095606-01
• MFCD00001634
• Menthan-3-one, trans
• Spectrum_001299
• rel-(2R,5S)-2-isopropyl-5-methylcyclohexanone
• (-)-Menthone,(S)
• MENTHONE [FHFI]
• SpecPlus_000437
• MENTHONE, L-
• L-MENTHONE [MI]
• Spectrum2_000691
• Spectrum3_001272
• Spectrum4_001648
• Spectrum5_000495
• (2S,5R)-2-isopropyl-5-methyl-cyclohexanone
• bmse000375
• (-)-Menthone, 90%
• 9NH5J4V8FN
• SCHEMBL21709
• BSPBio_002864
• KBioGR_002115
• KBioSS_001779
• L - menthan - 3 - one
• MENTHONE, (-)-
• SPECTRUM300564
• DivK1c_006533
• SPBio_000841
• (1S)-trans-p-menthan-3-one
• (-)-MENTHONE [FCC]
• CHEMBL276311
• DTXSID2044478
• KBio1_001477
• KBio2_001779
• KBio2_004347
• KBio2_006915
• KBio3_002364
• (-)-Menthone, analytical standard
• HY-N7916
• Tox21_111510
• Tox21_302153
• CCG-38562
• MFCD00136033
• AKOS006343213
• Tox21_111510_1
• LMPR0102090004
• LS-2354
• SDCCGMLS-0066582.P001
• 2-Isopropyl-5-methylcyclohexanone, trans
• NCGC00095606-02
• NCGC00178425-01
• NCGC00255957-01
• p-Menthan-3-one, (1R,4S)-(-)-
• AS-17440
• (2S,5R)2-isopropyl-5-methylcyclohexanone
• CS-0138798
• 1-METHYL-4-ISOPROPYLCYCLOHEXAN-3-ONE
• C00843
• EN300-383879
• (2S,5R)-2-Isopropyl-5-methylcyclohexan-1-one
• (2S, 5R)-trans-2-isopropyl-5-methylcyclohexanone
• Q424902
• SR-05000002387
• 5-Methyl-2-(1-methylethyl)-(2S,5R)-Cyclohexanone
• SR-05000002387-1
• W-108194
• 5-Methyl-2-(1-methylethyl)-(2S-trans)-Cyclohexanone
• (-)-Menthone, primary pharmaceutical reference standard
• Z1201619246
• Cyclohexanone, 5-methyl-2-(1-methylethyl)-, trans-(.+/-.)-
• 1/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s
• InChI=1/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9960	99.60%
Caco-2	+	0.6871	68.71%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7285	72.85%
OATP2B1 inhibitior	-	0.8425	84.25%
OATP1B1 inhibitior	+	0.9674	96.74%
OATP1B3 inhibitior	+	0.9577	95.77%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9392	93.92%
P-glycoprotein inhibitior	-	0.9784	97.84%
P-glycoprotein substrate	-	0.8022	80.22%
CYP3A4 substrate	-	0.6522	65.22%
CYP2C9 substrate	-	0.6168	61.68%
CYP2D6 substrate	-	0.7682	76.82%
CYP3A4 inhibition	-	0.9700	97.00%
CYP2C9 inhibition	-	0.9000	90.00%
CYP2C19 inhibition	-	0.9399	93.99%
CYP2D6 inhibition	-	0.9535	95.35%
CYP1A2 inhibition	-	0.7503	75.03%
CYP2C8 inhibition	-	0.9963	99.63%
CYP inhibitory promiscuity	-	0.9679	96.79%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.7053	70.53%
Eye corrosion	+	0.7224	72.24%
Eye irritation	+	0.9884	98.84%
Skin irritation	+	0.8622	86.22%
Skin corrosion	-	0.8439	84.39%
Ames mutagenesis	+	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7475	74.75%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	+	0.9500	95.00%
skin sensitisation	+	0.9334	93.34%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	-	0.9375	93.75%
Nephrotoxicity	+	0.6807	68.07%
Acute Oral Toxicity (c)	III	0.7891	78.91%
Estrogen receptor binding	-	0.9559	95.59%
Androgen receptor binding	-	0.7272	72.72%
Thyroid receptor binding	-	0.8887	88.87%
Glucocorticoid receptor binding	-	0.8706	87.06%
Aromatase binding	-	0.8411	84.11%
PPAR gamma	-	0.9284	92.84%
Honey bee toxicity	-	0.9063	90.63%
Biodegradation	+	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9304	93.04%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.47%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.25%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.24%	96.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.07%	90.71%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	84.27%	86.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.94%	97.25%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.77%	94.80%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.07%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.75%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.04%	93.56%

Plants that contains it

• Achillea cuneatiloba
• Aconitum leucostomum
• Actaea cimicifuga
• Actaea dahurica
• Actaea simplex
• Aiouea montana
• Akebia quinata
• Akebia trifoliata
• Aquilegia ecalcarata
• Artemisia argyi
• Artemisia montana
• Artemisia princeps
• Artemisia szowitziana
• Atractylodes lancea
• Atractylodes macrocephala
• Aucklandia costus
• Blumea axillaris
• Ceanothus velutinus
• Centella asiatica
• Chlorophytum borivilianum
• Clinopodium serpyllifolium subsp. fruticosum
• Conioselinum anthriscoides
• Conioselinum smithii
• Conioselinum tenuissimum
• Dipterocarpus dyeri
• Echinops grijsii
• Elsholtzia splendens
• Fragaria vesca
• Gamblea innovans
• Garcinia scortechinii
• Gardenia tubifera
• Hypericum perforatum
• Inula helenium
• Ipomoea cairica
• Isodon lophanthoides
• Kopsia grandifolia
• Lasianthus fordii
• Ledebouria socialis
• Leonurus japonicus
• Leuzea uniflora
• Lycopus europaeus
• Mentha × piperita
• Mentha arvensis
• Mentha canadensis
• Mentha pulegium
• Minthostachys mollis
• Nepeta tenuifolia
• Perilla frutescens
• Persea barbujana
• Pinellia ternata
• Scutellaria barbata
• Senna alexandrina
• Thymus quinquecostatus
• Thymus vulgaris
• Vitex negundo

Cross-Links

• PubChem: 26447
• NPASS: NPC45270
• LOTUS: LTS0020315
• wikiData: Q424902