(+)-Menthol

Details

• Internal ID: 1fbe88bf-7f9b-4f9c-86e2-6dbcafb8d7c1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Menthane monoterpenoids
• IUPAC Name: (1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexan-1-ol
• SMILES (Canonical): CC1CCC(C(C1)O)C(C)C
• SMILES (Isomeric): C[C@H]1CC[C@@H]([C@H](C1)O)C(C)C
• InChI: InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m0/s1
• InChI Key: NOOLISFMXDJSKH-AEJSXWLSSA-N
• Popularity: 32 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₂₀O
• Molecular Weight: 156.26 g/mol
• Exact Mass: 156.151415257 g/mol
• Topological Polar Surface Area (TPSA): 20.20 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.44
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 15356-60-2
• d-Menthol
• (1S,2R,5S)-(+)-Menthol
• (1S,2R,5S)-Menthol
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1S,2R,5S)-
• (1S,2R,5S)-2-Isopropyl-5-methylcyclohexanol
• Hexahydrothymol
• Menthol, (+)-
• (1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexan-1-ol
• (1S,2R,5S)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol
• Menthol, (1S,3S,4R)-(+)-
• UNII-C6B1OE8P3W
• C6B1OE8P3W
• rac-Menthol
• DTXSID8029733
• CHEBI:76306
• (+)-(1S,2R,5S)-menthol
• (+)-(1S,3S,4R)-menthol
• p-Menthan-3-ol
• EINECS 239-387-8
• MFCD00062983
• (1S,2R,5S)-5-methyl-2-(1-methylethyl)cyclohexanol
• 89-78-1
• EC 239-387-8
• Menthol, racemic
• 3-p-Menthanol
• D - menthol
• Racementhol [BAN:INN]
• (+)-p-Menthan-3-ol
• Fisherman's friend lozenges
• (1R,2S,5R)-Menthol
• Menthol, cis-1,3,trans-1,4-
• Fancol menthol
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1.alpha.,2.beta.,5.alpha.)-
• (DL)-Menthol
• (+) - menthol
• (.+/-.)-Menthol
• (1S)-(+)-menthol
• (+/-)-Menthol racemic
• MENTHOL, D-
• Ciclohexanol, 5-metil-2-(1-metiletil)-, (1r, 2s, 5r)-rel-
• SCHEMBL521946
• DTXCID409733
• GTPL2471
• CHEMBL2106989
• (1s, 2r, 5s)-(+)-menthol
• Menthol, (1S,3S,4R)-()-
• Tox21_201043
• AKOS006281173
• CS-W017993
• DB11344
• HY-W017277
• NCGC00248905-01
• NCGC00258596-01
• AS-69562
• (1S,2R,5S)-(+)-Menthol, 99%
• CAS-15356-60-2
• M0826
• M3170
• EN300-92162
• A815982
• (1S,2R,5S)-2-Isopropyl-5-methylcyclohexan-1-ol
• (1S,2R,5S)-5-methyl-2-propan-2-yl-1-cyclohexanol
• Q27084428
• (1S,2R,5S)-5-methyl-2-propan-2-yl-cyclohexan-1-ol
• F8889-8741
• Z1198149783
• 5.alpha.-Methyl-2.beta.-(1.alpha.-methylethyl)cyclohexanol
• Cyclohexanol,5-methyl-2-(1-methylethyl)-,(1S,2R,5S)-
• 2-Isopropyl-5-methylcyclohexanol, (1.alpha.,2.beta.,5.alpha.)-
• 5-Methyl-2-(1-methylethyl)cyclohexanol, (1.alpha.,2.beta.,5.alpha.)-
• Cyclohexanol, 2-isopropyl-5-methyl-, (1.alpha.,2.beta.,5.alpha.)-
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1S-(1alpha,2beta,5alpha))-
• (+)-Menthol, puriss. p.a., terpene standard for GC, >=99.0% (sum of enantiomers, GC)
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, [1S-(1.alpha.,2.beta.,5.alpha.)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9940	99.40%
Caco-2	+	0.6690	66.90%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6714	67.14%
OATP2B1 inhibitior	-	0.8429	84.29%
OATP1B1 inhibitior	+	0.9562	95.62%
OATP1B3 inhibitior	+	0.9500	95.00%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9437	94.37%
P-glycoprotein inhibitior	-	0.9709	97.09%
P-glycoprotein substrate	-	0.8708	87.08%
CYP3A4 substrate	-	0.6168	61.68%
CYP2C9 substrate	-	0.8151	81.51%
CYP2D6 substrate	-	0.6696	66.96%
CYP3A4 inhibition	-	0.9458	94.58%
CYP2C9 inhibition	-	0.8484	84.84%
CYP2C19 inhibition	-	0.9185	91.85%
CYP2D6 inhibition	-	0.9451	94.51%
CYP1A2 inhibition	-	0.7188	71.88%
CYP2C8 inhibition	-	0.9923	99.23%
CYP inhibitory promiscuity	-	0.9546	95.46%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.7397	73.97%
Eye corrosion	+	0.5163	51.63%
Eye irritation	+	0.9629	96.29%
Skin irritation	+	0.8623	86.23%
Skin corrosion	-	0.6193	61.93%
Ames mutagenesis	-	1.0000	100.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6231	62.31%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	+	0.8275	82.75%
skin sensitisation	+	0.8443	84.43%
Respiratory toxicity	-	0.7222	72.22%
Reproductive toxicity	-	0.6667	66.67%
Mitochondrial toxicity	-	0.8500	85.00%
Nephrotoxicity	-	0.5939	59.39%
Acute Oral Toxicity (c)	III	0.8431	84.31%
Estrogen receptor binding	-	0.9182	91.82%
Androgen receptor binding	-	0.7230	72.30%
Thyroid receptor binding	-	0.7964	79.64%
Glucocorticoid receptor binding	-	0.8709	87.09%
Aromatase binding	-	0.8947	89.47%
PPAR gamma	-	0.9385	93.85%
Honey bee toxicity	-	0.9134	91.34%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9059	90.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.26%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.50%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.84%	97.09%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	85.82%	95.58%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	84.85%	97.23%
CHEMBL2581	P07339	Cathepsin D	84.59%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	82.93%	95.93%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.88%	96.47%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.82%	85.14%

Plants that contains it

• Aconitum leucostomum
• Actaea cimicifuga
• Actaea dahurica
• Actaea simplex
• Agrimonia pilosa
• Aiouea montana
• Akebia quinata
• Akebia trifoliata
• Aquilegia ecalcarata
• Artemisia argyi
• Artemisia montana
• Artemisia princeps
• Artemisia szowitziana
• Blumea axillaris
• Cannabis sativa
• Capsicum annuum
• Ceanothus velutinus
• Chlorophytum borivilianum
• Conioselinum anthriscoides
• Conioselinum smithii
• Conioselinum tenuissimum
• Dipterocarpus dyeri
• Elsholtzia ciliata
• Fragaria vesca
• Gamblea innovans
• Garcinia scortechinii
• Gardenia tubifera
• Glycyrrhiza
• Ipomoea cairica
• Isodon lophanthoides
• Kopsia grandifolia
• Lasianthus fordii
• Ledebouria socialis
• Leonurus japonicus
• Lycopus europaeus
• Mentha arvensis
• Mentha canadensis
• Mosla chinensis
• Nepeta tenuifolia
• Perilla frutescens
• Persea barbujana
• Pinellia ternata
• Scutellaria barbata
• Senna alexandrina
• Thymus quinquecostatus
• Thymus vulgaris
• Vitex negundo
• Wurfbainia longiligularis
• Wurfbainia villosa
• Wurfbainia villosa var. xanthioides

Cross-Links

• PubChem: 165675
• NPASS: NPC84030
• LOTUS: LTS0229953
• wikiData: Q27084428