Neoisomenthol

Details

• Internal ID: ba3ccaf1-59a1-4be0-ade1-fcfc5f2ab136
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Menthane monoterpenoids
• IUPAC Name: (1R,2R,5R)-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-/m1/s1
• InChI Key: NOOLISFMXDJSKH-OPRDCNLKSA-N
• Popularity: 85 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

• (+)-neoisomenthol
• 20752-34-5
• DL-ISOMENTHOL
• iso-neomenthol
• (R,R,R)-Menthol
• (+/-)-Neoisomenthol
• (1R,2R,5R)-2-isopropyl-5-methylcyclohexanol
• d-neo-Menthol
• Isomenthol
• cis-1,3,cis-1,4-menthol
• (+-)-Isomenthol
• 491-02-1
• Neoisomenthol, (+)-
• UNII-90E7IB31QH
• (1R,2R,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol
• FEMA No. 2666
• 90E7IB31QH
• cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2R,5R)-
• (1R,2R,5R)-Isomenthol
• p-Menthan-3-ol
• EINECS 207-722-7
• EINECS 222-825-7
• (1R,2R,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol
• 3623-52-7
• BRN 3194262
• rel-(1R,2R,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol
• (1alpha,2alpha,5alpha)-5-methyl-2-(1-methylethyl)cyclohexanol
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5S)-rel-
• Hexahydrothymol
• (1R,2R,5R)-rel-2-Isopropyl-5-methylcyclohexanol
• rac-Menthol
• Menthol, racemic
• D - menthol
• (1)-Isomenthol
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1.alpha.,2.alpha.,5.alpha.)-
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1theta-(1alpha,2alpha,5alpha))-
• Racementhol [BAN:INN]
• (1R,2S,5R)-Menthol
• UNII-Q3I568EO1X
• Isoneomenthol
• CYCLOHEXANOL, 5-METHYL-2-(1-METHYLETHYL)-, (1R-(1.ALPHA.,2.ALPHA.,5.ALPHA.))-
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, [1R-(1.alpha.,2.alpha.,5.alpha.)]-
• menthol (iso-)
• 89-78-1
• MENTHOL, cis-1,3-cis-1,4-(+-)-
• 4-06-00-00152 (Beilstein Handbook Reference)
• (1R)-(+)-neoisomenthol
• (1R,3R,4R)-form
• Ciclohexanol, 5-metil-2-(1-metiletil)-, (1r, 2s, 5r)-rel-
• SCHEMBL1703569
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1.alpha.,2.beta.,5.alpha.)-
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1alpha,2beta,5beta)-(+/-)-
• CHEBI:18451
• NOOLISFMXDJSKH-OPRDCNLKSA-
• DTXSID80895815
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1-alpha,2-beta,5-beta)-(+-)-
• MFCD09834087
• LMPR0102090057
• NCGC00142588-01
• 490-99-3
• LS-89534
• MENTHOL, (1R,3R,4R)-(+)-
• CS-0239800
• EN300-219194
• Q27109029
• 2-Isopropyl-5-methylcyclohexanol, (1.alpha.,2.alpha.,5.alpha.)-
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, [1R-(1?,2?,5?)]-
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1-alpha,2-beta,5-beta)-(+)-
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1.alpha.,2.beta.,5.beta.)-(.+-.)-
• Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1.alpha.,2.beta.,5.beta.)-(.+.)-
• InChI=1/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9-,10-/m1/s1

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

• Agathosma betulina
• Clinopodium grandiflorum
• Mentha × piperita
• Mentha arvensis
• Mentha canadensis
• Mentha longifolia
• Minthostachys mollis

Cross-Links

• PubChem: 19244
• NPASS: NPC308453
• LOTUS: LTS0034777
• wikiData: Q27109029