(1S,2S,4S)-4-Isopropyl-1-methylcyclohexane-1,2,4-triol

Details

• Internal ID: c394fe6a-c236-4c66-9a83-713ac712094f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Menthane monoterpenoids
• IUPAC Name: (1S,2S,4S)-1-methyl-4-propan-2-ylcyclohexane-1,2,4-triol
• SMILES (Canonical): CC(C)C1(CCC(C(C1)O)(C)O)O
• SMILES (Isomeric): CC(C)[C@@]1(CC[C@]([C@H](C1)O)(C)O)O
• InChI: InChI=1S/C10H20O3/c1-7(2)10(13)5-4-9(3,12)8(11)6-10/h7-8,11-13H,4-6H2,1-3H3/t8-,9-,10-/m0/s1
• InChI Key: RKROZYQLIWCOBD-GUBZILKMSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₂₀O₃
• Molecular Weight: 188.26 g/mol
• Exact Mass: 188.14124450 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.67
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 36150-04-6
• (1s,2s,4s)-p-menthane-1,2,4-triol
• p-menthane-1,2,4-triol
• (1S,2S,4S)-4-Isopropyl-1-methylcyclohexane-1,2,4-triol
• RKROZYQLIWCOBD-GUBZILKMSA-N
• (1S,2S,4S)-1-methyl-4-propan-2-ylcyclohexane-1,2,4-triol
• (1S,2S,4S)-Trihydroxy-p-menthane
• AKOS032962328
• FS-9804
• 4-isopropyl-1-methylcyclohexane-1,2,4-triol
• p-Menthane-1,2,4-triol, (1S,2S,4S)-(+)-
• 1,2,4-Cyclohexanetriol, 1-methyl-4-(1-methylethyl)-, (1S,2S,4S)-
• 1,2,4-Cyclohexanetriol, 1-methyl-4-(1-methylethyl)-, [1S-(1.alpha.,2.beta.,4.beta.)]-
• InChI=1/C10H20O3/c1-7(2)10(13)5-4-9(3,12)8(11)6-10/h7-8,11-13H,4-6H2,1-3H3/t8-,9-,10-/m0/s
• rel-(1R,2R,4R)-1-Methyl-4-(1-methylethyl)-1,2,4-cyclohexanetriol; p-Menthane-1,2,4-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9456	94.56%
Caco-2	-	0.6651	66.51%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7446	74.46%
OATP2B1 inhibitior	-	0.8473	84.73%
OATP1B1 inhibitior	+	0.9618	96.18%
OATP1B3 inhibitior	+	0.9555	95.55%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9339	93.39%
P-glycoprotein inhibitior	-	0.9781	97.81%
P-glycoprotein substrate	-	0.8926	89.26%
CYP3A4 substrate	-	0.5576	55.76%
CYP2C9 substrate	-	0.8008	80.08%
CYP2D6 substrate	-	0.7440	74.40%
CYP3A4 inhibition	-	0.9021	90.21%
CYP2C9 inhibition	-	0.7084	70.84%
CYP2C19 inhibition	-	0.8340	83.40%
CYP2D6 inhibition	-	0.9492	94.92%
CYP1A2 inhibition	-	0.8254	82.54%
CYP2C8 inhibition	-	0.9878	98.78%
CYP inhibitory promiscuity	-	0.9759	97.59%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6647	66.47%
Eye corrosion	-	0.9572	95.72%
Eye irritation	+	0.9117	91.17%
Skin irritation	+	0.5712	57.12%
Skin corrosion	-	0.8976	89.76%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6999	69.99%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	-	0.5533	55.33%
skin sensitisation	+	0.5298	52.98%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.6232	62.32%
Acute Oral Toxicity (c)	III	0.7310	73.10%
Estrogen receptor binding	-	0.8177	81.77%
Androgen receptor binding	-	0.8285	82.85%
Thyroid receptor binding	-	0.6636	66.36%
Glucocorticoid receptor binding	-	0.7880	78.80%
Aromatase binding	-	0.7859	78.59%
PPAR gamma	-	0.8660	86.60%
Honey bee toxicity	-	0.8695	86.95%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.8682	86.82%

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	93.37%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.28%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	85.86%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.69%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.48%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.39%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.82%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	80.62%	95.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.10%	85.14%

Plants that contains it

• Artemisia suksdorfii
• Boswellia sacra
• Garcinia dulcis
• Zingiber mekongense

Cross-Links

• PubChem: 5326310
• LOTUS: LTS0269585
• wikiData: Q105238776