(1S,2R)-4-(2-hydroxypropan-2-yl)-1-methylcyclohex-3-ene-1,2-diol

Details

• Internal ID: e9cbab55-5d85-4fb0-85ef-a44ca6dd3dea
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Menthane monoterpenoids
• IUPAC Name: (1S,2R)-4-(2-hydroxypropan-2-yl)-1-methylcyclohex-3-ene-1,2-diol
• SMILES (Canonical): CC1(CCC(=CC1O)C(C)(C)O)O
• SMILES (Isomeric): C[C@@]1(CCC(=C[C@H]1O)C(C)(C)O)O
• InChI: InChI=1S/C10H18O3/c1-9(2,12)7-4-5-10(3,13)8(11)6-7/h6,8,11-13H,4-5H2,1-3H3/t8-,10+/m1/s1
• InChI Key: CYSRURFSGZEJNU-SCZZXKLOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₈O₃
• Molecular Weight: 186.25 g/mol
• Exact Mass: 186.125594432 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): 0.59
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• BDBM50379795

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9841	98.41%
Caco-2	+	0.5856	58.56%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6993	69.93%
OATP2B1 inhibitior	-	0.8494	84.94%
OATP1B1 inhibitior	+	0.9415	94.15%
OATP1B3 inhibitior	+	0.9668	96.68%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.9492	94.92%
P-glycoprotein inhibitior	-	0.9747	97.47%
P-glycoprotein substrate	-	0.8900	89.00%
CYP3A4 substrate	-	0.5146	51.46%
CYP2C9 substrate	-	0.7979	79.79%
CYP2D6 substrate	-	0.7542	75.42%
CYP3A4 inhibition	-	0.8561	85.61%
CYP2C9 inhibition	-	0.8150	81.50%
CYP2C19 inhibition	-	0.8140	81.40%
CYP2D6 inhibition	-	0.9139	91.39%
CYP1A2 inhibition	-	0.8773	87.73%
CYP2C8 inhibition	-	0.9314	93.14%
CYP inhibitory promiscuity	-	0.8784	87.84%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5926	59.26%
Eye corrosion	-	0.9782	97.82%
Eye irritation	+	0.7218	72.18%
Skin irritation	+	0.5916	59.16%
Skin corrosion	-	0.8779	87.79%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7882	78.82%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	+	0.6928	69.28%
skin sensitisation	+	0.6849	68.49%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.7566	75.66%
Acute Oral Toxicity (c)	III	0.7340	73.40%
Estrogen receptor binding	-	0.8058	80.58%
Androgen receptor binding	-	0.7633	76.33%
Thyroid receptor binding	-	0.7626	76.26%
Glucocorticoid receptor binding	-	0.6371	63.71%
Aromatase binding	-	0.8059	80.59%
PPAR gamma	-	0.8650	86.50%
Honey bee toxicity	-	0.8881	88.81%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.8689	86.89%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL239	Q07869	Peroxisome proliferator-activated receptor alpha	19500 nM	EC50	PMID: 1965200
CHEMBL3979	Q03181	Peroxisome proliferator-activated receptor delta	48500 nM	EC50	PMID: 8759172
CHEMBL235	P37231	Peroxisome proliferator-activated receptor gamma	21700 nM	EC50	PMID: 24369840

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.22%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.69%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.66%	91.11%
CHEMBL2581	P07339	Cathepsin D	87.72%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.58%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.76%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.56%	95.89%

Plants that contains it

• Asarum sieboldii

Cross-Links

• PubChem: 57404439
• NPASS: NPC82337
• ChEMBL: CHEMBL2011541
• LOTUS: LTS0037747
• wikiData: Q104972542