(1S,2S,4R)-Limonene-1,2-diol

Details

• Internal ID: b9a840a2-1f6e-4f0e-93d1-dfcd48440ea4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Menthane monoterpenoids
• IUPAC Name: (1S,2S,4R)-1-methyl-4-prop-1-en-2-ylcyclohexane-1,2-diol
• SMILES (Canonical): CC(=C)C1CCC(C(C1)O)(C)O
• SMILES (Isomeric): CC(=C)[C@@H]1CC[C@]([C@H](C1)O)(C)O
• InChI: InChI=1S/C10H18O2/c1-7(2)8-4-5-10(3,12)9(11)6-8/h8-9,11-12H,1,4-6H2,2-3H3/t8-,9+,10+/m1/s1
• InChI Key: WKZWTZTZWGWEGE-UTLUCORTSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.25 g/mol
• Exact Mass: 170.130679813 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.47
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• Limonene glycol
• 38630-75-0
• 8-p-Menthene-1,2-diol
• FEMA no. 4409
• (1S,2S,4R)-p-Menth-8-ene-1,2-diol
• 1,2-Cyclohexanediol, 1-methyl-4-(1-methylethenyl)-, (1S,2S,4R)-
• UNII-B9MU2A776W
• B9MU2A776W
• (+/-)-1-Hydroxyneodihydrocarveol
• Limonene-1,2-diol
• 8-p-Menthene-1,2-diol, (+/-)-
• (+/-)-(1S,2S,4R)-Limonene glycol
• (+/-)-(1S,2S,4R)-Limonene-1,2-diol
• (1S,2S,4R)-(+/-)-Limonene-1,2-diol
• (1S,2S,4R)-1-methyl-4-prop-1-en-2-ylcyclohexane-1,2-diol
• (1S,2S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol
• (1S,2S,4R)-menth-8-ene-1,2-diol
• 1,2-Cyclohexanediol, 1-methyl-4-(1-methylethenyl)-, (1S-(1alpha,2beta,4alpha))-
• d-Limonene-1,2-diol
• 8,9-p-Menthen-1,2-diol
• SCHEMBL1443876
• (+)-1-Hydroxyneodihydrocarveol
• (+)-Limonene-trans-1,2-diol
• CHEMBL4213960
• (+)-8-p-menthene-1,2-diol
• CHEBI:18515
• (+)-(1S,2S,4R)-Limonene glycol
• LMPR0102090016
• 8-P-MENTHENE-1,2-DIOL [FHFI]
• (1S,2S,4R)-(+)-Limonen-1,2-diol
• p-Menth-8-ene-1,2-diol (7CI, 8CI)
• 8-P-MENTHENE-1,2-DIOL, (+)-
• C07276
• (+)-(1S,2S,4R)-LIMONENE-1,2-DIOL
• A901211
• (1S,2S,4R)-(+)-Limonene-1,2-diol, >=97%
• Q27109038
• (1S,2S,4R)-4-isopropenyl-1-methylcyclohexane-1,2-diol
• (1S,2S,4R)-(+)-Limonene-1,2-diol, >=97.0% (GC)
• 1,2-CYCLOHEXANEDIOL, 1-METHYL-4-(1-METHYLETHENYL)-, (1S-(1.ALPHA.,2.BETA.,4.ALPHA.))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9844	98.44%
Caco-2	-	0.5508	55.08%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6584	65.84%
OATP2B1 inhibitior	-	0.8403	84.03%
OATP1B1 inhibitior	+	0.9659	96.59%
OATP1B3 inhibitior	+	0.9549	95.49%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.9395	93.95%
P-glycoprotein inhibitior	-	0.9853	98.53%
P-glycoprotein substrate	-	0.8450	84.50%
CYP3A4 substrate	+	0.5190	51.90%
CYP2C9 substrate	-	0.6063	60.63%
CYP2D6 substrate	-	0.7644	76.44%
CYP3A4 inhibition	-	0.8730	87.30%
CYP2C9 inhibition	-	0.8913	89.13%
CYP2C19 inhibition	-	0.7863	78.63%
CYP2D6 inhibition	-	0.9165	91.65%
CYP1A2 inhibition	-	0.8322	83.22%
CYP2C8 inhibition	-	0.9459	94.59%
CYP inhibitory promiscuity	-	0.9394	93.94%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.5905	59.05%
Eye corrosion	-	0.9573	95.73%
Eye irritation	+	0.8116	81.16%
Skin irritation	+	0.5256	52.56%
Skin corrosion	-	0.9358	93.58%
Ames mutagenesis	-	0.7837	78.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5987	59.87%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	+	0.5460	54.60%
skin sensitisation	+	0.6637	66.37%
Respiratory toxicity	-	0.7111	71.11%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.5342	53.42%
Acute Oral Toxicity (c)	III	0.7797	77.97%
Estrogen receptor binding	-	0.8460	84.60%
Androgen receptor binding	-	0.8041	80.41%
Thyroid receptor binding	-	0.7886	78.86%
Glucocorticoid receptor binding	-	0.6526	65.26%
Aromatase binding	-	0.8554	85.54%
PPAR gamma	-	0.8202	82.02%
Honey bee toxicity	-	0.8212	82.12%
Biodegradation	+	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9702	97.02%

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	96.40%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.14%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.51%	96.09%
CHEMBL206	P03372	Estrogen receptor alpha	87.83%	97.64%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.10%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.90%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.20%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.64%	82.69%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.40%	93.04%
CHEMBL2996	Q05655	Protein kinase C delta	83.86%	97.79%
CHEMBL1871	P10275	Androgen Receptor	83.62%	96.43%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.77%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.60%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.51%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	81.01%	90.17%

Plants that contains it

• Acer triflorum
• Boltonia asteroides
• Carum carvi
• Citrus medica
• Dalea purpurea
• Dracocephalum kotschyi
• Drimia sanguinea
• Prunus cerasoides
• Zaluzianskya capensis

Cross-Links

• PubChem: 441246
• NPASS: NPC253448
• LOTUS: LTS0093422
• wikiData: Q27109038