(-)-Isopulegol

Details

• Internal ID: 42fcf03e-568f-4123-84e2-fa8a4333cd24
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Menthane monoterpenoids
• IUPAC Name: (1R,2S,5R)-5-methyl-2-prop-1-en-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/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1
• InChI Key: ZYTMANIQRDEHIO-KXUCPTDWSA-N
• Popularity: 123 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25 g/mol
• Exact Mass: 154.135765193 g/mol
• Topological Polar Surface Area (TPSA): 20.20 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.36
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 89-79-2
• l-Isopulegol
• coolact P
• (1R,2S,5R)-5-METHYL-2-(PROP-1-EN-2-YL)CYCLOHEXAN-1-OL
• FEMA No. 2962
• 3TH92O3BXN
• (1R,2S,5R)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol
• DTXSID5047116
• NSC-231369
• RefChem:792269
• DTXCID501764296
• 201-940-6
• Isopulegol
• p-Menth-8-en-3-ol
• 50373-36-9
• (-)-L-Isopulegol
• Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)-
• MFCD00134655
• Isopulegol, (+/-)-
• NVG8YK55NL
• (1R,2S,5R)-2-Isopropenyl-5-methylcyclohexanol
• NSC1263
• p-Menth-8-en-3-ol, (1R,3R,4S)-(-)-
• NSC-1263
• iso-Pulegol
• (1R,3R,4S)-(-)-p-Menth-8-en-3-ol
• p-8(9)-Menthen-3-ol
• rel-(1R,2S,5R)-5-Methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol
• 59905-53-2
• Isopulegol (natural)
• (+/-)-(1alpha,2beta,5alpha)-5-methyl-2-(1-methylvinyl)cyclohexan-1-ol
• UNII-3TH92O3BXN
• rac-isopulegol
• Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)-rel-
• 1-isopulegol
• Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, [1R-(1.alpha.,2.beta.,5.alpha.)]-
• EINECS 201-940-6
• (+/-)-isopulegol
• AI3-02176
• ISOPULEGOL [FCC]
• UNII-NVG8YK55NL
• ISOPULEGOL [FHFI]
• (-)-Isopulegol, 99%
• EC 201-940-6
• SCHEMBL43859
• p-Menth-8(9)-en-3-ol
• (-)-Isopulegol, >=98%
• CHEMBL237994
• GTPL2462
• orb1311050
• CHEBI:70479
• ZYTMANIQRDEHIO-KXUCPTDWSA-
• (-)-Isopulegol, technical grade
• DTXSID90110001
• NSC 1263
• EINECS 256-557-7
• (-)-Isopulegol, analytical standard
• 5-Methyl-2-(1-methylethenyl)cyclohexanol, (1R-(1alpha,2beta,5alpha))-
• AKOS028109164
• Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R-(1alpha,2beta,5alpha))-
• AS-10358
• FI106423
• SY211633
• HY-121206
• (1R,3R,4S)-P-METH-8-EN-3-OL
• CS-0081229
• NS00127398
• (-)-Isopulegol 100 microg/mL in Acetonitrile
• E78611
• EN300-269447
• (1R,2S,5R)-2-isopropenyl-5-methyl-cyclohexanol
• F868911
• Q2103922
• (1R,2S,5R)-5-Methyl-2-(1-propen-2-yl)cyclohexanol
• (1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexanol
• 5-Methyl-2-(1-methylethenyl)-(1R,2S,5R)-Cyclohexanol
• (-)-Isopulegol, primary pharmaceutical reference standard
• 2-Isopropenyl-5-methylcyclohexanol-, (1R-(1alpha,2beta,5alpha))-
• (1)-(1alpha,2beta,5alpha)-5-Methyl-2-(1-methylvinyl)cyclohexan-1-ol
• InChI=1/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	+	0.6312	63.12%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5206	52.06%
OATP2B1 inhibitior	-	0.8385	83.85%
OATP1B1 inhibitior	+	0.9605	96.05%
OATP1B3 inhibitior	+	0.9260	92.60%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.9540	95.40%
P-glycoprotein inhibitior	-	0.9704	97.04%
P-glycoprotein substrate	-	0.8640	86.40%
CYP3A4 substrate	-	0.5975	59.75%
CYP2C9 substrate	-	0.8090	80.90%
CYP2D6 substrate	-	0.7021	70.21%
CYP3A4 inhibition	-	0.8482	84.82%
CYP2C9 inhibition	-	0.9173	91.73%
CYP2C19 inhibition	-	0.8559	85.59%
CYP2D6 inhibition	-	0.9258	92.58%
CYP1A2 inhibition	-	0.8078	80.78%
CYP2C8 inhibition	-	0.9778	97.78%
CYP inhibitory promiscuity	-	0.8831	88.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8328	83.28%
Carcinogenicity (trinary)	Non-required	0.6267	62.67%
Eye corrosion	-	0.8214	82.14%
Eye irritation	+	0.9633	96.33%
Skin irritation	+	0.7202	72.02%
Skin corrosion	-	0.8963	89.63%
Ames mutagenesis	-	0.8554	85.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6811	68.11%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	+	0.8335	83.35%
Respiratory toxicity	-	0.7778	77.78%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.8625	86.25%
Nephrotoxicity	+	0.5547	55.47%
Acute Oral Toxicity (c)	III	0.7959	79.59%
Estrogen receptor binding	-	0.9151	91.51%
Androgen receptor binding	-	0.8492	84.92%
Thyroid receptor binding	-	0.7966	79.66%
Glucocorticoid receptor binding	-	0.7448	74.48%
Aromatase binding	-	0.8487	84.87%
PPAR gamma	-	0.8716	87.16%
Honey bee toxicity	-	0.8532	85.32%
Biodegradation	+	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9822	98.22%

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	93.12%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.83%	97.25%
CHEMBL1951	P21397	Monoamine oxidase A	88.56%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.96%	97.09%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	80.61%	98.46%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.52%	92.94%

Plants that contains it

• Acicarpha tribuloides
• Aconitum palmatum
• Aconitum rotundifolium
• Aniba rosaeodora
• Ariocarpus fissuratus
• Bidens tripartita
• Bursera simaruba
• Carpesium faberi
• Cephalaria leucantha
• Cheirolophus arbutifolius
• Cissus quadrangularis
• Citrus hystrix
• Cleome trachysperma
• Clinopodium serpyllifolium subsp. fruticosum
• Codonopsis cordifolioidea
• Corydalis sewerzowi
• Corymbia citriodora
• Culcitium albifolium
• Dahlstedtia pentaphylla
• Delphinium denudatum
• Diplacus aurantiacus
• Ericameria laricifolia
• Eucalyptus brassiana
• Flemingia prostrata
• Genista sessilifolia
• Gomphostemma parviflorum
• Hasteola robusta
• Hippobroma longiflora
• Hypericum japonicum
• Juniperus communis
• Litsea cubeba
• Loranthus longiflorus
• Melaleuca glauca
• Mentha arvensis
• Mentha canadensis
• Mentha longifolia subsp. longifolia
• Mentha pulegium
• Onoseris alata
• Ormosia fordiana
• Orthosiphon wulfenioides
• Piper acutifolium
• Piper cubeba
• Podocarpus elatus
• Polygala senega
• Psilotum nudum
• Solanum scabrum
• Staehelina fruticosa
• Stevia rebaudiana
• Teucrium kotschyanum
• Trapa natans var. bispinosa
• Vachellia karroo
• Vellozia streptophylla
• Xyris indica
• Zanthoxylum bungeanum
• Zanthoxylum schinifolium

Cross-Links

• PubChem: 170833
• NPASS: NPC67508
• LOTUS: LTS0040417
• wikiData: Q2103922