rel-(+)-(1R,4S,6S)-5-Methylene-6-(1-methylethenyl)-2-cyclohexene-1,4-diol

Details

• Internal ID: 431002a4-1d43-473c-830a-f432b19927c7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Monocyclic monoterpenoids
• IUPAC Name: (1R,4S,6S)-5-methylidene-6-prop-1-en-2-ylcyclohex-2-ene-1,4-diol
• InChI: InChI=1S/C10H14O2/c1-6(2)10-7(3)8(11)4-5-9(10)12/h4-5,8-12H,1,3H2,2H3/t8-,9+,10-/m0/s1
• InChI Key: NEMBFIOCFSUBLI-AEJSXWLSSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22 g/mol
• Exact Mass: 166.099379685 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.03
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 32151-10-3
• (1R,4S,6S)-5-methylidene-6-prop-1-en-2-ylcyclohex-2-ene-1,4-diol
• DTXSID00185942
• (1S,4R,5S)-5-isopropenyl-6-methylene-cyclohex-2-ene-1,4-diol
• RefChem:930610
• DTXCID40108433
• rel-(+)-(1R,4S,6S)-5-Methylene-6-(1-methylethenyl)-2-cyclohexene-1,4-diol
• Piquerol B
• AC1L4PZ8
• AC1Q59G4
• CHEBI:8244
• C09887
• Q27108014
• (1R,4S,6S)-5-Methylidene-6-(prop-1-en-2-yl)cyclohex-2-ene-1,4-diol
• 2-Cyclohexene-1,4-diol, 5-methylene-6-(1-methylethenyl)-, (1alpha,4alpha,6alpha)-(+)-
• 2-Cyclohexene-1,4-diol, 5-methylene-6-(1-methylethenyl)-, (1.alpha.,4.alpha.,6.alpha.)-(+)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9936	99.36%
Caco-2	-	0.8084	80.84%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6766	67.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9344	93.44%
OATP1B3 inhibitior	+	0.9651	96.51%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9829	98.29%
P-glycoprotein inhibitior	-	0.9746	97.46%
P-glycoprotein substrate	-	0.9247	92.47%
CYP3A4 substrate	-	0.5956	59.56%
CYP2C9 substrate	-	0.8006	80.06%
CYP2D6 substrate	-	0.7623	76.23%
CYP3A4 inhibition	-	0.7496	74.96%
CYP2C9 inhibition	-	0.7992	79.92%
CYP2C19 inhibition	-	0.6579	65.79%
CYP2D6 inhibition	-	0.9316	93.16%
CYP1A2 inhibition	-	0.7598	75.98%
CYP2C8 inhibition	-	0.9673	96.73%
CYP inhibitory promiscuity	-	0.5423	54.23%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.5775	57.75%
Carcinogenicity (trinary)	Non-required	0.6266	62.66%
Eye corrosion	+	0.6357	63.57%
Eye irritation	+	0.7117	71.17%
Skin irritation	+	0.7082	70.82%
Skin corrosion	+	0.5678	56.78%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6882	68.82%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	+	0.9182	91.82%
Respiratory toxicity	-	0.7111	71.11%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.8625	86.25%
Nephrotoxicity	+	0.6159	61.59%
Acute Oral Toxicity (c)	III	0.6026	60.26%
Estrogen receptor binding	-	0.8448	84.48%
Androgen receptor binding	-	0.9064	90.64%
Thyroid receptor binding	-	0.7545	75.45%
Glucocorticoid receptor binding	-	0.8617	86.17%
Aromatase binding	-	0.8547	85.47%
PPAR gamma	-	0.8177	81.77%
Honey bee toxicity	-	0.8380	83.80%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8509	85.09%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.06%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.17%	96.09%
CHEMBL2581	P07339	Cathepsin D	84.37%	98.95%

Plants that contains it

• Piqueria trinervia

Cross-Links

• PubChem: 161734
• LOTUS: LTS0226332
• wikiData: Q27108014