(2Z,4E)-5-[(1R,3S)-1,3-dihydroxy-2,2-dimethyl-6-methylidenecyclohexyl]-3-methylpenta-2,4-dienoic acid

Details

• Internal ID: 0aa47e0e-5553-4df7-b04e-f68ccf88751a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2Z,4E)-5-[(1R,3S)-1,3-dihydroxy-2,2-dimethyl-6-methylidenecyclohexyl]-3-methylpenta-2,4-dienoic acid
• SMILES (Canonical): CC(=CC(=O)O)C=CC1(C(=C)CCC(C1(C)C)O)O
• SMILES (Isomeric): C/C(=C/C(=O)O)/C=C/[C@]1(C(=C)CC[C@@H](C1(C)C)O)O
• InChI: InChI=1S/C15H22O4/c1-10(9-13(17)18)7-8-15(19)11(2)5-6-12(16)14(15,3)4/h7-9,12,16,19H,2,5-6H2,1,3-4H3,(H,17,18)/b8-7+,10-9-/t12-,15+/m0/s1
• InChI Key: PIJGLJJHMTWEIU-FZIBRQLCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.04
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9531	95.31%
Caco-2	+	0.5831	58.31%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7598	75.98%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.9186	91.86%
OATP1B3 inhibitior	+	0.8369	83.69%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.6791	67.91%
P-glycoprotein inhibitior	-	0.9751	97.51%
P-glycoprotein substrate	-	0.8711	87.11%
CYP3A4 substrate	+	0.5945	59.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9052	90.52%
CYP3A4 inhibition	-	0.8625	86.25%
CYP2C9 inhibition	-	0.7377	73.77%
CYP2C19 inhibition	-	0.8091	80.91%
CYP2D6 inhibition	-	0.9318	93.18%
CYP1A2 inhibition	-	0.8968	89.68%
CYP2C8 inhibition	-	0.8724	87.24%
CYP inhibitory promiscuity	-	0.9243	92.43%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8953	89.53%
Carcinogenicity (trinary)	Non-required	0.6744	67.44%
Eye corrosion	-	0.9809	98.09%
Eye irritation	-	0.8305	83.05%
Skin irritation	+	0.5728	57.28%
Skin corrosion	-	0.8965	89.65%
Ames mutagenesis	-	0.7054	70.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5718	57.18%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	+	0.5496	54.96%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.4548	45.48%
Acute Oral Toxicity (c)	III	0.4794	47.94%
Estrogen receptor binding	-	0.5217	52.17%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.6243	62.43%
Glucocorticoid receptor binding	-	0.4844	48.44%
Aromatase binding	+	0.5340	53.40%
PPAR gamma	+	0.7006	70.06%
Honey bee toxicity	-	0.9118	91.18%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9454	94.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2061	P19793	Retinoid X receptor alpha	94.21%	91.67%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.67%	91.11%
CHEMBL1870	P28702	Retinoid X receptor beta	90.15%	95.00%
CHEMBL221	P23219	Cyclooxygenase-1	89.08%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.38%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	86.61%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.69%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.05%	95.56%
CHEMBL2004	P48443	Retinoid X receptor gamma	84.76%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	83.15%	83.82%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.34%	89.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 10423038
• LOTUS: LTS0043653
• wikiData: Q105209541