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

Details

• Internal ID: b6f03960-56aa-4c55-ba74-181cf2cc45c4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2E,4E)-5-[(1S,3S)-3-hydroxy-2,2-dimethyl-6-methylidenecyclohexyl]-3-methylpenta-2,4-dienoic acid
• SMILES (Canonical): CC(=CC(=O)O)C=CC1C(=C)CCC(C1(C)C)O
• SMILES (Isomeric): C/C(=C\C(=O)O)/C=C/[C@H]1C(=C)CC[C@@H](C1(C)C)O
• InChI: InChI=1S/C15H22O3/c1-10(9-14(17)18)5-7-12-11(2)6-8-13(16)15(12,3)4/h5,7,9,12-13,16H,2,6,8H2,1,3-4H3,(H,17,18)/b7-5+,10-9+/t12-,13-/m0/s1
• InChI Key: XDRODHLVFJLYRJ-OIKSQQPJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.93
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9935	99.35%
Caco-2	+	0.6462	64.62%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8330	83.30%
OATP2B1 inhibitior	-	0.8614	86.14%
OATP1B1 inhibitior	+	0.9105	91.05%
OATP1B3 inhibitior	+	0.9252	92.52%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.8204	82.04%
P-glycoprotein inhibitior	-	0.9653	96.53%
P-glycoprotein substrate	-	0.8377	83.77%
CYP3A4 substrate	+	0.5787	57.87%
CYP2C9 substrate	-	0.8100	81.00%
CYP2D6 substrate	-	0.9082	90.82%
CYP3A4 inhibition	-	0.8720	87.20%
CYP2C9 inhibition	-	0.8790	87.90%
CYP2C19 inhibition	-	0.9067	90.67%
CYP2D6 inhibition	-	0.9269	92.69%
CYP1A2 inhibition	-	0.9347	93.47%
CYP2C8 inhibition	-	0.8245	82.45%
CYP inhibitory promiscuity	-	0.9477	94.77%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8343	83.43%
Carcinogenicity (trinary)	Non-required	0.6417	64.17%
Eye corrosion	-	0.9754	97.54%
Eye irritation	-	0.9393	93.93%
Skin irritation	+	0.6508	65.08%
Skin corrosion	-	0.9149	91.49%
Ames mutagenesis	-	0.8554	85.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.3860	38.60%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	+	0.7798	77.98%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.5716	57.16%
Acute Oral Toxicity (c)	III	0.7591	75.91%
Estrogen receptor binding	-	0.6360	63.60%
Androgen receptor binding	-	0.6561	65.61%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.6130	61.30%
Aromatase binding	-	0.5354	53.54%
PPAR gamma	+	0.6552	65.52%
Honey bee toxicity	-	0.8383	83.83%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9449	94.49%

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	94.25%	91.67%
CHEMBL221	P23219	Cyclooxygenase-1	92.05%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.91%	91.11%
CHEMBL1870	P28702	Retinoid X receptor beta	90.99%	95.00%
CHEMBL340	P08684	Cytochrome P450 3A4	88.72%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.70%	96.09%
CHEMBL2004	P48443	Retinoid X receptor gamma	86.58%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.13%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	83.97%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.40%	95.56%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 14218556
• LOTUS: LTS0195838
• wikiData: Q105326017