(2Z)-2-[(4aR,8R,8aR)-8-hydroxy-4a,8-dimethyl-3-oxo-1,4,5,6,7,8a-hexahydronaphthalen-2-ylidene]propanoic acid

Details

• Internal ID: b176d142-58ed-4286-ad1a-e1e514d50884
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2Z)-2-[(4aR,8R,8aR)-8-hydroxy-4a,8-dimethyl-3-oxo-1,4,5,6,7,8a-hexahydronaphthalen-2-ylidene]propanoic acid
• SMILES (Canonical): CC(=C1CC2C(CCCC2(C)O)(CC1=O)C)C(=O)O
• SMILES (Isomeric): C/C(=C/1\C[C@@H]2[C@](CCC[C@@]2(C)O)(CC1=O)C)/C(=O)O
• InChI: InChI=1S/C15H22O4/c1-9(13(17)18)10-7-12-14(2,8-11(10)16)5-4-6-15(12,3)19/h12,19H,4-8H2,1-3H3,(H,17,18)/b10-9-/t12-,14-,15-/m1/s1
• InChI Key: CYQHVFHYCZDSIE-KGJNJRFFSA-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): 74.60 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.31
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9897	98.97%
Caco-2	+	0.6895	68.95%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8519	85.19%
OATP2B1 inhibitior	-	0.8528	85.28%
OATP1B1 inhibitior	+	0.9053	90.53%
OATP1B3 inhibitior	-	0.2952	29.52%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5842	58.42%
BSEP inhibitior	-	0.8217	82.17%
P-glycoprotein inhibitior	-	0.9143	91.43%
P-glycoprotein substrate	-	0.8816	88.16%
CYP3A4 substrate	+	0.5468	54.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9197	91.97%
CYP3A4 inhibition	-	0.7510	75.10%
CYP2C9 inhibition	-	0.9561	95.61%
CYP2C19 inhibition	-	0.9665	96.65%
CYP2D6 inhibition	-	0.9534	95.34%
CYP1A2 inhibition	-	0.9227	92.27%
CYP2C8 inhibition	-	0.9383	93.83%
CYP inhibitory promiscuity	-	0.9674	96.74%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6564	65.64%
Eye corrosion	-	0.9955	99.55%
Eye irritation	-	0.5090	50.90%
Skin irritation	+	0.6993	69.93%
Skin corrosion	-	0.9575	95.75%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6601	66.01%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.5166	51.66%
skin sensitisation	-	0.5323	53.23%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6669	66.69%
Acute Oral Toxicity (c)	III	0.7243	72.43%
Estrogen receptor binding	+	0.5694	56.94%
Androgen receptor binding	-	0.5091	50.91%
Thyroid receptor binding	+	0.5810	58.10%
Glucocorticoid receptor binding	+	0.5941	59.41%
Aromatase binding	-	0.5797	57.97%
PPAR gamma	+	0.6463	64.63%
Honey bee toxicity	-	0.9408	94.08%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9961	99.61%

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	91.94%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.88%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.07%	97.25%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	89.48%	93.04%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	88.76%	85.30%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.28%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.79%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	84.15%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.93%	96.09%
CHEMBL1902	P62942	FK506-binding protein 1A	83.07%	97.05%
CHEMBL3524	P56524	Histone deacetylase 4	81.95%	92.97%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.67%	93.03%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 101611296
• LOTUS: LTS0055935
• wikiData: Q104972497