[(4S,4aS,8aS)-4-hydroxy-4-(hydroxymethyl)-4a,8,8-trimethyl-5,6,7,8a-tetrahydro-1H-naphthalen-1-yl] (2E,4E,6E)-octa-2,4,6-trienoate

Details

• Internal ID: 958fd228-7835-421e-86c0-eb46f766e45a
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acid esters
• IUPAC Name: [(4S,4aS,8aS)-4-hydroxy-4-(hydroxymethyl)-4a,8,8-trimethyl-5,6,7,8a-tetrahydro-1H-naphthalen-1-yl] (2E,4E,6E)-octa-2,4,6-trienoate
• SMILES (Canonical): CC=CC=CC=CC(=O)OC1C=CC(C2(C1C(CCC2)(C)C)C)(CO)O
• SMILES (Isomeric): C/C=C/C=C/C=C/C(=O)OC1C=C[C@]([C@@]2([C@@H]1C(CCC2)(C)C)C)(CO)O
• InChI: InChI=1S/C22H32O4/c1-5-6-7-8-9-11-18(24)26-17-12-15-22(25,16-23)21(4)14-10-13-20(2,3)19(17)21/h5-9,11-12,15,17,19,23,25H,10,13-14,16H2,1-4H3/b6-5+,8-7+,11-9+/t17?,19-,21-,22+/m0/s1
• InChI Key: KKQZGPSOJHPQNX-ROIWYKLJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₄
• Molecular Weight: 360.50 g/mol
• Exact Mass: 360.23005950 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.71
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9753	97.53%
Caco-2	+	0.5121	51.21%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8934	89.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8112	81.12%
OATP1B3 inhibitior	+	0.8073	80.73%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7292	72.92%
BSEP inhibitior	+	0.6096	60.96%
P-glycoprotein inhibitior	-	0.7065	70.65%
P-glycoprotein substrate	-	0.7820	78.20%
CYP3A4 substrate	+	0.6463	64.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9115	91.15%
CYP3A4 inhibition	-	0.6903	69.03%
CYP2C9 inhibition	-	0.8520	85.20%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9589	95.89%
CYP1A2 inhibition	-	0.8156	81.56%
CYP2C8 inhibition	+	0.4458	44.58%
CYP inhibitory promiscuity	-	0.9432	94.32%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7583	75.83%
Eye corrosion	-	0.9938	99.38%
Eye irritation	-	0.9395	93.95%
Skin irritation	-	0.5972	59.72%
Skin corrosion	-	0.9713	97.13%
Ames mutagenesis	-	0.6170	61.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8540	85.40%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.5376	53.76%
skin sensitisation	-	0.8393	83.93%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7792	77.92%
Acute Oral Toxicity (c)	III	0.6820	68.20%
Estrogen receptor binding	+	0.8371	83.71%
Androgen receptor binding	+	0.5401	54.01%
Thyroid receptor binding	+	0.7403	74.03%
Glucocorticoid receptor binding	+	0.7708	77.08%
Aromatase binding	+	0.7665	76.65%
PPAR gamma	+	0.5807	58.07%
Honey bee toxicity	-	0.8700	87.00%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9872	98.72%

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	97.19%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.89%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.16%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.36%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.33%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.51%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.60%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.17%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.02%	82.69%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 46882364
• LOTUS: LTS0257203
• wikiData: Q105142324