(E)-5-[(1S,4aR,6R,8aS)-6-hydroxy-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid

Details

• Internal ID: 6ea49081-8500-471a-98d3-46710fd2a9f6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (E)-5-[(1S,4aR,6R,8aS)-6-hydroxy-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid
• InChI: InChI=1S/C20H32O3/c1-13(12-18(22)23)6-8-15-14(2)7-9-16-19(3,4)17(21)10-11-20(15,16)5/h7,12,15-17,21H,6,8-11H2,1-5H3,(H,22,23)/b13-12+/t15-,16-,17+,20-/m0/s1
• InChI Key: KFWGTOAALSCZHD-MILOQCLBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.50 g/mol
• Exact Mass: 320.23514488 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.57
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9965	99.65%
Caco-2	+	0.6771	67.71%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8401	84.01%
OATP2B1 inhibitior	-	0.8632	86.32%
OATP1B1 inhibitior	+	0.8893	88.93%
OATP1B3 inhibitior	+	0.9441	94.41%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.6417	64.17%
P-glycoprotein inhibitior	-	0.8324	83.24%
P-glycoprotein substrate	-	0.8345	83.45%
CYP3A4 substrate	+	0.6296	62.96%
CYP2C9 substrate	-	0.7928	79.28%
CYP2D6 substrate	-	0.9050	90.50%
CYP3A4 inhibition	-	0.7599	75.99%
CYP2C9 inhibition	-	0.9210	92.10%
CYP2C19 inhibition	-	0.9012	90.12%
CYP2D6 inhibition	-	0.9572	95.72%
CYP1A2 inhibition	-	0.9501	95.01%
CYP2C8 inhibition	-	0.7639	76.39%
CYP inhibitory promiscuity	-	0.8315	83.15%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6612	66.12%
Eye corrosion	-	0.9957	99.57%
Eye irritation	-	0.8628	86.28%
Skin irritation	+	0.6034	60.34%
Skin corrosion	-	0.9695	96.95%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7521	75.21%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.6620	66.20%
skin sensitisation	+	0.5964	59.64%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.8251	82.51%
Acute Oral Toxicity (c)	III	0.7784	77.84%
Estrogen receptor binding	+	0.6478	64.78%
Androgen receptor binding	+	0.5589	55.89%
Thyroid receptor binding	+	0.6385	63.85%
Glucocorticoid receptor binding	+	0.7009	70.09%
Aromatase binding	+	0.5380	53.80%
PPAR gamma	+	0.7152	71.52%
Honey bee toxicity	-	0.8697	86.97%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9954	99.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	93.75%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.06%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.24%	96.09%
CHEMBL2581	P07339	Cathepsin D	86.80%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.58%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	85.23%	83.82%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.63%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.67%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.68%	94.45%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.40%	94.62%

Plants that contains it

• Ericameria nauseosa var. nauseosa

Cross-Links

• PubChem: 162969783
• LOTUS: LTS0174387
• wikiData: Q105140582