[(1S,4R,4aR,8aS)-4-acetyloxy-5,5,8a-trimethyl-1-[(E)-3-oxobut-1-enyl]-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]methyl acetate

Details

• Internal ID: 5b32f036-31be-4636-b26b-e5eb5fc354c0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1S,4R,4aR,8aS)-4-acetyloxy-5,5,8a-trimethyl-1-[(E)-3-oxobut-1-enyl]-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]methyl acetate
• SMILES (Canonical): CC(=O)C=CC1C(=CC(C2C1(CCCC2(C)C)C)OC(=O)C)COC(=O)C
• SMILES (Isomeric): CC(=O)/C=C/[C@@H]1C(=C[C@H]([C@H]2[C@]1(CCCC2(C)C)C)OC(=O)C)COC(=O)C
• InChI: InChI=1S/C22H32O5/c1-14(23)8-9-18-17(13-26-15(2)24)12-19(27-16(3)25)20-21(4,5)10-7-11-22(18,20)6/h8-9,12,18-20H,7,10-11,13H2,1-6H3/b9-8+/t18-,19-,20-,22+/m1/s1
• InChI Key: VWSIRBHDCATCTC-SDMLLVAWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₅
• Molecular Weight: 376.50 g/mol
• Exact Mass: 376.22497412 g/mol
• Topological Polar Surface Area (TPSA): 69.70 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 4.02
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	+	0.6732	67.32%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8341	83.41%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8488	84.88%
OATP1B3 inhibitior	+	0.8168	81.68%
MATE1 inhibitior	-	0.6400	64.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.7220	72.20%
P-glycoprotein inhibitior	+	0.7114	71.14%
P-glycoprotein substrate	-	0.7562	75.62%
CYP3A4 substrate	+	0.6454	64.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9127	91.27%
CYP3A4 inhibition	-	0.8592	85.92%
CYP2C9 inhibition	-	0.6241	62.41%
CYP2C19 inhibition	-	0.7232	72.32%
CYP2D6 inhibition	-	0.8839	88.39%
CYP1A2 inhibition	-	0.7024	70.24%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.6425	64.25%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5514	55.14%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9414	94.14%
Skin irritation	-	0.6136	61.36%
Skin corrosion	-	0.9768	97.68%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4664	46.64%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.6851	68.51%
skin sensitisation	-	0.5600	56.00%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5080	50.80%
Acute Oral Toxicity (c)	III	0.7835	78.35%
Estrogen receptor binding	-	0.4924	49.24%
Androgen receptor binding	-	0.5225	52.25%
Thyroid receptor binding	+	0.6293	62.93%
Glucocorticoid receptor binding	+	0.7936	79.36%
Aromatase binding	-	0.6401	64.01%
PPAR gamma	+	0.6364	63.64%
Honey bee toxicity	-	0.7903	79.03%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	97.89%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.53%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.14%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.80%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.24%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.88%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	81.49%	91.19%
CHEMBL2581	P07339	Cathepsin D	81.08%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.87%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	80.06%	83.82%

Plants that contains it

• Rutidosis murchisonii

Cross-Links

• PubChem: 162955309
• LOTUS: LTS0063331
• wikiData: Q105298251