[(1R,2S,4aR,8S,8aR)-2-acetyloxy-3,8-dimethyl-6-oxo-5-propan-2-ylidene-1,2,4a,7,8,8a-hexahydronaphthalen-1-yl] acetate

Details

• Internal ID: 3f249ab1-2f24-44dd-88b3-186248f96aa3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1R,2S,4aR,8S,8aR)-2-acetyloxy-3,8-dimethyl-6-oxo-5-propan-2-ylidene-1,2,4a,7,8,8a-hexahydronaphthalen-1-yl] acetate
• SMILES (Canonical): CC1CC(=O)C(=C(C)C)C2C1C(C(C(=C2)C)OC(=O)C)OC(=O)C
• SMILES (Isomeric): C[C@H]1CC(=O)C(=C(C)C)[C@H]2[C@@H]1[C@H]([C@H](C(=C2)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C19H26O5/c1-9(2)16-14-7-11(4)18(23-12(5)20)19(24-13(6)21)17(14)10(3)8-15(16)22/h7,10,14,17-19H,8H2,1-6H3/t10-,14-,17+,18-,19+/m0/s1
• InChI Key: GIHHWTGPMYARCT-RBVNUJLISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₅
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.17802393 g/mol
• Topological Polar Surface Area (TPSA): 69.70 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.99
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9941	99.41%
Caco-2	+	0.8291	82.91%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7698	76.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9041	90.41%
OATP1B3 inhibitior	+	0.9387	93.87%
MATE1 inhibitior	+	0.6000	60.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.5726	57.26%
P-glycoprotein inhibitior	-	0.5104	51.04%
P-glycoprotein substrate	-	0.7715	77.15%
CYP3A4 substrate	+	0.5573	55.73%
CYP2C9 substrate	-	0.8058	80.58%
CYP2D6 substrate	-	0.9017	90.17%
CYP3A4 inhibition	-	0.6737	67.37%
CYP2C9 inhibition	-	0.7465	74.65%
CYP2C19 inhibition	-	0.7558	75.58%
CYP2D6 inhibition	-	0.8924	89.24%
CYP1A2 inhibition	-	0.7908	79.08%
CYP2C8 inhibition	-	0.8827	88.27%
CYP inhibitory promiscuity	-	0.6735	67.35%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8886	88.86%
Carcinogenicity (trinary)	Non-required	0.5060	50.60%
Eye corrosion	-	0.9818	98.18%
Eye irritation	-	0.6267	62.67%
Skin irritation	-	0.7931	79.31%
Skin corrosion	-	0.9839	98.39%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6627	66.27%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.7566	75.66%
skin sensitisation	+	0.5808	58.08%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.5714	57.14%
Acute Oral Toxicity (c)	III	0.5012	50.12%
Estrogen receptor binding	+	0.5344	53.44%
Androgen receptor binding	-	0.5506	55.06%
Thyroid receptor binding	-	0.6410	64.10%
Glucocorticoid receptor binding	-	0.6085	60.85%
Aromatase binding	-	0.7906	79.06%
PPAR gamma	-	0.5917	59.17%
Honey bee toxicity	-	0.8049	80.49%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5250	52.50%
Fish aquatic toxicity	+	0.9903	99.03%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	94.70%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.25%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.84%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.97%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.04%	96.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.72%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	82.54%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.61%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.11%	94.45%

Plants that contains it

• Marsupella emarginata

Cross-Links

• PubChem: 15923268
• LOTUS: LTS0057595
• wikiData: Q105008979