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

Details

• Internal ID: 7c55166e-8bd0-4585-9e79-c303af6b5c5a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1S,2R,4aR,8aR)-1-acetyloxy-1,4a-dimethyl-6-oxo-7-propan-2-ylidene-2,3,4,5,8,8a-hexahydronaphthalen-2-yl] 2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CCC2(CC(=O)C(=C(C)C)CC2C1(C)OC(=O)C)C
• SMILES (Isomeric): CC=C(C)C(=O)O[C@@H]1CC[C@@]2(CC(=O)C(=C(C)C)C[C@H]2[C@]1(C)OC(=O)C)C
• InChI: InChI=1S/C22H32O5/c1-8-14(4)20(25)26-19-9-10-21(6)12-17(24)16(13(2)3)11-18(21)22(19,7)27-15(5)23/h8,18-19H,9-12H2,1-7H3/t18-,19-,21-,22+/m1/s1
• InChI Key: DLLCYEYTXHAUTA-CZAYHTPWSA-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: 4.20
• Atomic LogP (AlogP): 4.30
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	+	0.7520	75.20%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8422	84.22%
OATP2B1 inhibitior	-	0.8636	86.36%
OATP1B1 inhibitior	+	0.8865	88.65%
OATP1B3 inhibitior	+	0.9078	90.78%
MATE1 inhibitior	+	0.7800	78.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7360	73.60%
P-glycoprotein inhibitior	+	0.6512	65.12%
P-glycoprotein substrate	-	0.7894	78.94%
CYP3A4 substrate	+	0.6546	65.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9075	90.75%
CYP3A4 inhibition	-	0.7028	70.28%
CYP2C9 inhibition	-	0.8853	88.53%
CYP2C19 inhibition	-	0.8250	82.50%
CYP2D6 inhibition	-	0.9482	94.82%
CYP1A2 inhibition	-	0.9075	90.75%
CYP2C8 inhibition	-	0.7430	74.30%
CYP inhibitory promiscuity	-	0.9049	90.49%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9343	93.43%
Carcinogenicity (trinary)	Non-required	0.5999	59.99%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.7506	75.06%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9748	97.48%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7370	73.70%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.5030	50.30%
skin sensitisation	+	0.4830	48.30%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.6888	68.88%
Acute Oral Toxicity (c)	III	0.5680	56.80%
Estrogen receptor binding	+	0.7990	79.90%
Androgen receptor binding	+	0.5512	55.12%
Thyroid receptor binding	+	0.6109	61.09%
Glucocorticoid receptor binding	+	0.5539	55.39%
Aromatase binding	-	0.5978	59.78%
PPAR gamma	+	0.6738	67.38%
Honey bee toxicity	-	0.7347	73.47%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
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
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.46%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.88%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.87%	91.11%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	94.67%	85.30%
CHEMBL4040	P28482	MAP kinase ERK2	91.23%	83.82%
CHEMBL2581	P07339	Cathepsin D	91.22%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.18%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.91%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	88.56%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.06%	89.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	87.29%	80.96%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.12%	93.00%
CHEMBL284	P27487	Dipeptidyl peptidase IV	86.73%	95.69%
CHEMBL299	P17252	Protein kinase C alpha	86.14%	98.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.65%	99.23%
CHEMBL1937	Q92769	Histone deacetylase 2	85.15%	94.75%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.25%	93.04%
CHEMBL3524	P56524	Histone deacetylase 4	82.35%	92.97%
CHEMBL1902	P62942	FK506-binding protein 1A	81.09%	97.05%
CHEMBL217	P14416	Dopamine D2 receptor	80.42%	95.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.40%	92.94%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.23%	92.62%

Plants that contains it

• Laggera tomentosa

Cross-Links

• PubChem: 162876297
• LOTUS: LTS0003556
• wikiData: Q104984440