[(4S,4aS,5S,8aS,9aS)-8a-hydroxy-9a-methoxy-3,4a,5-trimethyl-2-oxo-4,5,6,7,8,9-hexahydrobenzo[f][1]benzofuran-4-yl] (2R)-2-methylbutanoate

Details

• Internal ID: 43707110-0ff4-436d-83a2-33a7ecb8ab9a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(4S,4aS,5S,8aS,9aS)-8a-hydroxy-9a-methoxy-3,4a,5-trimethyl-2-oxo-4,5,6,7,8,9-hexahydrobenzo[f][1]benzofuran-4-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C2=C(C(=O)OC2(CC3(C1(C(CCC3)C)C)O)OC)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@@H]1C2=C(C(=O)O[C@]2(C[C@@]3([C@]1([C@H](CCC3)C)C)O)OC)C
• InChI: InChI=1S/C21H32O6/c1-7-12(2)17(22)26-16-15-14(4)18(23)27-21(15,25-6)11-20(24)10-8-9-13(3)19(16,20)5/h12-13,16,24H,7-11H2,1-6H3/t12-,13+,16-,19+,20+,21+/m1/s1
• InChI Key: UDVLOCQBYDZUGP-QHNFPCJYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₆
• Molecular Weight: 380.50 g/mol
• Exact Mass: 380.21988874 g/mol
• Topological Polar Surface Area (TPSA): 82.10 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.12
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9957	99.57%
Caco-2	+	0.8080	80.80%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7471	74.71%
OATP2B1 inhibitior	-	0.8609	86.09%
OATP1B1 inhibitior	+	0.8469	84.69%
OATP1B3 inhibitior	+	0.9381	93.81%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.5889	58.89%
P-glycoprotein inhibitior	-	0.5329	53.29%
P-glycoprotein substrate	-	0.7006	70.06%
CYP3A4 substrate	+	0.6521	65.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9041	90.41%
CYP3A4 inhibition	+	0.6913	69.13%
CYP2C9 inhibition	-	0.7440	74.40%
CYP2C19 inhibition	-	0.7854	78.54%
CYP2D6 inhibition	-	0.9385	93.85%
CYP1A2 inhibition	-	0.7488	74.88%
CYP2C8 inhibition	-	0.6011	60.11%
CYP inhibitory promiscuity	-	0.7854	78.54%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5674	56.74%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.8369	83.69%
Skin irritation	+	0.6148	61.48%
Skin corrosion	-	0.9255	92.55%
Ames mutagenesis	-	0.7054	70.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5068	50.68%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.5835	58.35%
skin sensitisation	-	0.8764	87.64%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.7044	70.44%
Acute Oral Toxicity (c)	II	0.3473	34.73%
Estrogen receptor binding	+	0.7977	79.77%
Androgen receptor binding	+	0.7067	70.67%
Thyroid receptor binding	+	0.6222	62.22%
Glucocorticoid receptor binding	+	0.6919	69.19%
Aromatase binding	+	0.6331	63.31%
PPAR gamma	+	0.5934	59.34%
Honey bee toxicity	-	0.8275	82.75%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9931	99.31%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.62%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.64%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.60%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.61%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.04%	95.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	91.84%	96.38%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.84%	96.47%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.29%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.76%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.64%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.53%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.48%	99.23%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.06%	95.71%
CHEMBL1937	Q92769	Histone deacetylase 2	84.09%	94.75%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.88%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	82.83%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.25%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.25%	91.07%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.21%	93.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.38%	86.33%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.22%	82.69%

Plants that contains it

• Ligularia sagitta

Cross-Links

• PubChem: 162961523
• LOTUS: LTS0157687
• wikiData: Q105270533