(6-hydroxy-5a,9-dimethyl-3-methylidene-2-oxo-4,5,6,7,8,9,9a,9b-octahydro-3aH-benzo[g][1]benzofuran-4-yl) 2,3-dihydroxy-2-methylbutanoate

Details

• Internal ID: 00824c19-b389-4509-ad04-d7597082be89
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (6-hydroxy-5a,9-dimethyl-3-methylidene-2-oxo-4,5,6,7,8,9,9a,9b-octahydro-3aH-benzo[g][1]benzofuran-4-yl) 2,3-dihydroxy-2-methylbutanoate
• SMILES (Canonical): CC1CCC(C2(C1C3C(C(C2)OC(=O)C(C)(C(C)O)O)C(=C)C(=O)O3)C)O
• SMILES (Isomeric): CC1CCC(C2(C1C3C(C(C2)OC(=O)C(C)(C(C)O)O)C(=C)C(=O)O3)C)O
• InChI: InChI=1S/C20H30O7/c1-9-6-7-13(22)19(4)8-12(26-18(24)20(5,25)11(3)21)14-10(2)17(23)27-16(14)15(9)19/h9,11-16,21-22,25H,2,6-8H2,1,3-5H3
• InChI Key: VUBMWJMJRVICBE-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₇
• Molecular Weight: 382.40 g/mol
• Exact Mass: 382.19915329 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 0.94
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9807	98.07%
Caco-2	-	0.5899	58.99%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7282	72.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8742	87.42%
OATP1B3 inhibitior	+	0.8337	83.37%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6803	68.03%
BSEP inhibitior	-	0.9248	92.48%
P-glycoprotein inhibitior	-	0.6900	69.00%
P-glycoprotein substrate	-	0.5549	55.49%
CYP3A4 substrate	+	0.6880	68.80%
CYP2C9 substrate	-	0.8144	81.44%
CYP2D6 substrate	-	0.8662	86.62%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.8152	81.52%
CYP2C19 inhibition	-	0.8211	82.11%
CYP2D6 inhibition	-	0.9543	95.43%
CYP1A2 inhibition	-	0.7011	70.11%
CYP2C8 inhibition	-	0.5941	59.41%
CYP inhibitory promiscuity	-	0.9675	96.75%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5574	55.74%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9443	94.43%
Skin irritation	+	0.6019	60.19%
Skin corrosion	-	0.9050	90.50%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6489	64.89%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.6783	67.83%
skin sensitisation	-	0.8243	82.43%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.5431	54.31%
Acute Oral Toxicity (c)	I	0.3701	37.01%
Estrogen receptor binding	+	0.8259	82.59%
Androgen receptor binding	+	0.6127	61.27%
Thyroid receptor binding	+	0.6460	64.60%
Glucocorticoid receptor binding	+	0.6860	68.60%
Aromatase binding	+	0.6880	68.80%
PPAR gamma	+	0.5788	57.88%
Honey bee toxicity	-	0.7302	73.02%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9960	99.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.76%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.55%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.36%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.58%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.06%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	94.58%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.87%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.14%	96.09%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	90.03%	92.88%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.90%	93.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.46%	96.47%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.68%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.35%	86.33%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	86.96%	94.97%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.67%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.22%	97.09%
CHEMBL5028	O14672	ADAM10	85.17%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.88%	99.23%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	84.74%	97.33%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	84.71%	95.71%
CHEMBL2996	Q05655	Protein kinase C delta	83.95%	97.79%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.11%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.06%	91.07%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.96%	96.77%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.30%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.58%	89.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.51%	93.03%

Plants that contains it

• Tithonia rotundifolia

Cross-Links

• PubChem: 101288306
• LOTUS: LTS0263490
• wikiData: Q105293176