[4,4a-bis(acetyloxymethyl)-4,5-dihydroxy-8-[2-hydroxy-2-(5-oxo-2H-furan-3-yl)ethyl]-7,8-dimethyl-2,3,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] 2-methylbutanoate

Details

• Internal ID: d5a502b7-49ab-4911-9ede-5bed6ce9c969
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [4,4a-bis(acetyloxymethyl)-4,5-dihydroxy-8-[2-hydroxy-2-(5-oxo-2H-furan-3-yl)ethyl]-7,8-dimethyl-2,3,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] 2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1CCC(C2(C1C(C(CC2O)C)(C)CC(C3=CC(=O)OC3)O)COC(=O)C)(COC(=O)C)O
• SMILES (Isomeric): CCC(C)C(=O)OC1CCC(C2(C1C(C(CC2O)C)(C)CC(C3=CC(=O)OC3)O)COC(=O)C)(COC(=O)C)O
• InChI: InChI=1S/C29H44O11/c1-7-16(2)26(35)40-22-8-9-28(36,14-38-18(4)30)29(15-39-19(5)31)23(33)10-17(3)27(6,25(22)29)12-21(32)20-11-24(34)37-13-20/h11,16-17,21-23,25,32-33,36H,7-10,12-15H2,1-6H3
• InChI Key: PCXVVBLCDMHQIP-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₄O₁₁
• Molecular Weight: 568.70 g/mol
• Exact Mass: 568.28836222 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.84
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9712	97.12%
Caco-2	-	0.7516	75.16%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7654	76.54%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.8784	87.84%
OATP1B3 inhibitior	+	0.9657	96.57%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9837	98.37%
P-glycoprotein inhibitior	+	0.7185	71.85%
P-glycoprotein substrate	+	0.6857	68.57%
CYP3A4 substrate	+	0.6966	69.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9109	91.09%
CYP3A4 inhibition	-	0.6424	64.24%
CYP2C9 inhibition	-	0.8059	80.59%
CYP2C19 inhibition	-	0.8432	84.32%
CYP2D6 inhibition	-	0.9310	93.10%
CYP1A2 inhibition	-	0.9051	90.51%
CYP2C8 inhibition	+	0.5182	51.82%
CYP inhibitory promiscuity	-	0.7982	79.82%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5599	55.99%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9171	91.71%
Skin irritation	+	0.6142	61.42%
Skin corrosion	-	0.9422	94.22%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5056	50.56%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.5149	51.49%
skin sensitisation	-	0.9326	93.26%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.7915	79.15%
Acute Oral Toxicity (c)	III	0.4559	45.59%
Estrogen receptor binding	+	0.8288	82.88%
Androgen receptor binding	+	0.7492	74.92%
Thyroid receptor binding	-	0.5510	55.10%
Glucocorticoid receptor binding	+	0.7368	73.68%
Aromatase binding	+	0.7269	72.69%
PPAR gamma	+	0.6089	60.89%
Honey bee toxicity	-	0.7065	70.65%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9906	99.06%

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	98.84%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.34%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.21%	97.25%
CHEMBL2581	P07339	Cathepsin D	97.16%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.83%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.45%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.56%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.74%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	91.40%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.54%	89.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.79%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.77%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.73%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.71%	96.77%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.33%	94.80%
CHEMBL1937	Q92769	Histone deacetylase 2	83.12%	94.75%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.93%	90.08%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.91%	96.47%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.31%	89.50%
CHEMBL5028	O14672	ADAM10	81.92%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.41%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.98%	99.23%

Plants that contains it

• Ajuga nipponensis

Cross-Links

• PubChem: 14314162
• LOTUS: LTS0138842
• wikiData: Q105206151