[(1R,2R,4S,4aR,5R,6S,8aR)-4,6-diacetyloxy-1-[2-acetyloxy-2-(furan-3-yl)ethyl]-4a-(acetyloxymethyl)-2-methylspiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxirane]-1-yl]methyl acetate

Details

• Internal ID: d669619f-c7e0-453c-9471-d42f39907b62
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: [(1R,2R,4S,4aR,5R,6S,8aR)-4,6-diacetyloxy-1-[2-acetyloxy-2-(furan-3-yl)ethyl]-4a-(acetyloxymethyl)-2-methylspiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxirane]-1-yl]methyl acetate
• SMILES (Canonical): CC1CC(C2(C(C1(CC(C3=COC=C3)OC(=O)C)COC(=O)C)CCC(C24CO4)OC(=O)C)COC(=O)C)OC(=O)C
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@@]2([C@@H]([C@]1(CC(C3=COC=C3)OC(=O)C)COC(=O)C)CC[C@@H]([C@]24CO4)OC(=O)C)COC(=O)C)OC(=O)C
• InChI: InChI=1S/C30H40O12/c1-17-11-27(42-22(6)35)29(15-38-19(3)32)25(7-8-26(41-21(5)34)30(29)16-39-30)28(17,14-37-18(2)31)12-24(40-20(4)33)23-9-10-36-13-23/h9-10,13,17,24-27H,7-8,11-12,14-16H2,1-6H3/t17-,24?,25-,26+,27+,28-,29+,30-/m1/s1
• InChI Key: JBHVBDJOSXIXLV-ACVNANFXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₀O₁₂
• Molecular Weight: 592.60 g/mol
• Exact Mass: 592.25197671 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 3.46
• H-Bond Acceptor: 12
• H-Bond Donor: 0
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9754	97.54%
Caco-2	-	0.7656	76.56%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7632	76.32%
OATP2B1 inhibitior	-	0.8578	85.78%
OATP1B1 inhibitior	+	0.8373	83.73%
OATP1B3 inhibitior	+	0.9612	96.12%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.9861	98.61%
P-glycoprotein inhibitior	+	0.8333	83.33%
P-glycoprotein substrate	+	0.5444	54.44%
CYP3A4 substrate	+	0.6578	65.78%
CYP2C9 substrate	-	0.5936	59.36%
CYP2D6 substrate	-	0.8262	82.62%
CYP3A4 inhibition	-	0.6325	63.25%
CYP2C9 inhibition	-	0.7524	75.24%
CYP2C19 inhibition	-	0.6319	63.19%
CYP2D6 inhibition	-	0.9389	93.89%
CYP1A2 inhibition	-	0.8616	86.16%
CYP2C8 inhibition	+	0.5945	59.45%
CYP inhibitory promiscuity	-	0.8227	82.27%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5091	50.91%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.8874	88.74%
Skin irritation	-	0.7487	74.87%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8784	87.84%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.6073	60.73%
skin sensitisation	-	0.8748	87.48%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.5836	58.36%
Acute Oral Toxicity (c)	III	0.4559	45.59%
Estrogen receptor binding	+	0.8817	88.17%
Androgen receptor binding	+	0.6526	65.26%
Thyroid receptor binding	+	0.6084	60.84%
Glucocorticoid receptor binding	+	0.8058	80.58%
Aromatase binding	+	0.6790	67.90%
PPAR gamma	+	0.6772	67.72%
Honey bee toxicity	-	0.7656	76.56%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6245	62.45%
Fish aquatic toxicity	+	0.9901	99.01%

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	98.63%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.12%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.24%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.17%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.52%	97.25%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.93%	94.80%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.12%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	88.76%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.87%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.34%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.30%	96.00%
CHEMBL2996	Q05655	Protein kinase C delta	83.01%	97.79%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.97%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.73%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.69%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	81.39%	90.17%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.35%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.03%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.04%	92.62%

Plants that contains it

• Teucrium gracile

Cross-Links

• PubChem: 101634639
• LOTUS: LTS0111440
• wikiData: Q105124359