[(1R,2S,3R,4aR,5S,6R,8S,8aR)-5-[(2R,3aS,5S,6aR)-5-hydroxy-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-2-yl]-8-acetyloxy-8a-(acetyloxymethyl)-3-hydroxy-5,6-dimethylspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2'-oxirane]-2-yl] 2-methylpropanoate

Details

• Internal ID: 3c6adef6-55c8-48a5-bfb4-8b0cd3c388af
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [(1R,2S,3R,4aR,5S,6R,8S,8aR)-5-[(2R,3aS,5S,6aR)-5-hydroxy-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-2-yl]-8-acetyloxy-8a-(acetyloxymethyl)-3-hydroxy-5,6-dimethylspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2'-oxirane]-2-yl] 2-methylpropanoate
• SMILES (Canonical): CC1CC(C2(C(C1(C)C3CC4CC(OC4O3)O)CC(C(C25CO5)OC(=O)C(C)C)O)COC(=O)C)OC(=O)C
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@@]2([C@@H]([C@@]1(C)[C@H]3C[C@H]4C[C@H](O[C@H]4O3)O)C[C@H]([C@@H]([C@]25CO5)OC(=O)C(C)C)O)COC(=O)C)OC(=O)C
• InChI: InChI=1S/C28H42O11/c1-13(2)24(33)39-23-18(31)10-19-26(6,20-8-17-9-22(32)38-25(17)37-20)14(3)7-21(36-16(5)30)27(19,11-34-15(4)29)28(23)12-35-28/h13-14,17-23,25,31-32H,7-12H2,1-6H3/t14-,17+,18-,19-,20-,21+,22+,23+,25-,26+,27+,28-/m1/s1
• InChI Key: SJOJHHWDKFCIBR-UVSKFGLDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₂O₁₁
• Molecular Weight: 554.60 g/mol
• Exact Mass: 554.27271215 g/mol
• Topological Polar Surface Area (TPSA): 150.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.70
• H-Bond Acceptor: 11
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9469	94.69%
Caco-2	-	0.7660	76.60%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7875	78.75%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.8821	88.21%
OATP1B3 inhibitior	+	0.9029	90.29%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6820	68.20%
P-glycoprotein inhibitior	+	0.6355	63.55%
P-glycoprotein substrate	+	0.5650	56.50%
CYP3A4 substrate	+	0.6728	67.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8620	86.20%
CYP3A4 inhibition	-	0.6782	67.82%
CYP2C9 inhibition	-	0.7773	77.73%
CYP2C19 inhibition	-	0.8083	80.83%
CYP2D6 inhibition	-	0.9460	94.60%
CYP1A2 inhibition	-	0.9326	93.26%
CYP2C8 inhibition	-	0.5746	57.46%
CYP inhibitory promiscuity	-	0.8981	89.81%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5036	50.36%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9119	91.19%
Skin irritation	-	0.7158	71.58%
Skin corrosion	-	0.9430	94.30%
Ames mutagenesis	-	0.5237	52.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6117	61.17%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	-	0.6108	61.08%
skin sensitisation	-	0.8625	86.25%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.6912	69.12%
Acute Oral Toxicity (c)	I	0.6893	68.93%
Estrogen receptor binding	+	0.8103	81.03%
Androgen receptor binding	+	0.7037	70.37%
Thyroid receptor binding	-	0.5436	54.36%
Glucocorticoid receptor binding	+	0.6498	64.98%
Aromatase binding	+	0.7180	71.80%
PPAR gamma	+	0.6975	69.75%
Honey bee toxicity	-	0.6927	69.27%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6955	69.55%
Fish aquatic toxicity	+	0.9806	98.06%

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	98.71%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.48%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.59%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.79%	94.45%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	93.91%	98.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.73%	85.14%
CHEMBL2581	P07339	Cathepsin D	93.35%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	93.34%	91.19%
CHEMBL2996	Q05655	Protein kinase C delta	91.17%	97.79%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	90.85%	95.71%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.50%	96.47%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	90.20%	89.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.79%	97.09%
CHEMBL299	P17252	Protein kinase C alpha	87.55%	98.03%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.55%	82.69%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	87.00%	82.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.97%	91.24%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.75%	89.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.64%	91.07%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.54%	96.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.39%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.33%	92.62%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.88%	97.21%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.42%	97.14%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.88%	94.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.62%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.86%	95.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.27%	97.36%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.11%	97.28%

Plants that contains it

• Ajuga salicifolia

Cross-Links

• PubChem: 162940649
• LOTUS: LTS0272540
• wikiData: Q105254456