[(4R,4aR,5S,7R,8S,8aR)-5-acetyloxy-7,8-dimethyl-8-[2-(5-oxo-2H-furan-3-yl)ethyl]spiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl 3-hydroxy-2-methylidenebutanoate

Details

• Internal ID: daf5d858-6509-45ad-b5f5-c29849d39cc7
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [(4R,4aR,5S,7R,8S,8aR)-5-acetyloxy-7,8-dimethyl-8-[2-(5-oxo-2H-furan-3-yl)ethyl]spiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl 3-hydroxy-2-methylidenebutanoate
• SMILES (Canonical): CC1CC(C2(C(C1(C)CCC3=CC(=O)OC3)CCCC24CO4)COC(=O)C(=C)C(C)O)OC(=O)C
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@@]2([C@@H]([C@@]1(C)CCC3=CC(=O)OC3)CCC[C@]24CO4)COC(=O)C(=C)C(C)O)OC(=O)C
• InChI: InChI=1S/C27H38O8/c1-16-11-22(35-19(4)29)27(15-33-24(31)17(2)18(3)28)21(7-6-9-26(27)14-34-26)25(16,5)10-8-20-12-23(30)32-13-20/h12,16,18,21-22,28H,2,6-11,13-15H2,1,3-5H3/t16-,18?,21-,22+,25+,26+,27+/m1/s1
• InChI Key: KACNHTHLIACRKY-GTKADIPGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₈O₈
• Molecular Weight: 490.60 g/mol
• Exact Mass: 490.25666817 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.26
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9737	97.37%
Caco-2	-	0.6953	69.53%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7744	77.44%
OATP2B1 inhibitior	-	0.8642	86.42%
OATP1B1 inhibitior	+	0.8270	82.70%
OATP1B3 inhibitior	+	0.9126	91.26%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	+	0.5229	52.29%
BSEP inhibitior	+	0.8967	89.67%
P-glycoprotein inhibitior	+	0.7150	71.50%
P-glycoprotein substrate	+	0.6089	60.89%
CYP3A4 substrate	+	0.7050	70.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8932	89.32%
CYP3A4 inhibition	-	0.6781	67.81%
CYP2C9 inhibition	-	0.7999	79.99%
CYP2C19 inhibition	-	0.8437	84.37%
CYP2D6 inhibition	-	0.9406	94.06%
CYP1A2 inhibition	-	0.7566	75.66%
CYP2C8 inhibition	+	0.6218	62.18%
CYP inhibitory promiscuity	-	0.9076	90.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5248	52.48%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.8879	88.79%
Skin irritation	-	0.5515	55.15%
Skin corrosion	-	0.9221	92.21%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8132	81.32%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.5678	56.78%
skin sensitisation	-	0.8167	81.67%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.4888	48.88%
Acute Oral Toxicity (c)	I	0.4080	40.80%
Estrogen receptor binding	+	0.8521	85.21%
Androgen receptor binding	+	0.6906	69.06%
Thyroid receptor binding	-	0.5248	52.48%
Glucocorticoid receptor binding	+	0.7967	79.67%
Aromatase binding	+	0.8363	83.63%
PPAR gamma	+	0.7270	72.70%
Honey bee toxicity	-	0.6616	66.16%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9956	99.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.73%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.82%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.73%	97.25%
CHEMBL2581	P07339	Cathepsin D	97.43%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.91%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	95.03%	82.69%
CHEMBL4040	P28482	MAP kinase ERK2	93.41%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.69%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.61%	89.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.17%	94.80%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.60%	96.47%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.26%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.26%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.08%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.12%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.89%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	85.13%	91.19%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.74%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.53%	93.04%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.42%	85.14%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	83.15%	86.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.86%	83.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.40%	91.07%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.90%	95.71%
CHEMBL5028	O14672	ADAM10	80.93%	97.50%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.43%	89.50%

Plants that contains it

• Ajuga decumbens

Cross-Links

• PubChem: 15276268
• LOTUS: LTS0087637
• wikiData: Q105137786