(4R,4aR,5S,7S,8R,8aR)-7-hydroxy-7,8-dimethyl-5-[(2S)-2-methylbutanoyl]oxy-8-[2-(5-oxo-2H-furan-3-yl)ethyl]spiro[1,2,3,5,6,8a-hexahydronaphthalene-4,2'-oxirane]-4a-carboxylic acid

Details

• Internal ID: 26175ab2-b96f-4b04-bac8-0688a02fb6fd
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: (4R,4aR,5S,7S,8R,8aR)-7-hydroxy-7,8-dimethyl-5-[(2S)-2-methylbutanoyl]oxy-8-[2-(5-oxo-2H-furan-3-yl)ethyl]spiro[1,2,3,5,6,8a-hexahydronaphthalene-4,2'-oxirane]-4a-carboxylic acid
• SMILES (Canonical): CCC(C)C(=O)OC1CC(C(C2C1(C3(CCC2)CO3)C(=O)O)(C)CCC4=CC(=O)OC4)(C)O
• SMILES (Isomeric): CC[C@H](C)C(=O)O[C@H]1C[C@]([C@]([C@@H]2[C@@]1([C@]3(CCC2)CO3)C(=O)O)(C)CCC4=CC(=O)OC4)(C)O
• InChI: InChI=1S/C25H36O8/c1-5-15(2)20(27)33-18-12-23(4,30)22(3,10-8-16-11-19(26)31-13-16)17-7-6-9-24(14-32-24)25(17,18)21(28)29/h11,15,17-18,30H,5-10,12-14H2,1-4H3,(H,28,29)/t15-,17+,18-,22+,23-,24-,25-/m0/s1
• InChI Key: HLXRXKZVYFPPMX-DQFVWIRPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₆O₈
• Molecular Weight: 464.50 g/mol
• Exact Mass: 464.24101810 g/mol
• Topological Polar Surface Area (TPSA): 123.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 3.01
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9850	98.50%
Caco-2	-	0.6030	60.30%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7839	78.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8355	83.55%
OATP1B3 inhibitior	+	0.9577	95.77%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.8684	86.84%
P-glycoprotein inhibitior	+	0.5996	59.96%
P-glycoprotein substrate	-	0.5119	51.19%
CYP3A4 substrate	+	0.6766	67.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9039	90.39%
CYP3A4 inhibition	+	0.5730	57.30%
CYP2C9 inhibition	-	0.7615	76.15%
CYP2C19 inhibition	-	0.8586	85.86%
CYP2D6 inhibition	-	0.9298	92.98%
CYP1A2 inhibition	-	0.8700	87.00%
CYP2C8 inhibition	+	0.5725	57.25%
CYP inhibitory promiscuity	-	0.8281	82.81%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4430	44.30%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9272	92.72%
Skin irritation	+	0.5146	51.46%
Skin corrosion	-	0.9366	93.66%
Ames mutagenesis	-	0.6624	66.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.5158	51.58%
skin sensitisation	-	0.8976	89.76%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.6467	64.67%
Acute Oral Toxicity (c)	I	0.3968	39.68%
Estrogen receptor binding	+	0.8254	82.54%
Androgen receptor binding	+	0.7337	73.37%
Thyroid receptor binding	+	0.5697	56.97%
Glucocorticoid receptor binding	+	0.8008	80.08%
Aromatase binding	+	0.8230	82.30%
PPAR gamma	+	0.5764	57.64%
Honey bee toxicity	-	0.7615	76.15%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9933	99.33%

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	98.48%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.72%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.60%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.35%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.21%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.76%	82.69%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.24%	96.47%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.21%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.89%	99.23%
CHEMBL226	P30542	Adenosine A1 receptor	89.47%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.39%	89.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.23%	96.38%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.27%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.13%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	86.89%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.40%	97.09%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.42%	95.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.23%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.21%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.82%	96.61%
CHEMBL1937	Q92769	Histone deacetylase 2	82.79%	94.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.14%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	81.12%	92.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.36%	96.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.31%	100.00%

Plants that contains it

• Scutellaria caucasica

Cross-Links

• PubChem: 162898791
• LOTUS: LTS0188890
• wikiData: Q105030390