2-[(3S,4aS,7R,8R,8aS)-3-acetyloxy-4,4,7,8a-tetramethylspiro[2,3,4a,5,6,7-hexahydro-1H-naphthalene-8,5'-oxolane]-2'-ylidene]acetic acid

Details

• Internal ID: b63512d3-c820-4a48-a6c3-5a984e9544a8
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Dicarboxylic acids and derivatives
• IUPAC Name: 2-[(3S,4aS,7R,8R,8aS)-3-acetyloxy-4,4,7,8a-tetramethylspiro[2,3,4a,5,6,7-hexahydro-1H-naphthalene-8,5'-oxolane]-2'-ylidene]acetic acid
• SMILES (Canonical): CC1CCC2C(C(CCC2(C13CCC(=CC(=O)O)O3)C)OC(=O)C)(C)C
• SMILES (Isomeric): C[C@@H]1CC[C@@H]2[C@@]([C@@]13CCC(=CC(=O)O)O3)(CC[C@@H](C2(C)C)OC(=O)C)C
• InChI: InChI=1S/C21H32O5/c1-13-6-7-16-19(3,4)17(25-14(2)22)9-10-20(16,5)21(13)11-8-15(26-21)12-18(23)24/h12-13,16-17H,6-11H2,1-5H3,(H,23,24)/t13-,16+,17+,20+,21-/m1/s1
• InChI Key: LLSQOJBRINBUMN-KUNMCDETSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₅
• Molecular Weight: 364.50 g/mol
• Exact Mass: 364.22497412 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.31
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9846	98.46%
Caco-2	+	0.6534	65.34%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7677	76.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8279	82.79%
OATP1B3 inhibitior	-	0.2273	22.73%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.5555	55.55%
P-glycoprotein inhibitior	+	0.6093	60.93%
P-glycoprotein substrate	-	0.8524	85.24%
CYP3A4 substrate	+	0.6360	63.60%
CYP2C9 substrate	-	0.8070	80.70%
CYP2D6 substrate	-	0.9018	90.18%
CYP3A4 inhibition	-	0.7409	74.09%
CYP2C9 inhibition	-	0.8415	84.15%
CYP2C19 inhibition	-	0.8313	83.13%
CYP2D6 inhibition	-	0.9616	96.16%
CYP1A2 inhibition	-	0.5898	58.98%
CYP2C8 inhibition	+	0.4606	46.06%
CYP inhibitory promiscuity	-	0.8896	88.96%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5759	57.59%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9544	95.44%
Skin irritation	+	0.5703	57.03%
Skin corrosion	-	0.8876	88.76%
Ames mutagenesis	-	0.6664	66.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.3767	37.67%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.7893	78.93%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.4840	48.40%
Acute Oral Toxicity (c)	III	0.3805	38.05%
Estrogen receptor binding	+	0.9114	91.14%
Androgen receptor binding	+	0.6786	67.86%
Thyroid receptor binding	+	0.7985	79.85%
Glucocorticoid receptor binding	+	0.7851	78.51%
Aromatase binding	+	0.7681	76.81%
PPAR gamma	+	0.7814	78.14%
Honey bee toxicity	-	0.6886	68.86%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5455	54.55%
Fish aquatic toxicity	+	0.9961	99.61%

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	95.73%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.73%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.07%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.73%	95.56%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	86.71%	89.05%
CHEMBL340	P08684	Cytochrome P450 3A4	85.55%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.16%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.23%	86.33%
CHEMBL5028	O14672	ADAM10	82.93%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.06%	95.89%

Plants that contains it

• Vitex negundo

Cross-Links

• PubChem: 162972774
• LOTUS: LTS0201708
• wikiData: Q105153713