dimethyl (3aR,4R,5S,7aR)-3a-methyl-5-[(Z)-2-methylbut-2-enoyl]oxy-1,4,5,6,7,7a-hexahydroindene-2,4-dicarboxylate

Details

• Internal ID: 802d5f08-e3a2-4bae-b766-6ea2fa37ff8f
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: dimethyl (3aR,4R,5S,7aR)-3a-methyl-5-[(Z)-2-methylbut-2-enoyl]oxy-1,4,5,6,7,7a-hexahydroindene-2,4-dicarboxylate
• SMILES (Canonical): CC=C(C)C(=O)OC1CCC2CC(=CC2(C1C(=O)OC)C)C(=O)OC
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1CC[C@@H]2CC(=C[C@@]2([C@H]1C(=O)OC)C)C(=O)OC
• InChI: InChI=1S/C19H26O6/c1-6-11(2)16(20)25-14-8-7-13-9-12(17(21)23-4)10-19(13,3)15(14)18(22)24-5/h6,10,13-15H,7-9H2,1-5H3/b11-6-/t13-,14+,15-,19+/m1/s1
• InChI Key: GTQAUWWSOKGAGH-REPNLMGLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₆
• Molecular Weight: 350.40 g/mol
• Exact Mass: 350.17293854 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.57
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9919	99.19%
Caco-2	+	0.8111	81.11%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7603	76.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8596	85.96%
OATP1B3 inhibitior	+	0.9631	96.31%
MATE1 inhibitior	+	0.6000	60.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.5661	56.61%
P-glycoprotein inhibitior	-	0.4335	43.35%
P-glycoprotein substrate	-	0.7247	72.47%
CYP3A4 substrate	+	0.6468	64.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9092	90.92%
CYP3A4 inhibition	-	0.7846	78.46%
CYP2C9 inhibition	-	0.9136	91.36%
CYP2C19 inhibition	-	0.9232	92.32%
CYP2D6 inhibition	-	0.9635	96.35%
CYP1A2 inhibition	-	0.7761	77.61%
CYP2C8 inhibition	-	0.6216	62.16%
CYP inhibitory promiscuity	-	0.9163	91.63%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8946	89.46%
Carcinogenicity (trinary)	Non-required	0.5989	59.89%
Eye corrosion	-	0.9776	97.76%
Eye irritation	-	0.9214	92.14%
Skin irritation	-	0.5266	52.66%
Skin corrosion	-	0.9443	94.43%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7907	79.07%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.7357	73.57%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.6541	65.41%
Acute Oral Toxicity (c)	III	0.5379	53.79%
Estrogen receptor binding	+	0.7772	77.72%
Androgen receptor binding	-	0.4904	49.04%
Thyroid receptor binding	+	0.5835	58.35%
Glucocorticoid receptor binding	+	0.7304	73.04%
Aromatase binding	-	0.6496	64.96%
PPAR gamma	-	0.5079	50.79%
Honey bee toxicity	-	0.7174	71.74%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9688	96.88%

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	97.21%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.11%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.86%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	88.67%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.44%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	85.16%	90.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.68%	91.07%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.21%	99.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.21%	94.33%

Plants that contains it

• Ligularia virgaurea

Cross-Links

• PubChem: 162960665
• LOTUS: LTS0201222
• wikiData: Q105019255