[(3aR,4R,9aR,9bR)-8-chloro-6-(hydroxymethyl)-9-methyl-3-methylidene-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-methylprop-2-enoate

Details

• Internal ID: 99730eaa-3fa8-44f2-ad0c-3cb5dee350fd
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: [(3aR,4R,9aR,9bR)-8-chloro-6-(hydroxymethyl)-9-methyl-3-methylidene-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-methylprop-2-enoate
• SMILES (Canonical): CC1=C(C(=O)C2=C(CC(C3C(C12)OC(=O)C3=C)OC(=O)C(=C)C)CO)Cl
• SMILES (Isomeric): CC1=C(C(=O)C2=C(C[C@H]([C@@H]3[C@@H]([C@@H]12)OC(=O)C3=C)OC(=O)C(=C)C)CO)Cl
• InChI: InChI=1S/C19H19ClO6/c1-7(2)18(23)25-11-5-10(6-21)14-13(8(3)15(20)16(14)22)17-12(11)9(4)19(24)26-17/h11-13,17,21H,1,4-6H2,2-3H3/t11-,12-,13+,17+/m1/s1
• InChI Key: KFPWRPCTAULPMU-FJZAXULXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₉ClO₆
• Molecular Weight: 378.80 g/mol
• Exact Mass: 378.0870160 g/mol
• Topological Polar Surface Area (TPSA): 89.90 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.98
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9901	99.01%
Caco-2	-	0.5319	53.19%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6120	61.20%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8950	89.50%
OATP1B3 inhibitior	+	0.9134	91.34%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9284	92.84%
P-glycoprotein inhibitior	-	0.7090	70.90%
P-glycoprotein substrate	-	0.6537	65.37%
CYP3A4 substrate	+	0.6588	65.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8864	88.64%
CYP3A4 inhibition	-	0.7166	71.66%
CYP2C9 inhibition	-	0.7453	74.53%
CYP2C19 inhibition	-	0.6992	69.92%
CYP2D6 inhibition	-	0.8975	89.75%
CYP1A2 inhibition	-	0.6862	68.62%
CYP2C8 inhibition	+	0.4814	48.14%
CYP inhibitory promiscuity	-	0.8189	81.89%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8199	81.99%
Carcinogenicity (trinary)	Non-required	0.5040	50.40%
Eye corrosion	-	0.9603	96.03%
Eye irritation	-	0.7918	79.18%
Skin irritation	-	0.6914	69.14%
Skin corrosion	-	0.8948	89.48%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5229	52.29%
Micronuclear	-	0.5967	59.67%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.7642	76.42%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.9222	92.22%
Acute Oral Toxicity (c)	III	0.4642	46.42%
Estrogen receptor binding	+	0.6913	69.13%
Androgen receptor binding	+	0.6146	61.46%
Thyroid receptor binding	+	0.5429	54.29%
Glucocorticoid receptor binding	+	0.7633	76.33%
Aromatase binding	-	0.6475	64.75%
PPAR gamma	+	0.6335	63.35%
Honey bee toxicity	-	0.6780	67.80%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5250	52.50%
Fish aquatic toxicity	+	0.9567	95.67%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.94%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.47%	91.11%
CHEMBL2581	P07339	Cathepsin D	89.36%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.90%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.76%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	84.78%	94.73%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.69%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.69%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.86%	91.19%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.46%	89.34%

Plants that contains it

• Mikania vitifolia

Cross-Links

• PubChem: 162919906
• LOTUS: LTS0008899
• wikiData: Q105140510