[(3aR,4R,5R,9aR,9bS)-5-acetyloxy-6,9-dimethyl-3-methylidene-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] (2R,3R)-2,3-dimethyloxirane-2-carboxylate

Details

• Internal ID: a7f46d26-89e1-4042-9007-8af24ce986b4
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [(3aR,4R,5R,9aR,9bS)-5-acetyloxy-6,9-dimethyl-3-methylidene-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] (2R,3R)-2,3-dimethyloxirane-2-carboxylate
• SMILES (Canonical): CC1C(O1)(C)C(=O)OC2C3C(C4C(=CC(=O)C4=C(C2OC(=O)C)C)C)OC(=O)C3=C
• SMILES (Isomeric): C[C@@H]1[C@](O1)(C)C(=O)O[C@@H]2[C@H]3[C@H]([C@@H]4C(=CC(=O)C4=C([C@H]2OC(=O)C)C)C)OC(=O)C3=C
• InChI: InChI=1S/C22H24O8/c1-8-7-13(24)15-9(2)17(27-12(5)23)19(29-21(26)22(6)11(4)30-22)16-10(3)20(25)28-18(16)14(8)15/h7,11,14,16-19H,3H2,1-2,4-6H3/t11-,14-,16-,17-,18+,19-,22-/m1/s1
• InChI Key: QEDRCVLPCKIQNE-CETNYNMCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₄O₈
• Molecular Weight: 416.40 g/mol
• Exact Mass: 416.14711772 g/mol
• Topological Polar Surface Area (TPSA): 109.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.58
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9835	98.35%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5875	58.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8627	86.27%
OATP1B3 inhibitior	+	0.9178	91.78%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8088	80.88%
P-glycoprotein inhibitior	+	0.7237	72.37%
P-glycoprotein substrate	-	0.5297	52.97%
CYP3A4 substrate	+	0.6473	64.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9060	90.60%
CYP3A4 inhibition	-	0.6124	61.24%
CYP2C9 inhibition	-	0.8949	89.49%
CYP2C19 inhibition	-	0.7982	79.82%
CYP2D6 inhibition	-	0.9356	93.56%
CYP1A2 inhibition	-	0.7258	72.58%
CYP2C8 inhibition	+	0.4576	45.76%
CYP inhibitory promiscuity	-	0.7825	78.25%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9043	90.43%
Carcinogenicity (trinary)	Non-required	0.4187	41.87%
Eye corrosion	-	0.9477	94.77%
Eye irritation	-	0.8670	86.70%
Skin irritation	-	0.6672	66.72%
Skin corrosion	-	0.9155	91.55%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4939	49.39%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.7066	70.66%
skin sensitisation	-	0.6289	62.89%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6072	60.72%
Acute Oral Toxicity (c)	III	0.3914	39.14%
Estrogen receptor binding	+	0.7991	79.91%
Androgen receptor binding	+	0.6989	69.89%
Thyroid receptor binding	+	0.6449	64.49%
Glucocorticoid receptor binding	+	0.6365	63.65%
Aromatase binding	+	0.5241	52.41%
PPAR gamma	+	0.7739	77.39%
Honey bee toxicity	-	0.6697	66.97%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5550	55.50%
Fish aquatic toxicity	+	0.9619	96.19%

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	94.28%	94.45%
CHEMBL2581	P07339	Cathepsin D	92.42%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.68%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.99%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.37%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.53%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.05%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.14%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.14%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.76%	97.14%

Plants that contains it

• Inula royleana
• Isodon lophanthoides
• Juniperus chinensis
• Peltodon longipes
• Plectranthus grandidentatus
• Premna serratifolia
• Prumnopitys ferruginea
• Salvia deserta
• Salvia nutans
• Salvia phlomoides
• Salvia pratensis
• Squamopappus skutchii

Cross-Links

• PubChem: 162926507
• LOTUS: LTS0173065
• wikiData: Q105148039