[(3aS,4R,5R,9S,9aS,9bS)-4-acetyloxy-9-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-5-yl] (2S,3R)-2,3-dimethyloxirane-2-carboxylate

Details

• Internal ID: 438cd78f-99b0-4773-8aa5-f8196563aedf
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [(3aS,4R,5R,9S,9aS,9bS)-4-acetyloxy-9-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-5-yl] (2S,3R)-2,3-dimethyloxirane-2-carboxylate
• InChI: InChI=1S/C22H26O8/c1-9-13-7-8-21(5,26)15(13)17-14(10(2)19(24)28-17)18(27-12(4)23)16(9)29-20(25)22(6)11(3)30-22/h7-8,11,14-18,26H,2H2,1,3-6H3/t11-,14+,15+,16-,17+,18-,21+,22+/m1/s1
• InChI Key: QDXPVFREXDFFGU-PCNMBPDASA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆O₈
• Molecular Weight: 418.40 g/mol
• Exact Mass: 418.16276778 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.37
• H-Bond Acceptor: 8
• 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	+	0.9744	97.44%
Caco-2	-	0.5567	55.67%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6307	63.07%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8667	86.67%
OATP1B3 inhibitior	+	0.8985	89.85%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7315	73.15%
P-glycoprotein inhibitior	+	0.6458	64.58%
P-glycoprotein substrate	-	0.5715	57.15%
CYP3A4 substrate	+	0.6507	65.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8979	89.79%
CYP3A4 inhibition	-	0.6574	65.74%
CYP2C9 inhibition	-	0.8911	89.11%
CYP2C19 inhibition	-	0.8444	84.44%
CYP2D6 inhibition	-	0.9378	93.78%
CYP1A2 inhibition	-	0.7918	79.18%
CYP2C8 inhibition	-	0.5590	55.90%
CYP inhibitory promiscuity	-	0.8919	89.19%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9143	91.43%
Carcinogenicity (trinary)	Danger	0.4659	46.59%
Eye corrosion	-	0.9577	95.77%
Eye irritation	-	0.8546	85.46%
Skin irritation	-	0.6408	64.08%
Skin corrosion	-	0.9114	91.14%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5422	54.22%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	+	0.7211	72.11%
skin sensitisation	-	0.6691	66.91%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.6791	67.91%
Acute Oral Toxicity (c)	III	0.3580	35.80%
Estrogen receptor binding	+	0.6839	68.39%
Androgen receptor binding	+	0.6701	67.01%
Thyroid receptor binding	+	0.6278	62.78%
Glucocorticoid receptor binding	+	0.5956	59.56%
Aromatase binding	-	0.4901	49.01%
PPAR gamma	+	0.6248	62.48%
Honey bee toxicity	-	0.7525	75.25%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5250	52.50%
Fish aquatic toxicity	+	0.9454	94.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.31%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.49%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.34%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.57%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.77%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.58%	98.95%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	89.43%	81.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.10%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.14%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.84%	91.11%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	81.00%	94.42%

Plants that contains it

• Balsamorhiza sagittata

Cross-Links

• PubChem: 162883313
• LOTUS: LTS0151761
• wikiData: Q105219025