[(3aR,4R,6R,6aS,9S,9aS,9bR)-6-(chloromethyl)-6,9-dihydroxy-9-methyl-3-methylidene-2-oxo-3a,4,5,6a,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (E)-4-hydroxy-2-methylbut-2-enoate

Details

• Internal ID: b755397a-7424-41b1-89e9-d9e863c50e5f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4R,6R,6aS,9S,9aS,9bR)-6-(chloromethyl)-6,9-dihydroxy-9-methyl-3-methylidene-2-oxo-3a,4,5,6a,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (E)-4-hydroxy-2-methylbut-2-enoate
• InChI: InChI=1S/C20H25ClO7/c1-10(5-7-22)17(23)27-13-8-20(26,9-21)12-4-6-19(3,25)15(12)16-14(13)11(2)18(24)28-16/h4-6,12-16,22,25-26H,2,7-9H2,1,3H3/b10-5+/t12-,13+,14+,15-,16+,19-,20-/m0/s1
• InChI Key: IXLMITLRFJSJRS-XIMQPRQKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₅ClO₇
• Molecular Weight: 412.90 g/mol
• Exact Mass: 412.1288808 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.86
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9802	98.02%
Caco-2	-	0.6965	69.65%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5470	54.70%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8691	86.91%
OATP1B3 inhibitior	+	0.9245	92.45%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6501	65.01%
P-glycoprotein inhibitior	-	0.5940	59.40%
P-glycoprotein substrate	-	0.6249	62.49%
CYP3A4 substrate	+	0.6748	67.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8896	88.96%
CYP3A4 inhibition	-	0.8009	80.09%
CYP2C9 inhibition	-	0.8597	85.97%
CYP2C19 inhibition	-	0.7809	78.09%
CYP2D6 inhibition	-	0.9077	90.77%
CYP1A2 inhibition	-	0.7605	76.05%
CYP2C8 inhibition	-	0.6016	60.16%
CYP inhibitory promiscuity	-	0.8902	89.02%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8244	82.44%
Carcinogenicity (trinary)	Non-required	0.5488	54.88%
Eye corrosion	-	0.9690	96.90%
Eye irritation	-	0.9614	96.14%
Skin irritation	-	0.6578	65.78%
Skin corrosion	-	0.8790	87.90%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4143	41.43%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.5803	58.03%
skin sensitisation	-	0.7316	73.16%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.7281	72.81%
Acute Oral Toxicity (c)	III	0.4918	49.18%
Estrogen receptor binding	+	0.8397	83.97%
Androgen receptor binding	+	0.5736	57.36%
Thyroid receptor binding	+	0.6546	65.46%
Glucocorticoid receptor binding	+	0.6721	67.21%
Aromatase binding	+	0.6487	64.87%
PPAR gamma	+	0.6711	67.11%
Honey bee toxicity	-	0.5694	56.94%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9005	90.05%

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	98.53%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.12%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.64%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	93.31%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.02%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.58%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.36%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.15%	91.07%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.79%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.72%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	80.34%	94.73%

Plants that contains it

• Eupatorium lindleyanum

Cross-Links

• PubChem: 162948412
• LOTUS: LTS0230702
• wikiData: Q105122246