[(3aS,5aR,6S,9bS)-9-(hydroxymethyl)-5a-methyl-3-methylidene-2-oxo-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-6-yl] 2-(hydroxymethyl)prop-2-enoate

Details

• Internal ID: 2cf8c191-a38b-469d-9d3c-4da76d5fe674
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3aS,5aR,6S,9bS)-9-(hydroxymethyl)-5a-methyl-3-methylidene-2-oxo-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-6-yl] 2-(hydroxymethyl)prop-2-enoate
• InChI: InChI=1S/C19H24O6/c1-10(8-20)17(22)24-14-5-4-12(9-21)15-16-13(6-7-19(14,15)3)11(2)18(23)25-16/h13-14,16,20-21H,1-2,4-9H2,3H3/t13-,14-,16-,19-/m0/s1
• InChI Key: ACBNGGPMOZZTFC-PWDMQXDWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₆
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.15728848 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.43
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9707	97.07%
Caco-2	+	0.5809	58.09%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8325	83.25%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.8634	86.34%
OATP1B3 inhibitior	+	0.9178	91.78%
MATE1 inhibitior	-	0.8212	82.12%
OCT2 inhibitior	-	0.5342	53.42%
BSEP inhibitior	-	0.8044	80.44%
P-glycoprotein inhibitior	-	0.6599	65.99%
P-glycoprotein substrate	-	0.7513	75.13%
CYP3A4 substrate	+	0.6736	67.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8649	86.49%
CYP3A4 inhibition	-	0.6748	67.48%
CYP2C9 inhibition	-	0.8547	85.47%
CYP2C19 inhibition	-	0.8564	85.64%
CYP2D6 inhibition	-	0.9362	93.62%
CYP1A2 inhibition	-	0.7307	73.07%
CYP2C8 inhibition	+	0.4812	48.12%
CYP inhibitory promiscuity	-	0.8127	81.27%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5145	51.45%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.7762	77.62%
Skin irritation	-	0.5406	54.06%
Skin corrosion	-	0.9336	93.36%
Ames mutagenesis	-	0.7240	72.40%
Human Ether-a-go-go-Related Gene inhibition	-	0.5325	53.25%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.5299	52.99%
skin sensitisation	-	0.9079	90.79%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.6571	65.71%
Acute Oral Toxicity (c)	III	0.5888	58.88%
Estrogen receptor binding	+	0.6206	62.06%
Androgen receptor binding	-	0.4834	48.34%
Thyroid receptor binding	-	0.5543	55.43%
Glucocorticoid receptor binding	+	0.6801	68.01%
Aromatase binding	+	0.6443	64.43%
PPAR gamma	+	0.5557	55.57%
Honey bee toxicity	-	0.8124	81.24%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9950	99.50%

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	96.98%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.21%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.56%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.93%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	88.73%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.32%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.67%	97.25%
CHEMBL2581	P07339	Cathepsin D	85.65%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.82%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.08%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.85%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.54%	92.62%

Plants that contains it

• Dimerostemma bishopii

Cross-Links

• PubChem: 162901489
• LOTUS: LTS0265686
• wikiData: Q104909008