(3aR,4S,5aS,6S,9bS)-4,6-dihydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one

Details

• Internal ID: ed93d6c6-15ad-4f01-b1d9-388d83470a00
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,4S,5aS,6S,9bS)-4,6-dihydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1=C2C3C(C(CC2(C(CC1)O)C)O)C(=C)C(=O)O3
• SMILES (Isomeric): CC1=C2[C@@H]3[C@@H]([C@H](C[C@@]2([C@H](CC1)O)C)O)C(=C)C(=O)O3
• InChI: InChI=1S/C15H20O4/c1-7-4-5-10(17)15(3)6-9(16)11-8(2)14(18)19-13(11)12(7)15/h9-11,13,16-17H,2,4-6H2,1,3H3/t9-,10-,11+,13-,15+/m0/s1
• InChI Key: YRNOGCOWCRFGDU-BPJKLTAVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.33
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9949	99.49%
Caco-2	+	0.6624	66.24%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6991	69.91%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.9172	91.72%
OATP1B3 inhibitior	+	0.8907	89.07%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5599	55.99%
BSEP inhibitior	-	0.9617	96.17%
P-glycoprotein inhibitior	-	0.8909	89.09%
P-glycoprotein substrate	-	0.8578	85.78%
CYP3A4 substrate	+	0.6025	60.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8379	83.79%
CYP3A4 inhibition	-	0.5502	55.02%
CYP2C9 inhibition	-	0.9183	91.83%
CYP2C19 inhibition	-	0.9352	93.52%
CYP2D6 inhibition	-	0.9485	94.85%
CYP1A2 inhibition	-	0.6718	67.18%
CYP2C8 inhibition	-	0.8691	86.91%
CYP inhibitory promiscuity	-	0.9367	93.67%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4826	48.26%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.6455	64.55%
Skin irritation	+	0.5935	59.35%
Skin corrosion	-	0.9008	90.08%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7549	75.49%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.6408	64.08%
skin sensitisation	-	0.7622	76.22%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.6454	64.54%
Acute Oral Toxicity (c)	I	0.3967	39.67%
Estrogen receptor binding	-	0.5412	54.12%
Androgen receptor binding	-	0.6009	60.09%
Thyroid receptor binding	+	0.5211	52.11%
Glucocorticoid receptor binding	+	0.6144	61.44%
Aromatase binding	-	0.7223	72.23%
PPAR gamma	-	0.5824	58.24%
Honey bee toxicity	-	0.8157	81.57%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9953	99.53%

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	92.19%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.04%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.12%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.36%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.08%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.90%	89.00%
CHEMBL1871	P10275	Androgen Receptor	84.77%	96.43%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.56%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.15%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.88%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.87%	95.89%

Plants that contains it

• Cassinia subtropica

Cross-Links

• PubChem: 14191301
• LOTUS: LTS0135485
• wikiData: Q105352913