(5aR,6R,9R)-6,9-dihydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one

Details

• Internal ID: e84f911b-3bd3-4df4-850d-d8a203fa3787
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (5aR,6R,9R)-6,9-dihydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC12CCC3C(C1C(CCC2O)(C)O)OC(=O)C3=C
• SMILES (Isomeric): C[C@@]12CCC3C(C1[C@](CC[C@H]2O)(C)O)OC(=O)C3=C
• InChI: InChI=1S/C15H22O4/c1-8-9-4-6-14(2)10(16)5-7-15(3,18)12(14)11(9)19-13(8)17/h9-12,16,18H,1,4-7H2,2-3H3/t9?,10-,11?,12?,14+,15-/m1/s1
• InChI Key: LVABKRFKENTQBT-VWNUJFTMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.41
• 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	+	0.9905	99.05%
Caco-2	+	0.6432	64.32%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6937	69.37%
OATP2B1 inhibitior	-	0.8542	85.42%
OATP1B1 inhibitior	+	0.8981	89.81%
OATP1B3 inhibitior	+	0.8475	84.75%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6170	61.70%
BSEP inhibitior	-	0.9633	96.33%
P-glycoprotein inhibitior	-	0.9147	91.47%
P-glycoprotein substrate	-	0.8658	86.58%
CYP3A4 substrate	+	0.6389	63.89%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8527	85.27%
CYP3A4 inhibition	-	0.5612	56.12%
CYP2C9 inhibition	-	0.9247	92.47%
CYP2C19 inhibition	-	0.8848	88.48%
CYP2D6 inhibition	-	0.9517	95.17%
CYP1A2 inhibition	-	0.6883	68.83%
CYP2C8 inhibition	-	0.8361	83.61%
CYP inhibitory promiscuity	-	0.9169	91.69%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4952	49.52%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.8593	85.93%
Skin irritation	+	0.6326	63.26%
Skin corrosion	-	0.8995	89.95%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5741	57.41%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.8875	88.75%
skin sensitisation	-	0.7613	76.13%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.5196	51.96%
Acute Oral Toxicity (c)	I	0.5236	52.36%
Estrogen receptor binding	+	0.7480	74.80%
Androgen receptor binding	+	0.6255	62.55%
Thyroid receptor binding	+	0.5360	53.60%
Glucocorticoid receptor binding	+	0.6944	69.44%
Aromatase binding	-	0.5810	58.10%
PPAR gamma	-	0.6807	68.07%
Honey bee toxicity	-	0.8650	86.50%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.44%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.43%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.70%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.38%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.59%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.89%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.90%	99.23%
CHEMBL2581	P07339	Cathepsin D	83.12%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.25%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.60%	95.89%

Plants that contains it

• Gynochthodes umbellata

Cross-Links

• PubChem: 5318148
• NPASS: NPC163651