(3aR,4aR,5R,8aR,9aR)-5-hydroxy-5,8a-dimethyl-3-methylidene-4,4a,9,9a-tetrahydro-3aH-benzo[f][1]benzofuran-2,8-dione

Details

• Internal ID: 3b838b59-0674-48cd-a140-98bf62408470
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,4aR,5R,8aR,9aR)-5-hydroxy-5,8a-dimethyl-3-methylidene-4,4a,9,9a-tetrahydro-3aH-benzo[f][1]benzofuran-2,8-dione
• InChI: InChI=1S/C15H18O4/c1-8-9-6-11-14(2,7-10(9)19-13(8)17)12(16)4-5-15(11,3)18/h4-5,9-11,18H,1,6-7H2,2-3H3/t9-,10-,11-,14-,15-/m1/s1
• InChI Key: SEHWANFWBQNVNV-KAILVDNBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.39
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9901	99.01%
Caco-2	+	0.5614	56.14%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7445	74.45%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.8974	89.74%
OATP1B3 inhibitior	+	0.8692	86.92%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9558	95.58%
P-glycoprotein inhibitior	-	0.9093	90.93%
P-glycoprotein substrate	-	0.8370	83.70%
CYP3A4 substrate	+	0.5739	57.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9014	90.14%
CYP3A4 inhibition	+	0.5442	54.42%
CYP2C9 inhibition	-	0.9001	90.01%
CYP2C19 inhibition	-	0.8950	89.50%
CYP2D6 inhibition	-	0.9508	95.08%
CYP1A2 inhibition	-	0.7273	72.73%
CYP2C8 inhibition	-	0.7809	78.09%
CYP inhibitory promiscuity	-	0.8588	85.88%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5066	50.66%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.8775	87.75%
Skin irritation	+	0.5194	51.94%
Skin corrosion	-	0.8513	85.13%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6810	68.10%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.7324	73.24%
skin sensitisation	-	0.6562	65.62%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.5728	57.28%
Acute Oral Toxicity (c)	III	0.5366	53.66%
Estrogen receptor binding	+	0.5942	59.42%
Androgen receptor binding	+	0.5451	54.51%
Thyroid receptor binding	-	0.4897	48.97%
Glucocorticoid receptor binding	-	0.6210	62.10%
Aromatase binding	-	0.7641	76.41%
PPAR gamma	-	0.5229	52.29%
Honey bee toxicity	-	0.8475	84.75%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	96.88%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.59%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.07%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.76%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.00%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.17%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.17%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.11%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.80%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	83.01%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.55%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	80.42%	97.79%

Plants that contains it

• Ferreyranthus fruticosus

Cross-Links

• PubChem: 14021280
• LOTUS: LTS0060610
• wikiData: Q105202708