(3aR,4aR,8R,8aS,9aR)-4a,8-dihydroxy-5,8a-dimethyl-3-methylidene-4,8,9,9a-tetrahydro-3aH-benzo[f][1]benzofuran-2,7-dione

Details

• Internal ID: e9e856ae-7036-479d-b2d7-da847e3b42bb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,4aR,8R,8aS,9aR)-4a,8-dihydroxy-5,8a-dimethyl-3-methylidene-4,8,9,9a-tetrahydro-3aH-benzo[f][1]benzofuran-2,7-dione
• InChI: InChI=1S/C15H18O5/c1-7-4-10(16)12(17)14(3)6-11-9(5-15(7,14)19)8(2)13(18)20-11/h4,9,11-12,17,19H,2,5-6H2,1,3H3/t9-,11-,12+,14+,15-/m1/s1
• InChI Key: DZBDVPICGOLHAO-HTZLXXLYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.51
• H-Bond Acceptor: 5
• 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	+	0.9692	96.92%
Caco-2	-	0.5762	57.62%
Blood Brain Barrier	+	0.7777	77.77%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6049	60.49%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.8923	89.23%
OATP1B3 inhibitior	+	0.9322	93.22%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9751	97.51%
P-glycoprotein inhibitior	-	0.9289	92.89%
P-glycoprotein substrate	-	0.8088	80.88%
CYP3A4 substrate	+	0.5940	59.40%
CYP2C9 substrate	-	0.7890	78.90%
CYP2D6 substrate	-	0.9032	90.32%
CYP3A4 inhibition	-	0.5815	58.15%
CYP2C9 inhibition	-	0.9026	90.26%
CYP2C19 inhibition	-	0.9130	91.30%
CYP2D6 inhibition	-	0.9414	94.14%
CYP1A2 inhibition	-	0.8713	87.13%
CYP2C8 inhibition	-	0.8406	84.06%
CYP inhibitory promiscuity	-	0.8860	88.60%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4602	46.02%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.8144	81.44%
Skin irritation	+	0.5315	53.15%
Skin corrosion	-	0.8698	86.98%
Ames mutagenesis	-	0.6624	66.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.6699	66.99%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.7158	71.58%
skin sensitisation	-	0.7711	77.11%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.6052	60.52%
Acute Oral Toxicity (c)	I	0.3926	39.26%
Estrogen receptor binding	+	0.6409	64.09%
Androgen receptor binding	+	0.6483	64.83%
Thyroid receptor binding	-	0.4931	49.31%
Glucocorticoid receptor binding	+	0.6031	60.31%
Aromatase binding	-	0.6411	64.11%
PPAR gamma	-	0.6018	60.18%
Honey bee toxicity	-	0.8530	85.30%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9929	99.29%

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	97.00%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.86%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.33%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.06%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.00%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	84.41%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.17%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.37%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.78%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.35%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.66%	96.09%

Plants that contains it

• Ferreyranthus fruticosus

Cross-Links

• PubChem: 162904159
• LOTUS: LTS0210333
• wikiData: Q104991698