(4S,4aR,5S,9aR)-4,9a-dihydroxy-3,4a,5-trimethyl-4,5,6,7-tetrahydrobenzo[f][1]benzofuran-2,8-dione

Details

• Internal ID: 32dff888-511e-4ffd-87ed-6b3b1da3e9d8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4S,4aR,5S,9aR)-4,9a-dihydroxy-3,4a,5-trimethyl-4,5,6,7-tetrahydrobenzo[f][1]benzofuran-2,8-dione
• SMILES (Canonical): CC1CCC(=O)C2=CC3(C(=C(C(=O)O3)C)C(C12C)O)O
• SMILES (Isomeric): C[C@H]1CCC(=O)C2=C[C@@]3(C(=C(C(=O)O3)C)[C@H]([C@]12C)O)O
• InChI: InChI=1S/C15H18O5/c1-7-4-5-10(16)9-6-15(19)11(8(2)13(18)20-15)12(17)14(7,9)3/h6-7,12,17,19H,4-5H2,1-3H3/t7-,12+,14+,15+/m0/s1
• InChI Key: KSIHDKSKQWRYLV-YQKRUCBRSA-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): 0.85
• 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	+	0.9698	96.98%
Caco-2	+	0.7895	78.95%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6762	67.62%
OATP2B1 inhibitior	-	0.8570	85.70%
OATP1B1 inhibitior	+	0.9084	90.84%
OATP1B3 inhibitior	+	0.9573	95.73%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5521	55.21%
BSEP inhibitior	-	0.8258	82.58%
P-glycoprotein inhibitior	-	0.9195	91.95%
P-glycoprotein substrate	-	0.7940	79.40%
CYP3A4 substrate	+	0.6078	60.78%
CYP2C9 substrate	-	0.7872	78.72%
CYP2D6 substrate	-	0.8844	88.44%
CYP3A4 inhibition	-	0.6953	69.53%
CYP2C9 inhibition	-	0.8685	86.85%
CYP2C19 inhibition	-	0.9574	95.74%
CYP2D6 inhibition	-	0.9398	93.98%
CYP1A2 inhibition	+	0.6012	60.12%
CYP2C8 inhibition	-	0.8467	84.67%
CYP inhibitory promiscuity	-	0.7855	78.55%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Danger	0.4650	46.50%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9299	92.99%
Skin irritation	+	0.6498	64.98%
Skin corrosion	-	0.7834	78.34%
Ames mutagenesis	-	0.6870	68.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6022	60.22%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.6232	62.32%
skin sensitisation	-	0.7799	77.99%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6063	60.63%
Acute Oral Toxicity (c)	III	0.4518	45.18%
Estrogen receptor binding	-	0.6267	62.67%
Androgen receptor binding	-	0.5480	54.80%
Thyroid receptor binding	-	0.5330	53.30%
Glucocorticoid receptor binding	-	0.5442	54.42%
Aromatase binding	-	0.6672	66.72%
PPAR gamma	-	0.7015	70.15%
Honey bee toxicity	-	0.8594	85.94%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9718	97.18%

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	96.18%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.37%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.35%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.83%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.78%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.49%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.40%	92.94%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.02%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.75%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.63%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.44%	97.14%

Plants that contains it

• Ligularia virgaurea

Cross-Links

• PubChem: 11161751
• LOTUS: LTS0220488
• wikiData: Q105145424