(4S,4aR,5S,9aR)-4,9a-dihydroxy-3,4a,5-trimethyl-5,6,7,9-tetrahydro-4H-benzo[f][1]benzofuran-2-one

Details

• Internal ID: 3a800a67-b4ad-433e-a367-2317a330dd10
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4S,4aR,5S,9aR)-4,9a-dihydroxy-3,4a,5-trimethyl-5,6,7,9-tetrahydro-4H-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1CCC=C2C1(C(C3=C(C(=O)OC3(C2)O)C)O)C
• SMILES (Isomeric): C[C@H]1CCC=C2[C@@]1([C@@H](C3=C(C(=O)O[C@@]3(C2)O)C)O)C
• InChI: InChI=1S/C15H20O4/c1-8-5-4-6-10-7-15(18)11(9(2)13(17)19-15)12(16)14(8,10)3/h6,8,12,16,18H,4-5,7H2,1-3H3/t8-,12+,14+,15+/m0/s1
• InChI Key: UGNQNRZIEYRXRE-AZEZGGBOSA-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: 1.00
• Atomic LogP (AlogP): 1.68
• 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	+	0.9836	98.36%
Caco-2	+	0.8395	83.95%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.9164	91.64%
OATP1B3 inhibitior	+	0.9572	95.72%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.7496	74.96%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.8024	80.24%
CYP3A4 substrate	+	0.5960	59.60%
CYP2C9 substrate	-	0.7943	79.43%
CYP2D6 substrate	-	0.8686	86.86%
CYP3A4 inhibition	-	0.6327	63.27%
CYP2C9 inhibition	-	0.9154	91.54%
CYP2C19 inhibition	-	0.9353	93.53%
CYP2D6 inhibition	-	0.9489	94.89%
CYP1A2 inhibition	-	0.6099	60.99%
CYP2C8 inhibition	-	0.7605	76.05%
CYP inhibitory promiscuity	-	0.8696	86.96%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4304	43.04%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.9370	93.70%
Skin irritation	+	0.7052	70.52%
Skin corrosion	-	0.9076	90.76%
Ames mutagenesis	-	0.6770	67.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5221	52.21%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5217	52.17%
skin sensitisation	-	0.8135	81.35%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.7031	70.31%
Acute Oral Toxicity (c)	I	0.4947	49.47%
Estrogen receptor binding	-	0.6076	60.76%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.4882	48.82%
Glucocorticoid receptor binding	+	0.5411	54.11%
Aromatase binding	-	0.5743	57.43%
PPAR gamma	+	0.5383	53.83%
Honey bee toxicity	-	0.8428	84.28%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9869	98.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.40%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.60%	91.11%
CHEMBL2581	P07339	Cathepsin D	89.94%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.82%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.37%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.03%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.63%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.53%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.44%	86.33%
CHEMBL4208	P20618	Proteasome component C5	83.14%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.35%	97.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.32%	96.77%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.31%	93.04%

Plants that contains it

• Packera toluccana

Cross-Links

• PubChem: 11572499
• LOTUS: LTS0078441
• wikiData: Q105272460