(3S,3aS,5aR,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-3,3a,4,5,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2,6-dione

Details

• Internal ID: 7abfdec5-021a-4769-a6d8-30f3e1b0ca21
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3S,3aS,5aR,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-3,3a,4,5,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2,6-dione
• SMILES (Canonical): CC1C2CCC3(C(C2OC1=O)C(CCC3=O)(C)O)C
• SMILES (Isomeric): C[C@H]1[C@@H]2CC[C@@]3([C@@H]([C@H]2OC1=O)[C@](CCC3=O)(C)O)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/h8-9,11-12,18H,4-7H2,1-3H3/t8-,9-,11-,12+,14-,15+/m0/s1
• InChI Key: SMEJXMYNQKQENF-WUDKWMPASA-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): 63.60 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.69
• 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	+	0.9834	98.34%
Caco-2	+	0.6676	66.76%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7279	72.79%
OATP2B1 inhibitior	-	0.8538	85.38%
OATP1B1 inhibitior	+	0.9344	93.44%
OATP1B3 inhibitior	+	0.8757	87.57%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6571	65.71%
BSEP inhibitior	-	0.9173	91.73%
P-glycoprotein inhibitior	-	0.8745	87.45%
P-glycoprotein substrate	-	0.9040	90.40%
CYP3A4 substrate	+	0.5817	58.17%
CYP2C9 substrate	-	0.8104	81.04%
CYP2D6 substrate	-	0.8535	85.35%
CYP3A4 inhibition	-	0.7224	72.24%
CYP2C9 inhibition	-	0.8834	88.34%
CYP2C19 inhibition	-	0.8858	88.58%
CYP2D6 inhibition	-	0.9784	97.84%
CYP1A2 inhibition	-	0.7894	78.94%
CYP2C8 inhibition	-	0.9199	91.99%
CYP inhibitory promiscuity	-	0.9877	98.77%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6210	62.10%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9058	90.58%
Skin irritation	+	0.6426	64.26%
Skin corrosion	-	0.7711	77.11%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7068	70.68%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.6982	69.82%
skin sensitisation	-	0.8907	89.07%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.5056	50.56%
Acute Oral Toxicity (c)	III	0.3465	34.65%
Estrogen receptor binding	+	0.6896	68.96%
Androgen receptor binding	+	0.5467	54.67%
Thyroid receptor binding	+	0.6107	61.07%
Glucocorticoid receptor binding	+	0.5690	56.90%
Aromatase binding	-	0.6960	69.60%
PPAR gamma	-	0.6520	65.20%
Honey bee toxicity	-	0.9101	91.01%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9760	97.60%

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	94.44%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.40%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.21%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.00%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.98%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.98%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.72%	96.09%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	80.16%	89.05%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162971514
• LOTUS: LTS0239735
• wikiData: Q105255860