(3aS,5S,5aR,8R,8aS,9aR)-5a,8-dihydroxy-5,8-dimethyl-1-methylidene-3a,4,5,6,7,8a,9,9a-octahydroazuleno[6,5-b]furan-2-one

Details

• Internal ID: 18dbd1bd-d203-4456-89b7-ee3bf1f68744
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,5S,5aR,8R,8aS,9aR)-5a,8-dihydroxy-5,8-dimethyl-1-methylidene-3a,4,5,6,7,8a,9,9a-octahydroazuleno[6,5-b]furan-2-one
• SMILES (Canonical): CC1CC2C(CC3C1(CCC3(C)O)O)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@H]1C[C@H]2[C@H](C[C@@H]3[C@]1(CC[C@@]3(C)O)O)C(=C)C(=O)O2
• InChI: InChI=1S/C15H22O4/c1-8-6-11-10(9(2)13(16)19-11)7-12-14(3,17)4-5-15(8,12)18/h8,10-12,17-18H,2,4-7H2,1,3H3/t8-,10+,11-,12-,14+,15+/m0/s1
• InChI Key: SFYCHZOHMRIYJL-WTBCFXLOSA-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): 66.80 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.41
• 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	+	0.9660	96.60%
Caco-2	+	0.7393	73.93%
Blood Brain Barrier	-	0.5223	52.23%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5241	52.41%
OATP2B1 inhibitior	-	0.8501	85.01%
OATP1B1 inhibitior	+	0.8843	88.43%
OATP1B3 inhibitior	+	0.9165	91.65%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6321	63.21%
BSEP inhibitior	-	0.9669	96.69%
P-glycoprotein inhibitior	-	0.9330	93.30%
P-glycoprotein substrate	-	0.9087	90.87%
CYP3A4 substrate	+	0.5744	57.44%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	-	0.8539	85.39%
CYP3A4 inhibition	-	0.7705	77.05%
CYP2C9 inhibition	-	0.8116	81.16%
CYP2C19 inhibition	-	0.8082	80.82%
CYP2D6 inhibition	-	0.9425	94.25%
CYP1A2 inhibition	+	0.5869	58.69%
CYP2C8 inhibition	-	0.8429	84.29%
CYP inhibitory promiscuity	-	0.9344	93.44%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5774	57.74%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.7747	77.47%
Skin irritation	+	0.5115	51.15%
Skin corrosion	-	0.8990	89.90%
Ames mutagenesis	-	0.6424	64.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.4593	45.93%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.6241	62.41%
skin sensitisation	-	0.7783	77.83%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.5499	54.99%
Acute Oral Toxicity (c)	II	0.3435	34.35%
Estrogen receptor binding	+	0.7613	76.13%
Androgen receptor binding	-	0.5416	54.16%
Thyroid receptor binding	+	0.6462	64.62%
Glucocorticoid receptor binding	+	0.7571	75.71%
Aromatase binding	-	0.5791	57.91%
PPAR gamma	+	0.6630	66.30%
Honey bee toxicity	-	0.8055	80.55%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9832	98.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.94%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	92.80%	97.79%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.61%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.28%	95.56%
CHEMBL299	P17252	Protein kinase C alpha	88.93%	98.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.74%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.72%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.61%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.46%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.74%	86.33%

Plants that contains it

• Picris asplenioides subsp. asplenioides

Cross-Links

• PubChem: 162888842
• LOTUS: LTS0158261
• wikiData: Q105252136