(3aR,5aS,8S,8aS)-3a,5a-dihydroxy-1,5,8-trimethyl-7,8,8a,9-tetrahydro-6H-azuleno[6,5-b]furan-2-one

Details

• Internal ID: 0b54e04d-74b1-4ffc-8b70-275003efd121
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aR,5aS,8S,8aS)-3a,5a-dihydroxy-1,5,8-trimethyl-7,8,8a,9-tetrahydro-6H-azuleno[6,5-b]furan-2-one
• SMILES (Canonical): CC1CCC2(C1CC3=C(C(=O)OC3(C=C2C)O)C)O
• SMILES (Isomeric): C[C@H]1CC[C@@]2([C@H]1CC3=C(C(=O)O[C@@]3(C=C2C)O)C)O
• InChI: InChI=1S/C15H20O4/c1-8-4-5-14(17)9(2)7-15(18)12(6-11(8)14)10(3)13(16)19-15/h7-8,11,17-18H,4-6H2,1-3H3/t8-,11-,14+,15+/m0/s1
• InChI Key: SEOLELWZKNPODR-YFZRIKAGSA-N
• Popularity: 2 references 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: 0.70
• Atomic LogP (AlogP): 1.68
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 2,4,4aalpha,5,6,7,7a,9a-Octahydro-3,5beta,8-trimethyl-7aalpha,9aalpha-dihydroxyazuleno[6,5-b]furan-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9885	98.85%
Caco-2	+	0.8565	85.65%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6398	63.98%
OATP2B1 inhibitior	-	0.8558	85.58%
OATP1B1 inhibitior	+	0.8929	89.29%
OATP1B3 inhibitior	+	0.9496	94.96%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6071	60.71%
BSEP inhibitior	-	0.8496	84.96%
P-glycoprotein inhibitior	-	0.9253	92.53%
P-glycoprotein substrate	-	0.8540	85.40%
CYP3A4 substrate	+	0.6096	60.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8768	87.68%
CYP3A4 inhibition	-	0.7103	71.03%
CYP2C9 inhibition	-	0.7357	73.57%
CYP2C19 inhibition	-	0.7670	76.70%
CYP2D6 inhibition	-	0.9534	95.34%
CYP1A2 inhibition	+	0.7187	71.87%
CYP2C8 inhibition	-	0.8682	86.82%
CYP inhibitory promiscuity	-	0.9459	94.59%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4970	49.70%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.7473	74.73%
Skin irritation	+	0.6062	60.62%
Skin corrosion	-	0.9138	91.38%
Ames mutagenesis	-	0.7670	76.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6166	61.66%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.5462	54.62%
skin sensitisation	-	0.8029	80.29%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.7881	78.81%
Acute Oral Toxicity (c)	II	0.3487	34.87%
Estrogen receptor binding	-	0.6677	66.77%
Androgen receptor binding	+	0.5913	59.13%
Thyroid receptor binding	+	0.6848	68.48%
Glucocorticoid receptor binding	+	0.6377	63.77%
Aromatase binding	-	0.7245	72.45%
PPAR gamma	+	0.5220	52.20%
Honey bee toxicity	-	0.8920	89.20%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9744	97.44%

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	97.02%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.85%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.58%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.48%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.04%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.60%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.04%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.93%	99.23%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.14%	94.80%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.97%	100.00%

Plants that contains it

• Daphne aurantiaca

Cross-Links

• PubChem: 46211180
• NPASS: NPC287015
• ChEMBL: CHEMBL1095577
• LOTUS: LTS0204303
• wikiData: Q105251379