(3S,3aS,6S,6aS,9aS,9bR)-6a-hydroxy-3,6,9a-trimethyl-3,3a,4,5,6,9b-hexahydroazuleno[8,7-b]furan-2,9-dione

Details

• Internal ID: e240ad7f-c8e7-4bc9-a958-f1c8343478c1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: (3S,3aS,6S,6aS,9aS,9bR)-6a-hydroxy-3,6,9a-trimethyl-3,3a,4,5,6,9b-hexahydroazuleno[8,7-b]furan-2,9-dione
• SMILES (Canonical): CC1CCC2C(C(=O)OC2C3(C1(C=CC3=O)O)C)C
• SMILES (Isomeric): C[C@H]1CC[C@H]2[C@@H](C(=O)O[C@H]2[C@]3([C@]1(C=CC3=O)O)C)C
• InChI: InChI=1S/C15H20O4/c1-8-4-5-10-9(2)13(17)19-12(10)14(3)11(16)6-7-15(8,14)18/h6-10,12,18H,4-5H2,1-3H3/t8-,9-,10-,12+,14-,15+/m0/s1
• InChI Key: OYBKYXUMZIXQDT-DMFLFAPQSA-N
• Popularity: 3 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): 63.60 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.47
• 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	+	0.9666	96.66%
Caco-2	+	0.5980	59.80%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5565	55.65%
OATP2B1 inhibitior	-	0.8531	85.31%
OATP1B1 inhibitior	+	0.9060	90.60%
OATP1B3 inhibitior	+	0.9020	90.20%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7821	78.21%
BSEP inhibitior	-	0.9528	95.28%
P-glycoprotein inhibitior	-	0.8988	89.88%
P-glycoprotein substrate	-	0.7645	76.45%
CYP3A4 substrate	+	0.5941	59.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9037	90.37%
CYP3A4 inhibition	-	0.8007	80.07%
CYP2C9 inhibition	-	0.8318	83.18%
CYP2C19 inhibition	-	0.8787	87.87%
CYP2D6 inhibition	-	0.9593	95.93%
CYP1A2 inhibition	+	0.5912	59.12%
CYP2C8 inhibition	-	0.9302	93.02%
CYP inhibitory promiscuity	-	0.9682	96.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5342	53.42%
Eye corrosion	-	0.9658	96.58%
Eye irritation	-	0.9685	96.85%
Skin irritation	+	0.5341	53.41%
Skin corrosion	-	0.6198	61.98%
Ames mutagenesis	-	0.7940	79.40%
Human Ether-a-go-go-Related Gene inhibition	-	0.6342	63.42%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.5671	56.71%
skin sensitisation	-	0.7600	76.00%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.4855	48.55%
Acute Oral Toxicity (c)	II	0.4341	43.41%
Estrogen receptor binding	+	0.6860	68.60%
Androgen receptor binding	+	0.6019	60.19%
Thyroid receptor binding	-	0.5064	50.64%
Glucocorticoid receptor binding	+	0.5543	55.43%
Aromatase binding	-	0.5666	56.66%
PPAR gamma	-	0.6374	63.74%
Honey bee toxicity	-	0.9251	92.51%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9539	95.39%

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	95.16%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.18%	97.25%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	89.55%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.27%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.27%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.20%	97.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.43%	94.80%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.54%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.99%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.27%	99.23%

Plants that contains it

• Dendrobium chrysanthum

Cross-Links

• PubChem: 10989149
• NPASS: NPC265863