(3S,3aR,6S,6aS,9aS,9bR)-3,6a-dihydroxy-3-(hydroxymethyl)-6,9a-dimethyl-4,5,6,9b-tetrahydro-3aH-azuleno[8,7-b]furan-2,9-dione

Details

• Internal ID: a3b1d181-4242-4b5d-826e-31885ca8f43f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: (3S,3aR,6S,6aS,9aS,9bR)-3,6a-dihydroxy-3-(hydroxymethyl)-6,9a-dimethyl-4,5,6,9b-tetrahydro-3aH-azuleno[8,7-b]furan-2,9-dione
• SMILES (Canonical): CC1CCC2C(C3(C1(C=CC3=O)O)C)OC(=O)C2(CO)O
• SMILES (Isomeric): C[C@H]1CC[C@@H]2[C@H]([C@]3([C@]1(C=CC3=O)O)C)OC(=O)[C@]2(CO)O
• InChI: InChI=1S/C15H20O6/c1-8-3-4-9-11(21-12(18)14(9,19)7-16)13(2)10(17)5-6-15(8,13)20/h5-6,8-9,11,16,19-20H,3-4,7H2,1-2H3/t8-,9+,11+,13-,14+,15+/m0/s1
• InChI Key: LXSZIMHCXDHCLA-VOKLROIKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₆
• Molecular Weight: 296.31 g/mol
• Exact Mass: 296.12598835 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.44
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9159	91.59%
Caco-2	-	0.5765	57.65%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7418	74.18%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.8954	89.54%
OATP1B3 inhibitior	+	0.9555	95.55%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6859	68.59%
BSEP inhibitior	-	0.9467	94.67%
P-glycoprotein inhibitior	-	0.9393	93.93%
P-glycoprotein substrate	-	0.7843	78.43%
CYP3A4 substrate	+	0.6149	61.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8982	89.82%
CYP3A4 inhibition	-	0.6201	62.01%
CYP2C9 inhibition	-	0.8304	83.04%
CYP2C19 inhibition	-	0.8584	85.84%
CYP2D6 inhibition	-	0.9589	95.89%
CYP1A2 inhibition	-	0.7258	72.58%
CYP2C8 inhibition	-	0.8849	88.49%
CYP inhibitory promiscuity	-	0.9842	98.42%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6350	63.50%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9884	98.84%
Skin irritation	-	0.5397	53.97%
Skin corrosion	-	0.9292	92.92%
Ames mutagenesis	-	0.6070	60.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.7548	75.48%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.5835	58.35%
skin sensitisation	-	0.9230	92.30%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.4829	48.29%
Acute Oral Toxicity (c)	III	0.4156	41.56%
Estrogen receptor binding	+	0.6853	68.53%
Androgen receptor binding	+	0.6005	60.05%
Thyroid receptor binding	+	0.5591	55.91%
Glucocorticoid receptor binding	+	0.7291	72.91%
Aromatase binding	+	0.6947	69.47%
PPAR gamma	-	0.6114	61.14%
Honey bee toxicity	-	0.9418	94.18%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9405	94.05%

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	93.50%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.81%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.46%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.41%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.50%	93.04%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.44%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.21%	97.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.27%	94.80%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.95%	85.14%
CHEMBL2581	P07339	Cathepsin D	80.21%	98.95%

Plants that contains it

• Dichrocephala integrifolia

Cross-Links

• PubChem: 11522200
• LOTUS: LTS0007811
• wikiData: Q105159065