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

Details

• Internal ID: a74278b4-2a0c-40d0-af9b-2fd93871e3ba
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,5R,6aR,8S,9aR,9bS)-5,8-dihydroxy-3,6,9-trimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): C=C1C2CC(C(=C)C2C3C(CC1O)C(=C)C(=O)O3)O
• SMILES (Isomeric): C=C1[C@@H]2C[C@@H](C(=C)[C@@H]2[C@@H]3[C@@H](C[C@H]1O)C(=C)C(=O)O3)O
• InChI: InChI=1S/C15H18O4/c1-6-9-4-12(17)8(3)13(9)14-10(5-11(6)16)7(2)15(18)19-14/h9-14,16-17H,1-5H2/t9-,10-,11+,12-,13-,14-/m0/s1
• InChI Key: PNMKDWVKEBNNFG-XQZGEAEESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.96
• 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	+	0.9787	97.87%
Caco-2	-	0.6600	66.00%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5226	52.26%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.9206	92.06%
OATP1B3 inhibitior	+	0.9472	94.72%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9682	96.82%
P-glycoprotein inhibitior	-	0.9400	94.00%
P-glycoprotein substrate	-	0.9154	91.54%
CYP3A4 substrate	-	0.5402	54.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7973	79.73%
CYP3A4 inhibition	-	0.8867	88.67%
CYP2C9 inhibition	-	0.9074	90.74%
CYP2C19 inhibition	-	0.8323	83.23%
CYP2D6 inhibition	-	0.9149	91.49%
CYP1A2 inhibition	-	0.8282	82.82%
CYP2C8 inhibition	-	0.9252	92.52%
CYP inhibitory promiscuity	-	0.9050	90.50%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9142	91.42%
Carcinogenicity (trinary)	Non-required	0.5654	56.54%
Eye corrosion	-	0.9263	92.63%
Eye irritation	+	0.6797	67.97%
Skin irritation	-	0.6100	61.00%
Skin corrosion	-	0.8907	89.07%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7993	79.93%
Micronuclear	-	0.5041	50.41%
Hepatotoxicity	+	0.8802	88.02%
skin sensitisation	-	0.6966	69.66%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6802	68.02%
Acute Oral Toxicity (c)	III	0.3886	38.86%
Estrogen receptor binding	+	0.6026	60.26%
Androgen receptor binding	+	0.5818	58.18%
Thyroid receptor binding	-	0.5164	51.64%
Glucocorticoid receptor binding	+	0.7416	74.16%
Aromatase binding	-	0.6715	67.15%
PPAR gamma	-	0.7544	75.44%
Honey bee toxicity	-	0.6998	69.98%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.8878	88.78%

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	91.58%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.37%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.97%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.09%	95.56%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.23%	96.61%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.41%	96.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.80%	89.34%

Plants that contains it

• Crepidiastrum sonchifolium subsp. sonchifolium
• Lactuca quercina
• Lactuca serriola
• Lactuca virosa

Cross-Links

• PubChem: 101938089
• LOTUS: LTS0064728
• wikiData: Q105212039