(3S,6aR,9aR,9bS)-5,8-dihydroxy-3-methyl-6,9-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

Details

• Internal ID: b93045b7-dd37-4fe6-95e7-1135e260bae2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3S,6aR,9aR,9bS)-5,8-dihydroxy-3-methyl-6,9-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1C2CC(C(=C)C3CC(C(=C)C3C2OC1=O)O)O
• SMILES (Isomeric): C[C@H]1C2CC(C(=C)[C@@H]3CC(C(=C)[C@@H]3[C@H]2OC1=O)O)O
• InChI: InChI=1S/C15H20O4/c1-6-9-4-12(17)8(3)13(9)14-10(5-11(6)16)7(2)15(18)19-14/h7,9-14,16-17H,1,3-5H2,2H3/t7-,9-,10?,11?,12?,13-,14-/m0/s1
• InChI Key: GLMKTMOFCGDFFQ-LAEOIKMWSA-N
• Popularity: 0 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: 0.30
• Atomic LogP (AlogP): 1.04
• 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	+	0.9874	98.74%
Caco-2	-	0.6714	67.14%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5123	51.23%
OATP2B1 inhibitior	-	0.8561	85.61%
OATP1B1 inhibitior	+	0.9152	91.52%
OATP1B3 inhibitior	+	0.9534	95.34%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9762	97.62%
P-glycoprotein inhibitior	-	0.9379	93.79%
P-glycoprotein substrate	-	0.8134	81.34%
CYP3A4 substrate	+	0.5336	53.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8313	83.13%
CYP3A4 inhibition	-	0.9144	91.44%
CYP2C9 inhibition	-	0.8972	89.72%
CYP2C19 inhibition	-	0.8102	81.02%
CYP2D6 inhibition	-	0.9188	91.88%
CYP1A2 inhibition	-	0.7085	70.85%
CYP2C8 inhibition	-	0.9473	94.73%
CYP inhibitory promiscuity	-	0.8997	89.97%
UGT catelyzed	+	0.7362	73.62%
Carcinogenicity (binary)	-	0.9142	91.42%
Carcinogenicity (trinary)	Non-required	0.5804	58.04%
Eye corrosion	-	0.9522	95.22%
Eye irritation	-	0.8146	81.46%
Skin irritation	-	0.5798	57.98%
Skin corrosion	-	0.8682	86.82%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7592	75.92%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.7677	76.77%
skin sensitisation	-	0.7137	71.37%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.6698	66.98%
Acute Oral Toxicity (c)	III	0.4482	44.82%
Estrogen receptor binding	-	0.5158	51.58%
Androgen receptor binding	+	0.5572	55.72%
Thyroid receptor binding	+	0.5267	52.67%
Glucocorticoid receptor binding	+	0.6450	64.50%
Aromatase binding	-	0.6802	68.02%
PPAR gamma	-	0.7780	77.80%
Honey bee toxicity	-	0.8168	81.68%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9447	94.47%

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	91.43%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.72%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.13%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.40%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.79%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.05%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.97%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.62%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.98%	90.71%
CHEMBL1871	P10275	Androgen Receptor	80.31%	96.43%

Plants that contains it

• Arctotis fastuosa

Cross-Links

• PubChem: 163053546
• LOTUS: LTS0258571
• wikiData: Q105011053