(3S,3aS,6aS,9R,9aS,9bS)-6a,9-dihydroxy-3,9-dimethyl-6-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2-one

Details

• Internal ID: 0f7fcbab-8a9d-4d14-b8df-947b9639ac06
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3S,3aS,6aS,9R,9aS,9bS)-6a,9-dihydroxy-3,9-dimethyl-6-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1C2CCC(=C)C3(C=CC(C3C2OC1=O)(C)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]2CCC(=C)[C@@]3(C=C[C@@]([C@@H]3[C@H]2OC1=O)(C)O)O
• InChI: InChI=1S/C15H20O4/c1-8-4-5-10-9(2)13(16)19-11(10)12-14(3,17)6-7-15(8,12)18/h6-7,9-12,17-18H,1,4-5H2,2-3H3/t9-,10-,11-,12-,14+,15+/m0/s1
• InChI Key: RXOIKFWKDNBHPU-OOAGNDBOSA-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: 0.70
• Atomic LogP (AlogP): 1.18
• 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	+	0.9434	94.34%
Caco-2	-	0.6823	68.23%
Blood Brain Barrier	+	0.5027	50.27%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5086	50.86%
OATP2B1 inhibitior	-	0.8544	85.44%
OATP1B1 inhibitior	+	0.9162	91.62%
OATP1B3 inhibitior	+	0.9165	91.65%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8071	80.71%
BSEP inhibitior	-	0.9284	92.84%
P-glycoprotein inhibitior	-	0.9076	90.76%
P-glycoprotein substrate	-	0.8758	87.58%
CYP3A4 substrate	+	0.5748	57.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8639	86.39%
CYP3A4 inhibition	-	0.8053	80.53%
CYP2C9 inhibition	-	0.7751	77.51%
CYP2C19 inhibition	-	0.7763	77.63%
CYP2D6 inhibition	-	0.9050	90.50%
CYP1A2 inhibition	+	0.5823	58.23%
CYP2C8 inhibition	-	0.9036	90.36%
CYP inhibitory promiscuity	-	0.7877	78.77%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9525	95.25%
Carcinogenicity (trinary)	Non-required	0.5369	53.69%
Eye corrosion	-	0.9729	97.29%
Eye irritation	-	0.8513	85.13%
Skin irritation	-	0.5408	54.08%
Skin corrosion	-	0.8004	80.04%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4597	45.97%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.7982	79.82%
skin sensitisation	-	0.7074	70.74%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.4812	48.12%
Acute Oral Toxicity (c)	III	0.3633	36.33%
Estrogen receptor binding	+	0.6879	68.79%
Androgen receptor binding	+	0.6445	64.45%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6379	63.79%
Aromatase binding	-	0.6152	61.52%
PPAR gamma	-	0.6479	64.79%
Honey bee toxicity	-	0.8697	86.97%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9465	94.65%

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	96.06%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.67%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.72%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.10%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.51%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.25%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.59%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.06%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	80.48%	91.49%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.34%	93.04%

Plants that contains it

• Artemisia adamsii

Cross-Links

• PubChem: 162889445
• LOTUS: LTS0147781
• wikiData: Q105247194