(3aS,6aR,8S,9S,9aR,9bR)-8-hydroxy-9-methyl-3,6-dimethylidene-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: 2786d2f8-0336-45f7-b094-42446e1008a1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,6aR,8S,9S,9aR,9bR)-8-hydroxy-9-methyl-3,6-dimethylidene-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1C(CC2C1C3C(CCC2=C)C(=C)C(=O)O3)O
• SMILES (Isomeric): C[C@@H]1[C@H](C[C@@H]2[C@H]1[C@@H]3[C@@H](CCC2=C)C(=C)C(=O)O3)O
• InChI: InChI=1S/C15H20O3/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h9-14,16H,1-2,4-6H2,3H3/t9-,10+,11+,12+,13+,14+/m1/s1
• InChI Key: DNYGRDBARHAWAJ-ORWNZLQRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.07
• H-Bond Acceptor: 3
• 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	+	0.9958	99.58%
Caco-2	+	0.7336	73.36%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5275	52.75%
OATP2B1 inhibitior	-	0.8535	85.35%
OATP1B1 inhibitior	+	0.8261	82.61%
OATP1B3 inhibitior	+	0.9491	94.91%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.9424	94.24%
P-glycoprotein inhibitior	-	0.9260	92.60%
P-glycoprotein substrate	-	0.8502	85.02%
CYP3A4 substrate	+	0.5427	54.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8285	82.85%
CYP3A4 inhibition	-	0.8259	82.59%
CYP2C9 inhibition	-	0.9431	94.31%
CYP2C19 inhibition	-	0.7913	79.13%
CYP2D6 inhibition	-	0.9418	94.18%
CYP1A2 inhibition	+	0.5462	54.62%
CYP2C8 inhibition	-	0.8739	87.39%
CYP inhibitory promiscuity	-	0.9536	95.36%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6118	61.18%
Eye corrosion	-	0.9290	92.90%
Eye irritation	+	0.6081	60.81%
Skin irritation	-	0.5320	53.20%
Skin corrosion	-	0.9126	91.26%
Ames mutagenesis	-	0.7370	73.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6798	67.98%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.9000	90.00%
skin sensitisation	-	0.6151	61.51%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.5900	59.00%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.6091	60.91%
Acute Oral Toxicity (c)	III	0.5409	54.09%
Estrogen receptor binding	-	0.5135	51.35%
Androgen receptor binding	+	0.5903	59.03%
Thyroid receptor binding	-	0.6135	61.35%
Glucocorticoid receptor binding	+	0.6674	66.74%
Aromatase binding	-	0.7794	77.94%
PPAR gamma	-	0.7697	76.97%
Honey bee toxicity	-	0.8240	82.40%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9511	95.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.56%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.68%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.13%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.06%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.86%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.82%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	83.35%	91.49%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.23%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.16%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.34%	92.94%

Plants that contains it

• Ainsliaea fragrans

Cross-Links

• PubChem: 163069975
• LOTUS: LTS0225197
• wikiData: Q104985849