(3aS,6aR,9R,9aS,9bS)-9-hydroxy-9-methyl-3,6-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one

Details

• Internal ID: 5cd6112a-75bf-4d47-bd59-79122f9fa51c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,6aR,9R,9aS,9bS)-9-hydroxy-9-methyl-3,6-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1(CCC2C1C3C(CCC2=C)C(=C)C(=O)O3)O
• SMILES (Isomeric): C[C@]1(CC[C@@H]2[C@H]1[C@@H]3[C@@H](CCC2=C)C(=C)C(=O)O3)O
• InChI: InChI=1S/C15H20O3/c1-8-4-5-11-9(2)14(16)18-13(11)12-10(8)6-7-15(12,3)17/h10-13,17H,1-2,4-7H2,3H3/t10-,11-,12-,13-,15+/m0/s1
• InChI Key: QRVGCXGOIPXKQE-MJDBTJCESA-N
• Popularity: 1 reference 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: 1.80
• Atomic LogP (AlogP): 2.21
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• SCHEMBL17147754

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9936	99.36%
Caco-2	+	0.6597	65.97%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5768	57.68%
OATP2B1 inhibitior	-	0.8536	85.36%
OATP1B1 inhibitior	+	0.8472	84.72%
OATP1B3 inhibitior	+	0.9323	93.23%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.9659	96.59%
P-glycoprotein inhibitior	-	0.8964	89.64%
P-glycoprotein substrate	-	0.9095	90.95%
CYP3A4 substrate	+	0.6008	60.08%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	-	0.8539	85.39%
CYP3A4 inhibition	-	0.8348	83.48%
CYP2C9 inhibition	-	0.8336	83.36%
CYP2C19 inhibition	-	0.6537	65.37%
CYP2D6 inhibition	-	0.9538	95.38%
CYP1A2 inhibition	+	0.6734	67.34%
CYP2C8 inhibition	-	0.7262	72.62%
CYP inhibitory promiscuity	-	0.9582	95.82%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5028	50.28%
Eye corrosion	-	0.9762	97.62%
Eye irritation	-	0.6417	64.17%
Skin irritation	+	0.5564	55.64%
Skin corrosion	-	0.8804	88.04%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5745	57.45%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.8574	85.74%
skin sensitisation	-	0.7270	72.70%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.6723	67.23%
Acute Oral Toxicity (c)	III	0.3819	38.19%
Estrogen receptor binding	+	0.7370	73.70%
Androgen receptor binding	+	0.7029	70.29%
Thyroid receptor binding	-	0.5497	54.97%
Glucocorticoid receptor binding	+	0.6736	67.36%
Aromatase binding	-	0.7076	70.76%
PPAR gamma	-	0.7260	72.60%
Honey bee toxicity	-	0.8687	86.87%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9789	97.89%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.41%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.98%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.19%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.93%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.80%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.87%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.75%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.80%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	82.33%	97.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.94%	95.89%

Plants that contains it

• Arctotis auriculata
• Casuarina equisetifolia
• Mollugo pentaphylla

Cross-Links

• PubChem: 14466196
• NPASS: NPC245665
• ChEMBL: CHEMBL2206435
• LOTUS: LTS0022764
• wikiData: Q105226655