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

Details

• Internal ID: 751dcf16-ddb4-484e-9e69-84cbf3f8487c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aR,4R,6aS,9aR,9bR)-4-hydroxy-9-methyl-3,6-dimethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1=CCC2C1C3C(C(CC2=C)O)C(=C)C(=O)O3
• SMILES (Isomeric): CC1=CC[C@H]2[C@H]1[C@@H]3[C@@H]([C@@H](CC2=C)O)C(=C)C(=O)O3
• InChI: InChI=1S/C15H18O3/c1-7-4-5-10-8(2)6-11(16)13-9(3)15(17)18-14(13)12(7)10/h4,10-14,16H,2-3,5-6H2,1H3/t10-,11-,12+,13-,14-/m1/s1
• InChI Key: YNKRYYFPKLHACH-RKQHYHRCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.99
• 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	+	0.9964	99.64%
Caco-2	+	0.5427	54.27%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.7571	75.71%
Subcellular localzation	Mitochondria	0.4401	44.01%
OATP2B1 inhibitior	-	0.8578	85.78%
OATP1B1 inhibitior	+	0.9110	91.10%
OATP1B3 inhibitior	+	0.9561	95.61%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9586	95.86%
P-glycoprotein inhibitior	-	0.9003	90.03%
P-glycoprotein substrate	-	0.8767	87.67%
CYP3A4 substrate	+	0.5376	53.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8285	82.85%
CYP3A4 inhibition	-	0.8628	86.28%
CYP2C9 inhibition	-	0.9442	94.42%
CYP2C19 inhibition	-	0.8262	82.62%
CYP2D6 inhibition	-	0.9595	95.95%
CYP1A2 inhibition	-	0.6052	60.52%
CYP2C8 inhibition	-	0.9346	93.46%
CYP inhibitory promiscuity	-	0.9339	93.39%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5092	50.92%
Eye corrosion	-	0.8955	89.55%
Eye irritation	-	0.5521	55.21%
Skin irritation	+	0.5375	53.75%
Skin corrosion	-	0.8286	82.86%
Ames mutagenesis	-	0.6370	63.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5804	58.04%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.6908	69.08%
skin sensitisation	-	0.6421	64.21%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5836	58.36%
Acute Oral Toxicity (c)	III	0.4768	47.68%
Estrogen receptor binding	-	0.5279	52.79%
Androgen receptor binding	+	0.5658	56.58%
Thyroid receptor binding	-	0.5633	56.33%
Glucocorticoid receptor binding	+	0.5902	59.02%
Aromatase binding	-	0.8016	80.16%
PPAR gamma	-	0.7470	74.70%
Honey bee toxicity	-	0.8038	80.38%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9352	93.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.28%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.93%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.05%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.65%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	86.38%	94.73%
CHEMBL2581	P07339	Cathepsin D	85.54%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.02%	89.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.15%	93.56%
CHEMBL221	P23219	Cyclooxygenase-1	81.72%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.69%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.03%	95.89%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.26%	93.03%

Plants that contains it

• Picradeniopsis schaffneri

Cross-Links

• PubChem: 162984882
• LOTUS: LTS0267803
• wikiData: Q105350984