(3aR,5aR,8aR,9R,9aS)-9-hydroxy-1,5,8-trimethylidene-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,5-b]furan-2-one

Details

• Internal ID: a81c1c2b-9200-4154-8a02-088674e6c47e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: (3aR,5aR,8aR,9R,9aS)-9-hydroxy-1,5,8-trimethylidene-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,5-b]furan-2-one
• SMILES (Canonical): C=C1CCC2C1C(C3C(CC2=C)OC(=O)C3=C)O
• SMILES (Isomeric): C=C1CC[C@@H]2[C@H]1[C@H]([C@H]3[C@@H](CC2=C)OC(=O)C3=C)O
• InChI: InChI=1S/C15H18O3/c1-7-4-5-10-8(2)6-11-13(14(16)12(7)10)9(3)15(17)18-11/h10-14,16H,1-6H2/t10-,11+,12-,13+,14+/m0/s1
• InChI Key: BFJZGJOZEZXOIT-MEBFFEOJSA-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: 1.60
• 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	+	0.9878	98.78%
Caco-2	-	0.5305	53.05%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5222	52.22%
OATP2B1 inhibitior	-	0.8551	85.51%
OATP1B1 inhibitior	+	0.9234	92.34%
OATP1B3 inhibitior	+	0.9548	95.48%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.9204	92.04%
P-glycoprotein inhibitior	-	0.9046	90.46%
P-glycoprotein substrate	-	0.9319	93.19%
CYP3A4 substrate	+	0.5146	51.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7973	79.73%
CYP3A4 inhibition	-	0.8583	85.83%
CYP2C9 inhibition	-	0.9050	90.50%
CYP2C19 inhibition	-	0.7801	78.01%
CYP2D6 inhibition	-	0.9354	93.54%
CYP1A2 inhibition	-	0.6103	61.03%
CYP2C8 inhibition	-	0.9084	90.84%
CYP inhibitory promiscuity	-	0.9293	92.93%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5813	58.13%
Eye corrosion	-	0.7524	75.24%
Eye irritation	+	0.5703	57.03%
Skin irritation	-	0.6385	63.85%
Skin corrosion	-	0.9323	93.23%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6865	68.65%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.7533	75.33%
skin sensitisation	-	0.7049	70.49%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.7111	71.11%
Acute Oral Toxicity (c)	III	0.4500	45.00%
Estrogen receptor binding	+	0.6013	60.13%
Androgen receptor binding	+	0.5360	53.60%
Thyroid receptor binding	-	0.5336	53.36%
Glucocorticoid receptor binding	+	0.7579	75.79%
Aromatase binding	-	0.7163	71.63%
PPAR gamma	-	0.6161	61.61%
Honey bee toxicity	-	0.7981	79.81%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9162	91.62%

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	92.39%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.17%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.75%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.63%	99.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.89%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.63%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.21%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.10%	100.00%

Plants that contains it

• Cyathocline purpurea

Cross-Links

• PubChem: 15857815
• LOTUS: LTS0000684
• wikiData: Q104934300