(1R,3aR,5aR,8aR,9aR)-8-(hydroxymethyl)-1-methyl-5-methylidene-1,3a,4,5a,6,8a,9,9a-octahydroazuleno[6,5-b]furan-2-one

Details

• Internal ID: a796b55f-842b-432e-9427-6b153d1a8559
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (1R,3aR,5aR,8aR,9aR)-8-(hydroxymethyl)-1-methyl-5-methylidene-1,3a,4,5a,6,8a,9,9a-octahydroazuleno[6,5-b]furan-2-one
• SMILES (Canonical): CC1C2CC3C(CC=C3CO)C(=C)CC2OC1=O
• SMILES (Isomeric): C[C@@H]1[C@H]2C[C@@H]3[C@@H](CC=C3CO)C(=C)C[C@H]2OC1=O
• InChI: InChI=1S/C15H20O3/c1-8-5-14-12(9(2)15(17)18-14)6-13-10(7-16)3-4-11(8)13/h3,9,11-14,16H,1,4-7H2,2H3/t9-,11+,12-,13+,14-/m1/s1
• InChI Key: GRXWMNZAVGFDPM-RMTQGBGSSA-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: 1.20
• Atomic LogP (AlogP): 2.07
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9918	99.18%
Caco-2	+	0.6861	68.61%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5685	56.85%
OATP2B1 inhibitior	-	0.8580	85.80%
OATP1B1 inhibitior	+	0.8906	89.06%
OATP1B3 inhibitior	+	0.9575	95.75%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8772	87.72%
P-glycoprotein inhibitior	-	0.9152	91.52%
P-glycoprotein substrate	-	0.7362	73.62%
CYP3A4 substrate	+	0.5456	54.56%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8497	84.97%
CYP3A4 inhibition	-	0.8636	86.36%
CYP2C9 inhibition	-	0.8736	87.36%
CYP2C19 inhibition	-	0.7870	78.70%
CYP2D6 inhibition	-	0.9381	93.81%
CYP1A2 inhibition	-	0.6290	62.90%
CYP2C8 inhibition	-	0.8767	87.67%
CYP inhibitory promiscuity	-	0.8528	85.28%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9417	94.17%
Carcinogenicity (trinary)	Non-required	0.6651	66.51%
Eye corrosion	-	0.9519	95.19%
Eye irritation	-	0.9007	90.07%
Skin irritation	-	0.6216	62.16%
Skin corrosion	-	0.8942	89.42%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6294	62.94%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.6783	67.83%
skin sensitisation	-	0.7066	70.66%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.6255	62.55%
Acute Oral Toxicity (c)	III	0.5213	52.13%
Estrogen receptor binding	-	0.5570	55.70%
Androgen receptor binding	+	0.5630	56.30%
Thyroid receptor binding	-	0.6320	63.20%
Glucocorticoid receptor binding	+	0.6489	64.89%
Aromatase binding	-	0.7182	71.82%
PPAR gamma	-	0.7581	75.81%
Honey bee toxicity	-	0.8050	80.50%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9627	96.27%

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	93.44%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.31%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.02%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.60%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.42%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.60%	96.95%
CHEMBL2581	P07339	Cathepsin D	84.71%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.86%	100.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.17%	89.34%

Plants that contains it

• Stevia samaipatensis

Cross-Links

• PubChem: 163035129
• LOTUS: LTS0157192
• wikiData: Q105016826