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

Details

• Internal ID: 1f2b0113-dd1c-455a-94eb-b9868bb8804e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3S,3aS,5R,6aR,9aR,9bS)-5-hydroxy-3-methyl-6,9-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1C2CC(C(=C)C3CCC(=C)C3C2OC1=O)O
• SMILES (Isomeric): C[C@H]1[C@@H]2C[C@H](C(=C)[C@@H]3CCC(=C)[C@@H]3[C@H]2OC1=O)O
• InChI: InChI=1S/C15H20O3/c1-7-4-5-10-8(2)12(16)6-11-9(3)15(17)18-14(11)13(7)10/h9-14,16H,1-2,4-6H2,3H3/t9-,10-,11-,12+,13-,14-/m0/s1
• InChI Key: NMUKFBVCUMTQOB-GAURVVSWSA-N
• Popularity: 2 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: 1.60
• 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	+	0.9944	99.44%
Caco-2	+	0.6381	63.81%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5499	54.99%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.8948	89.48%
OATP1B3 inhibitior	+	0.9557	95.57%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.9447	94.47%
P-glycoprotein inhibitior	-	0.9236	92.36%
P-glycoprotein substrate	-	0.7490	74.90%
CYP3A4 substrate	+	0.5625	56.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8313	83.13%
CYP3A4 inhibition	-	0.9034	90.34%
CYP2C9 inhibition	-	0.9235	92.35%
CYP2C19 inhibition	-	0.7907	79.07%
CYP2D6 inhibition	-	0.9214	92.14%
CYP1A2 inhibition	-	0.5596	55.96%
CYP2C8 inhibition	-	0.8969	89.69%
CYP inhibitory promiscuity	-	0.9362	93.62%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5959	59.59%
Eye corrosion	-	0.9167	91.67%
Eye irritation	-	0.6152	61.52%
Skin irritation	-	0.5541	55.41%
Skin corrosion	-	0.8670	86.70%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7730	77.30%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.6208	62.08%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5712	57.12%
Acute Oral Toxicity (c)	III	0.5238	52.38%
Estrogen receptor binding	-	0.6007	60.07%
Androgen receptor binding	+	0.5686	56.86%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5423	54.23%
Aromatase binding	-	0.7778	77.78%
PPAR gamma	-	0.7826	78.26%
Honey bee toxicity	-	0.8228	82.28%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.8810	88.10%

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	91.36%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	90.37%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.98%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.29%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.29%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.44%	95.56%
CHEMBL1871	P10275	Androgen Receptor	85.04%	96.43%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.26%	99.23%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	82.61%	98.46%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.44%	89.00%
CHEMBL1978	P11511	Cytochrome P450 19A1	81.79%	91.76%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.52%	90.71%

Plants that contains it

• Picris hieracioides

Cross-Links

• PubChem: 162968993
• LOTUS: LTS0178241
• wikiData: Q105181969