(3aS,6aS,9R,9aS,9bS)-6a,9-dihydroxy-9-methyl-3,6-dimethylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: 1abd94cd-f919-4d83-99d5-8e22bcc6379b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,6aS,9R,9aS,9bS)-6a,9-dihydroxy-9-methyl-3,6-dimethylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1(C=CC2(C1C3C(CCC2=C)C(=C)C(=O)O3)O)O
• SMILES (Isomeric): C[C@]1(C=C[C@@]2([C@H]1[C@@H]3[C@@H](CCC2=C)C(=C)C(=O)O3)O)O
• InChI: InChI=1S/C15H18O4/c1-8-4-5-10-9(2)13(16)19-11(10)12-14(3,17)6-7-15(8,12)18/h6-7,10-12,17-18H,1-2,4-5H2,3H3/t10-,11-,12-,14+,15+/m0/s1
• InChI Key: OOFQAUVGYPFQPZ-JQPXUNLUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.10
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9332	93.32%
Caco-2	-	0.6476	64.76%
Blood Brain Barrier	-	0.6473	64.73%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5769	57.69%
OATP2B1 inhibitior	-	0.8551	85.51%
OATP1B1 inhibitior	+	0.8948	89.48%
OATP1B3 inhibitior	+	0.9408	94.08%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7821	78.21%
BSEP inhibitior	-	0.9794	97.94%
P-glycoprotein inhibitior	-	0.8713	87.13%
P-glycoprotein substrate	-	0.9193	91.93%
CYP3A4 substrate	+	0.5578	55.78%
CYP2C9 substrate	-	0.8223	82.23%
CYP2D6 substrate	-	0.8552	85.52%
CYP3A4 inhibition	-	0.8534	85.34%
CYP2C9 inhibition	-	0.7781	77.81%
CYP2C19 inhibition	-	0.7530	75.30%
CYP2D6 inhibition	-	0.9059	90.59%
CYP1A2 inhibition	-	0.5728	57.28%
CYP2C8 inhibition	-	0.7765	77.65%
CYP inhibitory promiscuity	-	0.7810	78.10%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9425	94.25%
Carcinogenicity (trinary)	Non-required	0.4728	47.28%
Eye corrosion	-	0.9494	94.94%
Eye irritation	-	0.8517	85.17%
Skin irritation	-	0.5909	59.09%
Skin corrosion	-	0.8236	82.36%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3683	36.83%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.8324	83.24%
skin sensitisation	-	0.7299	72.99%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5754	57.54%
Acute Oral Toxicity (c)	III	0.3799	37.99%
Estrogen receptor binding	+	0.5940	59.40%
Androgen receptor binding	+	0.6515	65.15%
Thyroid receptor binding	-	0.5463	54.63%
Glucocorticoid receptor binding	+	0.5556	55.56%
Aromatase binding	-	0.5427	54.27%
PPAR gamma	-	0.6037	60.37%
Honey bee toxicity	-	0.8858	88.58%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.8655	86.55%

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	95.62%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.66%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.56%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.28%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.29%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.11%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.62%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.62%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.66%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.46%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.65%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	80.21%	91.49%

Plants that contains it

• Artemisia rutifolia

Cross-Links

• PubChem: 163043492
• LOTUS: LTS0253949
• wikiData: Q105195345