(3aS,6R,6aR,9aR,9bS)-6-hydroxy-6,9-dimethyl-3-methylidene-3a,4,5,6a,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione

Details

• Internal ID: 923ae82b-39ec-4ba1-bcfd-c49701e3072e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,6R,6aR,9aR,9bS)-6-hydroxy-6,9-dimethyl-3-methylidene-3a,4,5,6a,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
• SMILES (Canonical): CC1=CC(=O)C2C1C3C(CCC2(C)O)C(=C)C(=O)O3
• SMILES (Isomeric): CC1=CC(=O)[C@@H]2[C@H]1[C@@H]3[C@@H](CC[C@@]2(C)O)C(=C)C(=O)O3
• InChI: InChI=1S/C15H18O4/c1-7-6-10(16)12-11(7)13-9(4-5-15(12,3)18)8(2)14(17)19-13/h6,9,11-13,18H,2,4-5H2,1,3H3/t9-,11-,12+,13-,15+/m0/s1
• InChI Key: HARKXFOTIYQCLZ-OHJULZJPSA-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): 63.60 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.39
• H-Bond Acceptor: 4
• 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	+	0.9885	98.85%
Caco-2	+	0.6206	62.06%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5876	58.76%
OATP2B1 inhibitior	-	0.8556	85.56%
OATP1B1 inhibitior	+	0.8285	82.85%
OATP1B3 inhibitior	+	0.9174	91.74%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7271	72.71%
BSEP inhibitior	-	0.9750	97.50%
P-glycoprotein inhibitior	-	0.8871	88.71%
P-glycoprotein substrate	-	0.7609	76.09%
CYP3A4 substrate	+	0.6062	60.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9043	90.43%
CYP3A4 inhibition	-	0.7628	76.28%
CYP2C9 inhibition	-	0.8985	89.85%
CYP2C19 inhibition	-	0.9164	91.64%
CYP2D6 inhibition	-	0.9349	93.49%
CYP1A2 inhibition	-	0.6615	66.15%
CYP2C8 inhibition	-	0.6668	66.68%
CYP inhibitory promiscuity	-	0.9774	97.74%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5557	55.57%
Eye corrosion	-	0.9666	96.66%
Eye irritation	-	0.7991	79.91%
Skin irritation	+	0.5119	51.19%
Skin corrosion	-	0.7311	73.11%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4323	43.23%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.8908	89.08%
skin sensitisation	-	0.6919	69.19%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.6053	60.53%
Acute Oral Toxicity (c)	II	0.3531	35.31%
Estrogen receptor binding	+	0.6443	64.43%
Androgen receptor binding	+	0.6851	68.51%
Thyroid receptor binding	-	0.5101	51.01%
Glucocorticoid receptor binding	-	0.5931	59.31%
Aromatase binding	-	0.7552	75.52%
PPAR gamma	-	0.6098	60.98%
Honey bee toxicity	-	0.8838	88.38%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9426	94.26%

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	93.09%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.70%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.26%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.53%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.31%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.06%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.53%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.97%	95.89%
CHEMBL2581	P07339	Cathepsin D	80.78%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.75%	89.00%

Plants that contains it

• Kaunia longipetiolata

Cross-Links

• PubChem: 162900230
• LOTUS: LTS0117648
• wikiData: Q105025009