3-Hydroxy-6,9-dimethylidene-3-(2-oxopropyl)-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one

Details

• Internal ID: 64cf74cd-92ce-47ff-b34e-f1bf1f2c8b85
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 3-hydroxy-6,9-dimethylidene-3-(2-oxopropyl)-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC(=O)CC1(C2CCC(=C)C3CCC(=C)C3C2OC1=O)O
• SMILES (Isomeric): CC(=O)CC1(C2CCC(=C)C3CCC(=C)C3C2OC1=O)O
• InChI: InChI=1S/C17H22O4/c1-9-5-7-13-15(14-10(2)4-6-12(9)14)21-16(19)17(13,20)8-11(3)18/h12-15,20H,1-2,4-8H2,3H3
• InChI Key: JPMPVNCPOBTSBR-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₄
• Molecular Weight: 290.40 g/mol
• Exact Mass: 290.15180918 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.17
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9671	96.71%
Caco-2	-	0.7198	71.98%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7204	72.04%
OATP2B1 inhibitior	-	0.8567	85.67%
OATP1B1 inhibitior	+	0.8940	89.40%
OATP1B3 inhibitior	+	0.9432	94.32%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6592	65.92%
BSEP inhibitior	-	0.9037	90.37%
P-glycoprotein inhibitior	-	0.8192	81.92%
P-glycoprotein substrate	-	0.7829	78.29%
CYP3A4 substrate	+	0.5713	57.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8652	86.52%
CYP3A4 inhibition	-	0.8290	82.90%
CYP2C9 inhibition	-	0.8424	84.24%
CYP2C19 inhibition	-	0.7957	79.57%
CYP2D6 inhibition	-	0.9452	94.52%
CYP1A2 inhibition	-	0.7235	72.35%
CYP2C8 inhibition	-	0.8674	86.74%
CYP inhibitory promiscuity	-	0.9676	96.76%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5324	53.24%
Eye corrosion	-	0.9709	97.09%
Eye irritation	-	0.6441	64.41%
Skin irritation	-	0.5279	52.79%
Skin corrosion	-	0.8932	89.32%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7012	70.12%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.7086	70.86%
skin sensitisation	-	0.8021	80.21%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.5211	52.11%
Acute Oral Toxicity (c)	III	0.3683	36.83%
Estrogen receptor binding	-	0.5989	59.89%
Androgen receptor binding	+	0.5641	56.41%
Thyroid receptor binding	-	0.5213	52.13%
Glucocorticoid receptor binding	+	0.5801	58.01%
Aromatase binding	-	0.7915	79.15%
PPAR gamma	-	0.6809	68.09%
Honey bee toxicity	-	0.9205	92.05%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9676	96.76%

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	95.65%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.63%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.56%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.52%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.09%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.32%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.42%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	81.57%	83.82%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.49%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.01%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	80.37%	91.19%

Plants that contains it

• Aucklandia costus

Cross-Links

• PubChem: 85353728
• LOTUS: LTS0148187
• wikiData: Q105132940