4,7-Dihydroxy-3,9-dimethyl-6-methylidene-3,3a,4,5,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-2-one

Details

• Internal ID: e9f04764-6569-46d3-bdeb-b79c5f6958ba
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 4,7-dihydroxy-3,9-dimethyl-6-methylidene-3,3a,4,5,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1C2C(CC(=C)C3C(C=C(C3C2OC1=O)C)O)O
• SMILES (Isomeric): CC1C2C(CC(=C)C3C(C=C(C3C2OC1=O)C)O)O
• InChI: InChI=1S/C15H20O4/c1-6-4-10(17)13-8(3)15(18)19-14(13)12-7(2)5-9(16)11(6)12/h5,8-14,16-17H,1,4H2,2-3H3
• InChI Key: LHEKNORJBDXZLE-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.04
• 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	+	0.9713	97.13%
Caco-2	-	0.6929	69.29%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4801	48.01%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.8721	87.21%
OATP1B3 inhibitior	+	0.9520	95.20%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9660	96.60%
P-glycoprotein inhibitior	-	0.9073	90.73%
P-glycoprotein substrate	-	0.8182	81.82%
CYP3A4 substrate	+	0.5251	52.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8313	83.13%
CYP3A4 inhibition	-	0.7351	73.51%
CYP2C9 inhibition	-	0.8744	87.44%
CYP2C19 inhibition	-	0.8174	81.74%
CYP2D6 inhibition	-	0.9340	93.40%
CYP1A2 inhibition	-	0.7678	76.78%
CYP2C8 inhibition	-	0.9345	93.45%
CYP inhibitory promiscuity	-	0.8478	84.78%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9525	95.25%
Carcinogenicity (trinary)	Non-required	0.4553	45.53%
Eye corrosion	-	0.9529	95.29%
Eye irritation	-	0.8386	83.86%
Skin irritation	-	0.5905	59.05%
Skin corrosion	-	0.8631	86.31%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5744	57.44%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.6837	68.37%
skin sensitisation	-	0.7150	71.50%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7299	72.99%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7262	72.62%
Acute Oral Toxicity (c)	II	0.3916	39.16%
Estrogen receptor binding	-	0.6997	69.97%
Androgen receptor binding	-	0.6208	62.08%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.6201	62.01%
Aromatase binding	-	0.8390	83.90%
PPAR gamma	-	0.8444	84.44%
Honey bee toxicity	-	0.8159	81.59%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.8421	84.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	90.67%	91.49%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.99%	94.80%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.97%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.71%	95.56%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	86.55%	86.00%
CHEMBL2581	P07339	Cathepsin D	86.08%	98.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.94%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.06%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.57%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.83%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.44%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.53%	86.33%

Plants that contains it

• Seriphidium fragrans

Cross-Links

• PubChem: 4979241
• LOTUS: LTS0273765
• wikiData: Q105151728