(6,9-Dihydroxy-6,9-dimethyl-3-methylidene-2-oxo-3a,4,5,6a,9a,9b-hexahydroazuleno[4,5-b]furan-5-yl) acetate

Details

• Internal ID: a691fe74-24d4-4912-a013-1e3fa487e0ff
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (6,9-dihydroxy-6,9-dimethyl-3-methylidene-2-oxo-3a,4,5,6a,9a,9b-hexahydroazuleno[4,5-b]furan-5-yl) acetate
• SMILES (Canonical): CC(=O)OC1CC2C(C3C(C1(C)O)C=CC3(C)O)OC(=O)C2=C
• SMILES (Isomeric): CC(=O)OC1CC2C(C3C(C1(C)O)C=CC3(C)O)OC(=O)C2=C
• InChI: InChI=1S/C17H22O6/c1-8-10-7-12(22-9(2)18)17(4,21)11-5-6-16(3,20)13(11)14(10)23-15(8)19/h5-6,10-14,20-21H,1,7H2,2-4H3
• InChI Key: NIBHTNDTDSUJGV-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₆
• Molecular Weight: 322.40 g/mol
• Exact Mass: 322.14163842 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.72
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9772	97.72%
Caco-2	-	0.6849	68.49%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5729	57.29%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.8640	86.40%
OATP1B3 inhibitior	+	0.8444	84.44%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9641	96.41%
P-glycoprotein inhibitior	-	0.7636	76.36%
P-glycoprotein substrate	-	0.8245	82.45%
CYP3A4 substrate	+	0.6508	65.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8998	89.98%
CYP3A4 inhibition	-	0.6819	68.19%
CYP2C9 inhibition	-	0.8516	85.16%
CYP2C19 inhibition	-	0.8299	82.99%
CYP2D6 inhibition	-	0.9517	95.17%
CYP1A2 inhibition	-	0.7017	70.17%
CYP2C8 inhibition	-	0.6599	65.99%
CYP inhibitory promiscuity	-	0.9296	92.96%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5147	51.47%
Eye corrosion	-	0.9735	97.35%
Eye irritation	-	0.9612	96.12%
Skin irritation	-	0.5982	59.82%
Skin corrosion	-	0.8757	87.57%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4406	44.06%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.7001	70.01%
skin sensitisation	-	0.7095	70.95%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5930	59.30%
Acute Oral Toxicity (c)	III	0.3562	35.62%
Estrogen receptor binding	+	0.7605	76.05%
Androgen receptor binding	+	0.5366	53.66%
Thyroid receptor binding	+	0.5819	58.19%
Glucocorticoid receptor binding	-	0.4768	47.68%
Aromatase binding	-	0.5325	53.25%
PPAR gamma	+	0.6325	63.25%
Honey bee toxicity	-	0.6569	65.69%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9521	95.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.73%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.39%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.85%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.45%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.03%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.18%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.71%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.56%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.09%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	86.53%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.45%	94.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.15%	97.25%

Plants that contains it

• Anthemis cretica subsp. carpatica

Cross-Links

• PubChem: 85241134
• LOTUS: LTS0209958
• wikiData: Q105179722