(6S,6aS,9aS,9bR)-6a-hydroxy-3-(hydroxymethyl)-6,9a-dimethyl-4,5,6,9b-tetrahydroazuleno[8,7-b]furan-2,9-dione

Details

• Internal ID: ec44cbca-c1e0-46cf-9569-558fab05f2c6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: (6S,6aS,9aS,9bR)-6a-hydroxy-3-(hydroxymethyl)-6,9a-dimethyl-4,5,6,9b-tetrahydroazuleno[8,7-b]furan-2,9-dione
• InChI: InChI=1S/C15H18O5/c1-8-3-4-9-10(7-16)13(18)20-12(9)14(2)11(17)5-6-15(8,14)19/h5-6,8,12,16,19H,3-4,7H2,1-2H3/t8-,12+,14-,15+/m0/s1
• InChI Key: KCWWJJPMWLFJRS-VLBDWWMKSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.51
• H-Bond Acceptor: 5
• 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	+	0.9752	97.52%
Caco-2	+	0.5556	55.56%
Blood Brain Barrier	+	0.6369	63.69%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7726	77.26%
OATP2B1 inhibitior	-	0.8551	85.51%
OATP1B1 inhibitior	+	0.8663	86.63%
OATP1B3 inhibitior	+	0.9476	94.76%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5125	51.25%
BSEP inhibitior	-	0.9141	91.41%
P-glycoprotein inhibitior	-	0.9381	93.81%
P-glycoprotein substrate	-	0.8125	81.25%
CYP3A4 substrate	+	0.5802	58.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9156	91.56%
CYP3A4 inhibition	-	0.6420	64.20%
CYP2C9 inhibition	-	0.7136	71.36%
CYP2C19 inhibition	-	0.8594	85.94%
CYP2D6 inhibition	-	0.9198	91.98%
CYP1A2 inhibition	+	0.5341	53.41%
CYP2C8 inhibition	-	0.8545	85.45%
CYP inhibitory promiscuity	-	0.8869	88.69%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5394	53.94%
Eye corrosion	-	0.9834	98.34%
Eye irritation	-	0.9428	94.28%
Skin irritation	-	0.5425	54.25%
Skin corrosion	-	0.9300	93.00%
Ames mutagenesis	-	0.6170	61.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6514	65.14%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5157	51.57%
skin sensitisation	-	0.8737	87.37%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6580	65.80%
Acute Oral Toxicity (c)	III	0.4521	45.21%
Estrogen receptor binding	+	0.5740	57.40%
Androgen receptor binding	+	0.5788	57.88%
Thyroid receptor binding	-	0.5452	54.52%
Glucocorticoid receptor binding	+	0.6583	65.83%
Aromatase binding	+	0.5936	59.36%
PPAR gamma	+	0.5924	59.24%
Honey bee toxicity	-	0.9511	95.11%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9895	98.95%

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	97.07%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.88%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.46%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.91%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.22%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.82%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.59%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.99%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.11%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.90%	93.04%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.47%	86.33%

Plants that contains it

• Dichrocephala integrifolia

Cross-Links

• PubChem: 15605026
• LOTUS: LTS0099179
• wikiData: Q105138990