[(3R,3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3-methyl-6,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-4-yl] 4-hydroxy-3-methylbut-2-enoate

Details

• Internal ID: de69d5c5-e6bf-45e5-81fb-80465e092e0c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3R,3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3-methyl-6,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-4-yl] 4-hydroxy-3-methylbut-2-enoate
• InChI: InChI=1S/C20H26O6/c1-9(8-21)5-16(23)25-15-6-10(2)13-7-14(22)11(3)17(13)19-18(15)12(4)20(24)26-19/h5,12-15,17-19,21-22H,2-3,6-8H2,1,4H3/t12-,13+,14+,15+,17+,18-,19-/m1/s1
• InChI Key: DTHPKFOZPQHUHF-MPXQTMFQSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.40 g/mol
• Exact Mass: 362.17293854 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.53
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9759	97.59%
Caco-2	-	0.5792	57.92%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6048	60.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8739	87.39%
OATP1B3 inhibitior	+	0.9521	95.21%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7203	72.03%
P-glycoprotein inhibitior	-	0.7532	75.32%
P-glycoprotein substrate	+	0.5520	55.20%
CYP3A4 substrate	+	0.6566	65.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9015	90.15%
CYP3A4 inhibition	-	0.5984	59.84%
CYP2C9 inhibition	-	0.8433	84.33%
CYP2C19 inhibition	-	0.8412	84.12%
CYP2D6 inhibition	-	0.9314	93.14%
CYP1A2 inhibition	-	0.7083	70.83%
CYP2C8 inhibition	-	0.8281	82.81%
CYP inhibitory promiscuity	-	0.8664	86.64%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6168	61.68%
Eye corrosion	-	0.9724	97.24%
Eye irritation	-	0.8790	87.90%
Skin irritation	-	0.6678	66.78%
Skin corrosion	-	0.9270	92.70%
Ames mutagenesis	-	0.5154	51.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6455	64.55%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.6677	66.77%
skin sensitisation	-	0.7754	77.54%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.6069	60.69%
Acute Oral Toxicity (c)	III	0.4604	46.04%
Estrogen receptor binding	+	0.5970	59.70%
Androgen receptor binding	+	0.6642	66.42%
Thyroid receptor binding	+	0.5601	56.01%
Glucocorticoid receptor binding	+	0.6349	63.49%
Aromatase binding	-	0.5183	51.83%
PPAR gamma	-	0.6008	60.08%
Honey bee toxicity	-	0.6007	60.07%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9520	95.20%

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	94.96%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	92.82%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.26%	96.09%
CHEMBL2581	P07339	Cathepsin D	89.44%	98.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.53%	89.34%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.11%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.56%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.22%	86.33%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	84.50%	92.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.77%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.88%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.28%	100.00%

Plants that contains it

• Saussurea pulchella

Cross-Links

• PubChem: 163083500
• LOTUS: LTS0234477
• wikiData: Q104988736