[(3aR,4R,6aR,9S,9aR,9bR)-9-methyl-3,6-dimethylidene-2,8-dioxo-3a,4,5,6a,7,9,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate

Details

• Internal ID: 6dc02ce6-a5a0-4f9d-9dc5-19c62dc5cbd4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4R,6aR,9S,9aR,9bR)-9-methyl-3,6-dimethylidene-2,8-dioxo-3a,4,5,6a,7,9,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate
• InChI: InChI=1S/C20H24O7/c1-9-6-15(26-20(25)12(8-22)4-5-21)17-11(3)19(24)27-18(17)16-10(2)14(23)7-13(9)16/h4,10,13,15-18,21-22H,1,3,5-8H2,2H3/b12-4+/t10-,13+,15-,16+,17-,18-/m1/s1
• InChI Key: RSMYKTKKFRLXQD-VDRIGBRRSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₇
• Molecular Weight: 376.40 g/mol
• Exact Mass: 376.15220310 g/mol
• Topological Polar Surface Area (TPSA): 110.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.71
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9352	93.52%
Caco-2	-	0.6189	61.89%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6379	63.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8727	87.27%
OATP1B3 inhibitior	+	0.9571	95.71%
MATE1 inhibitior	-	0.7812	78.12%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5275	52.75%
P-glycoprotein inhibitior	-	0.5462	54.62%
P-glycoprotein substrate	-	0.6919	69.19%
CYP3A4 substrate	+	0.6165	61.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9063	90.63%
CYP3A4 inhibition	-	0.8148	81.48%
CYP2C9 inhibition	-	0.8240	82.40%
CYP2C19 inhibition	-	0.7640	76.40%
CYP2D6 inhibition	-	0.9248	92.48%
CYP1A2 inhibition	-	0.6900	69.00%
CYP2C8 inhibition	-	0.7443	74.43%
CYP inhibitory promiscuity	-	0.7903	79.03%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6195	61.95%
Eye corrosion	-	0.9704	97.04%
Eye irritation	-	0.6886	68.86%
Skin irritation	-	0.6540	65.40%
Skin corrosion	-	0.8957	89.57%
Ames mutagenesis	-	0.5854	58.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4194	41.94%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8121	81.21%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6385	63.85%
Acute Oral Toxicity (c)	III	0.4465	44.65%
Estrogen receptor binding	+	0.8148	81.48%
Androgen receptor binding	+	0.6101	61.01%
Thyroid receptor binding	+	0.5365	53.65%
Glucocorticoid receptor binding	+	0.6788	67.88%
Aromatase binding	+	0.6329	63.29%
PPAR gamma	+	0.5211	52.11%
Honey bee toxicity	-	0.7326	73.26%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9565	95.65%

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	95.42%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.38%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.01%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.00%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	82.26%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.13%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.10%	99.23%
CHEMBL2581	P07339	Cathepsin D	80.61%	98.95%

Plants that contains it

• Brickellia californica

Cross-Links

• PubChem: 14845496
• LOTUS: LTS0168052
• wikiData: Q105244763