(3aS,6aR,8S,9aR,9bS)-3,6,9-trimethylidene-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one

Details

• Internal ID: 53e8c3f3-f924-48a2-8c9b-28ccb6c946f4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,6aR,8S,9aR,9bS)-3,6,9-trimethylidene-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): C=C1CCC2C(C3C1CC(C3=C)OC4C(C(C(C(O4)CO)O)O)O)OC(=O)C2=C
• SMILES (Isomeric): C=C1CC[C@@H]2[C@@H]([C@@H]3[C@H]1C[C@@H](C3=C)O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC(=O)C2=C
• InChI: InChI=1S/C21H28O8/c1-8-4-5-11-9(2)20(26)29-19(11)15-10(3)13(6-12(8)15)27-21-18(25)17(24)16(23)14(7-22)28-21/h11-19,21-25H,1-7H2/t11-,12-,13-,14+,15-,16+,17-,18+,19-,21-/m0/s1
• InChI Key: OIOLZODVFMMERF-NUBWYMJQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₈
• Molecular Weight: 408.40 g/mol
• Exact Mass: 408.17841785 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.19
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6233	62.33%
Caco-2	-	0.8217	82.17%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7747	77.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8221	82.21%
OATP1B3 inhibitior	+	0.9558	95.58%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5833	58.33%
P-glycoprotein inhibitior	-	0.7807	78.07%
P-glycoprotein substrate	-	0.8148	81.48%
CYP3A4 substrate	+	0.6220	62.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8596	85.96%
CYP3A4 inhibition	-	0.9412	94.12%
CYP2C9 inhibition	-	0.8819	88.19%
CYP2C19 inhibition	-	0.8133	81.33%
CYP2D6 inhibition	-	0.8800	88.00%
CYP1A2 inhibition	-	0.7959	79.59%
CYP2C8 inhibition	-	0.6887	68.87%
CYP inhibitory promiscuity	-	0.8902	89.02%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7462	74.62%
Eye corrosion	-	0.9778	97.78%
Eye irritation	-	0.8948	89.48%
Skin irritation	-	0.7800	78.00%
Skin corrosion	-	0.9487	94.87%
Ames mutagenesis	-	0.6923	69.23%
Human Ether-a-go-go-Related Gene inhibition	-	0.4736	47.36%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8515	85.15%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.5436	54.36%
Acute Oral Toxicity (c)	III	0.4362	43.62%
Estrogen receptor binding	+	0.6249	62.49%
Androgen receptor binding	+	0.5986	59.86%
Thyroid receptor binding	+	0.5785	57.85%
Glucocorticoid receptor binding	-	0.4803	48.03%
Aromatase binding	+	0.6450	64.50%
PPAR gamma	+	0.5570	55.70%
Honey bee toxicity	-	0.6391	63.91%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8484	84.84%

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	96.14%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.93%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.03%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.99%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.01%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.34%	92.94%
CHEMBL2996	Q05655	Protein kinase C delta	82.25%	97.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.95%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.42%	94.45%

Plants that contains it

• Ainsliaea uniflora

Cross-Links

• PubChem: 162908328
• LOTUS: LTS0102195
• wikiData: Q105192642