1,5,8-Trimethylidene-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,5-b]furan-2-one

Details

• Internal ID: eb49b3ce-b033-49e8-acde-e7416a78463a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 1,5,8-trimethylidene-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,5-b]furan-2-one
• SMILES (Canonical): C=C1CC2C(CC3C1CC(C3=C)OC4C(C(C(C(O4)CO)O)O)O)C(=C)C(=O)O2
• SMILES (Isomeric): C=C1CC2C(CC3C1CC(C3=C)OC4C(C(C(C(O4)CO)O)O)O)C(=C)C(=O)O2
• InChI: InChI=1S/C21H28O8/c1-8-4-15-13(10(3)20(26)27-15)5-12-9(2)14(6-11(8)12)28-21-19(25)18(24)17(23)16(7-22)29-21/h11-19,21-25H,1-7H2
• InChI Key: HYHULTLAIDHNLO-UHFFFAOYSA-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	+	0.6496	64.96%
Caco-2	-	0.8137	81.37%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7079	70.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8487	84.87%
OATP1B3 inhibitior	+	0.9619	96.19%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7573	75.73%
P-glycoprotein inhibitior	-	0.7708	77.08%
P-glycoprotein substrate	-	0.8358	83.58%
CYP3A4 substrate	+	0.6078	60.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8596	85.96%
CYP3A4 inhibition	-	0.9022	90.22%
CYP2C9 inhibition	-	0.9084	90.84%
CYP2C19 inhibition	-	0.8254	82.54%
CYP2D6 inhibition	-	0.9057	90.57%
CYP1A2 inhibition	-	0.8541	85.41%
CYP2C8 inhibition	-	0.7497	74.97%
CYP inhibitory promiscuity	-	0.8715	87.15%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7551	75.51%
Eye corrosion	-	0.9810	98.10%
Eye irritation	-	0.9185	91.85%
Skin irritation	-	0.7846	78.46%
Skin corrosion	-	0.9482	94.82%
Ames mutagenesis	-	0.5628	56.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.4792	47.92%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.7071	70.71%
skin sensitisation	-	0.8492	84.92%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.6417	64.17%
Acute Oral Toxicity (c)	III	0.4075	40.75%
Estrogen receptor binding	+	0.6487	64.87%
Androgen receptor binding	+	0.6014	60.14%
Thyroid receptor binding	+	0.5657	56.57%
Glucocorticoid receptor binding	-	0.4703	47.03%
Aromatase binding	+	0.6449	64.49%
PPAR gamma	+	0.5915	59.15%
Honey bee toxicity	-	0.5918	59.18%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8974	89.74%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	92.08%	97.09%
CHEMBL220	P22303	Acetylcholinesterase	91.96%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.91%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.98%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.18%	85.14%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.44%	95.83%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.03%	95.56%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.13%	91.24%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.01%	97.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.93%	94.00%
CHEMBL2581	P07339	Cathepsin D	80.25%	98.95%

Plants that contains it

• Pertya triloba

Cross-Links

• PubChem: 85134965
• LOTUS: LTS0269633
• wikiData: Q105035329