[8,9-Dihydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate

Details

• Internal ID: a2659bba-abd5-4cb0-915b-5daba870f671
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [8,9-dihydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
• SMILES (Canonical): C=C1CC(C2C(C3C1CC(C3(CO)O)O)OC(=O)C2=C)OC(=O)C(=C)CO
• SMILES (Isomeric): C=C1CC(C2C(C3C1CC(C3(CO)O)O)OC(=O)C2=C)OC(=O)C(=C)CO
• InChI: InChI=1S/C19H24O8/c1-8-4-12(26-17(23)9(2)6-20)14-10(3)18(24)27-16(14)15-11(8)5-13(22)19(15,25)7-21/h11-16,20-22,25H,1-7H2
• InChI Key: WXULAPKWBLTYSL-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₈
• Molecular Weight: 380.40 g/mol
• Exact Mass: 380.14711772 g/mol
• Topological Polar Surface Area (TPSA): 134.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.78
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6910	69.10%
Caco-2	-	0.8163	81.63%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6216	62.16%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8886	88.86%
OATP1B3 inhibitior	+	0.9633	96.33%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9584	95.84%
P-glycoprotein inhibitior	-	0.7729	77.29%
P-glycoprotein substrate	-	0.5799	57.99%
CYP3A4 substrate	+	0.6505	65.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8416	84.16%
CYP3A4 inhibition	-	0.9210	92.10%
CYP2C9 inhibition	-	0.8460	84.60%
CYP2C19 inhibition	-	0.7965	79.65%
CYP2D6 inhibition	-	0.9191	91.91%
CYP1A2 inhibition	-	0.8438	84.38%
CYP2C8 inhibition	-	0.7047	70.47%
CYP inhibitory promiscuity	-	0.9538	95.38%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6741	67.41%
Eye corrosion	-	0.9816	98.16%
Eye irritation	-	0.7884	78.84%
Skin irritation	-	0.7397	73.97%
Skin corrosion	-	0.9300	93.00%
Ames mutagenesis	-	0.6054	60.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4759	47.59%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.8483	84.83%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.8001	80.01%
Acute Oral Toxicity (c)	III	0.4298	42.98%
Estrogen receptor binding	+	0.7037	70.37%
Androgen receptor binding	+	0.6704	67.04%
Thyroid receptor binding	+	0.5280	52.80%
Glucocorticoid receptor binding	+	0.6792	67.92%
Aromatase binding	+	0.5956	59.56%
PPAR gamma	+	0.6244	62.44%
Honey bee toxicity	-	0.6352	63.52%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8991	89.91%

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	97.56%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.51%	97.09%
CHEMBL299	P17252	Protein kinase C alpha	91.02%	98.03%
CHEMBL2996	Q05655	Protein kinase C delta	90.74%	97.79%
CHEMBL221	P23219	Cyclooxygenase-1	90.21%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.88%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.90%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.22%	86.33%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.68%	90.08%
CHEMBL340	P08684	Cytochrome P450 3A4	81.97%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.28%	95.56%

Plants that contains it

• Saussurea candicans

Cross-Links

• PubChem: 14021491
• LOTUS: LTS0238398
• wikiData: Q105314953