1alpha,3alpha,4beta-Trihydroxy-8alpha-acetoxyguai-9,11(13)-dien-6alpha,12-olide

Details

• Internal ID: 205c86ea-7132-44e2-96ea-ee5dc32084bc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4S,6aS,8R,9R,9aR,9bS)-6a,8,9-trihydroxy-6,9-dimethyl-3-methylidene-2-oxo-3a,4,7,8,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] acetate
• SMILES (Canonical): CC1=CC(C2C(C3C1(CC(C3(C)O)O)O)OC(=O)C2=C)OC(=O)C
• SMILES (Isomeric): CC1=C[C@@H]([C@@H]2[C@@H]([C@@H]3[C@]1(C[C@H]([C@]3(C)O)O)O)OC(=O)C2=C)OC(=O)C
• InChI: InChI=1S/C17H22O7/c1-7-5-10(23-9(3)18)12-8(2)15(20)24-13(12)14-16(4,21)11(19)6-17(7,14)22/h5,10-14,19,21-22H,2,6H2,1,3-4H3/t10-,11+,12+,13-,14-,16-,17+/m0/s1
• InChI Key: KWODTFNUHIUBMF-AHZUSZHVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₇
• Molecular Weight: 338.40 g/mol
• Exact Mass: 338.13655304 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.16
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8947	89.47%
Caco-2	-	0.6566	65.66%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.4554	45.54%
OATP2B1 inhibitior	-	0.8578	85.78%
OATP1B1 inhibitior	+	0.8986	89.86%
OATP1B3 inhibitior	+	0.9276	92.76%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9598	95.98%
P-glycoprotein inhibitior	-	0.8471	84.71%
P-glycoprotein substrate	-	0.7266	72.66%
CYP3A4 substrate	+	0.6537	65.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8894	88.94%
CYP3A4 inhibition	-	0.6256	62.56%
CYP2C9 inhibition	-	0.8000	80.00%
CYP2C19 inhibition	-	0.7840	78.40%
CYP2D6 inhibition	-	0.9321	93.21%
CYP1A2 inhibition	-	0.7428	74.28%
CYP2C8 inhibition	-	0.7563	75.63%
CYP inhibitory promiscuity	-	0.9390	93.90%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5531	55.31%
Eye corrosion	-	0.9817	98.17%
Eye irritation	-	0.8939	89.39%
Skin irritation	-	0.6037	60.37%
Skin corrosion	-	0.8879	88.79%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5491	54.91%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.7700	77.00%
skin sensitisation	-	0.7804	78.04%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.7198	71.98%
Acute Oral Toxicity (c)	III	0.3735	37.35%
Estrogen receptor binding	+	0.6786	67.86%
Androgen receptor binding	+	0.5280	52.80%
Thyroid receptor binding	+	0.5332	53.32%
Glucocorticoid receptor binding	+	0.6314	63.14%
Aromatase binding	-	0.6047	60.47%
PPAR gamma	-	0.5292	52.92%
Honey bee toxicity	-	0.7720	77.20%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5850	58.50%
Fish aquatic toxicity	+	0.9321	93.21%

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	95.80%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.42%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.59%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.03%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.76%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.22%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.50%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	81.73%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.56%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.86%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.06%	94.00%

Plants that contains it

• Artemisia suksdorfii

Cross-Links

• PubChem: 21589792
• LOTUS: LTS0040447
• wikiData: Q105147040