(3a-Hydroxy-5a,9-dimethyl-3-methylidene-2-oxo-4,5,6,7,8,9b-hexahydrobenzo[g][1]benzofuran-7-yl) acetate

Details

• Internal ID: b85a506f-bb01-47eb-a59f-c9eb41e13544
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3a-hydroxy-5a,9-dimethyl-3-methylidene-2-oxo-4,5,6,7,8,9b-hexahydrobenzo[g][1]benzofuran-7-yl) acetate
• SMILES (Canonical): CC1=C2C3C(CCC2(CC(C1)OC(=O)C)C)(C(=C)C(=O)O3)O
• SMILES (Isomeric): CC1=C2C3C(CCC2(CC(C1)OC(=O)C)C)(C(=C)C(=O)O3)O
• InChI: InChI=1S/C17H22O5/c1-9-7-12(21-11(3)18)8-16(4)5-6-17(20)10(2)15(19)22-14(17)13(9)16/h12,14,20H,2,5-8H2,1,3-4H3
• InChI Key: DOHRVHAOURGWKT-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.14672380 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 2.04
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9935	99.35%
Caco-2	+	0.6951	69.51%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7456	74.56%
OATP2B1 inhibitior	-	0.8537	85.37%
OATP1B1 inhibitior	+	0.8822	88.22%
OATP1B3 inhibitior	-	0.2194	21.94%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5803	58.03%
BSEP inhibitior	-	0.9186	91.86%
P-glycoprotein inhibitior	-	0.7649	76.49%
P-glycoprotein substrate	-	0.8514	85.14%
CYP3A4 substrate	+	0.6480	64.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8912	89.12%
CYP3A4 inhibition	+	0.5090	50.90%
CYP2C9 inhibition	-	0.7809	78.09%
CYP2C19 inhibition	-	0.8401	84.01%
CYP2D6 inhibition	-	0.9542	95.42%
CYP1A2 inhibition	-	0.6456	64.56%
CYP2C8 inhibition	-	0.8093	80.93%
CYP inhibitory promiscuity	-	0.9568	95.68%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5410	54.10%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.6461	64.61%
Skin irritation	+	0.6410	64.10%
Skin corrosion	-	0.9027	90.27%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7258	72.58%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.5693	56.93%
skin sensitisation	-	0.8421	84.21%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.6818	68.18%
Acute Oral Toxicity (c)	IV	0.4221	42.21%
Estrogen receptor binding	-	0.4844	48.44%
Androgen receptor binding	-	0.5297	52.97%
Thyroid receptor binding	+	0.5490	54.90%
Glucocorticoid receptor binding	+	0.6190	61.90%
Aromatase binding	+	0.6180	61.80%
PPAR gamma	-	0.5852	58.52%
Honey bee toxicity	-	0.7590	75.90%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.9958	99.58%

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	96.11%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.54%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.93%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.65%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	88.34%	91.19%
CHEMBL2581	P07339	Cathepsin D	85.93%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.28%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.33%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.29%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.08%	96.95%

Plants that contains it

• Sphaeranthus suaveolens

Cross-Links

• PubChem: 14589097
• LOTUS: LTS0263233
• wikiData: Q104985994