(4,9a-dihydroxy-3,4a,5-trimethyl-2-oxo-5,6,7,9-tetrahydro-4H-benzo[f][1]benzofuran-6-yl) acetate

Details

• Internal ID: 4c500895-a081-4631-96d5-5db69572c56b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4,9a-dihydroxy-3,4a,5-trimethyl-2-oxo-5,6,7,9-tetrahydro-4H-benzo[f][1]benzofuran-6-yl) acetate
• SMILES (Canonical): CC1C(CC=C2C1(C(C3=C(C(=O)OC3(C2)O)C)O)C)OC(=O)C
• SMILES (Isomeric): CC1C(CC=C2C1(C(C3=C(C(=O)OC3(C2)O)C)O)C)OC(=O)C
• InChI: InChI=1S/C17H22O6/c1-8-13-14(19)16(4)9(2)12(22-10(3)18)6-5-11(16)7-17(13,21)23-15(8)20/h5,9,12,14,19,21H,6-7H2,1-4H3
• InChI Key: MQTMOQGPHULVBH-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₆
• Molecular Weight: 322.40 g/mol
• Exact Mass: 322.14163842 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.22
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9771	97.71%
Caco-2	+	0.6712	67.12%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6712	67.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9113	91.13%
OATP1B3 inhibitior	+	0.9421	94.21%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7136	71.36%
P-glycoprotein inhibitior	-	0.7773	77.73%
P-glycoprotein substrate	-	0.7389	73.89%
CYP3A4 substrate	+	0.6628	66.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8919	89.19%
CYP3A4 inhibition	-	0.5567	55.67%
CYP2C9 inhibition	-	0.8715	87.15%
CYP2C19 inhibition	-	0.9387	93.87%
CYP2D6 inhibition	-	0.9402	94.02%
CYP1A2 inhibition	-	0.7206	72.06%
CYP2C8 inhibition	-	0.7618	76.18%
CYP inhibitory promiscuity	-	0.7311	73.11%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Danger	0.4877	48.77%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9722	97.22%
Skin irritation	+	0.5392	53.92%
Skin corrosion	-	0.9036	90.36%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5695	56.95%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.6015	60.15%
skin sensitisation	-	0.7998	79.98%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.7554	75.54%
Acute Oral Toxicity (c)	I	0.4042	40.42%
Estrogen receptor binding	+	0.6672	66.72%
Androgen receptor binding	+	0.5245	52.45%
Thyroid receptor binding	+	0.6041	60.41%
Glucocorticoid receptor binding	+	0.5948	59.48%
Aromatase binding	+	0.6425	64.25%
PPAR gamma	-	0.5442	54.42%
Honey bee toxicity	-	0.7306	73.06%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5150	51.50%
Fish aquatic toxicity	+	0.9814	98.14%

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	97.20%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.58%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.04%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.90%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.89%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	88.09%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.03%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.86%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.89%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.70%	97.14%
CHEMBL3401	O75469	Pregnane X receptor	81.22%	94.73%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.11%	91.07%

Plants that contains it

• Packera toluccana

Cross-Links

• PubChem: 14890410
• LOTUS: LTS0206629
• wikiData: Q105170270