[(5S,7S)-7-hydroxy-3,5-dimethyl-9-propanoyloxy-5,6,7,8-tetrahydrobenzo[f][1]benzofuran-4-yl]methyl propanoate

Details

• Internal ID: 6a91176c-a76f-4eaf-9a4e-bf279b52f21e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(5S,7S)-7-hydroxy-3,5-dimethyl-9-propanoyloxy-5,6,7,8-tetrahydrobenzo[f][1]benzofuran-4-yl]methyl propanoate
• SMILES (Canonical): CCC(=O)OCC1=C2C(=COC2=C(C3=C1C(CC(C3)O)C)OC(=O)CC)C
• SMILES (Isomeric): CCC(=O)OCC1=C2C(=COC2=C(C3=C1[C@H](C[C@@H](C3)O)C)OC(=O)CC)C
• InChI: InChI=1S/C21H26O6/c1-5-16(23)25-10-15-18-11(3)7-13(22)8-14(18)20(27-17(24)6-2)21-19(15)12(4)9-26-21/h9,11,13,22H,5-8,10H2,1-4H3/t11-,13-/m0/s1
• InChI Key: XVMJURDWENMOTK-AAEUAGOBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆O₆
• Molecular Weight: 374.40 g/mol
• Exact Mass: 374.17293854 g/mol
• Topological Polar Surface Area (TPSA): 86.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.92
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 5

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	+	0.5670	56.70%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7742	77.42%
OATP2B1 inhibitior	-	0.8584	85.84%
OATP1B1 inhibitior	+	0.8544	85.44%
OATP1B3 inhibitior	+	0.8756	87.56%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8886	88.86%
P-glycoprotein inhibitior	-	0.5232	52.32%
P-glycoprotein substrate	-	0.6678	66.78%
CYP3A4 substrate	+	0.5991	59.91%
CYP2C9 substrate	-	0.7996	79.96%
CYP2D6 substrate	-	0.7794	77.94%
CYP3A4 inhibition	-	0.5417	54.17%
CYP2C9 inhibition	+	0.7548	75.48%
CYP2C19 inhibition	+	0.6889	68.89%
CYP2D6 inhibition	-	0.9389	93.89%
CYP1A2 inhibition	+	0.7498	74.98%
CYP2C8 inhibition	+	0.6463	64.63%
CYP inhibitory promiscuity	-	0.6282	62.82%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5890	58.90%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.8470	84.70%
Skin irritation	-	0.8511	85.11%
Skin corrosion	-	0.9715	97.15%
Ames mutagenesis	-	0.5145	51.45%
Human Ether-a-go-go-Related Gene inhibition	-	0.5730	57.30%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8049	80.49%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.9557	95.57%
Acute Oral Toxicity (c)	III	0.6424	64.24%
Estrogen receptor binding	+	0.6601	66.01%
Androgen receptor binding	+	0.6921	69.21%
Thyroid receptor binding	-	0.6167	61.67%
Glucocorticoid receptor binding	+	0.7776	77.76%
Aromatase binding	-	0.5654	56.54%
PPAR gamma	+	0.7665	76.65%
Honey bee toxicity	-	0.7543	75.43%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9956	99.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	96.31%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.76%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.63%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.59%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.69%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.71%	99.17%
CHEMBL221	P23219	Cyclooxygenase-1	87.73%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.28%	86.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.21%	96.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.38%	94.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	80.96%	93.65%

Plants that contains it

• Senecio lydenburgensis

Cross-Links

• PubChem: 163190735
• LOTUS: LTS0016040
• wikiData: Q105342974