[(1S,4aS,7aS)-4-[[(2R,3S,4R,6S)-3,4-dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl] 3-methylbutanoate

Details

• Internal ID: 3d9a3936-dfcc-44bc-96f3-e87173ec2e2e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(1S,4aS,7aS)-4-[[(2R,3S,4R,6S)-3,4-dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl] 3-methylbutanoate
• SMILES (Canonical): CC(C)CC(=O)OC1C2C(CC=C2CO)C(=CO1)COC3C(C(CC(O3)COC4C(C(C(C(O4)CO)O)O)O)O)O
• SMILES (Isomeric): CC(C)CC(=O)O[C@H]1[C@H]2[C@H](CC=C2CO)C(=CO1)CO[C@H]3[C@H]([C@@H](C[C@H](O3)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
• InChI: InChI=1S/C27H42O14/c1-12(2)5-19(31)41-25-20-13(7-28)3-4-16(20)14(9-36-25)10-37-26-21(32)17(30)6-15(39-26)11-38-27-24(35)23(34)22(33)18(8-29)40-27/h3,9,12,15-18,20-30,32-35H,4-8,10-11H2,1-2H3/t15-,16+,17+,18+,20+,21-,22+,23-,24+,25-,26+,27+/m0/s1
• InChI Key: QHFLEHBNWPQUDX-BOVNTEGRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₂O₁₄
• Molecular Weight: 590.60 g/mol
• Exact Mass: 590.25745601 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -2.60
• Atomic LogP (AlogP): -1.96
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6863	68.63%
Caco-2	-	0.8553	85.53%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7766	77.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8329	83.29%
OATP1B3 inhibitior	+	0.9325	93.25%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8600	86.00%
P-glycoprotein inhibitior	-	0.5647	56.47%
P-glycoprotein substrate	-	0.5110	51.10%
CYP3A4 substrate	+	0.6531	65.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8757	87.57%
CYP3A4 inhibition	-	0.9093	90.93%
CYP2C9 inhibition	-	0.9154	91.54%
CYP2C19 inhibition	-	0.8494	84.94%
CYP2D6 inhibition	-	0.8622	86.22%
CYP1A2 inhibition	-	0.8773	87.73%
CYP2C8 inhibition	+	0.4829	48.29%
CYP inhibitory promiscuity	-	0.8955	89.55%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7012	70.12%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9400	94.00%
Skin irritation	-	0.7734	77.34%
Skin corrosion	-	0.9560	95.60%
Ames mutagenesis	-	0.5082	50.82%
Human Ether-a-go-go-Related Gene inhibition	+	0.7409	74.09%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6771	67.71%
skin sensitisation	-	0.8706	87.06%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.4509	45.09%
Acute Oral Toxicity (c)	III	0.5223	52.23%
Estrogen receptor binding	+	0.7297	72.97%
Androgen receptor binding	+	0.6552	65.52%
Thyroid receptor binding	-	0.5605	56.05%
Glucocorticoid receptor binding	-	0.4883	48.83%
Aromatase binding	+	0.5673	56.73%
PPAR gamma	+	0.5477	54.77%
Honey bee toxicity	-	0.7798	77.98%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9224	92.24%

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	97.99%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.79%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.53%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	92.46%	95.93%
CHEMBL2581	P07339	Cathepsin D	92.23%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.31%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.82%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.05%	94.45%
CHEMBL5255	O00206	Toll-like receptor 4	86.80%	92.50%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.16%	97.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.92%	96.95%
CHEMBL3401	O75469	Pregnane X receptor	83.88%	94.73%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.05%	93.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.35%	97.25%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.87%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.53%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.82%	99.17%
CHEMBL2996	Q05655	Protein kinase C delta	80.58%	97.79%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.06%	89.62%

Plants that contains it

• Penstemon richardsonii
• Penstemon serrulatus

Cross-Links

• PubChem: 101285190
• LOTUS: LTS0233559
• wikiData: Q104392297