2-Acetylacteoside

Details

• Internal ID: e9e59b17-dbf0-4635-b71b-3a2dabc6d039
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4S,5R,6R)-5-acetyloxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C)OCCC3=CC(=C(C=C3)O)O)CO)OC(=O)C=CC4=CC(=C(C=C4)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]([C@H](O[C@H]([C@@H]2OC(=O)C)OCCC3=CC(=C(C=C3)O)O)CO)OC(=O)/C=C/C4=CC(=C(C=C4)O)O)O)O)O
• InChI: InChI=1S/C31H38O16/c1-14-24(39)25(40)26(41)30(43-14)47-28-27(46-23(38)8-5-16-3-6-18(34)20(36)11-16)22(13-32)45-31(29(28)44-15(2)33)42-10-9-17-4-7-19(35)21(37)12-17/h3-8,11-12,14,22,24-32,34-37,39-41H,9-10,13H2,1-2H3/b8-5+/t14-,22+,24-,25+,26+,27+,28-,29+,30-,31+/m0/s1
• InChI Key: ALERZNQPBWWLMW-OMRKUVHCSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₈O₁₆
• Molecular Weight: 666.60 g/mol
• Exact Mass: 666.21598512 g/mol
• Topological Polar Surface Area (TPSA): 251.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -0.45
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

• 94492-24-7
• 2'-Acetylacteoside
• [(2R,3R,4S,5R,6R)-5-acetyloxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• MFCD25977378
• MS-31037
• PD124371
• (2R,3R,4S,5R,6R)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-2-(hydroxymethyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8373	83.73%
Caco-2	-	0.8969	89.69%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.7684	76.84%
OATP2B1 inhibitior	-	0.7262	72.62%
OATP1B1 inhibitior	+	0.8736	87.36%
OATP1B3 inhibitior	+	0.9366	93.66%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9072	90.72%
P-glycoprotein inhibitior	+	0.5763	57.63%
P-glycoprotein substrate	-	0.5952	59.52%
CYP3A4 substrate	+	0.6634	66.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8729	87.29%
CYP3A4 inhibition	-	0.8012	80.12%
CYP2C9 inhibition	-	0.6940	69.40%
CYP2C19 inhibition	-	0.8573	85.73%
CYP2D6 inhibition	-	0.9190	91.90%
CYP1A2 inhibition	-	0.8568	85.68%
CYP2C8 inhibition	+	0.7042	70.42%
CYP inhibitory promiscuity	-	0.7570	75.70%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.7213	72.13%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9199	91.99%
Skin irritation	-	0.8586	85.86%
Skin corrosion	-	0.9519	95.19%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8018	80.18%
Micronuclear	-	0.6467	64.67%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8452	84.52%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8964	89.64%
Acute Oral Toxicity (c)	III	0.7934	79.34%
Estrogen receptor binding	+	0.8081	80.81%
Androgen receptor binding	-	0.6142	61.42%
Thyroid receptor binding	+	0.5391	53.91%
Glucocorticoid receptor binding	+	0.6337	63.37%
Aromatase binding	-	0.5233	52.33%
PPAR gamma	+	0.6966	69.66%
Honey bee toxicity	-	0.6593	65.93%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.8673	86.73%

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	99.74%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.17%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.44%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.55%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.49%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	94.74%	94.73%
CHEMBL2581	P07339	Cathepsin D	93.92%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.36%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.12%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.78%	86.92%
CHEMBL3194	P02766	Transthyretin	89.79%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.02%	94.45%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	84.65%	96.37%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.36%	80.78%
CHEMBL226	P30542	Adenosine A1 receptor	83.47%	95.93%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.90%	97.36%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.18%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.17%	95.50%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.58%	94.80%
CHEMBL4208	P20618	Proteasome component C5	80.26%	90.00%

Plants that contains it

• Aeginetia indica
• Brandisia hancei
• Callicarpa macrophylla
• Cistanche deserticola
• Cistanche phelypaea
• Cistanche salsa
• Harpagophytum procumbens
• Pedicularis densispica
• Rosa rugosa

Cross-Links

• PubChem: 21629996
• NPASS: NPC83268
• LOTUS: LTS0215850
• wikiData: Q104914069