Avenacoside B

Details

• Internal ID: 1bcdbb06-ae8f-4b93-ad08-1f09ecaa235f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)-2-[(1S,2S,4S,5'S,6S,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethyl-5'-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]spiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxolane]-16-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C2C(CC3C2(CCC4C3CC=C5C4(CCC(C5)OC6C(C(C(C(O6)CO)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)O)O)O)O)OC9C(C(C(C(O9)C)O)O)O)C)C)OC11CCC(O1)(C)COC1C(C(C(C(O1)CO)O)O)O
• SMILES (Isomeric): C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O)C)C)O[C@]11CC[C@@](O1)(C)CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• InChI: InChI=1S/C57H92O28/c1-21-33-28(84-57(21)13-12-54(3,85-57)20-74-49-41(69)39(67)35(63)29(16-58)77-49)15-27-25-7-6-23-14-24(8-10-55(23,4)26(25)9-11-56(27,33)5)76-53-48(83-50-42(70)38(66)34(62)22(2)75-50)44(72)46(32(19-61)80-53)81-52-45(73)47(37(65)31(18-60)79-52)82-51-43(71)40(68)36(64)30(17-59)78-51/h6,21-22,24-53,58-73H,7-20H2,1-5H3/t21-,22-,24-,25+,26-,27-,28-,29+,30+,31+,32+,33-,34-,35+,36+,37+,38+,39-,40-,41+,42+,43+,44-,45+,46+,47-,48+,49+,50-,51-,52-,53+,54-,55-,56-,57-/m0/s1
• InChI Key: NMIRRCSMDCNCKV-ZRCSLNBESA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₇H₉₂O₂₈
• Molecular Weight: 1225.30 g/mol
• Exact Mass: 1224.57751227 g/mol
• Topological Polar Surface Area (TPSA): 434.00 Ų
• XlogP: -3.60
• Atomic LogP (AlogP): -5.02
• H-Bond Acceptor: 28
• H-Bond Donor: 16
• Rotatable Bonds: 15

Synonyms

• (3beta,22S,25S)-3-{[6-deoxy-alpha-L-mannopyranosyl-(1->2)-[beta-D-glucopyranosyl-(1->3)-beta-D-glucopyranosyl-(1->4)]-beta-D-glucopyranosyl]oxy}-22,25-epoxyfurost-5-en-26-yl beta-D-glucopyranoside
• nuatigenin 3-O-{alpha-L-rhamnopyranosyl-(1->2)-[beta-D-glucopyranosyl-(1->3)-beta-D-glucopyranosyl-(1->4)]-beta-D-glucopyranoside} 26-O-beta-D-glucopyranoside
• Nuatigenin 3-O-{alpha-L-rhamnopyranosyl-(1->2)-[beta-D-glucopyranosyl-(1->3)-beta-D-glucopyranosyl-(1->4)]-beta-D-glucopyranoside}-26-O-beta-D-glucopyranoside
• CHEBI:2938
• CHEMBL4635475
• C08888
• Q27105893

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7196	71.96%
Caco-2	-	0.8795	87.95%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7739	77.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8726	87.26%
OATP1B3 inhibitior	+	0.8663	86.63%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.9233	92.33%
P-glycoprotein inhibitior	+	0.7418	74.18%
P-glycoprotein substrate	+	0.6073	60.73%
CYP3A4 substrate	+	0.7490	74.90%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8216	82.16%
CYP3A4 inhibition	-	0.9460	94.60%
CYP2C9 inhibition	-	0.9118	91.18%
CYP2C19 inhibition	-	0.9113	91.13%
CYP2D6 inhibition	-	0.9360	93.60%
CYP1A2 inhibition	-	0.8848	88.48%
CYP2C8 inhibition	+	0.7840	78.40%
CYP inhibitory promiscuity	-	0.8774	87.74%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5291	52.91%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9012	90.12%
Skin irritation	-	0.5662	56.62%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8527	85.27%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.9125	91.25%
skin sensitisation	-	0.9240	92.40%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.8511	85.11%
Acute Oral Toxicity (c)	III	0.4459	44.59%
Estrogen receptor binding	+	0.8474	84.74%
Androgen receptor binding	+	0.7331	73.31%
Thyroid receptor binding	+	0.5938	59.38%
Glucocorticoid receptor binding	+	0.7476	74.76%
Aromatase binding	+	0.6655	66.55%
PPAR gamma	+	0.8205	82.05%
Honey bee toxicity	-	0.6224	62.24%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9442	94.42%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.69%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	96.31%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.20%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.26%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.15%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.19%	96.61%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	89.89%	89.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.69%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.98%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.83%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.13%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.77%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.32%	97.25%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.89%	92.94%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.81%	95.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.03%	93.56%
CHEMBL1871	P10275	Androgen Receptor	82.89%	96.43%
CHEMBL5255	O00206	Toll-like receptor 4	82.55%	92.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.77%	91.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.72%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	80.99%	94.75%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.90%	97.50%
CHEMBL5028	O14672	ADAM10	80.34%	97.50%

Plants that contains it

• Avena sativa

Cross-Links

• PubChem: 71581002
• LOTUS: LTS0170131
• wikiData: Q27105893