Aculeoside B

Details

• Internal ID: b71d820a-3443-4ec1-b6b8-eca683388155
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: [(2R,3S,4S,5R,6R)-3,4-diacetyloxy-5-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-[(1S,2S,3'S,4S,5'R,6S,7S,8R,9S,12S,13R,14R,16R)-16-hydroxy-5',7,9,13-tetramethyl-3'-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-14-yl]oxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC1CC(C2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(C(CC(C6)O)OC7C(C(C(C(O7)COC(=O)C)OC(=O)C)OC(=O)C)OC8C(C(C(C(O8)C)O)OC9C(C(C(C(O9)CO)O)O)O)O)C)C)C)OC1)OC1C(C(C(C(O1)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5([C@@H](C[C@@H](C6)O)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)COC(=O)C)OC(=O)C)OC(=O)C)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)C)C)C)OC1)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• InChI: InChI=1S/C57H88O27/c1-21-13-37(81-51-44(69)42(67)40(65)33(17-58)77-51)57(73-19-21)22(2)38-32(84-57)16-31-29-10-9-27-14-28(63)15-36(56(27,8)30(29)11-12-55(31,38)7)80-54-50(49(76-26(6)62)47(75-25(5)61)35(79-54)20-72-24(4)60)83-53-46(71)48(39(64)23(3)74-53)82-52-45(70)43(68)41(66)34(18-59)78-52/h9,21-23,28-54,58-59,63-71H,10-20H2,1-8H3/t21-,22+,23+,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+/m1/s1
• InChI Key: YWDANXPOTPLHIH-IWCGVCDDSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₇H₈₈O₂₇
• Molecular Weight: 1205.30 g/mol
• Exact Mass: 1204.55129753 g/mol
• Topological Polar Surface Area (TPSA): 394.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -2.31
• H-Bond Acceptor: 27
• H-Bond Donor: 11
• Rotatable Bonds: 14

Synonyms

• 214056-88-9
• (-)-Aculeoside B
• CHEMBL504592
• beta-D-Galactopyranoside, (1beta,3beta,23S,25R)-23-(beta-D-glucopyranosyloxy)-3-hydroxyspirost-5-en-1-yl O-beta-D-glucopyranosyl-(1-3)-O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-, 3,4,6-triacetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8056	80.56%
Caco-2	-	0.8723	87.23%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8501	85.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8385	83.85%
OATP1B3 inhibitior	+	0.9025	90.25%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5521	55.21%
BSEP inhibitior	+	0.9696	96.96%
P-glycoprotein inhibitior	+	0.7486	74.86%
P-glycoprotein substrate	+	0.6400	64.00%
CYP3A4 substrate	+	0.7607	76.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8766	87.66%
CYP3A4 inhibition	-	0.8389	83.89%
CYP2C9 inhibition	-	0.9095	90.95%
CYP2C19 inhibition	-	0.9382	93.82%
CYP2D6 inhibition	-	0.9468	94.68%
CYP1A2 inhibition	-	0.9168	91.68%
CYP2C8 inhibition	+	0.7946	79.46%
CYP inhibitory promiscuity	-	0.9561	95.61%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4754	47.54%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.8998	89.98%
Skin irritation	+	0.5722	57.22%
Skin corrosion	-	0.9383	93.83%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7878	78.78%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.8195	81.95%
skin sensitisation	-	0.9306	93.06%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.6429	64.29%
Acute Oral Toxicity (c)	III	0.4809	48.09%
Estrogen receptor binding	+	0.8100	81.00%
Androgen receptor binding	+	0.7513	75.13%
Thyroid receptor binding	+	0.6050	60.50%
Glucocorticoid receptor binding	+	0.7875	78.75%
Aromatase binding	+	0.6318	63.18%
PPAR gamma	+	0.8309	83.09%
Honey bee toxicity	-	0.5751	57.51%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5945	59.45%
Fish aquatic toxicity	+	0.9587	95.87%

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	99.04%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.02%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.44%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	95.61%	92.50%
CHEMBL226	P30542	Adenosine A1 receptor	95.15%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.98%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	94.49%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.35%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.05%	96.61%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.10%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.05%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.54%	97.09%
CHEMBL1914	P06276	Butyrylcholinesterase	90.21%	95.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.38%	93.04%
CHEMBL1871	P10275	Androgen Receptor	85.97%	96.43%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.79%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	84.23%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	83.61%	91.19%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.44%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.27%	96.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.02%	92.94%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.73%	93.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.28%	95.89%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.02%	97.28%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.68%	91.24%
CHEMBL2581	P07339	Cathepsin D	81.51%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.73%	95.50%
CHEMBL5028	O14672	ADAM10	80.28%	97.50%

Plants that contains it

• Adina eurhyncha
• Agave parryi var. huachucensis
• Aloe vera
• Angiopteris helferiana
• Anisomeles indica
• Anomospermum grandifolium
• Catunaregam longispina
• Centaurea diffusa
• Clarkia unguiculata
• Dahlstedtia pinnata
• Daphne papyracea
• Dermatophyllum secundiflorum
• Erinus alpinus
• Fritillaria taipaiensis
• Geranium macrorrhizum
• Gypothamnium pinifolium
• Hypolaena fastigiata
• Maclura pomifera
• Meryta denhamii
• Mimosa invisa
• Morinda citrifolia
• Pedicularis densispica
• Penianthus zenkeri
• Ruscus aculeatus
• Senecio macrophyllus
• Solanum chacoense
• Stenostomum acutatum
• Timonius eximius

Cross-Links

• PubChem: 154169
• NPASS: NPC164957
• LOTUS: LTS0132319
• wikiData: Q105366450