Aculeatiside A

Details

• Internal ID: 877c42ba-55b8-445f-a323-942898bda231
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(1S,2S,4S,5'S,6S,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethyl-5'-[[(2R,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]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-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)C)O)O)O)O)OC8C(C(C(C(O8)C)O)O)O)C)C)OC19CCC(O9)(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)C)O)O)O)O)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)C)C)O[C@]19CC[C@@](O9)(C)CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• InChI: InChI=1S/C51H82O22/c1-20-31-28(72-51(20)14-13-48(4,73-51)19-64-44-38(60)37(59)34(56)29(17-52)68-44)16-27-25-8-7-23-15-24(9-11-49(23,5)26(25)10-12-50(27,31)6)67-47-43(71-46-40(62)36(58)33(55)22(3)66-46)41(63)42(30(18-53)69-47)70-45-39(61)35(57)32(54)21(2)65-45/h7,20-22,24-47,52-63H,8-19H2,1-6H3/t20-,21-,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-/m0/s1
• InChI Key: CAQVTBKPDXKPJU-DXFNOYLOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₁H₈₂O₂₂
• Molecular Weight: 1047.20 g/mol
• Exact Mass: 1046.52977424 g/mol
• Topological Polar Surface Area (TPSA): 335.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.82
• H-Bond Acceptor: 22
• H-Bond Donor: 12
• Rotatable Bonds: 11

Synonyms

• C51-H82-O22
• 86848-73-9
• beta-D-Glucopyranoside, (3beta,22alpha,25S)-22,25-epoxy-26-(beta-D-glucopyranosyloxy)furost-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-(6-deoxy-alpha-L-mannopyranosyl-(1->4))-
• beta-D-Glucopyranoside, (3beta,22alpha,25S)-22,25-epoxy-26-(beta-D-glucopyranosyloxy)furost-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(6-deoxy-alpha-L-mannopyranosyl-(1-4))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7196	71.96%
Caco-2	-	0.8868	88.68%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7739	77.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8764	87.64%
OATP1B3 inhibitior	+	0.8663	86.63%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.8377	83.77%
P-glycoprotein inhibitior	+	0.7434	74.34%
P-glycoprotein substrate	+	0.5705	57.05%
CYP3A4 substrate	+	0.7479	74.79%
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	+	0.7662	76.62%
CYP inhibitory promiscuity	-	0.8774	87.74%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5291	52.91%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9051	90.51%
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	+	0.8413	84.13%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.9250	92.50%
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	-	0.8360	83.60%
Acute Oral Toxicity (c)	III	0.4459	44.59%
Estrogen receptor binding	+	0.8589	85.89%
Androgen receptor binding	+	0.7289	72.89%
Thyroid receptor binding	+	0.5620	56.20%
Glucocorticoid receptor binding	+	0.7286	72.86%
Aromatase binding	+	0.6844	68.44%
PPAR gamma	+	0.8053	80.53%
Honey bee toxicity	-	0.6200	62.00%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
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	98.63%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	96.34%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.73%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.26%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.15%	100.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	90.88%	89.05%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.52%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.69%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.29%	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	85.96%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.11%	86.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.81%	95.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.36%	92.94%
CHEMBL1871	P10275	Androgen Receptor	82.89%	96.43%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	82.43%	86.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.14%	92.50%
CHEMBL332	P03956	Matrix metalloproteinase-1	81.66%	94.50%
CHEMBL1937	Q92769	Histone deacetylase 2	80.99%	94.75%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.39%	93.56%
CHEMBL5028	O14672	ADAM10	80.34%	97.50%

Plants that contains it

• Solanum abutiloides
• Solanum aculeatissimum

Cross-Links

• PubChem: 159012
• NPASS: NPC41850
• LOTUS: LTS0082479
• wikiData: Q104951773