Isoastragaloside I

Details

• Internal ID: 67c5ae47-4df3-45f7-8f49-7588dbb932ee
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(3R,4S,5R,6S)-5-acetyloxy-4-hydroxy-6-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]oxan-3-yl] acetate
• SMILES (Canonical): CC(=O)OC1COC(C(C1O)OC(=O)C)OC2CCC34CC35CCC6(C(C(CC6(C5CC(C4C2(C)C)OC7C(C(C(C(O7)CO)O)O)O)C)O)C8(CCC(O8)C(C)(C)O)C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1CO[C@H]([C@@H]([C@H]1O)OC(=O)C)O[C@H]2CC[C@]34C[C@]35CC[C@@]6([C@H]([C@H](C[C@]6([C@@H]5C[C@@H]([C@H]4C2(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)O)[C@]8(CC[C@H](O8)C(C)(C)O)C)C
• InChI: InChI=1S/C45H72O16/c1-21(47)56-26-19-55-38(34(31(26)51)57-22(2)48)60-28-11-13-45-20-44(45)15-14-41(7)35(43(9)12-10-29(61-43)40(5,6)54)23(49)17-42(41,8)27(44)16-24(36(45)39(28,3)4)58-37-33(53)32(52)30(50)25(18-46)59-37/h23-38,46,49-54H,10-20H2,1-9H3/t23-,24-,25+,26+,27-,28-,29-,30+,31-,32-,33+,34+,35-,36-,37+,38-,41+,42-,43+,44-,45+/m0/s1
• InChI Key: HVPKALQHGQMJER-XOUPSZAESA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₇₂O₁₆
• Molecular Weight: 869.00 g/mol
• Exact Mass: 868.48203620 g/mol
• Topological Polar Surface Area (TPSA): 240.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 1.87
• H-Bond Acceptor: 16
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

• 84676-88-0
• Isoastragaloside-I
• IsoastragalosideI
• [(3R,4S,5R,6S)-5-acetyloxy-4-hydroxy-6-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]oxan-3-yl] acetate
• HY-N0887
• MFCD17214429
• CS-3717
• NCGC00485977-01
• AS-56993
• C17793

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6958	69.58%
Caco-2	-	0.8790	87.90%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7771	77.71%
OATP2B1 inhibitior	-	0.8771	87.71%
OATP1B1 inhibitior	+	0.8135	81.35%
OATP1B3 inhibitior	+	0.9416	94.16%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7287	72.87%
BSEP inhibitior	+	0.7552	75.52%
P-glycoprotein inhibitior	+	0.7725	77.25%
P-glycoprotein substrate	+	0.5619	56.19%
CYP3A4 substrate	+	0.7421	74.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8835	88.35%
CYP3A4 inhibition	-	0.7216	72.16%
CYP2C9 inhibition	-	0.7822	78.22%
CYP2C19 inhibition	-	0.8524	85.24%
CYP2D6 inhibition	-	0.9466	94.66%
CYP1A2 inhibition	-	0.9082	90.82%
CYP2C8 inhibition	+	0.7043	70.43%
CYP inhibitory promiscuity	-	0.9558	95.58%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6430	64.30%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9061	90.61%
Skin irritation	-	0.7028	70.28%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	-	0.5970	59.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6707	67.07%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.6800	68.00%
skin sensitisation	-	0.9164	91.64%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.9366	93.66%
Acute Oral Toxicity (c)	I	0.6455	64.55%
Estrogen receptor binding	+	0.7337	73.37%
Androgen receptor binding	+	0.7449	74.49%
Thyroid receptor binding	-	0.5864	58.64%
Glucocorticoid receptor binding	+	0.7564	75.64%
Aromatase binding	+	0.6704	67.04%
PPAR gamma	+	0.7920	79.20%
Honey bee toxicity	-	0.6035	60.35%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9297	92.97%

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	98.48%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.29%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.46%	94.45%
CHEMBL220	P22303	Acetylcholinesterase	95.31%	94.45%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	95.08%	83.57%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	93.72%	96.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.58%	96.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.88%	96.21%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.86%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.71%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.48%	96.77%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.44%	91.24%
CHEMBL2581	P07339	Cathepsin D	87.36%	98.95%
CHEMBL259	P32245	Melanocortin receptor 4	87.23%	95.38%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	86.97%	82.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.49%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.47%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.91%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.45%	91.07%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.16%	100.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.16%	98.75%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.09%	95.50%
CHEMBL2996	Q05655	Protein kinase C delta	83.67%	97.79%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.04%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.83%	92.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.33%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.93%	96.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.12%	95.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.47%	95.89%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.42%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	80.23%	95.93%
CHEMBL340	P08684	Cytochrome P450 3A4	80.09%	91.19%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.09%	97.28%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.01%	97.21%

Plants that contains it

• Astragalus mongholicus
• Hedysarum polybotrys

Cross-Links

• PubChem: 60148697
• NPASS: NPC89518