Astramembrannin I

Details

• Internal ID: 0a195960-e1c6-41e6-bf1d-9ce601aa24c4
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-9-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1(C(CCC23C1C(CC4C2(C3)CCC5(C4(CC(C5C6(CCC(O6)C(C)(C)O)C)O)C)C)OC7C(C(C(C(O7)CO)O)O)O)OC8C(C(C(CO8)O)O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@]34C[C@@]35CC[C@@H](C([C@@H]5[C@H](C[C@H]4[C@@]1(C[C@@H]([C@@H]2[C@@]6(CC[C@@H](O6)C(C)(C)O)C)O)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)(C)C)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O
• InChI: InChI=1S/C41H68O14/c1-35(2)24(54-33-29(48)26(45)20(44)17-51-33)9-11-41-18-40(41)13-12-37(5)31(39(7)10-8-25(55-39)36(3,4)50)19(43)15-38(37,6)23(40)14-21(32(35)41)52-34-30(49)28(47)27(46)22(16-42)53-34/h19-34,42-50H,8-18H2,1-7H3/t19-,20+,21-,22+,23-,24-,25+,26-,27+,28-,29+,30+,31-,32-,33-,34+,37+,38-,39-,40-,41+/m0/s1
• InChI Key: QMNWISYXSJWHRY-AUJDEUPOSA-N
• Popularity: 667 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₈O₁₄
• Molecular Weight: 785.00 g/mol
• Exact Mass: 784.46090684 g/mol
• Topological Polar Surface Area (TPSA): 228.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.72
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

• 83207-58-3
• Astragaloside-A
• Cyclosiversioside F
• Astramembrannin I
• Astragalin A
• Astragaloside IV
• UNII-3A592W8XKE
• 3A592W8XKE
• (2R,3R,4S,5S,6R)-2-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-9-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• (2R,3R,4S,5S,6R)-2-(((2aR,3R,4S,5aS,5bS,7S,7aR,9S,11aR,12aS)-4-Hydroxy-3-((2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl)-2a,5a,8,8-tetramethyl-9-(((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)hexadecahydrocyclopenta[a]cyclopropa[e]phenanthren-7-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• C41-H68-O14
• (+)-ASTRAGALOSIDE A
• DTXSID301347884
• HMS3884H17
• HY-N0099
• s2415
• AKOS022168196
• CCG-270471
• CS-3710
• BRD-K08188887-001-02-4
• Q27256953
• .BETA.-D-GLUCOPYRANOSIDE, (3.BETA.,6.ALPHA.,16.BETA.,24R)-20,24-EPOXY-16,25-DIHYDROXY-3-(.BETA.-D-XYLOPYRANOSYLOXY)-9,19-CYCLOLANOSTAN-6-YL-
• beta-D-Glucopyranoside, (3beta,6alpha,16beta,24R)-20,24-epoxy-16,25-dihydroxy-3-(beta-D-xylopyranosyloxy)-9,19-cyclolanostan-6-yl

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6581	65.81%
Caco-2	-	0.8686	86.86%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6782	67.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8381	83.81%
OATP1B3 inhibitior	+	0.9422	94.22%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.7885	78.85%
P-glycoprotein inhibitior	+	0.7497	74.97%
P-glycoprotein substrate	-	0.5266	52.66%
CYP3A4 substrate	+	0.7267	72.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8361	83.61%
CYP3A4 inhibition	-	0.8783	87.83%
CYP2C9 inhibition	-	0.8009	80.09%
CYP2C19 inhibition	-	0.8368	83.68%
CYP2D6 inhibition	-	0.9401	94.01%
CYP1A2 inhibition	-	0.8971	89.71%
CYP2C8 inhibition	+	0.6865	68.65%
CYP inhibitory promiscuity	-	0.9329	93.29%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6399	63.99%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9083	90.83%
Skin irritation	-	0.7237	72.37%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	0.6170	61.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7494	74.94%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6641	66.41%
skin sensitisation	-	0.9098	90.98%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.9533	95.33%
Acute Oral Toxicity (c)	I	0.6658	66.58%
Estrogen receptor binding	+	0.5975	59.75%
Androgen receptor binding	+	0.7428	74.28%
Thyroid receptor binding	-	0.5763	57.63%
Glucocorticoid receptor binding	+	0.6019	60.19%
Aromatase binding	+	0.6578	65.78%
PPAR gamma	+	0.6954	69.54%
Honey bee toxicity	-	0.6245	62.45%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8633	86.33%

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	98.86%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.31%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.82%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.60%	96.61%
CHEMBL220	P22303	Acetylcholinesterase	93.35%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	93.02%	95.93%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	92.92%	83.57%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.94%	96.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.67%	96.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.25%	96.95%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	90.16%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.96%	94.45%
CHEMBL259	P32245	Melanocortin receptor 4	89.62%	95.38%
CHEMBL1977	P11473	Vitamin D receptor	89.15%	99.43%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.71%	86.33%
CHEMBL3589	P55263	Adenosine kinase	86.39%	98.05%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.80%	95.50%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.77%	92.88%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.46%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.46%	92.94%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.25%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.76%	95.89%
CHEMBL2996	Q05655	Protein kinase C delta	83.56%	97.79%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.87%	92.62%
CHEMBL204	P00734	Thrombin	82.81%	96.01%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.34%	89.00%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	82.25%	95.58%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.05%	97.14%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.82%	82.50%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	80.74%	92.86%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.38%	100.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.38%	97.33%
CHEMBL1871	P10275	Androgen Receptor	80.32%	96.43%
CHEMBL237	P41145	Kappa opioid receptor	80.22%	98.10%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.15%	91.24%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.09%	85.14%

Plants that contains it

• Astragalus basineri
• Astragalus globiceps
• Astragalus mongholicus
• Astragalus pterocephalus
• Astragalus trimestris
• Hedysarum polybotrys

Cross-Links

• PubChem: 13943299
• NPASS: NPC212474
• LOTUS: LTS0240791
• wikiData: Q27256953