[4,5-dihydroxy-2-[[(1S,3R,6S,11S,14S,16R)-14-hydroxy-15-[(5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-oxapentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-yl]oxy]oxan-3-yl] acetate

Details

• Internal ID: 0508bc36-15e4-4276-9919-6fc76cb006d1
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [4,5-dihydroxy-2-[[(1S,3R,6S,11S,14S,16R)-14-hydroxy-15-[(5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-oxapentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-yl]oxy]oxan-3-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(C(COC1OC2CCC34C(C2(C)C)C(CC5C3(O4)CCC6(C5(CC(C6C7(CCC(O7)C(C)(C)O)C)O)C)C)OC8C(C(C(C(O8)CO)O)O)O)O)O
• SMILES (Isomeric): CC(=O)OC1C(C(COC1O[C@H]2CC[C@@]34C(C2(C)C)C(C[C@@H]5[C@@]3(O4)CC[C@]6(C5(C[C@@H](C6C7(CC[C@H](O7)C(C)(C)O)C)O)C)C)OC8C(C(C(C(O8)CO)O)O)O)O)O
• InChI: InChI=1S/C42H68O16/c1-19(44)53-31-27(47)21(46)18-52-35(31)56-25-10-12-42-33(36(25,2)3)22(54-34-30(50)29(49)28(48)23(17-43)55-34)15-24-39(7)16-20(45)32(38(39,6)13-14-41(24,42)58-42)40(8)11-9-26(57-40)37(4,5)51/h20-35,43,45-51H,9-18H2,1-8H3/t20-,21?,22?,23?,24-,25-,26-,27?,28?,29?,30?,31?,32?,33?,34?,35?,38+,39?,40?,41-,42+/m0/s1
• InChI Key: FPMKTOHSPZKRET-ZTXGWKAVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₈O₁₆
• Molecular Weight: 829.00 g/mol
• Exact Mass: 828.45073608 g/mol
• Topological Polar Surface Area (TPSA): 247.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.43
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

• SCHEMBL13907095
• NCI60_013940
• (2S,3BS,7S,9aR,10aS,12aR)-7-[(2-O-acetylpentopyranosyl)oxy]-2-hydroxy-1-[(5S)-5-(1-hydroxy-1-methylethyl)-2-methyltetrahydrofuran-2-yl]-3a,6,6,12a-tetramethyltetradecahydro-1H-cyclopenta[1,2]phenanthro[4a,4b-b]oxiren-5-yl hexopyranoside
• [4,5-dihydroxy-2-[hydroxy-[(5S)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydrofuran-2-yl]-tetramethyl-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-[?]yl]oxy-tetrahydropyran-3-yl] acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7239	72.39%
Caco-2	-	0.8805	88.05%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7430	74.30%
OATP2B1 inhibitior	-	0.8730	87.30%
OATP1B1 inhibitior	+	0.8193	81.93%
OATP1B3 inhibitior	+	0.9385	93.85%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7037	70.37%
BSEP inhibitior	-	0.5341	53.41%
P-glycoprotein inhibitior	+	0.7717	77.17%
P-glycoprotein substrate	+	0.5670	56.70%
CYP3A4 substrate	+	0.7464	74.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8808	88.08%
CYP3A4 inhibition	-	0.7700	77.00%
CYP2C9 inhibition	-	0.7726	77.26%
CYP2C19 inhibition	-	0.8222	82.22%
CYP2D6 inhibition	-	0.9356	93.56%
CYP1A2 inhibition	-	0.8890	88.90%
CYP2C8 inhibition	+	0.7110	71.10%
CYP inhibitory promiscuity	-	0.9531	95.31%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6571	65.71%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9082	90.82%
Skin irritation	-	0.7039	70.39%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.6170	61.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7604	76.04%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.6459	64.59%
skin sensitisation	-	0.8985	89.85%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.8769	87.69%
Acute Oral Toxicity (c)	I	0.6168	61.68%
Estrogen receptor binding	+	0.6453	64.53%
Androgen receptor binding	+	0.7421	74.21%
Thyroid receptor binding	-	0.5810	58.10%
Glucocorticoid receptor binding	+	0.7048	70.48%
Aromatase binding	+	0.6871	68.71%
PPAR gamma	+	0.7578	75.78%
Honey bee toxicity	-	0.5985	59.85%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9028	90.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.84%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.65%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.14%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.06%	96.61%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.31%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.07%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.91%	96.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.39%	94.45%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.77%	91.24%
CHEMBL220	P22303	Acetylcholinesterase	89.01%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.95%	86.33%
CHEMBL259	P32245	Melanocortin receptor 4	88.42%	95.38%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.31%	96.21%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	86.84%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.24%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.20%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.93%	89.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.92%	97.28%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	85.92%	82.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.71%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	84.50%	92.50%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	84.05%	97.33%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.93%	92.88%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.57%	95.89%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.10%	95.71%
CHEMBL340	P08684	Cytochrome P450 3A4	82.66%	91.19%
CHEMBL2581	P07339	Cathepsin D	82.65%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	81.99%	97.79%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.88%	92.62%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.75%	91.07%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.46%	93.04%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.44%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.96%	94.00%

Plants that contains it

• Astragalus lehmannianus
• Astragalus melanophrurius
• Astragalus microcephalus
• Astragalus mongholicus
• Astragalus oleifolius
• Astragalus trigonus
• Astragalus trimestris
• Waltheria communis

Cross-Links

• PubChem: 369514
• LOTUS: LTS0126386
• wikiData: Q104999255