[(2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-3-acetyloxy-5-hydroxy-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-17-hydroxy-10,13-dimethyl-17-[(2S)-6-methyl-3-oxoheptan-2-yl]-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]oxan-4-yl]oxy-4,5-dihydroxyoxan-3-yl] 3,4,5-trimethoxybenzoate

Details

• Internal ID: 3d5d7555-8fcc-437c-91bb-f5aa863f3711
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: [(2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-3-acetyloxy-5-hydroxy-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-17-hydroxy-10,13-dimethyl-17-[(2S)-6-methyl-3-oxoheptan-2-yl]-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]oxan-4-yl]oxy-4,5-dihydroxyoxan-3-yl] 3,4,5-trimethoxybenzoate
• SMILES (Canonical): CC(C)CCC(=O)C(C)C1(C(CC2C1(CCC3C2CC=C4C3(CCC(C4)OC5C(C(C(C(O5)CO)O)O)O)C)C)OC6C(C(C(CO6)O)OC7C(C(C(CO7)O)O)OC(=O)C8=CC(=C(C(=C8)OC)OC)OC)OC(=O)C)O
• SMILES (Isomeric): C[C@H](C(=O)CCC(C)C)[C@]1([C@H](C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)C)O[C@H]6[C@@H]([C@H]([C@H](CO6)O)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O)OC(=O)C8=CC(=C(C(=C8)OC)OC)OC)OC(=O)C)O
• InChI: InChI=1S/C55H82O22/c1-25(2)10-13-34(58)26(3)55(66)40(21-33-31-12-11-29-20-30(14-16-53(29,5)32(31)15-17-54(33,55)6)73-50-44(64)43(63)42(62)39(22-56)74-50)75-52-48(72-27(4)57)45(36(60)24-71-52)77-51-47(41(61)35(59)23-70-51)76-49(65)28-18-37(67-7)46(69-9)38(19-28)68-8/h11,18-19,25-26,30-33,35-36,39-45,47-48,50-52,56,59-64,66H,10,12-17,20-24H2,1-9H3/t26-,30+,31-,32+,33+,35-,36+,39-,40+,41+,42-,43+,44-,45+,47-,48-,50-,51+,52+,53+,54+,55-/m1/s1
• InChI Key: FLAULGUSZSPUPV-RSLQRIQLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₅H₈₂O₂₂
• Molecular Weight: 1095.20 g/mol
• Exact Mass: 1094.52977424 g/mol
• Topological Polar Surface Area (TPSA): 315.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 1.87
• H-Bond Acceptor: 22
• H-Bond Donor: 8
• Rotatable Bonds: 18

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8937	89.37%
Caco-2	-	0.8655	86.55%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7777	77.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8146	81.46%
OATP1B3 inhibitior	+	0.8332	83.32%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9459	94.59%
P-glycoprotein inhibitior	+	0.7493	74.93%
P-glycoprotein substrate	+	0.7576	75.76%
CYP3A4 substrate	+	0.7586	75.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8751	87.51%
CYP3A4 inhibition	-	0.7864	78.64%
CYP2C9 inhibition	-	0.8020	80.20%
CYP2C19 inhibition	-	0.8263	82.63%
CYP2D6 inhibition	-	0.9159	91.59%
CYP1A2 inhibition	-	0.7495	74.95%
CYP2C8 inhibition	+	0.8213	82.13%
CYP inhibitory promiscuity	-	0.9326	93.26%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5968	59.68%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.8999	89.99%
Skin irritation	-	0.6897	68.97%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.6878	68.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7684	76.84%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8884	88.84%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.9292	92.92%
Acute Oral Toxicity (c)	I	0.3830	38.30%
Estrogen receptor binding	+	0.7829	78.29%
Androgen receptor binding	+	0.7528	75.28%
Thyroid receptor binding	+	0.6301	63.01%
Glucocorticoid receptor binding	+	0.8011	80.11%
Aromatase binding	+	0.6310	63.10%
PPAR gamma	+	0.8341	83.41%
Honey bee toxicity	-	0.6104	61.04%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5787	57.87%
Fish aquatic toxicity	+	0.9835	98.35%

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	99.54%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.03%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.50%	97.25%
CHEMBL4302	P08183	P-glycoprotein 1	94.35%	92.98%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	94.33%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.22%	99.17%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	93.71%	95.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.44%	89.00%
CHEMBL2581	P07339	Cathepsin D	93.14%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.42%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.91%	97.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.29%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.17%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	90.11%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.96%	91.07%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.64%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.37%	85.14%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.32%	91.24%
CHEMBL226	P30542	Adenosine A1 receptor	88.39%	95.93%
CHEMBL4581	P52732	Kinesin-like protein 1	88.28%	93.18%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.23%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.13%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	86.99%	92.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.56%	94.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.94%	89.05%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.32%	89.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.11%	93.56%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.83%	96.90%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.82%	95.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.76%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	83.35%	94.75%
CHEMBL4208	P20618	Proteasome component C5	83.22%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.17%	95.56%
CHEMBL5028	O14672	ADAM10	81.81%	97.50%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.18%	97.21%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.77%	92.88%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.62%	94.33%

Plants that contains it

• Ornithogalum thyrsoides

Cross-Links

• PubChem: 11105150
• LOTUS: LTS0268262
• wikiData: Q104996903