[(3S,8R,9S,10R,12R,13S,14S,17S)-17-acetyl-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-12-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: ebdf49e7-4a3d-4cc2-86a6-6e520b441b72
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: [(3S,8R,9S,10R,12R,13S,14S,17S)-17-acetyl-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-12-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC2C(CC=C3C2(CCC(C3)OC4CC(C(C(O4)C)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)OC7C(C(C(C(O7)C)O)OC)O)OC)OC)OC)C)C8(C1(C(CC8)C(=O)C)C)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@@H]1C[C@H]2[C@@H](CC=C3[C@@]2(CC[C@@H](C3)O[C@H]4C[C@@H]([C@@H]([C@H](O4)C)O[C@H]5C[C@@H]([C@@H]([C@H](O5)C)O[C@H]6C[C@@H]([C@@H]([C@H](O6)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C)O)OC)O)OC)OC)OC)C)[C@@]8([C@]1([C@H](CC8)C(=O)C)C)O
• InChI: InChI=1S/C54H86O18/c1-14-26(2)50(58)69-40-22-36-35(54(59)20-18-34(27(3)55)53(40,54)9)16-15-32-21-33(17-19-52(32,36)8)68-41-23-37(60-10)46(29(5)64-41)70-42-24-38(61-11)47(30(6)65-42)71-43-25-39(62-12)48(31(7)66-43)72-51-45(57)49(63-13)44(56)28(4)67-51/h14-15,28-31,33-49,51,56-57,59H,16-25H2,1-13H3/b26-14+/t28-,29-,30-,31-,33+,34-,35-,36+,37+,38+,39+,40-,41+,42+,43+,44-,45-,46-,47-,48-,49+,51+,52+,53+,54+/m1/s1
• InChI Key: KRNYAGXXMXIIDU-CSARZLOFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₆O₁₈
• Molecular Weight: 1023.20 g/mol
• Exact Mass: 1022.58141589 g/mol
• Topological Polar Surface Area (TPSA): 215.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 5.23
• H-Bond Acceptor: 18
• H-Bond Donor: 3
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9426	94.26%
Caco-2	-	0.8651	86.51%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7305	73.05%
OATP2B1 inhibitior	-	0.8725	87.25%
OATP1B1 inhibitior	+	0.8649	86.49%
OATP1B3 inhibitior	+	0.9218	92.18%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6374	63.74%
BSEP inhibitior	+	0.9847	98.47%
P-glycoprotein inhibitior	+	0.7531	75.31%
P-glycoprotein substrate	+	0.7426	74.26%
CYP3A4 substrate	+	0.7353	73.53%
CYP2C9 substrate	-	0.8019	80.19%
CYP2D6 substrate	-	0.9048	90.48%
CYP3A4 inhibition	-	0.8515	85.15%
CYP2C9 inhibition	-	0.9153	91.53%
CYP2C19 inhibition	-	0.9382	93.82%
CYP2D6 inhibition	-	0.9466	94.66%
CYP1A2 inhibition	-	0.8666	86.66%
CYP2C8 inhibition	+	0.6593	65.93%
CYP inhibitory promiscuity	-	0.9532	95.32%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5261	52.61%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9031	90.31%
Skin irritation	+	0.5649	56.49%
Skin corrosion	-	0.9199	91.99%
Ames mutagenesis	-	0.7054	70.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7834	78.34%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.6676	66.76%
skin sensitisation	-	0.8778	87.78%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.6703	67.03%
Acute Oral Toxicity (c)	I	0.3844	38.44%
Estrogen receptor binding	+	0.8409	84.09%
Androgen receptor binding	+	0.7482	74.82%
Thyroid receptor binding	+	0.6051	60.51%
Glucocorticoid receptor binding	+	0.8228	82.28%
Aromatase binding	+	0.7334	73.34%
PPAR gamma	+	0.8496	84.96%
Honey bee toxicity	-	0.6273	62.73%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5845	58.45%
Fish aquatic toxicity	+	0.9550	95.50%

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	98.57%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.04%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.33%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.46%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.74%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.34%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.07%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.84%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	88.32%	91.19%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.46%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	86.10%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.76%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.09%	91.07%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.43%	97.09%
CHEMBL2581	P07339	Cathepsin D	83.59%	98.95%
CHEMBL5028	O14672	ADAM10	82.33%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.15%	99.23%
CHEMBL226	P30542	Adenosine A1 receptor	82.13%	95.93%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.10%	94.62%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	80.20%	98.99%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.13%	97.14%

Plants that contains it

• Hoodia gordonii
• Lupinus polyphyllus
• Polyspora chrysandra

Cross-Links

• PubChem: 16733366
• LOTUS: LTS0004327
• wikiData: Q105299553