[(1S)-1-[(3S,8S,9R,10R,12R,13R,14R,17S)-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,3R,4R,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-8,14,17-trihydroxy-10,13-dimethyl-12-[(E)-2-methylbut-2-enoyl]oxy-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-17-yl]ethyl] benzoate

Details

• Internal ID: 0dd58297-e9e8-4db7-b794-cb06fbf296ce
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: [(1S)-1-[(3S,8S,9R,10R,12R,13R,14R,17S)-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,3R,4R,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-8,14,17-trihydroxy-10,13-dimethyl-12-[(E)-2-methylbut-2-enoyl]oxy-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-17-yl]ethyl] benzoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC2C3(CCC(CC3=CCC2(C4(C1(C(CC4)(C(C)OC(=O)C5=CC=CC=C5)O)C)O)O)OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)OC8C(C(C(C(O8)C)O)OC)O)OC)OC)C
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@@H]1C[C@@H]2[C@]3(CC[C@@H](CC3=CC[C@]2([C@@]4([C@]1([C@@](CC4)([C@H](C)OC(=O)C5=CC=CC=C5)O)C)O)O)O[C@H]6C[C@@H]([C@@H]([C@H](O6)C)O[C@H]7C[C@@H]([C@@H]([C@H](O7)C)O[C@H]8[C@@H]([C@@H]([C@@H]([C@H](O8)C)O)OC)O)OC)OC)C
• InChI: InChI=1S/C54H80O18/c1-12-28(2)47(57)70-39-27-38-50(7)20-19-35(24-34(50)18-21-53(38,60)54(61)23-22-52(59,51(39,54)8)32(6)68-48(58)33-16-14-13-15-17-33)69-40-25-36(62-9)44(30(4)65-40)71-41-26-37(63-10)45(31(5)66-41)72-49-43(56)46(64-11)42(55)29(3)67-49/h12-18,29-32,35-46,49,55-56,59-61H,19-27H2,1-11H3/b28-12+/t29-,30-,31-,32+,35+,36+,37+,38-,39-,40+,41+,42-,43-,44-,45-,46-,49+,50+,51-,52-,53+,54-/m1/s1
• InChI Key: VNPWBOBXORHSDJ-TWPMGTLBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₀O₁₈
• Molecular Weight: 1017.20 g/mol
• Exact Mass: 1016.53446570 g/mol
• Topological Polar Surface Area (TPSA): 237.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 4.58
• H-Bond Acceptor: 18
• H-Bond Donor: 5
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9136	91.36%
Caco-2	-	0.8644	86.44%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7085	70.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8374	83.74%
OATP1B3 inhibitior	+	0.9122	91.22%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7874	78.74%
BSEP inhibitior	+	0.9948	99.48%
P-glycoprotein inhibitior	+	0.7494	74.94%
P-glycoprotein substrate	+	0.7737	77.37%
CYP3A4 substrate	+	0.7409	74.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8800	88.00%
CYP3A4 inhibition	-	0.7482	74.82%
CYP2C9 inhibition	-	0.8927	89.27%
CYP2C19 inhibition	-	0.9044	90.44%
CYP2D6 inhibition	-	0.9288	92.88%
CYP1A2 inhibition	-	0.8304	83.04%
CYP2C8 inhibition	+	0.7682	76.82%
CYP inhibitory promiscuity	-	0.9574	95.74%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5356	53.56%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9008	90.08%
Skin irritation	-	0.5164	51.64%
Skin corrosion	-	0.9256	92.56%
Ames mutagenesis	-	0.5670	56.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7904	79.04%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8713	87.13%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.8879	88.79%
Acute Oral Toxicity (c)	II	0.4595	45.95%
Estrogen receptor binding	+	0.7886	78.86%
Androgen receptor binding	+	0.7576	75.76%
Thyroid receptor binding	+	0.6579	65.79%
Glucocorticoid receptor binding	+	0.7977	79.77%
Aromatase binding	+	0.6456	64.56%
PPAR gamma	+	0.8262	82.62%
Honey bee toxicity	-	0.6077	60.77%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5745	57.45%
Fish aquatic toxicity	+	0.9830	98.30%

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	97.03%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.91%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.85%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.48%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.67%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.12%	95.56%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	92.82%	83.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.36%	99.23%
CHEMBL226	P30542	Adenosine A1 receptor	90.33%	95.93%
CHEMBL221	P23219	Cyclooxygenase-1	89.81%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.77%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.36%	91.07%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.89%	97.14%
CHEMBL5028	O14672	ADAM10	88.32%	97.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	88.04%	94.08%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	87.85%	100.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.83%	94.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.70%	96.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.68%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.45%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.67%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.12%	100.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	84.11%	94.23%
CHEMBL340	P08684	Cytochrome P450 3A4	82.78%	91.19%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.86%	93.56%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.70%	95.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.29%	93.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.10%	95.71%

Plants that contains it

• Orbea variegata

Cross-Links

• PubChem: 101923687
• LOTUS: LTS0199809
• wikiData: Q105289838