1-[(3S,5S,8S,9R,10R,12R,13R,14R,17S)-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4R,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-4-methoxy-6-methyloxan-2-yl]oxy-5,8,14,17-tetrahydroxy-10,13-dimethyl-12-[(E)-3-phenylprop-2-enoyl]oxy-2,3,4,9,11,12,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl (E)-2-methylbut-2-enoate

Details

• Internal ID: 7e398b4e-58ee-4e18-ad19-8d25801e6969
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: 1-[(3S,5S,8S,9R,10R,12R,13R,14R,17S)-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4R,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-4-methoxy-6-methyloxan-2-yl]oxy-5,8,14,17-tetrahydroxy-10,13-dimethyl-12-[(E)-3-phenylprop-2-enoyl]oxy-2,3,4,9,11,12,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC(C)C1(CCC2(C1(C(CC3C2(C=CC4(C3(CCC(C4)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)OC8C(C(C(C(O8)C)O)OC)O)OC)OC)OC)C)O)O)OC(=O)C=CC9=CC=CC=C9)C)O)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)OC(C)[C@@]1(CC[C@]2([C@@]1([C@@H](C[C@H]3[C@]2(C=C[C@@]4([C@@]3(CC[C@@H](C4)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]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)OC)C)O)O)OC(=O)/C=C/C9=CC=CC=C9)C)O)O
• InChI: InChI=1S/C63H94O22/c1-14-33(2)56(67)80-38(7)61(69)26-27-63(71)59(61,9)45(82-46(64)21-20-39-18-16-15-17-19-39)31-44-58(8)23-22-40(32-60(58,68)24-25-62(44,63)70)81-47-28-41(72-10)52(35(4)76-47)83-48-29-42(73-11)53(36(5)77-48)84-49-30-43(74-12)54(37(6)78-49)85-57-51(66)55(75-13)50(65)34(3)79-57/h14-21,24-25,34-38,40-45,47-55,57,65-66,68-71H,22-23,26-32H2,1-13H3/b21-20+,33-14+/t34-,35-,36-,37-,38?,40+,41+,42+,43-,44-,45-,47+,48+,49+,50-,51-,52-,53-,54-,55-,57+,58-,59-,60-,61-,62+,63-/m1/s1
• InChI Key: MJCJBEOEBGINOT-ASUWCIHHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₃H₉₄O₂₂
• Molecular Weight: 1203.40 g/mol
• Exact Mass: 1202.62367462 g/mol
• Topological Polar Surface Area (TPSA): 285.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 4.49
• H-Bond Acceptor: 22
• H-Bond Donor: 6
• Rotatable Bonds: 18

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8815	88.15%
Caco-2	-	0.8600	86.00%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6452	64.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8230	82.30%
OATP1B3 inhibitior	+	0.8980	89.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8124	81.24%
BSEP inhibitior	+	0.9783	97.83%
P-glycoprotein inhibitior	+	0.7452	74.52%
P-glycoprotein substrate	+	0.7999	79.99%
CYP3A4 substrate	+	0.7444	74.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8918	89.18%
CYP3A4 inhibition	-	0.7720	77.20%
CYP2C9 inhibition	-	0.8911	89.11%
CYP2C19 inhibition	-	0.8856	88.56%
CYP2D6 inhibition	-	0.9336	93.36%
CYP1A2 inhibition	-	0.8250	82.50%
CYP2C8 inhibition	+	0.7897	78.97%
CYP inhibitory promiscuity	-	0.9600	96.00%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5757	57.57%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.8976	89.76%
Skin irritation	-	0.5311	53.11%
Skin corrosion	-	0.9277	92.77%
Ames mutagenesis	-	0.6640	66.40%
Human Ether-a-go-go-Related Gene inhibition	+	0.8041	80.41%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.5343	53.43%
skin sensitisation	-	0.8663	86.63%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.9534	95.34%
Acute Oral Toxicity (c)	II	0.4464	44.64%
Estrogen receptor binding	+	0.7112	71.12%
Androgen receptor binding	+	0.7693	76.93%
Thyroid receptor binding	+	0.7066	70.66%
Glucocorticoid receptor binding	+	0.7990	79.90%
Aromatase binding	+	0.6552	65.52%
PPAR gamma	+	0.8129	81.29%
Honey bee toxicity	-	0.6300	63.00%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6845	68.45%
Fish aquatic toxicity	+	0.9810	98.10%

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	99.33%	91.11%
CHEMBL4302	P08183	P-glycoprotein 1	96.89%	92.98%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.27%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.23%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.22%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.12%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.96%	89.00%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	93.13%	89.44%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	92.71%	94.62%
CHEMBL2581	P07339	Cathepsin D	90.15%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.95%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	89.78%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.63%	97.09%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	88.49%	94.23%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.11%	91.07%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	87.95%	83.00%
CHEMBL5028	O14672	ADAM10	87.81%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.77%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.94%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.73%	99.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	86.36%	94.08%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.61%	97.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.54%	95.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.25%	93.56%
CHEMBL226	P30542	Adenosine A1 receptor	85.12%	95.93%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	84.71%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.92%	92.62%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.00%	97.36%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.95%	100.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.83%	93.99%

Plants that contains it

• Gymnema sylvestre

Cross-Links

• PubChem: 101948680
• LOTUS: LTS0027247
• wikiData: Q105165347