(1S,3'S,4R,4'S,5'S,6S,7R,8R,12R,13R,14R,16R)-14-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3',16-dihydroxy-7-(hydroxymethyl)-5',13-dimethyl-4'-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-2(9),18-diene-6,2'-oxane]-3-one

Details

• Internal ID: bb4f2928-28bf-46ab-8a53-16c85323eb0a
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (1S,3'S,4R,4'S,5'S,6S,7R,8R,12R,13R,14R,16R)-14-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3',16-dihydroxy-7-(hydroxymethyl)-5',13-dimethyl-4'-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-2(9),18-diene-6,2'-oxane]-3-one
• SMILES (Canonical): CC1COC2(C(C3C(O2)C(=O)C4=C3CCC5C4CC=C6C5(C(CC(C6)O)OC7C(C(C(CO7)O)OC8C(C(C(CO8)O)O)O)OC9C(C(C(C(O9)C)O)OC2C(C(CO2)(CO)O)O)O)C)CO)C(C1OC1C(C(C(C(O1)C)O)O)O)O
• SMILES (Isomeric): C[C@H]1CO[C@]2([C@H]([C@H]3[C@@H](O2)C(=O)C4=C3CC[C@@H]5[C@@H]4CC=C6[C@@]5([C@@H](C[C@@H](C6)O)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O[C@H]2[C@@H]([C@](CO2)(CO)O)O)O)C)CO)[C@H]([C@H]1O[C@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O)O)O)O
• InChI: InChI=1S/C53H80O28/c1-17-12-73-53(44(67)39(17)77-47-37(65)35(63)31(59)18(2)74-47)25(11-54)30-23-7-8-24-22(29(23)34(62)41(30)81-53)6-5-20-9-21(56)10-28(51(20,24)4)76-49-43(40(27(58)14-71-49)78-46-36(64)33(61)26(57)13-70-46)80-48-38(66)42(32(60)19(3)75-48)79-50-45(68)52(69,15-55)16-72-50/h5,17-19,21-22,24-28,30-33,35-50,54-61,63-69H,6-16H2,1-4H3/t17-,18-,19-,21+,22-,24+,25-,26+,27-,28+,30-,31-,32-,33-,35+,36+,37+,38+,39-,40-,41+,42+,43+,44-,45-,46-,47-,48-,49-,50-,51-,52+,53-/m0/s1
• InChI Key: LTWMDDYNUKKCPA-YOTHLHBZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₀O₂₈
• Molecular Weight: 1165.20 g/mol
• Exact Mass: 1164.48361189 g/mol
• Topological Polar Surface Area (TPSA): 431.00 Ų
• XlogP: -7.00
• Atomic LogP (AlogP): -6.45
• H-Bond Acceptor: 28
• H-Bond Donor: 15
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8294	82.94%
Caco-2	-	0.8779	87.79%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8220	82.20%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8284	82.84%
OATP1B3 inhibitior	+	0.8670	86.70%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.9499	94.99%
P-glycoprotein inhibitior	+	0.7420	74.20%
P-glycoprotein substrate	+	0.7377	73.77%
CYP3A4 substrate	+	0.7510	75.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8843	88.43%
CYP3A4 inhibition	-	0.9196	91.96%
CYP2C9 inhibition	-	0.9244	92.44%
CYP2C19 inhibition	-	0.9343	93.43%
CYP2D6 inhibition	-	0.9378	93.78%
CYP1A2 inhibition	-	0.9172	91.72%
CYP2C8 inhibition	+	0.8074	80.74%
CYP inhibitory promiscuity	-	0.9444	94.44%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5179	51.79%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9028	90.28%
Skin irritation	+	0.5497	54.97%
Skin corrosion	-	0.9408	94.08%
Ames mutagenesis	-	0.5424	54.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7942	79.42%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.5052	50.52%
skin sensitisation	-	0.9231	92.31%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.7757	77.57%
Acute Oral Toxicity (c)	I	0.4770	47.70%
Estrogen receptor binding	+	0.8451	84.51%
Androgen receptor binding	+	0.7644	76.44%
Thyroid receptor binding	+	0.6216	62.16%
Glucocorticoid receptor binding	+	0.7464	74.64%
Aromatase binding	+	0.6156	61.56%
PPAR gamma	+	0.8216	82.16%
Honey bee toxicity	-	0.6073	60.73%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9416	94.16%

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	99.26%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	98.99%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.92%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.89%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.35%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.31%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.16%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.67%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.47%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.55%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.82%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.13%	97.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.12%	97.25%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	89.00%	92.88%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.46%	91.24%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.06%	91.07%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.89%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.82%	92.94%
CHEMBL2243	O00519	Anandamide amidohydrolase	85.32%	97.53%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.97%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.88%	97.36%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.92%	96.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.96%	96.61%

Plants that contains it

• Trillium tschonoskii

Cross-Links

• PubChem: 163098923
• LOTUS: LTS0174973
• wikiData: Q105157228