[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11S,12aR,14bS)-10-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-8,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate

Details

• Internal ID: 99c5f605-3453-4044-a5d2-f4cce311f558
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11S,12aR,14bS)-10-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-8,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CC(C5C4(CC(C(C5(C)CO)OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)O)O)O)O)O)OC8C(C(C(CO8)O)O)O)O)C)O)C)C2C1)C)C(=O)OC9C(C(C(C(O9)CO)O)O)O)C
• SMILES (Isomeric): C[C@@]12CC[C@]3(CCC(C[C@H]3C1=CC[C@H]4[C@]2(C[C@H]([C@@H]5[C@@]4(C[C@@H]([C@@H]([C@@]5(C)CO)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O)O[C@H]8[C@@H]([C@H]([C@H](CO8)O)O)O)O)C)O)C)(C)C)C(=O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O
• InChI: InChI=1S/C53H86O25/c1-48(2)9-11-53(47(70)78-45-39(69)35(65)32(62)27(17-55)74-45)12-10-51(5)21(22(53)13-48)7-8-29-49(3)14-24(58)42(50(4,20-56)41(49)23(57)15-52(29,51)6)77-46-40(76-44-37(67)30(60)25(59)18-71-44)36(66)33(63)28(75-46)19-72-43-38(68)34(64)31(61)26(16-54)73-43/h7,22-46,54-69H,8-20H2,1-6H3/t22-,23+,24-,25-,26+,27+,28+,29+,30-,31+,32+,33+,34-,35-,36-,37+,38+,39+,40+,41+,42-,43+,44-,45-,46-,49+,50-,51+,52+,53-/m0/s1
• InChI Key: SJKRZKLSDBFOIV-GOCRSBGVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₆O₂₅
• Molecular Weight: 1123.20 g/mol
• Exact Mass: 1122.54581822 g/mol
• Topological Polar Surface Area (TPSA): 415.00 Ų
• XlogP: -3.10
• Atomic LogP (AlogP): -4.48
• H-Bond Acceptor: 25
• H-Bond Donor: 16
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8849	88.49%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8648	86.48%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.8607	86.07%
P-glycoprotein inhibitior	+	0.7461	74.61%
P-glycoprotein substrate	-	0.5116	51.16%
CYP3A4 substrate	+	0.7215	72.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9300	93.00%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.8933	89.33%
CYP2C8 inhibition	+	0.6913	69.13%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9015	90.15%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7780	77.80%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.6605	66.05%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.8013	80.13%
Androgen receptor binding	+	0.7526	75.26%
Thyroid receptor binding	+	0.5225	52.25%
Glucocorticoid receptor binding	+	0.7482	74.82%
Aromatase binding	+	0.6476	64.76%
PPAR gamma	+	0.8104	81.04%
Honey bee toxicity	-	0.6619	66.19%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6550	65.50%
Fish aquatic toxicity	+	0.9411	94.11%

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	99.30%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.53%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.14%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.95%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.14%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.14%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.11%	96.77%
CHEMBL2581	P07339	Cathepsin D	90.07%	98.95%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.94%	97.36%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	89.33%	83.57%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.46%	95.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.33%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.34%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	85.93%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.42%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.49%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.00%	96.90%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	81.95%	95.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.73%	92.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.33%	94.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.30%	89.00%

Plants that contains it

• Amaranthus caudatus

Cross-Links

• PubChem: 101945197
• LOTUS: LTS0101781
• wikiData: Q105254379