Saikosaponin BK1

Details

• Internal ID: 7f67784e-5761-4989-a227-3ad61cb2e443
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[(2R,3S,4R,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aS,14aR,14bS)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,14a-dodecahydropicen-3-yl]oxy]-4,5-dihydroxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OC3CCC4(C(C3(C)C)CCC5(C4C=CC6=C7CC(CCC7(C(CC65C)O)CO)(C)C)C)C)COC8C(C(C(C(O8)CO)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)O[C@H]3CC[C@]4([C@H](C3(C)C)CC[C@@]5([C@@H]4C=CC6=C7CC(CC[C@@]7([C@@H](C[C@]65C)O)CO)(C)C)C)C)CO[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O
• InChI: InChI=1S/C48H78O17/c1-22-31(52)33(54)37(58)41(61-22)65-39-26(20-60-40-36(57)34(55)32(53)25(19-49)62-40)63-42(38(59)35(39)56)64-30-12-13-45(6)27(44(30,4)5)11-14-46(7)28(45)10-9-23-24-17-43(2,3)15-16-48(24,21-50)29(51)18-47(23,46)8/h9-10,22,25-42,49-59H,11-21H2,1-8H3/t22-,25+,26+,27-,28+,29+,30-,31-,32+,33+,34-,35+,36+,37+,38+,39+,40+,41-,42-,45-,46+,47+,48+/m0/s1
• InChI Key: PYJMYPPFWASOJX-YSNVVKQWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₈O₁₇
• Molecular Weight: 927.10 g/mol
• Exact Mass: 926.52390102 g/mol
• Topological Polar Surface Area (TPSA): 278.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 0.53
• H-Bond Acceptor: 17
• H-Bond Donor: 11
• Rotatable Bonds: 9

Synonyms

• 110352-77-7
• (2S,3R,4R,5R,6S)-2-[(2R,3S,4R,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aS,14aR,14bS)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,14a-dodecahydropicen-3-yl]oxy]-4,5-dihydroxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• C08976
• CHEBI:8997
• DTXSID40331683
• Q27108209

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7084	70.84%
Caco-2	-	0.8854	88.54%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.7876	78.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8009	80.09%
OATP1B3 inhibitior	-	0.4367	43.67%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.7890	78.90%
P-glycoprotein inhibitior	+	0.7479	74.79%
P-glycoprotein substrate	-	0.5170	51.70%
CYP3A4 substrate	+	0.7357	73.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8401	84.01%
CYP3A4 inhibition	-	0.9345	93.45%
CYP2C9 inhibition	-	0.8819	88.19%
CYP2C19 inhibition	-	0.8988	89.88%
CYP2D6 inhibition	-	0.9401	94.01%
CYP1A2 inhibition	-	0.8923	89.23%
CYP2C8 inhibition	+	0.7080	70.80%
CYP inhibitory promiscuity	-	0.9600	96.00%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6252	62.52%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9064	90.64%
Skin irritation	-	0.6425	64.25%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7377	73.77%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8896	88.96%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.8510	85.10%
Acute Oral Toxicity (c)	III	0.7434	74.34%
Estrogen receptor binding	+	0.7808	78.08%
Androgen receptor binding	+	0.7274	72.74%
Thyroid receptor binding	-	0.5404	54.04%
Glucocorticoid receptor binding	+	0.6462	64.62%
Aromatase binding	+	0.6604	66.04%
PPAR gamma	+	0.7698	76.98%
Honey bee toxicity	-	0.6466	64.66%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5850	58.50%
Fish aquatic toxicity	+	0.9174	91.74%

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	98.93%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.67%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.84%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.68%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	92.20%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.02%	100.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.16%	97.36%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.19%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	88.19%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.13%	95.89%
CHEMBL1871	P10275	Androgen Receptor	86.88%	96.43%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.27%	95.50%
CHEMBL2581	P07339	Cathepsin D	85.24%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	83.78%	94.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.51%	92.94%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.39%	93.04%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.07%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.49%	89.00%

Plants that contains it

• Bupleurum chinense
• Bupleurum falcatum
• Bupleurum scorzonerifolium

Cross-Links

• PubChem: 441945
• NPASS: NPC205432
• LOTUS: LTS0165734
• wikiData: Q27108209