6''-O-Acetylsaikosaponin D

Details

• Internal ID: 692a8136-786a-47e9-92b0-32f8ae4ea8ec
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[(2R,3R,4S,5S,6R)-3,5-dihydroxy-2-[[(1S,2R,4S,5R,8R,9R,10S,13S,14R,17S,18R)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-10-yl]oxy]-6-methyloxan-4-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2(C)CO)CCC4(C3C=CC56C4(CC(C7(C5CC(CC7)(C)C)CO6)O)C)C)C)O)OC8C(C(C(C(O8)COC(=O)C)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@]3([C@H]([C@]2(C)CO)CC[C@@]4([C@@H]3C=C[C@@]56[C@]4(C[C@H]([C@@]7([C@H]5CC(CC7)(C)C)CO6)O)C)C)C)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)COC(=O)C)O)O)O)O
• InChI: InChI=1S/C44H70O14/c1-22-30(48)35(58-36-33(51)32(50)31(49)24(56-36)19-53-23(2)46)34(52)37(55-22)57-29-11-12-39(5)25(40(29,6)20-45)9-13-41(7)26(39)10-14-44-27-17-38(3,4)15-16-43(27,21-54-44)28(47)18-42(41,44)8/h10,14,22,24-37,45,47-52H,9,11-13,15-21H2,1-8H3/t22-,24-,25-,26-,27-,28-,29+,30+,31-,32+,33-,34-,35+,36+,37+,39+,40+,41-,42+,43-,44+/m1/s1
• InChI Key: WDWZBAMDKXKRBA-YBZZVAQVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₇₀O₁₄
• Molecular Weight: 823.00 g/mol
• Exact Mass: 822.47655690 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.35
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• 64340-45-0
• [(2R,3S,4S,5R,6S)-6-[(2R,3R,4S,5S,6R)-3,5-Dihydroxy-2-[[(1S,2R,4S,5R,8R,9R,10S,13S,14R,17S,18R)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-10-yl]oxy]-6-methyloxan-4-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• 6''-Acetylsaikosaponin d
• CHEMBL3613726
• AKOS040761110

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7235	72.35%
Caco-2	-	0.8787	87.87%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7561	75.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8314	83.14%
OATP1B3 inhibitior	+	0.9009	90.09%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.7600	76.00%
P-glycoprotein inhibitior	+	0.7608	76.08%
P-glycoprotein substrate	+	0.5447	54.47%
CYP3A4 substrate	+	0.7338	73.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8785	87.85%
CYP3A4 inhibition	-	0.9130	91.30%
CYP2C9 inhibition	-	0.8588	85.88%
CYP2C19 inhibition	-	0.8720	87.20%
CYP2D6 inhibition	-	0.9479	94.79%
CYP1A2 inhibition	-	0.9165	91.65%
CYP2C8 inhibition	+	0.7098	70.98%
CYP inhibitory promiscuity	-	0.9568	95.68%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6305	63.05%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9061	90.61%
Skin irritation	-	0.6279	62.79%
Skin corrosion	-	0.9429	94.29%
Ames mutagenesis	-	0.6970	69.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6495	64.95%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.6012	60.12%
skin sensitisation	-	0.9113	91.13%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.7433	74.33%
Acute Oral Toxicity (c)	I	0.6357	63.57%
Estrogen receptor binding	+	0.7486	74.86%
Androgen receptor binding	+	0.7521	75.21%
Thyroid receptor binding	-	0.5521	55.21%
Glucocorticoid receptor binding	+	0.7130	71.30%
Aromatase binding	+	0.6500	65.00%
PPAR gamma	+	0.7667	76.67%
Honey bee toxicity	-	0.6877	68.77%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9406	94.06%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.11%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.09%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.15%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.75%	97.36%
CHEMBL226	P30542	Adenosine A1 receptor	93.26%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.18%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.19%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.25%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.26%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.88%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.74%	100.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.42%	96.38%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	86.97%	97.47%
CHEMBL1914	P06276	Butyrylcholinesterase	86.58%	95.00%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	86.09%	92.78%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.94%	95.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.89%	93.04%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.06%	94.33%
CHEMBL5028	O14672	ADAM10	83.00%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	82.94%	92.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.66%	100.00%
CHEMBL2581	P07339	Cathepsin D	82.16%	98.95%
CHEMBL2243	O00519	Anandamide amidohydrolase	81.27%	97.53%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.91%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.29%	92.62%

Plants that contains it

• Bupleurum chinense
• Bupleurum falcatum
• Bupleurum kunmingense
• Bupleurum marginatum
• Bupleurum polyclonum
• Bupleurum scorzonerifolium

Cross-Links

• PubChem: 21637630
• NPASS: NPC40133
• ChEMBL: CHEMBL3613726
• LOTUS: LTS0147344
• wikiData: Q104402596