Buddlejasaponin IV

Details

• Internal ID: c26b79fd-f107-4e7c-ae45-1517ae43f76c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-2-[[(1S,2S,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-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 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)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)CO)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[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O
• InChI: InChI=1S/C48H78O18/c1-22-30(53)37(65-39-35(58)33(56)31(54)23(18-49)62-39)38(66-40-36(59)34(57)32(55)24(19-50)63-40)41(61-22)64-29-10-11-43(4)25(44(29,5)20-51)8-12-45(6)26(43)9-13-48-27-16-42(2,3)14-15-47(27,21-60-48)28(52)17-46(45,48)7/h9,13,22-41,49-59H,8,10-12,14-21H2,1-7H3/t22-,23-,24-,25-,26-,27-,28+,29+,30+,31-,32-,33+,34+,35-,36-,37+,38-,39+,40+,41+,43+,44+,45-,46+,47-,48+/m1/s1
• InChI Key: IRJDRINEGANBIK-ARKKLDSOSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₈O₁₈
• Molecular Weight: 943.10 g/mol
• Exact Mass: 942.51881563 g/mol
• Topological Polar Surface Area (TPSA): 287.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): -0.40
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 9

Synonyms

• 139523-30-1
• Saikosaponin 1
• HZ7J643R5F
• (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-2-[[(1S,2S,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-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• beta-D-Galactopyranoside, (3beta,4alpha,16beta)-13,28-epoxy-16,23-dihydroxyolean-11-en-3-yl O-beta-D-glucopyranosyl-(1-2)-O-(beta-D-glucopyranosyl-(1-3))-6-deoxy-
• BUDDLEOGLUCOSIDE IV
• UNII-HZ7J643R5F
• CHEMBL510087
• DTXSID901315819
• AKOS040760309
• HY-125131
• CS-0089422
• (3.BETA.,4.ALPHA.,16.BETA.)-13,28-EPOXY-16,23-DIHYDROXYOLEAN-11-EN-3-YL O-.BETA.-D-GLUCOPYRANOSYL-(1->2)-O-(.BETA.-D-GLUCOPYRANOSYL-(1->3))-6-DEOXY-.BETA.-D-GALACTOPYRANOSIDE
• .BETA.-D-GALACTOPYRANOSIDE, (3.BETA.,4.ALPHA.,16.BETA.)-13,28-EPOXY-16,23-DIHYDROXYOLEAN-11-EN-3-YL O-.BETA.-D-GLUCOPYRANOSYL-(1->2)-O-(.BETA.-D-GLUCOPYRANOSYL-(1->3))-6-DEOXY-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6441	64.41%
Caco-2	-	0.8833	88.33%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6663	66.63%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8406	84.06%
OATP1B3 inhibitior	+	0.9158	91.58%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.6369	63.69%
P-glycoprotein inhibitior	+	0.7525	75.25%
P-glycoprotein substrate	+	0.5102	51.02%
CYP3A4 substrate	+	0.7268	72.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8287	82.87%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.8634	86.34%
CYP2C19 inhibition	-	0.8659	86.59%
CYP2D6 inhibition	-	0.9457	94.57%
CYP1A2 inhibition	-	0.9115	91.15%
CYP2C8 inhibition	+	0.6898	68.98%
CYP inhibitory promiscuity	-	0.9473	94.73%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6210	62.10%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9050	90.50%
Skin irritation	-	0.6612	66.12%
Skin corrosion	-	0.9452	94.52%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7368	73.68%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.5439	54.39%
skin sensitisation	-	0.9108	91.08%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.6992	69.92%
Acute Oral Toxicity (c)	I	0.7129	71.29%
Estrogen receptor binding	+	0.7702	77.02%
Androgen receptor binding	+	0.7568	75.68%
Thyroid receptor binding	-	0.5465	54.65%
Glucocorticoid receptor binding	+	0.6373	63.73%
Aromatase binding	+	0.6485	64.85%
PPAR gamma	+	0.7534	75.34%
Honey bee toxicity	-	0.6503	65.03%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9152	91.52%

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	96.86%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.27%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	94.48%	97.36%
CHEMBL226	P30542	Adenosine A1 receptor	93.93%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.30%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.94%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.33%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.19%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.77%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.29%	100.00%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	85.09%	97.47%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.64%	89.00%
CHEMBL2243	O00519	Anandamide amidohydrolase	84.35%	97.53%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.34%	92.94%
CHEMBL2581	P07339	Cathepsin D	82.95%	98.95%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	82.08%	92.78%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.55%	94.00%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	81.39%	97.86%

Plants that contains it

• Buddleja japonica
• Buddleja officinalis
• Bupleurum chinense
• Bupleurum falcatum
• Bupleurum fruticosum
• Bupleurum gibraltaricum
• Bupleurum rigidum
• Bupleurum scorzonerifolium
• Clinopodium chinense
• Clinopodium gracile
• Clinopodium micranthum
• Clinopodium vulgare
• Heteromorpha arborescens var. abyssinica
• Verbascum densiflorum

Cross-Links

• PubChem: 153940
• NPASS: NPC110494
• ChEMBL: CHEMBL510087
• LOTUS: LTS0131219
• wikiData: Q104402286