Isotheasaponin B1

Details

• Internal ID: 6a4b86ae-2573-42c2-9944-a4d4a4410aab
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8a-(acetyloxymethyl)-8,9-dihydroxy-4,4,6a,6b,11,11,14b-heptamethyl-10-[(E)-3-phenylprop-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC(=O)OCC12C(CC(C(C1O)OC(=O)C=CC3=CC=CC=C3)(C)C)C4=CCC5C6(CCC(C(C6CCC5(C4(CC2O)C)C)(C)C)OC7C(C(C(C(O7)C(=O)O)O)OC8C(C(C(CO8)O)O)OC9C(C(C(CO9)O)O)O)OC1C(C(C(C(O1)CO)O)O)O)C
• SMILES (Isomeric): CC(=O)OC[C@@]12[C@@H](C[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)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)CO)O)O)O)C)C)[C@@H]1CC([C@H]([C@@H]2O)OC(=O)/C=C/C1=CC=CC=C1)(C)C)C)O
• InChI: InChI=1S/C63H92O26/c1-28(65)82-27-63-31(22-58(2,3)52(51(63)77)85-39(69)17-14-29-12-10-9-11-13-29)30-15-16-36-60(6)20-19-38(59(4,5)35(60)18-21-61(36,7)62(30,8)23-37(63)68)84-57-50(89-55-45(75)43(73)42(72)34(24-64)83-55)47(46(76)48(87-57)53(78)79)86-56-49(41(71)33(67)26-81-56)88-54-44(74)40(70)32(66)25-80-54/h9-15,17,31-38,40-52,54-57,64,66-68,70-77H,16,18-27H2,1-8H3,(H,78,79)/b17-14+/t31-,32+,33-,34+,35-,36+,37+,38-,40-,41-,42-,43-,44+,45+,46-,47-,48-,49+,50+,51-,52-,54-,55-,56-,57+,60-,61+,62+,63-/m0/s1
• InChI Key: KOQFKNITQTWNHB-WXLDJIECSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₆₃H₉₂O₂₆
• Molecular Weight: 1265.40 g/mol
• Exact Mass: 1264.58768304 g/mol
• Topological Polar Surface Area (TPSA): 407.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): -0.44
• H-Bond Acceptor: 25
• H-Bond Donor: 13
• Rotatable Bonds: 15

Synonyms

• (+)-Isotheasaponin B1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8071	80.71%
Caco-2	-	0.8625	86.25%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8508	85.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7427	74.27%
OATP1B3 inhibitior	-	0.4332	43.32%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5776	57.76%
BSEP inhibitior	+	0.9772	97.72%
P-glycoprotein inhibitior	+	0.7442	74.42%
P-glycoprotein substrate	+	0.6499	64.99%
CYP3A4 substrate	+	0.7498	74.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8869	88.69%
CYP3A4 inhibition	-	0.6485	64.85%
CYP2C9 inhibition	-	0.8438	84.38%
CYP2C19 inhibition	-	0.8858	88.58%
CYP2D6 inhibition	-	0.9350	93.50%
CYP1A2 inhibition	-	0.8417	84.17%
CYP2C8 inhibition	+	0.8538	85.38%
CYP inhibitory promiscuity	-	0.9590	95.90%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6075	60.75%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.8972	89.72%
Skin irritation	-	0.6315	63.15%
Skin corrosion	-	0.9465	94.65%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7716	77.16%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8967	89.67%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.9051	90.51%
Acute Oral Toxicity (c)	III	0.7534	75.34%
Estrogen receptor binding	+	0.6594	65.94%
Androgen receptor binding	+	0.7596	75.96%
Thyroid receptor binding	+	0.6942	69.42%
Glucocorticoid receptor binding	+	0.7971	79.71%
Aromatase binding	+	0.6651	66.51%
PPAR gamma	+	0.8137	81.37%
Honey bee toxicity	-	0.6246	62.46%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5145	51.45%
Fish aquatic toxicity	+	0.9824	98.24%

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	98.46%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.36%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.77%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	94.98%	90.17%
CHEMBL2581	P07339	Cathepsin D	93.81%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.33%	95.56%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	93.05%	89.44%
CHEMBL5028	O14672	ADAM10	92.36%	97.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	92.04%	94.62%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	91.68%	91.65%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	90.11%	94.08%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.86%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.41%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.64%	94.45%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	86.70%	89.67%
CHEMBL1937	Q92769	Histone deacetylase 2	86.23%	94.75%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.91%	93.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.51%	96.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.90%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.14%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.94%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.87%	100.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.05%	94.23%
CHEMBL3401	O75469	Pregnane X receptor	80.26%	94.73%

Plants that contains it

• Camellia sinensis

Cross-Links

• PubChem: 101402534
• LOTUS: LTS0063948
• wikiData: Q105143940