DipsacosideB

Details

• Internal ID: 4c8497b7-111f-4d3e-b72c-ab4c2e8346df
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] 10-[4,5-dihydroxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-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): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)CO)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)OC8C(C(C(C(O8)COC9C(C(C(C(O9)CO)O)O)O)O)O)O)C)C)C)O)O)O)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)CO)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)OC8C(C(C(C(O8)COC9C(C(C(C(O9)CO)O)O)O)O)O)O)C)C)C)O)O)O)O)O
• InChI: InChI=1S/C53H86O22/c1-23-32(57)36(61)40(65)44(70-23)74-42-33(58)26(56)20-68-46(42)73-31-11-12-49(4)29(50(31,5)22-55)10-13-52(7)30(49)9-8-24-25-18-48(2,3)14-16-53(25,17-15-51(24,52)6)47(67)75-45-41(66)38(63)35(60)28(72-45)21-69-43-39(64)37(62)34(59)27(19-54)71-43/h8,23,25-46,54-66H,9-22H2,1-7H3
• InChI Key: GFPLPBCJRRNZHM-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₆O₂₂
• Molecular Weight: 1075.20 g/mol
• Exact Mass: 1074.56107437 g/mol
• Topological Polar Surface Area (TPSA): 354.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -1.40
• H-Bond Acceptor: 22
• H-Bond Donor: 13
• Rotatable Bonds: 11

Synonyms

• Glycoside L-G3;Tauroside G3
• 942997-00-4
• BCP10264
• [3,4,5-Trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] 10-[4,5-dihydroxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-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
• [3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl] 10-[4,5-dihydroxy-3-(3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-tetrahydropyran-2-yl]oxy-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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8885	88.85%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9207	92.07%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.7594	75.94%
P-glycoprotein inhibitior	+	0.7473	74.73%
P-glycoprotein substrate	-	0.5453	54.53%
CYP3A4 substrate	+	0.7376	73.76%
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	+	0.7299	72.99%
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	-	0.9021	90.21%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7577	75.77%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.8317	83.17%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.7912	79.12%
Androgen receptor binding	+	0.7382	73.82%
Thyroid receptor binding	+	0.5246	52.46%
Glucocorticoid receptor binding	+	0.7521	75.21%
Aromatase binding	+	0.6718	67.18%
PPAR gamma	+	0.8126	81.26%
Honey bee toxicity	-	0.6696	66.96%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5650	56.50%
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	98.40%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	96.34%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.07%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.72%	96.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	92.75%	95.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.61%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.03%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.38%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.21%	86.92%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.08%	96.77%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.79%	95.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.64%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.31%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.81%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	84.79%	95.93%
CHEMBL2581	P07339	Cathepsin D	84.07%	98.95%
CHEMBL5028	O14672	ADAM10	81.89%	97.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.51%	96.90%
CHEMBL5255	O00206	Toll-like receptor 4	80.83%	92.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.37%	91.07%

Plants that contains it

• Cephalaria procera
• Clematis tibetana
• Decaisnea fargesii
• Hedera canariensis
• Hedera helix
• Kalopanax septemlobus
• Lonicera japonica
• Medicago polymorpha
• Nigella damascena

Cross-Links

• PubChem: 14284443
• LOTUS: LTS0125941
• wikiData: Q105007691