Bacopaside I

Details

• Internal ID: 763b14b1-8498-4b5d-b74a-cdcc5c52d580
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5-hydroxy-2-[[(1S,2R,5R,7S,10R,11R,14R,15S,16S,17R,20R)-16-hydroxy-2,6,6,10,16-pentamethyl-17-(2-methylprop-1-enyl)-19,21-dioxahexacyclo[18.2.1.01,14.02,11.05,10.015,20]tricosan-7-yl]oxy]oxan-4-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl hydrogen sulfate
• SMILES (Canonical): CC(=CC1COC23CC4(CO2)C(C3C1(C)O)CCC5C4(CCC6C5(CCC(C6(C)C)OC7C(C(C(CO7)O)OC8C(C(C(C(O8)COS(=O)(=O)O)O)O)O)OC9C(C(C(O9)CO)O)O)C)C)C
• SMILES (Isomeric): CC(=C[C@@H]1CO[C@]23C[C@]4(CO2)[C@@H]([C@H]3[C@@]1(C)O)CC[C@H]5[C@]4(CC[C@@H]6[C@@]5(CC[C@@H](C6(C)C)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)COS(=O)(=O)O)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H](O9)CO)O)O)C)C)C
• InChI: InChI=1S/C46H74O20S/c1-21(2)14-22-16-59-46-19-45(20-60-46)23(37(46)44(22,7)54)8-9-28-42(5)12-11-29(41(3,4)27(42)10-13-43(28,45)6)64-40-36(66-38-33(52)30(49)25(15-47)62-38)35(24(48)17-58-40)65-39-34(53)32(51)31(50)26(63-39)18-61-67(55,56)57/h14,22-40,47-54H,8-13,15-20H2,1-7H3,(H,55,56,57)/t22-,23-,24+,25+,26-,27+,28-,29+,30+,31-,32+,33-,34-,35+,36-,37+,38+,39+,40+,42+,43-,44+,45+,46-/m1/s1
• InChI Key: SKFWOYHZBNAJGA-YAOMZRCFSA-N
• Popularity: 28 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₇₄O₂₀S
• Molecular Weight: 979.10 g/mol
• Exact Mass: 978.44941592 g/mol
• Topological Polar Surface Area (TPSA): 308.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.29
• H-Bond Acceptor: 19
• H-Bond Donor: 9
• Rotatable Bonds: 11

Synonyms

• 382148-47-2
• Bacopaside I, (-)-
• BACOPASIDE I(SH)
• UNII-36B8WUA361
• 36B8WUA361
• Bacopaside I (constituent of bacopa) [DSC]
• [(2R,3S,4S,5R,6S)-6-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5-hydroxy-2-[[(1S,2R,5R,7S,10R,11R,14R,15S,16S,17R,20R)-16-hydroxy-2,6,6,10,16-pentamethyl-17-(2-methylprop-1-enyl)-19,21-dioxahexacyclo[18.2.1.01,14.02,11.05,10.015,20]tricosan-7-yl]oxy]oxan-4-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl hydrogen sulfate
• 3-O-alpha-L-arabinofuranosyl-(1-2)-(6-O-sulphonyl-beta-D-glucopyranosyl-(1-3))-alpha-L-arabinopyranosyl pseudo-jujubogenin
• HY-N4246
• AKOS040760286
• AS-82791
• CS-0032525
• Q27256548

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8007	80.07%
Caco-2	-	0.8806	88.06%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.4949	49.49%
OATP2B1 inhibitior	-	0.8774	87.74%
OATP1B1 inhibitior	+	0.8227	82.27%
OATP1B3 inhibitior	+	0.9306	93.06%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7528	75.28%
P-glycoprotein inhibitior	+	0.7543	75.43%
P-glycoprotein substrate	+	0.5853	58.53%
CYP3A4 substrate	+	0.7524	75.24%
CYP2C9 substrate	-	0.8002	80.02%
CYP2D6 substrate	-	0.8537	85.37%
CYP3A4 inhibition	-	0.8370	83.70%
CYP2C9 inhibition	-	0.7521	75.21%
CYP2C19 inhibition	-	0.7185	71.85%
CYP2D6 inhibition	-	0.8706	87.06%
CYP1A2 inhibition	-	0.7463	74.63%
CYP2C8 inhibition	+	0.7147	71.47%
CYP inhibitory promiscuity	-	0.8771	87.71%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.5800	58.00%
Carcinogenicity (trinary)	Non-required	0.5478	54.78%
Eye corrosion	-	0.9794	97.94%
Eye irritation	-	0.9035	90.35%
Skin irritation	-	0.7477	74.77%
Skin corrosion	-	0.9064	90.64%
Ames mutagenesis	-	0.6054	60.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7322	73.22%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8407	84.07%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.8163	81.63%
Acute Oral Toxicity (c)	III	0.5760	57.60%
Estrogen receptor binding	+	0.8017	80.17%
Androgen receptor binding	+	0.7567	75.67%
Thyroid receptor binding	-	0.5116	51.16%
Glucocorticoid receptor binding	+	0.7404	74.04%
Aromatase binding	+	0.6230	62.30%
PPAR gamma	+	0.7983	79.83%
Honey bee toxicity	-	0.5663	56.63%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5055	50.55%
Fish aquatic toxicity	+	0.9854	98.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL325	Q13547	Histone deacetylase 1	96.93%	95.92%
CHEMBL226	P30542	Adenosine A1 receptor	96.63%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.02%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.32%	98.95%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.31%	96.38%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	91.84%	95.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.83%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.62%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.48%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	90.88%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.78%	100.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	89.69%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.37%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.36%	97.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.21%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.00%	94.45%
CHEMBL3524	P56524	Histone deacetylase 4	88.47%	92.97%
CHEMBL5255	O00206	Toll-like receptor 4	88.34%	92.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.26%	94.33%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	87.24%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.02%	91.24%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.74%	95.83%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.38%	89.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.96%	97.28%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.60%	96.90%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.57%	96.61%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.31%	91.03%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.61%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.52%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.39%	96.00%
CHEMBL1871	P10275	Androgen Receptor	81.89%	96.43%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	81.89%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.79%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	81.50%	91.19%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.49%	82.69%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	80.92%	85.49%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.50%	96.77%

Plants that contains it

• Aglaia elliptica
• Bacopa monnieri
• Catananche caerulea
• Cirsium wallichii
• Corydalis calliantha
• Fritillaria cirrhosa
• Phebalium whitei
• Quassia indica
• Rosa agrestis
• Rumex nepalensis
• Salvia urolepis
• Strychnos lucida
• Vitis betulifolia

Cross-Links

• PubChem: 21599442
• NPASS: NPC295232
• LOTUS: LTS0087888
• wikiData: Q27256548