Bacopaside X

Details

• Internal ID: 74803bac-5789-400f-a3bf-de8d945172d5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(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,18R,20S)-16-hydroxy-2,6,6,10,16-pentamethyl-18-(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-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(=CC1CC(C2C3CCC4C5(CCC(C(C5CCC4(C36CC2(O1)OC6)C)(C)C)OC7C(C(C(CO7)O)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(O9)CO)O)O)C)(C)O)C
• SMILES (Isomeric): CC(=C[C@H]1C[C@]([C@@H]2[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@]36C[C@@]2(O1)OC6)C)(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)CO)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H](O9)CO)O)O)C)(C)O)C
• InChI: InChI=1S/C46H74O17/c1-21(2)14-22-15-44(7,55)37-23-8-9-28-42(5)12-11-29(41(3,4)27(42)10-13-43(28,6)45(23)19-46(37,63-22)57-20-45)60-40-36(62-38-33(53)31(51)26(17-48)59-38)35(24(49)18-56-40)61-39-34(54)32(52)30(50)25(16-47)58-39/h14,22-40,47-55H,8-13,15-20H2,1-7H3/t22-,23+,24-,25+,26-,27-,28+,29-,30+,31-,32-,33+,34+,35-,36+,37-,38-,39-,40-,42-,43+,44-,45-,46-/m0/s1
• InChI Key: RANQPHKSRUUPKK-GPUGMLHBSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₇₄O₁₇
• Molecular Weight: 899.10 g/mol
• Exact Mass: 898.49260089 g/mol
• Topological Polar Surface Area (TPSA): 256.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 0.61
• H-Bond Acceptor: 17
• H-Bond Donor: 9
• Rotatable Bonds: 9

Synonyms

• 94443-88-6
• BacopasideVII
• Bacopaside X, (-)-
• UNII-P1040545PX
• P1040545PX
• Jujubogenin isomer of bacopasaponin C (bacopaside X) (constituent of bacopa) [DSC]
• bacopaside VII
• CHEMBL506315
• DTXSID00442623
• HY-N5140
• AKOS040760289
• MS-31678
• CS-0032549
• Q27285975
• (2S,3R,4S,5S,6R)-2-[(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,18R,20S)-16-hydroxy-2,6,6,10,16-pentamethyl-18-(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-6-(hydroxymethyl)oxane-3,4,5-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7395	73.95%
Caco-2	-	0.8864	88.64%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7487	74.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8369	83.69%
OATP1B3 inhibitior	+	0.8885	88.85%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.5857	58.57%
P-glycoprotein inhibitior	+	0.7541	75.41%
P-glycoprotein substrate	-	0.5164	51.64%
CYP3A4 substrate	+	0.7493	74.93%
CYP2C9 substrate	-	0.7915	79.15%
CYP2D6 substrate	-	0.8348	83.48%
CYP3A4 inhibition	-	0.9226	92.26%
CYP2C9 inhibition	-	0.8642	86.42%
CYP2C19 inhibition	-	0.9010	90.10%
CYP2D6 inhibition	-	0.9274	92.74%
CYP1A2 inhibition	-	0.9012	90.12%
CYP2C8 inhibition	+	0.7013	70.13%
CYP inhibitory promiscuity	-	0.9197	91.97%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5717	57.17%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9058	90.58%
Skin irritation	-	0.5769	57.69%
Skin corrosion	-	0.9449	94.49%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8035	80.35%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8994	89.94%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.7642	76.42%
Acute Oral Toxicity (c)	I	0.6698	66.98%
Estrogen receptor binding	+	0.7648	76.48%
Androgen receptor binding	+	0.7629	76.29%
Thyroid receptor binding	-	0.5644	56.44%
Glucocorticoid receptor binding	+	0.6649	66.49%
Aromatase binding	+	0.6580	65.80%
PPAR gamma	+	0.7532	75.32%
Honey bee toxicity	-	0.5695	56.95%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9306	93.06%

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	96.98%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.68%	91.11%
CHEMBL325	Q13547	Histone deacetylase 1	94.80%	95.92%
CHEMBL226	P30542	Adenosine A1 receptor	93.94%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.74%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.60%	96.61%
CHEMBL1937	Q92769	Histone deacetylase 2	92.22%	94.75%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.53%	91.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.41%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.07%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.98%	95.50%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	88.77%	89.05%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.22%	100.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	87.52%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.89%	95.89%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	86.72%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.66%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.17%	97.14%
CHEMBL3589	P55263	Adenosine kinase	85.91%	98.05%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	85.90%	97.47%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.08%	92.94%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.06%	92.62%
CHEMBL5555	O00767	Acyl-CoA desaturase	84.71%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	84.40%	90.17%
CHEMBL3524	P56524	Histone deacetylase 4	84.29%	92.97%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.07%	89.00%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	83.39%	95.36%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.19%	98.75%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	81.87%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.71%	95.56%
CHEMBL259	P32245	Melanocortin receptor 4	81.17%	95.38%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.15%	100.00%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	80.80%	89.44%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.73%	91.03%
CHEMBL237	P41145	Kappa opioid receptor	80.54%	98.10%

Plants that contains it

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

Cross-Links

• PubChem: 10629555
• NPASS: NPC100048
• LOTUS: LTS0275809
• wikiData: Q27285975