ardisicrenoside A

Details

• Internal ID: abb2f0ff-70a5-48e2-9a69-2368e0c51882
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[(3S,4S,5R,6S)-4-hydroxy-6-[[(1S,2R,4S,5R,8R,10S,13R,14R,17S,18R,20S)-2-hydroxy-20-(hydroxymethyl)-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-10-yl]oxy]-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3COC(C(C3O)OC4C(C(C(C(O4)CO)O)O)O)OC5CCC6(C(C5(C)C)CCC7(C6CCC89C7(CC(C1(C8CC(CC1)(C)CO)CO9)O)C)C)C)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@H]3CO[C@H]([C@@H]([C@H]3O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O[C@H]5CC[C@@]6([C@H]7CC[C@@]89[C@@H]1C[C@@](CC[C@]1(CO8)[C@@H](C[C@]9([C@@]7(CC[C@H]6C5(C)C)C)C)O)(C)CO)C)CO)O)O)O)O)O
• InChI: InChI=1S/C53H88O22/c1-23-32(58)36(62)39(65)43(69-23)75-42-38(64)34(60)25(19-55)71-46(42)72-26-20-67-45(41(35(26)61)74-44-40(66)37(63)33(59)24(18-54)70-44)73-31-10-11-49(5)27(47(31,2)3)8-12-50(6)28(49)9-13-53-29-16-48(4,21-56)14-15-52(29,22-68-53)30(57)17-51(50,53)7/h23-46,54-66H,8-22H2,1-7H3/t23-,24+,25+,26-,27-,28+,29+,30+,31-,32-,33+,34+,35-,36+,37-,38-,39+,40+,41+,42+,43-,44-,45-,46-,48-,49-,50+,51-,52+,53-/m0/s1
• InChI Key: LTTSWSWZQNISIB-LLEYBADXSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₈O₂₂
• Molecular Weight: 1077.30 g/mol
• Exact Mass: 1076.57672443 g/mol
• Topological Polar Surface Area (TPSA): 346.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.71
• H-Bond Acceptor: 22
• H-Bond Donor: 13
• Rotatable Bonds: 11

Synonyms

• 160824-52-2
• CHEMBL373378
• HY-N8199
• AKOS040761370
• CS-0140296

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5489	54.89%
Caco-2	-	0.8841	88.41%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6239	62.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8192	81.92%
OATP1B3 inhibitior	+	0.9351	93.51%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.7340	73.40%
P-glycoprotein inhibitior	+	0.7435	74.35%
P-glycoprotein substrate	+	0.5426	54.26%
CYP3A4 substrate	+	0.7451	74.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8237	82.37%
CYP3A4 inhibition	-	0.9474	94.74%
CYP2C9 inhibition	-	0.8579	85.79%
CYP2C19 inhibition	-	0.8572	85.72%
CYP2D6 inhibition	-	0.9505	95.05%
CYP1A2 inhibition	-	0.9122	91.22%
CYP2C8 inhibition	+	0.7152	71.52%
CYP inhibitory promiscuity	-	0.9632	96.32%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6416	64.16%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9017	90.17%
Skin irritation	-	0.7052	70.52%
Skin corrosion	-	0.9482	94.82%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7667	76.67%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.9225	92.25%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.8308	83.08%
Acute Oral Toxicity (c)	I	0.7071	70.71%
Estrogen receptor binding	+	0.7982	79.82%
Androgen receptor binding	+	0.7486	74.86%
Thyroid receptor binding	-	0.5104	51.04%
Glucocorticoid receptor binding	+	0.6529	65.29%
Aromatase binding	+	0.6464	64.64%
PPAR gamma	+	0.7793	77.93%
Honey bee toxicity	-	0.5556	55.56%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8283	82.83%

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	95.59%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	94.47%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.65%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.87%	97.36%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.58%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.60%	97.09%
CHEMBL332	P03956	Matrix metalloproteinase-1	88.46%	94.50%
CHEMBL2581	P07339	Cathepsin D	87.93%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	87.67%	90.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.14%	95.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.94%	96.61%
CHEMBL2243	O00519	Anandamide amidohydrolase	86.90%	97.53%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.89%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.83%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.07%	96.21%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	85.10%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.57%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.22%	95.89%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.15%	91.24%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	83.59%	89.44%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	82.91%	95.36%
CHEMBL259	P32245	Melanocortin receptor 4	82.61%	95.38%
CHEMBL4073	P09237	Matrix metalloproteinase 7	82.03%	97.56%
CHEMBL233	P35372	Mu opioid receptor	81.86%	97.93%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.65%	92.88%
CHEMBL3589	P55263	Adenosine kinase	81.31%	98.05%
CHEMBL1937	Q92769	Histone deacetylase 2	81.25%	94.75%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.13%	91.03%
CHEMBL237	P41145	Kappa opioid receptor	80.78%	98.10%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	80.74%	89.05%
CHEMBL1977	P11473	Vitamin D receptor	80.17%	99.43%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.15%	94.00%

Plants that contains it

• Ardisia crenata
• Ardisia japonica
• Ardisia mamillata
• Myrsine seguinii

Cross-Links

• PubChem: 10260582
• NPASS: NPC267238
• LOTUS: LTS0240580
• wikiData: Q104401552