Ardicrenin

Details

• Internal ID: 2b8a64ba-35a3-4797-8c32-f9d1200bd459
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (4S,5R,10S,13R,14R,20S,22S)-22-hydroxy-4,5,9,9,13,20-hexamethyl-10-[(2S,3R,4S,5S)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosane-20-carbaldehyde
• SMILES (Canonical): CC1C(C(C(C(O1)OC2COC(C(C2OC3C(C(C(C(O3)CO)O)O)O)OC4C(C(C(C(O4)CO)O)O)O)OC5CCC6(C(C5(C)C)CCC7(C6CCC89C7(CCC1(C8CC(CC1O)(C)C=O)CO9)C)C)C)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2CO[C@H]([C@@H]([C@H]2O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)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]7CCC89C1C[C@](C[C@@H](C1(CC[C@]8([C@@]7(CCC6C5(C)C)C)C)CO9)O)(C)C=O)C)O)O)O
• InChI: InChI=1S/C53H86O22/c1-23-32(58)35(61)38(64)43(69-23)72-26-20-67-46(42(75-45-40(66)37(63)34(60)25(19-55)71-45)41(26)74-44-39(65)36(62)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)17-30(57)52(29,22-68-53)15-14-51(50,53)7/h21,23-46,54-55,57-66H,8-20,22H2,1-7H3/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: AWHOLZVUVDYTBG-AZDDWXAASA-N
• Popularity: 3 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): 343.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.50
• H-Bond Acceptor: 22
• H-Bond Donor: 12
• Rotatable Bonds: 11

Synonyms

• 143016-77-7
• Cyclamiretin A-3-O-(alpha-L-rhamnopyranosyl-(1-4)-beta-D-glucopyranosyl-(1-4))(beta-D-glucopyranosyl-(1-2))-alpha-L-arabinopyranoside
• Oleanan-29-al, 3-((O-6-deoxy-alpha-L-mannopyranosyl-(1-4)-O-beta-D-glucopyranosyl-(1-4)-O-(beta-D-glucopyranosyl-(1-2))-alpha-L-arabinopyranosyl)oxy)-13,28-epoxy-22-hydroxy-, (3beta,20beta,22alpha)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6397	63.97%
Caco-2	-	0.8828	88.28%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7227	72.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7960	79.60%
OATP1B3 inhibitior	+	0.9276	92.76%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.7393	73.93%
P-glycoprotein inhibitior	+	0.7490	74.90%
P-glycoprotein substrate	+	0.5306	53.06%
CYP3A4 substrate	+	0.7436	74.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8272	82.72%
CYP3A4 inhibition	-	0.9228	92.28%
CYP2C9 inhibition	-	0.8526	85.26%
CYP2C19 inhibition	-	0.8627	86.27%
CYP2D6 inhibition	-	0.9523	95.23%
CYP1A2 inhibition	-	0.9157	91.57%
CYP2C8 inhibition	+	0.6833	68.33%
CYP inhibitory promiscuity	-	0.9693	96.93%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6545	65.45%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9028	90.28%
Skin irritation	-	0.6766	67.66%
Skin corrosion	-	0.9455	94.55%
Ames mutagenesis	-	0.5570	55.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7793	77.93%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.8123	81.23%
skin sensitisation	-	0.9229	92.29%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8057	80.57%
Acute Oral Toxicity (c)	I	0.6300	63.00%
Estrogen receptor binding	+	0.7582	75.82%
Androgen receptor binding	+	0.7470	74.70%
Thyroid receptor binding	-	0.5348	53.48%
Glucocorticoid receptor binding	+	0.6945	69.45%
Aromatase binding	+	0.6564	65.64%
PPAR gamma	+	0.7629	76.29%
Honey bee toxicity	-	0.5622	56.22%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5145	51.45%
Fish aquatic toxicity	+	0.8764	87.64%

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	94.65%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.63%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	92.49%	95.93%
CHEMBL203	P00533	Epidermal growth factor receptor erbB1	92.41%	97.34%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.98%	91.24%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.51%	97.36%
CHEMBL1951	P21397	Monoamine oxidase A	90.03%	91.49%
CHEMBL2581	P07339	Cathepsin D	88.97%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.71%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.73%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	86.20%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.00%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.57%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.88%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.81%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.24%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.66%	95.56%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.81%	97.53%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.45%	92.94%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.16%	96.21%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	81.75%	89.44%
CHEMBL4302	P08183	P-glycoprotein 1	81.44%	92.98%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.21%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.17%	86.33%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.38%	91.03%
CHEMBL5028	O14672	ADAM10	80.36%	97.50%

Plants that contains it

• Ardisia crenata

Cross-Links

• PubChem: 3083371
• LOTUS: LTS0176203
• wikiData: Q104920052