Cascaroside A

Details

• Internal ID: 2f4005fe-905f-487a-a08d-3e1bdec4abe3
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (10S)-1-hydroxy-3-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-10H-anthracen-9-one
• SMILES (Canonical): C1=CC2=C(C(=C1)OC3C(C(C(C(O3)CO)O)O)O)C(=O)C4=C(C2C5C(C(C(C(O5)CO)O)O)O)C=C(C=C4O)CO
• SMILES (Isomeric): C1=CC2=C(C(=C1)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)C4=C([C@H]2[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C=C(C=C4O)CO
• InChI: InChI=1S/C27H32O14/c28-6-9-4-11-16(26-24(37)22(35)19(32)14(7-29)39-26)10-2-1-3-13(18(10)21(34)17(11)12(31)5-9)40-27-25(38)23(36)20(33)15(8-30)41-27/h1-5,14-16,19-20,22-33,35-38H,6-8H2/t14-,15-,16+,19-,20-,22+,23+,24-,25-,26+,27-/m1/s1
• InChI Key: MNAYRSRTNMVAPR-ZHVWOXMGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₁₄
• Molecular Weight: 580.50 g/mol
• Exact Mass: 580.17920569 g/mol
• Topological Polar Surface Area (TPSA): 247.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -3.42
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

• 53823-08-8
• UNII-AI50I7OZY7
• AI50I7OZY7
• CASCAROSIDEA
• 50814-04-5
• DTXSID40202107
• (10S)-1-hydroxy-3-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-10H-anthracen-9-one
• 9(10H)-Anthracenone, 10-beta-D-glucopyranosyl-8-(beta-D-glucopyranosyloxy)-1-hydroxy-3-(hydroxymethyl)-, (10S)-
• 8-O-(beta-D-Glucopyranosyl)barbaloins
• CHEBI:3446
• DTXCID00124598
• LMPK13040003
• CASCAROSIDE A (CONSTITUENT OF CASCARA SAGRADA)
• Q27106082
• CASCAROSIDE A (CONSTITUENT OF CASCARA SAGRADA) [DSC]
• 9(10H)-ANTHRACENONE, 10-.BETA.-D-GLUCOPYRANOSYL-8-(.BETA.-D-GLUCOPYRANOSYLOXY)-1-HYDROXY-3-(HYDROXYMETHYL)-, (10S)-
• 9(10H)-Anthracenone, 10-beta-D-glucopyranosyl-8-(beta-D-glucopyranosyloxy)-1-hydroxy-3-(hydroxymethyl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9136	91.36%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.7074	70.74%
OATP1B1 inhibitior	-	0.3783	37.83%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6332	63.32%
P-glycoprotein inhibitior	-	0.5506	55.06%
P-glycoprotein substrate	-	0.7850	78.50%
CYP3A4 substrate	+	0.6469	64.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8529	85.29%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.9315	93.15%
CYP2C19 inhibition	-	0.9047	90.47%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9180	91.80%
CYP2C8 inhibition	+	0.5864	58.64%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.9061	90.61%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.7536	75.36%
Human Ether-a-go-go-Related Gene inhibition	+	0.8205	82.05%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.6845	68.45%
Androgen receptor binding	+	0.5197	51.97%
Thyroid receptor binding	-	0.5594	55.94%
Glucocorticoid receptor binding	-	0.6368	63.68%
Aromatase binding	+	0.5261	52.61%
PPAR gamma	+	0.6608	66.08%
Honey bee toxicity	-	0.7495	74.95%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6150	61.50%
Fish aquatic toxicity	+	0.7958	79.58%

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	99.11%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.06%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.79%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.55%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.73%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	88.34%	94.73%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.20%	96.61%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.96%	94.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.72%	96.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.57%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.36%	95.89%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	85.74%	89.67%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.67%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.11%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.24%	99.17%
CHEMBL220	P22303	Acetylcholinesterase	80.67%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	80.30%	95.93%

Plants that contains it

• Baccharis sulcata
• Blechnum fluviatile
• Frangula purshiana
• Fridericia triplinervia
• Garcinia smeathmanii
• Maclura tinctoria
• Magnolia figo
• Ravenia spectabilis
• Stevia berlandieri

Cross-Links

• PubChem: 442727
• NPASS: NPC44220
• LOTUS: LTS0158995
• wikiData: Q27106082