3-O-[alpha-L-arabinopyranosyl(1->6)]-2-acetamido-2-deoxy-beta-D-glucopyranosyl echinocystic acid

Details

• Internal ID: 396c4e9c-9854-4aa7-b19c-245c91d9de15
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• SMILES (Canonical): CC(=O)NC1C(C(C(OC1OC2CCC3(C(C2(C)C)CCC4(C3CC=C5C4(CC(C6(C5CC(CC6)(C)C)C(=O)O)O)C)C)C)COC7C(C(C(CO7)O)O)O)O)O
• SMILES (Isomeric): CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]4([C@@H]3CC=C5[C@]4(C[C@H]([C@@]6([C@H]5CC(CC6)(C)C)C(=O)O)O)C)C)C)CO[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O)O)O
• InChI: InChI=1S/C43H69NO13/c1-21(45)44-30-33(50)32(49)25(20-55-36-34(51)31(48)24(46)19-54-36)56-35(30)57-29-12-13-40(6)26(39(29,4)5)11-14-41(7)27(40)10-9-22-23-17-38(2,3)15-16-43(23,37(52)53)28(47)18-42(22,41)8/h9,23-36,46-51H,10-20H2,1-8H3,(H,44,45)(H,52,53)/t23-,24-,25+,26-,27+,28+,29-,30+,31-,32+,33+,34+,35-,36-,40-,41+,42+,43+/m0/s1
• InChI Key: LRMCXUYYLPHGOS-CJXDOCFZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₆₉NO₁₃
• Molecular Weight: 808.00 g/mol
• Exact Mass: 807.47689126 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.64
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• 3-O-[alpha-L-arabinopyranosyl(1->6)]-2-acetamido-2-deoxy-beta-D-glucopyranosyl echinocystic acid
• CHEMBL1765595
• Q27136278
• (4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5666	56.66%
Caco-2	-	0.8828	88.28%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7448	74.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7386	73.86%
OATP1B3 inhibitior	+	0.8857	88.57%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8026	80.26%
BSEP inhibitior	+	0.8432	84.32%
P-glycoprotein inhibitior	+	0.7654	76.54%
P-glycoprotein substrate	+	0.5223	52.23%
CYP3A4 substrate	+	0.7329	73.29%
CYP2C9 substrate	-	0.8153	81.53%
CYP2D6 substrate	-	0.8736	87.36%
CYP3A4 inhibition	-	0.9011	90.11%
CYP2C9 inhibition	-	0.8972	89.72%
CYP2C19 inhibition	-	0.8991	89.91%
CYP2D6 inhibition	-	0.9528	95.28%
CYP1A2 inhibition	-	0.9026	90.26%
CYP2C8 inhibition	+	0.6917	69.17%
CYP inhibitory promiscuity	-	0.8828	88.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5112	51.12%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9119	91.19%
Skin irritation	-	0.7189	71.89%
Skin corrosion	-	0.9306	93.06%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6796	67.96%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	-	0.7554	75.54%
skin sensitisation	-	0.8563	85.63%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.8282	82.82%
Acute Oral Toxicity (c)	III	0.6857	68.57%
Estrogen receptor binding	+	0.7648	76.48%
Androgen receptor binding	+	0.7197	71.97%
Thyroid receptor binding	-	0.6114	61.14%
Glucocorticoid receptor binding	+	0.6932	69.32%
Aromatase binding	+	0.6846	68.46%
PPAR gamma	+	0.7596	75.96%
Honey bee toxicity	-	0.7286	72.86%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6350	63.50%
Fish aquatic toxicity	+	0.9507	95.07%

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	98.25%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.63%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.02%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.29%	97.09%
CHEMBL5028	O14672	ADAM10	88.40%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	86.13%	92.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.50%	94.33%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	85.25%	95.17%
CHEMBL5957	P21589	5'-nucleotidase	83.37%	97.78%
CHEMBL221	P23219	Cyclooxygenase-1	83.35%	90.17%
CHEMBL2581	P07339	Cathepsin D	82.63%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.33%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.25%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	81.64%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.25%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.87%	89.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.08%	95.50%

Plants that contains it

• Albizia inundata

Cross-Links

• PubChem: 14217288
• NPASS: NPC75318
• ChEMBL: CHEMBL1765595
• LOTUS: LTS0252459
• wikiData: Q27136278