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

Details

• Internal ID: b2c5c8bf-e426-431b-849e-f4e44fe36b61
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (4aS,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-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(CCC6(C5CC(CC6)(C)C)C(=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(CC[C@@]6([C@H]5CC(CC6)(C)C)C(=O)O)C)C)C)CO[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O)O)O
• InChI: InChI=1S/C43H69NO12/c1-22(45)44-30-33(49)32(48)26(21-54-36-34(50)31(47)25(46)20-53-36)55-35(30)56-29-12-13-40(6)27(39(29,4)5)11-14-42(8)28(40)10-9-23-24-19-38(2,3)15-17-43(24,37(51)52)18-16-41(23,42)7/h9,24-36,46-50H,10-21H2,1-8H3,(H,44,45)(H,51,52)/t24-,25-,26+,27-,28+,29-,30+,31-,32+,33+,34+,35-,36-,40-,41+,42+,43-/m0/s1
• InChI Key: MBMJMOODCJFAET-NLZUOQEQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₆₉NO₁₂
• Molecular Weight: 792.00 g/mol
• Exact Mass: 791.48197664 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.66
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• 3-O-[alpha-L-arabinopyranosyl-(1->6)]-2-acetamido-2-deoxy-beta-D-glucopyranosyl oleanolic acid
• CHEMBL1765593
• Q27136276
• (4aS,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-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
• 3beta-[6-O-(alpha-L-Arabinopyranosyl)-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyloxy]oleana-12-ene-28-oic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5666	56.66%
Caco-2	-	0.8801	88.01%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7448	74.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3239	32.39%
OATP1B3 inhibitior	+	0.8857	88.57%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8026	80.26%
BSEP inhibitior	+	0.8298	82.98%
P-glycoprotein inhibitior	+	0.7672	76.72%
P-glycoprotein substrate	-	0.5661	56.61%
CYP3A4 substrate	+	0.7284	72.84%
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	+	0.6849	68.49%
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	-	0.9131	91.31%
Skin irritation	-	0.7189	71.89%
Skin corrosion	-	0.9306	93.06%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6465	64.65%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	-	0.8346	83.46%
skin sensitisation	-	0.8563	85.63%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.7759	77.59%
Acute Oral Toxicity (c)	III	0.6857	68.57%
Estrogen receptor binding	+	0.7489	74.89%
Androgen receptor binding	+	0.7172	71.72%
Thyroid receptor binding	-	0.6317	63.17%
Glucocorticoid receptor binding	+	0.6949	69.49%
Aromatase binding	+	0.6836	68.36%
PPAR gamma	+	0.7535	75.35%
Honey bee toxicity	-	0.7322	73.22%
Biodegradation	-	0.7000	70.00%
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	98.62%	91.11%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	97.31%	95.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.24%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.91%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.35%	94.45%
CHEMBL2581	P07339	Cathepsin D	89.19%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	87.57%	92.50%
CHEMBL5028	O14672	ADAM10	85.99%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	85.18%	90.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.29%	94.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.01%	99.17%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.00%	96.90%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.57%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.06%	95.56%
CHEMBL5957	P21589	5'-nucleotidase	81.55%	97.78%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.75%	96.77%

Plants that contains it

• Albizia inundata

Cross-Links

• PubChem: 10795385
• NPASS: NPC73829
• ChEMBL: CHEMBL1765593