I(2)-D-Glucopyranosiduronic acid, (3I(2),21I(2))-28-(I(2)-D-glucopyranosyloxy)-21-hydroxy-28-oxoolean-12-en-3-yl O-I(2)-D-galactopyranosyl-(1a3)-O-[I(2)-D-glucopyranosyl-(1a2)]-

Details

• Internal ID: 8d31d619-7a05-468f-a5b4-bb2fe1e164cd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aR,10S,12aS,14aR,14bR)-10-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1(CC2C3=CCC4C5(CCC(C(C5CCC4(C3(CCC2(CC1O)C(=O)OC6C(C(C(C(O6)CO)O)O)O)C)C)(C)C)OC7C(C(C(C(O7)C(=O)O)O)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)CO)O)O)O)C)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC([C@H](C5)O)(C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O[C@H]8[C@@H]([C@H]([C@H]([C@H](O8)CO)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O
• InChI: InChI=1S/C54H86O25/c1-49(2)16-22-21-8-9-27-51(5)12-11-29(50(3,4)26(51)10-13-53(27,7)52(21,6)14-15-54(22,17-28(49)58)48(71)79-46-38(67)35(64)32(61)25(20-57)74-46)75-47-42(78-45-37(66)34(63)31(60)24(19-56)73-45)40(39(68)41(77-47)43(69)70)76-44-36(65)33(62)30(59)23(18-55)72-44/h8,22-42,44-47,55-68H,9-20H2,1-7H3,(H,69,70)/t22-,23+,24+,25+,26-,27+,28-,29-,30-,31+,32+,33-,34-,35-,36+,37+,38+,39-,40-,41-,42+,44-,45-,46-,47+,51-,52+,53+,54+/m0/s1
• InChI Key: KBENXYXTLIQDHO-GYEKFMRNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₆O₂₅
• Molecular Weight: 1135.20 g/mol
• Exact Mass: 1134.54581822 g/mol
• Topological Polar Surface Area (TPSA): 411.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -2.97
• H-Bond Acceptor: 24
• H-Bond Donor: 15
• Rotatable Bonds: 12

Synonyms

• DTXSID501099689
• 358732-35-1
• beta-D-Glucopyranosiduronic acid, (3beta,21beta)-28-(beta-D-glucopyranosyloxy)-21-hydroxy-28-oxoolean-12-en-3-yl O-beta-D-galactopyranosyl-(1-->3)-O-[beta-D-glucopyranosyl-(1-->2)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7601	76.01%
Caco-2	-	0.8816	88.16%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7433	74.33%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.8322	83.22%
P-glycoprotein inhibitior	+	0.7475	74.75%
P-glycoprotein substrate	-	0.7532	75.32%
CYP3A4 substrate	+	0.7260	72.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8776	87.76%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.8704	87.04%
CYP2C19 inhibition	-	0.9216	92.16%
CYP2D6 inhibition	-	0.9491	94.91%
CYP1A2 inhibition	-	0.9009	90.09%
CYP2C8 inhibition	+	0.7585	75.85%
CYP inhibitory promiscuity	-	0.9733	97.33%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6024	60.24%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9002	90.02%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6894	68.94%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.9322	93.22%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.8678	86.78%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.7748	77.48%
Androgen receptor binding	+	0.7465	74.65%
Thyroid receptor binding	-	0.4925	49.25%
Glucocorticoid receptor binding	+	0.7643	76.43%
Aromatase binding	+	0.6282	62.82%
PPAR gamma	+	0.8071	80.71%
Honey bee toxicity	-	0.6823	68.23%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5655	56.55%
Fish aquatic toxicity	+	0.9585	95.85%

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	96.94%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.88%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.57%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.95%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.14%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.18%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.37%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	85.45%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.84%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.47%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.21%	86.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.77%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.62%	94.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.30%	95.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.10%	97.36%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.39%	95.89%

Plants that contains it

• Calendula officinalis

Cross-Links

• PubChem: 101105728
• NPASS: NPC114318
• LOTUS: LTS0227652
• wikiData: Q105138151