hederagenin 28-O-beta-D-glucopyranosyl ester

Details

• Internal ID: 94603aab-3923-4dc5-b95f-11bb5e4528f9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)CO)O)C)C)C2C1)C)C(=O)OC6C(C(C(C(O6)CO)O)O)O)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(CC5)(C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)(C)CO)O
• InChI: InChI=1S/C36H58O9/c1-31(2)13-15-36(30(43)45-29-28(42)27(41)26(40)22(18-37)44-29)16-14-34(5)20(21(36)17-31)7-8-24-32(3)11-10-25(39)33(4,19-38)23(32)9-12-35(24,34)6/h7,21-29,37-42H,8-19H2,1-6H3/t21-,22+,23+,24+,25-,26+,27-,28+,29-,32-,33-,34+,35+,36-/m0/s1
• InChI Key: WJMMBVSOQPALFO-DLQTVUGOSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₈O₉
• Molecular Weight: 634.80 g/mol
• Exact Mass: 634.40808342 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 3.46
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• 53931-25-2
• O-glucopyranosylepiederagenin, 28-
• CHEBI:67947
• CHEMBL1910843
• hederagenin 28-O-beta-D-glucopyranoside
• [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• 28-Glc-hederagenin
• hederagenin-28-O-B-glucoside
• O-glucopyranosylepiederagenin,28-
• hederagenin-28-O-beta-D-glucoside
• HY-N2190
• BDBM50235150
• AKOS037515154
• Hederagenin-28-beta-D-glucopyranoside
• MS-30883
• PD125694
• CS-0019498
• Q27136424
• 1-O-[3beta,23-dihydroxy-28-oxoolean-12-en-28-yl]-beta-D-glucopyranose
• 3beta,23-Dihydroxyoleana-12-ene-28-oic acid beta-D-glucopyranosyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8280	82.80%
Caco-2	-	0.8247	82.47%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8569	85.69%
OATP2B1 inhibitior	-	0.5773	57.73%
OATP1B1 inhibitior	+	0.8690	86.90%
OATP1B3 inhibitior	-	0.5000	50.00%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	-	0.6042	60.42%
P-glycoprotein inhibitior	+	0.6784	67.84%
P-glycoprotein substrate	-	0.8404	84.04%
CYP3A4 substrate	+	0.6998	69.98%
CYP2C9 substrate	-	0.8050	80.50%
CYP2D6 substrate	-	0.8436	84.36%
CYP3A4 inhibition	-	0.8968	89.68%
CYP2C9 inhibition	-	0.8549	85.49%
CYP2C19 inhibition	-	0.8686	86.86%
CYP2D6 inhibition	-	0.9356	93.56%
CYP1A2 inhibition	-	0.8265	82.65%
CYP2C8 inhibition	+	0.5440	54.40%
CYP inhibitory promiscuity	-	0.9540	95.40%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6921	69.21%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9184	91.84%
Skin irritation	-	0.6263	62.63%
Skin corrosion	-	0.9494	94.94%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7079	70.79%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8865	88.65%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.6591	65.91%
Acute Oral Toxicity (c)	III	0.8000	80.00%
Estrogen receptor binding	+	0.6478	64.78%
Androgen receptor binding	+	0.7264	72.64%
Thyroid receptor binding	-	0.5636	56.36%
Glucocorticoid receptor binding	+	0.6960	69.60%
Aromatase binding	+	0.6569	65.69%
PPAR gamma	+	0.6147	61.47%
Honey bee toxicity	-	0.7719	77.19%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6850	68.50%
Fish aquatic toxicity	+	0.9499	94.99%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4081	P13726	Coagulation factor III	6.46 nM; 0.28 nM	IC50; IC50	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.90%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.05%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.97%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.46%	96.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.94%	95.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.01%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.47%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.30%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.29%	97.36%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.06%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.91%	96.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.69%	96.77%
CHEMBL5255	O00206	Toll-like receptor 4	82.18%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.87%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.83%	94.33%

Plants that contains it

• Artemisia umbelliformis
• Eleutherococcus senticosus
• Juglans regia
• Kalopanax septemlobus
• Onopordum anatolicum
• Salix japonica
• Tiliacora triandra
• Viburnum ayavacense

Cross-Links

• PubChem: 21120798
• NPASS: NPC237503
• ChEMBL: CHEMBL1910843
• LOTUS: LTS0070501
• wikiData: Q27136424