Malonyl ginsenoside Rd

Details

• Internal ID: 236e78cd-4b67-4e34-9c92-0819fc2fa214
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: 3-[[(2R,3S,4S,5R,6S)-6-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-4,4,8,10,14-pentamethyl-17-[(2S)-6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3-oxopropanoic acid
• SMILES (Canonical): CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)COC(=O)CC(=O)O)O)O)O)C)C)O)C)OC7C(C(C(C(O7)CO)O)O)O)C
• SMILES (Isomeric): CC(=CCC[C@@](C)([C@H]1CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)COC(=O)CC(=O)O)O)O)O)C)C)O)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C
• InChI: InChI=1S/C51H84O21/c1-23(2)10-9-14-51(8,72-45-42(65)38(61)35(58)26(20-52)67-45)24-11-16-50(7)34(24)25(54)18-30-48(5)15-13-31(47(3,4)29(48)12-17-49(30,50)6)70-46-43(40(63)36(59)27(21-53)68-46)71-44-41(64)39(62)37(60)28(69-44)22-66-33(57)19-32(55)56/h10,24-31,34-46,52-54,58-65H,9,11-22H2,1-8H3,(H,55,56)/t24-,25+,26+,27+,28+,29-,30+,31-,34-,35+,36+,37+,38-,39-,40-,41+,42+,43+,44-,45-,46-,48-,49+,50+,51-/m0/s1
• InChI Key: OSXWNRAKZUNVDR-QHEGXUBCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₁H₈₄O₂₁
• Molecular Weight: 1033.20 g/mol
• Exact Mass: 1032.55050968 g/mol
• Topological Polar Surface Area (TPSA): 342.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): -0.00
• H-Bond Acceptor: 20
• H-Bond Donor: 12
• Rotatable Bonds: 16

Synonyms

• CHEMBL4209166
• BDBM50450907

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7431	74.31%
Caco-2	-	0.8861	88.61%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8360	83.60%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7794	77.94%
OATP1B3 inhibitior	+	0.8203	82.03%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5776	57.76%
BSEP inhibitior	+	0.8801	88.01%
P-glycoprotein inhibitior	+	0.7483	74.83%
P-glycoprotein substrate	-	0.6474	64.74%
CYP3A4 substrate	+	0.7364	73.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8862	88.62%
CYP3A4 inhibition	-	0.8860	88.60%
CYP2C9 inhibition	-	0.8463	84.63%
CYP2C19 inhibition	-	0.9234	92.34%
CYP2D6 inhibition	-	0.9476	94.76%
CYP1A2 inhibition	-	0.9169	91.69%
CYP2C8 inhibition	+	0.7103	71.03%
CYP inhibitory promiscuity	-	0.9609	96.09%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6365	63.65%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9015	90.15%
Skin irritation	-	0.5364	53.64%
Skin corrosion	-	0.9432	94.32%
Ames mutagenesis	-	0.7470	74.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7787	77.87%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.5870	58.70%
skin sensitisation	-	0.9102	91.02%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.7135	71.35%
Acute Oral Toxicity (c)	III	0.5258	52.58%
Estrogen receptor binding	+	0.8172	81.72%
Androgen receptor binding	+	0.7510	75.10%
Thyroid receptor binding	+	0.5216	52.16%
Glucocorticoid receptor binding	+	0.7909	79.09%
Aromatase binding	+	0.6446	64.46%
PPAR gamma	+	0.8114	81.14%
Honey bee toxicity	-	0.5871	58.71%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9586	95.86%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3038455	P54646	AMPK alpha2/beta1/gamma1	16.8 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.40%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.06%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.29%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.79%	97.25%
CHEMBL220	P22303	Acetylcholinesterase	90.63%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.50%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	90.00%	92.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.97%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.86%	86.33%
CHEMBL5028	O14672	ADAM10	89.09%	97.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.76%	97.36%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.68%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.31%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.69%	95.89%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	86.32%	96.90%
CHEMBL2581	P07339	Cathepsin D	85.64%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.59%	99.17%
CHEMBL226	P30542	Adenosine A1 receptor	84.78%	95.93%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.59%	95.83%
CHEMBL340	P08684	Cytochrome P450 3A4	84.01%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.00%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.47%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.74%	93.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	82.42%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.39%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.32%	97.14%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.21%	91.24%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.51%	97.50%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.47%	96.38%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.45%	93.04%

Plants that contains it

• Panax ginseng
• Panax japonicus
• Panax notoginseng
• Panax quinquefolius

Cross-Links

• PubChem: 14162967
• NPASS: NPC241381
• LOTUS: LTS0166517
• wikiData: Q104391628