3-[[(2R,3S,4S,5R,6S)-6-[(2R,3R,4S,5S,6R)-2-[[(8R,10R)-17-[(2S)-2-[(2S,3R,4S,5S,6R)-6-[[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-6-methylhept-5-en-2-yl]-12-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3-oxopropanoic acid

Details

• Internal ID: a4a8a9a4-cbcf-491c-8415-4552494d8ca7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: 3-[[(2R,3S,4S,5R,6S)-6-[(2R,3R,4S,5S,6R)-2-[[(8R,10R)-17-[(2S)-2-[(2S,3R,4S,5S,6R)-6-[[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-6-methylhept-5-en-2-yl]-12-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)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)COC8C(C(C(O8)CO)O)O)O)O)O)C
• SMILES (Isomeric): CC(=CCC[C@@](C)(C1CCC2(C1C(CC3[C@]2(CCC4[C@@]3(CCC(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[C@@H]8[C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)C
• InChI: InChI=1S/C56H92O25/c1-24(2)10-9-14-56(8,81-50-46(72)42(68)40(66)30(78-50)23-74-48-44(70)38(64)28(21-58)75-48)25-11-16-55(7)36(25)26(59)18-32-53(5)15-13-33(52(3,4)31(53)12-17-54(32,55)6)79-51-47(43(69)37(63)27(20-57)76-51)80-49-45(71)41(67)39(65)29(77-49)22-73-35(62)19-34(60)61/h10,25-33,36-51,57-59,63-72H,9,11-23H2,1-8H3,(H,60,61)/t25?,26?,27-,28-,29-,30-,31?,32?,33?,36?,37-,38-,39-,40-,41+,42+,43+,44+,45-,46-,47-,48+,49+,50+,51+,53+,54-,55?,56+/m1/s1
• InChI Key: UOFHLCPZXZURFL-TYRBHPFPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₆H₉₂O₂₅
• Molecular Weight: 1165.30 g/mol
• Exact Mass: 1164.59276842 g/mol
• Topological Polar Surface Area (TPSA): 400.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -1.54
• H-Bond Acceptor: 24
• H-Bond Donor: 14
• Rotatable Bonds: 19

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7917	79.17%
Caco-2	-	0.8849	88.49%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8458	84.58%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7900	79.00%
OATP1B3 inhibitior	+	0.8881	88.81%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.9299	92.99%
P-glycoprotein inhibitior	+	0.7460	74.60%
P-glycoprotein substrate	-	0.5861	58.61%
CYP3A4 substrate	+	0.7401	74.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8862	88.62%
CYP3A4 inhibition	-	0.8360	83.60%
CYP2C9 inhibition	-	0.8351	83.51%
CYP2C19 inhibition	-	0.9177	91.77%
CYP2D6 inhibition	-	0.9396	93.96%
CYP1A2 inhibition	-	0.9135	91.35%
CYP2C8 inhibition	+	0.7342	73.42%
CYP inhibitory promiscuity	-	0.9470	94.70%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5431	54.31%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.8989	89.89%
Skin irritation	-	0.5151	51.51%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.7570	75.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7840	78.40%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.6568	65.68%
skin sensitisation	-	0.9076	90.76%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6236	62.36%
Acute Oral Toxicity (c)	I	0.4634	46.34%
Estrogen receptor binding	+	0.7780	77.80%
Androgen receptor binding	+	0.7533	75.33%
Thyroid receptor binding	+	0.5916	59.16%
Glucocorticoid receptor binding	+	0.7905	79.05%
Aromatase binding	+	0.6730	67.30%
PPAR gamma	+	0.8207	82.07%
Honey bee toxicity	-	0.5837	58.37%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9655	96.55%

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	97.58%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.21%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.63%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.50%	97.25%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	91.56%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.18%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	90.52%	92.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.50%	97.09%
CHEMBL5028	O14672	ADAM10	89.09%	97.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.76%	97.36%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	87.75%	96.90%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.68%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.31%	94.33%
CHEMBL220	P22303	Acetylcholinesterase	87.30%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.63%	95.89%
CHEMBL2581	P07339	Cathepsin D	85.98%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.69%	99.17%
CHEMBL226	P30542	Adenosine A1 receptor	85.17%	95.93%
CHEMBL340	P08684	Cytochrome P450 3A4	83.62%	91.19%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.60%	95.83%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.47%	89.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	82.52%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.39%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.84%	91.24%
CHEMBL221	P23219	Cyclooxygenase-1	81.67%	90.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.32%	97.14%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.94%	97.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.68%	93.04%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.51%	85.14%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.48%	93.00%

Plants that contains it

• Panax ginseng

Cross-Links

• PubChem: 11968724
• NPASS: NPC120216