Details of the Drug

General Information of Drug (ID: DM46FVD)

Drug Name
Ginsenoside Re
Synonyms
Chikusetsusaponin IVc; Ginsenoside B2; Ginsenoside Re; PWAOOJDMFUQOKB-WCZZMFLVSA-N; Panaxoside RE; SCHEMBL669738; TR-036967; ZINC242620164; ginsenoside-Re; (20S)-ginsenoside Re; 2-O-(6-Deoxy-alpha-L-mannopyranosyl)-(3beta,6alpha,12beta)-20-(beta-D-glucopyranosyloxy)-3,12-dihydroxydammar-24-en-6-yl-beta-D-glucopyranoside; 46F3R0BL3I; 51542-56-4; 52286-59-6; AKOS025310861; BDBM50378779; CHEBI:77148; CHEMBL510095; CS-3838; CTK8F0918; DB14815; EINECS 257-814-6; HY-N0044; MFCD00133369; NSC 308877; NSC-308877; UNII-46F3R0BL3I; s3811
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 4 Molecular Weight (mw) 947.2
Logarithm of the Partition Coefficient (xlogp) 1.6
Rotatable Bond Count (rotbonds) 12
Hydrogen Bond Donor Count (hbonddonor) 12
Hydrogen Bond Acceptor Count (hbondacc) 18
Chemical Identifiers
Formula
C48H82O18
IUPAC Name
(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-2-[[(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-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-6-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
Canonical SMILES
CC1C(C(C(C(O1)OC2C(C(C(OC2OC3CC4(C(CC(C5C4(CCC5C(C)(CCC=C(C)C)OC6C(C(C(C(O6)CO)O)O)O)C)O)C7(C3C(C(CC7)O)(C)C)C)C)CO)O)O)O)O)O
InChI
InChI=1S/C48H82O18/c1-21(2)11-10-14-48(9,66-42-38(60)35(57)32(54)26(19-49)63-42)23-12-16-46(7)30(23)24(51)17-28-45(6)15-13-29(52)44(4,5)40(45)25(18-47(28,46)8)62-43-39(36(58)33(55)27(20-50)64-43)65-41-37(59)34(56)31(53)22(3)61-41/h11,22-43,49-60H,10,12-20H2,1-9H3/t22-,23-,24+,25-,26+,27+,28+,29-,30-,31-,32+,33+,34+,35-,36-,37+,38+,39+,40-,41-,42-,43+,45+,46+,47+,48-/m0/s1
InChIKey
PWAOOJDMFUQOKB-WCZZMFLVSA-N
Cross-matching ID
PubChem CID
441921
ChEBI ID
CHEMBL77148
CAS Number
52286-59-6
UNII
46F3R0BL3I
DrugBank ID
DB14815
INTEDE ID
DR2495
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Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Alpha-L-rhamnosidase (lrA) DEBI82Z A0A1V8Q7P3_9BIF Substrate [1]
Beta-glucosidase (bglA) DE9N4OU C6WCL5_ACTMD Substrate [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
5'-AMP-activated protein kinase catalytic subunit alpha-1 (PRKAA1) OT7TNF0L AAPK1_HUMAN Post-Translational Modifications [3]
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Regulation of Drug Effects [4]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Regulation of Drug Effects [4]
Glucose-6-phosphatase catalytic subunit 1 (G6PC1) OTJ6FM9F G6PC1_HUMAN Gene/Protein Processing [3]
Immunity-related GTPase family M protein (IRGM) OTKD3O5Z IRGM_HUMAN Gene/Protein Processing [5]
Nuclear receptor subfamily 0 group B member 2 (NR0B2) OT7UVICX NR0B2_HUMAN Gene/Protein Processing [3]
Phosphoenolpyruvate carboxykinase, cytosolic (PCK1) OTNWEJ5Y PCKGC_HUMAN Gene/Protein Processing [3]
Potassium voltage-gated channel subfamily E member 1 (KCNE1) OTZNQUW9 KCNE1_HUMAN Gene/Protein Processing [6]
Protein c-Fos (FOS) OTJBUVWS FOS_HUMAN Gene/Protein Processing [7]
Serine/threonine-protein kinase STK11 (STK11) OT1YZSP3 STK11_HUMAN Post-Translational Modifications [3]
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References

1 Metabolism of rutin and poncirin by human intestinal microbiota and cloning of their metabolizing alpha-L-rhamnosidase from Bifidobacterium dentium. J Microbiol Biotechnol. 2015 Jan;25(1):18-25.
2 Characterization of the ginsenoside-transforming recombinant beta-glucosidase from Actinosynnema mirum and bioconversion of major ginsenosides into minor ginsenosides. Appl Microbiol Biotechnol. 2013 Jan;97(2):649-59.
3 Ginsenoside Re lowers blood glucose and lipid levels via activation of AMP-activated protein kinase in HepG2 cells and high-fat diet fed mice. Int J Mol Med. 2012 Jan;29(1):73-80. doi: 10.3892/ijmm.2011.805. Epub 2011 Oct 3.
4 Molecular mechanisms governing different pharmacokinetics of ginsenosides and potential for ginsenoside-perpetrated herb-drug interactions on OATP1B3. Br J Pharmacol. 2015 Feb;172(4):1059-73. doi: 10.1111/bph.12971. Epub 2015 Jan 20.
5 Ginsenoside Re enhances survival of human CD4+ T cells through regulation of autophagy. Int Immunopharmacol. 2010 May;10(5):626-31. doi: 10.1016/j.intimp.2010.03.002. Epub 2010 Mar 15.
6 Ginsenosides may enhance the functionality of human embryonic stem cell-derived cardiomyocytes in vitro. Reprod Sci. 2014 Oct;21(10):1312-8. doi: 10.1177/1933719114525269. Epub 2014 Mar 10.
7 Metabolism of ginsenoside Re by human intestinal microflora and its estrogenic effect. Biol Pharm Bull. 2005 Oct;28(10):1903-8. doi: 10.1248/bpb.28.1903.