Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2124)
Drug Name
PNA-D-glucopyranoside
Synonyms
P-nitrophenyl-alpha-D-glucopyranoside; A-D-glucopyranoside; p-Nitrophenyl-.beta.-galactoside; (2R,3S,4S,5S,6S)-2-(Hydroxymethyl)-6-(4-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triol; 2-(hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4,5-triol; 2-(hydroxymethyl)-6-(4-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triol; 4-Nitrophenyl-; 6-(hydroxymethyl)-2-(4-nitrophenoxy)-2H-3,4,5,6-tetrahydropyran-3,4,5-triol; p-NITROPHENYL-beta-D-GALACTOPYRANOSIDE; p-Nitrophenyl-alpha-D-glucopyranoside; p-Nitrophenyl-beta-D-glucopyranoside
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 301.25 Topological Polar Surface Area 145
Heavy Atom Count 21 Rotatable Bond Count 3
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
259380
CAS Number
3150-24-1
Formula
C12H15NO8
Canonical SMILES
C1=CC(=CC=C1[N+](=O)[O-])OC2C(C(C(C(O2)CO)O)O)O
InChI
1S/C12H15NO8/c14-5-8-9(15)10(16)11(17)12(21-8)20-7-3-1-6(2-4-7)13(18)19/h1-4,8-12,14-17H,5H2
InChIKey
IFBHRQDFSNCLOZ-UHFFFAOYSA-N
The Predicted Metabolic Roadmap of This Drug
The Full List of Predicted Drug Metabolites (PDM) of This Drug
PDM Name PDM ID PubChem ID Reaction PDM Level Biosystem
p-nitrophenol DM004005
980
Hydrolysis - Glycoside hydrolysis 1 Human
PNA-D-glucopyranoside M2 PDM007633
206
Hydrolysis - Glycoside hydrolysis 1 Human
PNA-D-glucopyranoside M3 PDM007634 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
PNA-D-glucopyranoside M4 PDM007635 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
PNA-D-glucopyranoside M5 PDM007636 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
PNA-D-glucopyranoside M6 PDM007637 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
PNA-D-glucopyranoside M7 PDM007638 N. A. Conjugation - Sulfation of primary alcohol 1 Human
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-galactosidase (bgaB) DME1139 Victivallis vadensis
A0A2U1B4D0_9BACT
3.2.1.23
[2]
Beta-galactosidase (bgaB) DME1140 Bifidobacterium adolescentis
BGAL_BIFAA
3.2.1.23
[3]
Glucosidase II beta (PRKCSH) DME0546 Homo sapiens
GLU2B_HUMAN
3.2.1.84
[4]
Neutral alpha-glucosidase AB (GANAB) DME0547 Homo sapiens
GANAB_HUMAN
3.2.1.207
[4]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Beta-galactosidase (bgaB) DME1140 Km = 60000 microM
BGAL_BIFAA
[3]
Neutral alpha-glucosidase AB (GANAB) DME0547 Km = 0.5 microM
GANAB_HUMAN
[4]
Glucosidase II beta (PRKCSH) DME0546 Km = 0.5 microM
GLU2B_HUMAN
[4]
References
1 PubChem 2019 update: improved access to chemical data. Nucleic Acids Res. 2019 Jan 8; 47(D1):D1102-1109. (PubChem CID: 92969)
2 Identification and characterization of a novel beta-galactosidase from Victivallis vadensis ATCC BAA-548, an anaerobic fecal bacterium. J Microbiol. 2012 Dec;50(6):1034-40.
3 Beta-galactosidase from Bifidobacterium adolescentis DSM20083 prefers beta(1,4)-galactosides over lactose. Appl Microbiol Biotechnol. 2004 Dec;66(3):276-84.
4 The heterodimeric structure of glucosidase II is required for its activity, solubility, and localization in vivo. Glycobiology. 2000 Aug;10(8):815-27.

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