Molecule

2,5-bis(hydroxymethyl)-3,4-dihydroxypyrrolidine

AlkaPlorer ID: AK019532

Synonym: '2,5-Dihydroxymethyl-3,4-dihydroxypyrrolidine', 'DMDP', '2R,5R-Dihydroxymethyl-3R,4R-dihydroxy-pyrrolidine', '2,5-Dideoxy-2,5-imino-D-glucitol', '(+)-2,5-Dideoxy-2,5-imino-D-mannitol', '(+)-2,5-Dideoxy-2,5-imino-D-glucitol'

IUPAC Name: (2R,3R,4R,5R)-2,5-bis(hydroxymethyl)pyrrolidin-1-ium-3,4-diol

Structure

SMILES: OC[C@H]1[NH2+][C@H](CO)[C@@H](O)[C@@H]1O

InChI: InChI=1S/C6H13NO4/c8-1-3-5(10)6(11)4(2-9)7-3/h3-11H,1-2H2/p+1/t3-,4-,5-,6-/m1/s1

InChIKey: PFYHYHZGDNWFIF-KVTDHHQDSA-O

Reference

Antihyperglycemic Effects of N-Containing Sugars from Xanthocercis zambesiaca, Morus bombycis, Aglaonema treubii, and Castanospermum australe in Streptozotocin-Diabetic Mice

PubChem CID: 36687813

LOTUS: LTS0012425

SuperNatural Ⅲ: SN0284371-05

NPASS: NPC8087

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Castanospermum australe	Castanospermum	Fabaceae	Fabales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Lactuca floridana	Lactuca	Asteraceae	Asterales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Glycyrrhiza glabra	Glycyrrhiza	Fabaceae	Fabales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
None	Aglaonema	Araceae	Alismatales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Xanthocercis zambesiaca	Xanthocercis	Fabaceae	Fabales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Angylocalyx pynaertii	Angylocalyx	Fabaceae	Fabales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Hyacinthus orientalis	Hyacinthus	Hyacinthaceae	Asparagales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Glycyrrhiza uralensis	Glycyrrhiza	Fabaceae	Fabales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Scorzoneroides autumnalis	Scorzoneroides	Asteraceae	Asterales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Commelina communis	Commelina	Commelinaceae	Commelinales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Derris elliptica	Derris	Fabaceae	Fabales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Morus bombycis	Morus	Moraceae	Rosales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 164.181

TPSA？: 97.53000000000002

MolLogP？: -3.992999999999998

Number of H-Donors: 5

Number of H-Acceptors: 4

RingCount: 1

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Bos taurus	Alpha-glucosidase	IC50	170000.0	nM	10.1021/jm00048a006
Bos taurus	Alpha-L-fucosidase 1	Inhibition	50.0	%	10.1021/np9705726
Bos taurus	Beta-galactosidase	IC50	3300.0	nM	10.1021/jm00048a006
Bos taurus	Beta-galactosidase	IC50	nan	nM	10.1021/jm00048a006
Caldicellulosiruptor saccharolyticus	Beta-glucosidase A	IC50	34000.0	nM	10.1021/jm00048a006
Caldicellulosiruptor saccharolyticus	Beta-glucosidase A	IC50	nan	nM	10.1021/jm00048a006
Canavalia ensiformis	Alpha-mannosidase	Inhibition	50.0	%	10.1016/j.bmc.2016.10.015
Homo sapiens	Alpha-L-fucosidase I	IC50	nan	nM	10.1021/jm00048a006
Homo sapiens	Beta-glucosidase	IC50	150000.0	nM	10.1016/j.bmc.2008.01.032
Homo sapiens	Beta-glucosidase	Ki	200.0	nM	10.1039/C3MD00033H
Homo sapiens	Glycogen debranching enzyme	IC50	9800.0	nM	10.1016/j.bmc.2008.01.032
Homo sapiens	Lysosomal alpha-glucosidase	Delta Tm	0.0	degrees C	10.1016/j.bmc.2022.117129
Homo sapiens	Lysosomal alpha-glucosidase	Delta Tm	0.9	degrees C	10.1016/j.bmc.2022.117129
Homo sapiens	Lysosomal alpha-glucosidase	Delta Tm	6.9	degrees C	10.1016/j.bmc.2022.117129
Homo sapiens	Maltase-glucoamylase	IC50	50000.0	nM	10.1021/jm00013a012
Homo sapiens	MOLT-4	CC50	100000.0	ug.mL-1	10.1021/jm00013a012
Homo sapiens	MOLT-4	EC50	100000.0	ug.mL-1	10.1021/jm00013a012
Homo sapiens	MT4	CC50	100000.0	ug.mL-1	10.1021/jm00013a012
Homo sapiens	MT4	EC50	100000.0	ug.mL-1	10.1021/jm00013a012
Homo sapiens	Neutral alpha-glucosidase AB	IC50	nan	nM	10.1021/jm00048a006
Mus musculus	Mus musculus	Activity	nan	None	10.1021/np970277l
Mus musculus	Neutral alpha-glucosidase C	IC50	91000.0	nM	10.1021/jm00048a006
Rattus norvegicus	Acidic alpha-glucosidase	IC50	92000.0	nM	10.1021/jm00048a006
Rattus norvegicus	Acidic alpha-glucosidase	IC50	92000.0	nM	10.1021/np9705726
Rattus norvegicus	Acidic alpha-glucosidase	IC50	290000.0	nM	10.1021/np9705726
Rattus norvegicus	Acidic alpha-glucosidase	IC50	nan	nM	10.1021/jm00048a006
Rattus norvegicus	Alpha-mannosidase 2C1	IC50	260000.0	nM	10.1021/jm00013a012
Rattus norvegicus	Beta-galactosidase	IC50	3600.0	nM	10.1021/jm00048a006
Rattus norvegicus	Beta-galactosidase	IC50	nan	nM	10.1021/jm00048a006
Rattus norvegicus	Lactase-glycosylceramidase	IC50	3600.0	nM	10.1021/jm00013a012
Rattus norvegicus	Lactase-glycosylceramidase	IC50	3600.0	nM	10.1021/np9705726
Rattus norvegicus	Mannosidase 2 alpha 1	IC50	50000.0	nM	10.1021/jm00013a012
Rattus norvegicus	Mannosidase 2, alpha B1	IC50	50000.0	nM	10.1021/jm00013a012
Rattus norvegicus	Sucrase-isomaltase	IC50	44000.0	nM	10.1021/jm00013a012
Rattus norvegicus	Sucrase-isomaltase	IC50	64000.0	nM	10.1016/j.bmc.2008.01.032
Rattus norvegicus	Sucrase-isomaltase	IC50	90000.0	nM	10.1016/j.bmc.2008.01.032
Rattus norvegicus	Sucrase-isomaltase	IC50	91000.0	nM	10.1021/jm00013a012
Rattus norvegicus	Sucrase-isomaltase	IC50	91000.0	nM	10.1021/np9705726
Rattus norvegicus	Sucrase-isomaltase	IC50	290000.0	nM	10.1016/j.bmc.2008.01.032
Rattus norvegicus	Sucrase-isomaltase	Inhibition	50.0	%	10.1021/np9705726
Rattus norvegicus	Trehalase	IC50	200000.0	nM	10.1021/jm00048a006
Rattus norvegicus	Trehalase	IC50	360000.0	nM	10.1021/jm00013a012
Rattus norvegicus	Trehalase	IC50	360000.0	nM	10.1021/jm00048a006
Saccharomyces cerevisiae	Alpha-glucosidase MAL62	IC50	2000.0	nM	10.1021/np010360f
Sus scrofa	Uncharacterized protein	IC50	200000.0	nM	10.1021/np010360f
Sus scrofa	Uncharacterized protein	IC50	500000.0	nM	10.1021/np9705726
None	Unchecked	Activity	nan	None	10.1021/np50098a020
None	Unchecked	IC50	1100.0	nM	10.1016/j.bmc.2008.01.032
None	Unchecked	IC50	2000.0	nM	10.1021/np010360f
None	Unchecked	IC50	2500.0	nM	10.1021/np9705726
None	Unchecked	IC50	7800.0	nM	10.1016/j.bmc.2016.10.015
None	Unchecked	IC50	9700.0	nM	10.1016/j.bmc.2016.10.015
None	Unchecked	IC50	10000.0	nM	10.1016/j.bmc.2016.10.015
None	Unchecked	IC50	11000.0	nM	10.1021/np9705726
None	Unchecked	IC50	34000.0	nM	10.1021/jm00013a012
None	Unchecked	IC50	50000.0	nM	10.1021/jm00013a012
None	Unchecked	IC50	92000.0	nM	10.1021/jm00013a012
None	Unchecked	IC50	116000.0	nM	10.1016/j.bmc.2016.10.015
None	Unchecked	IC50	200000.0	nM	10.1021/np9705726
None	Unchecked	IC50	360000.0	nM	10.1021/np9705726
None	Unchecked	IC50	370000.0	nM	10.1016/j.bmc.2008.01.032
None	Unchecked	IC50	721000.0	nM	10.1016/j.bmc.2016.10.015
None	Unchecked	IC50	nan	nM	10.1021/jm00048a006
None	Unchecked	Inhibition	50.0	%	10.1016/j.bmc.2008.01.032
None	Unchecked	Inhibition	50.0	%	10.1016/j.bmc.2016.10.015
None	Unchecked	Ki	200.0	nM	10.1016/j.bmcl.2010.05.084
None	Unchecked	Ki	7000.0	nM	10.1021/np9705726
None	Unchecked	Ki	10000.0	nM	10.1021/np9705726