HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
Huagongshe Open Program:[email protected]AI access: llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.7.8
  1. Home
  2. /Compound

2-(Hydroxymethyl)piperidine-3,4,5-triol

HCID 1374
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
19130-96-2
Standard SMILES
OCC1NCC(O)C(O)C1O
InChIKey
LXBIFEVIBLOUGU-UHFFFAOYSA-N
Molecular formula
C6H13NO4
Average molar mass
163.17 g/mol
Monoisotopic mass
163.0844579

Overview

1-deoxynojirimycin (unspec. stereochemistry) has been reported in Bacillus subtilis, Commelina, and other organisms with data available.

Names & identifiers

Preferred name
2-(Hydroxymethyl)piperidine-3,4,5-triol
IUPAC
2-(hydroxymethyl)piperidine-3,4,5-triol
English name
1-Deoxynojirimycin
Molecular formula
C6H13NO4
Molecular weight
163.17

Names & synonyms

2-(hydroxymethyl)piperidine-3,4,5-triolRefChem:1061869CHEBI:72490DTXCID40218026DTXSID5086487170956-02-42-hydroxymethyl-3,4,5-trihydroxypiperidine1oim1-Deoxy-NojirimycinS-GIDuvoglustat (hydrochloride)Antibiotic S-GI
Show more names
DNJSepetaprostDEOXYNOJIRIMYCINmoranolineDNMDuvoglustatEIEE31moranolinbay-h5595
1-DeoxygulonojirimycinLopac0_000444CHEMBL11510SCHEMBL2163281SCHEMBL77970511-Deoxygalactonojirimycin (DGJ)(2S,3R,4R,5S)-2-(Hydroxymethyl)-3,4,5-piperidinetriolLXBIFEVIBLOUGU-UHFFFAOYSA-N

Database identifiers

CAS
19130-96-2
PubChem CID
1374
ChEMBL
CHEMBL11510
Nikkaji
J1.676.303I

Properties

Computed structural properties

XLogP
-2.3
Topological polar surface area
93 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
5
Rotatable bonds
1
Heavy atoms
11
Formal charge
0
Complexity
132

Experimental & physicochemical properties

LogP-1.80
Melting Point206 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
195 · 195-196°C
Boiling point
361.1 · 361.1±42.0 °C(Predicted)
Density
1.456 · 1.456±0.06 g/cm3(Predicted)
vapor pressure
0 Pa · 0Pa at 25℃
RTECS
4350300 · TN4350300
storage temp.
-20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility
25 mg/ml) · Soluble in Water up to 25 mg/ml).
pka
13.77 · 13.77±0.70(Predicted)
form
Powder
color
White
Water Solubility
Soluble in water, dimethyl sulfoxide and methanol.

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
1
hs_code
29329990
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
24/25
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319-H335
REACH Registrations
Inactive
Precautionary statements
P271-P280

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm
Applications · 5 items

DescriptionDeoxynojirimycin (19130-96-2) inhibits α-glucosidase I and II.1,2 Inhibits human immunodeficiency virus envelope glycoprotein-mediated membrane fusion at the CXCR4 binding step.3 May be used to produce an affinity ligand for purifying glucosidase 1.4 Deoxynojirimycin was used to inhibit ER glucosidases I and II allowing for the discovery of a second mechanism for deglucosylation of N-linked oligosaccharides in PhaR1.7, a mouse lymphoma cell line.5

Occurrence1-Deoxynojirimycin (DNJ), a product of fermentation, exists in mulberry leaves and Commelina communis (dayflower) as well as is isolated from several bacterial strains such as Bacillus and Streptomyces species. Mulberry, a common deciduous plant, belongs to the genus Morus (Moraceae family). Numerous researchers have reported the DJN contents in different parts and various varieties of mulberry. Various mulberry varieties contain DNJ contents ranging between 0.68 and 2.78 mg/gm, while this fraction varies between 1.57 and 3.48 mg/gm in different Chinese mulberry leaves. Moreover, mulberry shoots contain the highest contents of DNJ, followed by young mulberry leaves. Mature leaves of mulberry contain the least content of DNJ. All the mulberry leave groups showed a 1–2-fold increase in DNJ contents compared to unfermented mulberry leaf powder extract (UFMLE). Additionally, fermented mulberry leaf powder extract exhibited higher α-glucosidase activity than UFMLE. DNJ-rich food products can be prepared by fermenting mulberry leaves using the above-mentioned fermenting agents[6].

UsesDeoxynojirimycin inhibits mammalian glucosidase 1. As well, it inhibits intestinal and lysosmal alpha-glucosidases, beta-glucosidase from sweet almonds, pancreatic alpha-amylase and amyloglucosidase.

UsesAn inhibitor of α-glucosidase I and II

UsesAn alpha-glucosidase inhibitor. Interferes with normal processing of N-linked glycoproteins.(+)-1-Deoxynojirimycin acts as an inhibitor of alfa-glucosidase I and II and maltase-glucoamylase. It also inhibits mammalian glucosidase, intestinal and lysosmal, beta-glucosidase from sweet almonds, pancreatic alfa-amylase and amyloglucosidase. Further, it serves as a enzyme enhancer for the treatment of Fabry and Pompe disease.

Related reactions

2 records
New reaction record
HRID 695495 reaction equation
HRID 695495As reactantTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
HRID 2051760 reaction equation
HRID 2051760As reactantuspto-grants-1980_01

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
BRN
3588039 · 3588039
Stability
2 years · Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 3 months.
Major Application
food and beveragespharmaceutical
Cosmetics Ingredients Functions
SKIN PROTECTINGSKIN CONDITIONING - MISCELLANEOUS
InChI
1S/C6H13NO4/c8-2-3-5(10)6(11)4(9)1-7-3/h3-11H,1-2H2/t3-,4+,5-,6-/m1/s1
InChIKey
LXBIFEVIBLOUGU-JGWLITMVSA-N
SMILES
OC[C@H]1NC[C@H](O)[C@@H](O)[C@@H]1O
LogP
-1.8 · -1.8
CAS DataBase Reference
19130 · 19130-96-2(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
56898 FLE · FZ56898FLE
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
271 · P271-P280
Safety Statements
24 · 24/25
WGK Germany
1 · 1
HS Code
29329990 · 29329990
Storage Class
11 · 11 - Combustible Solids
REACH Registrations
Inactive

Suppliers102 total

北京华美互利生物化工010-56205725 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
西安天朗源生物科技有限公司17749038280 17749038280 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
成都普睿法药物研发有限公司82633860 18982077548 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
成都添福瑞生物科技有限公司18030648795 18030648795 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
上海诗丹德标准技术服务有限公司021-021-57127007-6622-6622 17621252073 · [email protected]
天津万象恒远科技有限公司15722085254 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
成都普菲德生物技术有限公司028-82610909 13388174823 · [email protected]
嘉兴市艾森化工有限公司0573-85285100 18627885956 · [email protected]
深圳虹彩祥根生物科技有限公司+86-0755-89668383 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
长沙上禾生物科技有限公司0731-84213302 18975842720 · [email protected]
长沙禾普生物科技有限公司0731-88202122 13187036806;13187036806 · [email protected]
杰达维(上海)医药科技发展有限公司/J & W PharmLab021-64340559 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
成都锦然生物科技有限公司028-83311324 1278112614 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
深圳康特腾科技有限公司86-0755-86635001 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
成都瑞芬思德丹生物科技有限公司2355253622; 18981954830 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
上海昶衍化工科技有限公司021-20242659 18930833303 · [email protected]
苏州爱玛特生物科技有限公司0512-56316828 4008675858 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海卓因生物科技有限公司021-61317773 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
南京百得生物科技有限公司025-85553958 13951088118
江苏倍达医药科技有限公司0512-63009836 18994340901 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
湖北康恩化学有限公司180-64105258 18064105258 · [email protected]

Additional notes

DefinitionChEBI: An optically active form of 2-(hydroxymethyl)piperidine-3,4,5-triol having 2R,3R,4R,5S-configuration.