Mizoribine - Moligand™, ≥98% , GMP synthase [glutamine-hydrolyzing] inhibitor, CAS No.50924-49-7, GMP synthase [glutamine-hydrolyzing] inhibitor

CAS: 50924-49-7 Cat. No.: M129842 Molecular Weight: 259.22 EC Number: 637-144-4

GRADE & PURITY Moligand™, ≥98%

Synonyms

4-Carbamoyl-1-beta-D-ribofuranosyl-imidazolium-5-olate | HE-69 | HMS3262E12 | Mizoribine (Bredinin) | N-Methyl-5-phenyl-5-ethylbarbituric acid | SCHEMBL7118 | BRN 4151713 | HY-17470 | J-521362 | 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofu

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Mizoribine is an imidazole nucleoside, selectively inhibits inosine monophosphate synthetase and guanosine monophosphate synthetase
An imidazole nucleoside immunosuppressant agent.

Specifications

Synonyms

4-Carbamoyl-1-beta-D-ribofuranosyl-imidazolium-5-olate | HE-69 | HMS3262E12 | Mizoribine (Bredinin) | N-Methyl-5-phenyl-5-ethylbarbituric acid | SCHEMBL7118 | BRN 4151713 | HY-17470 | J-521362 | 1-((2R, 3R, 4S, 5R)-3, 4-dihydroxy-5-(hydroxymethyl)tetrahydrofu

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Mizoribine is an imidazole nucleoside immunosuppressant agent that was first isolated from the mold Eupenicillium brefeldimium with antibiotic and cytotoxic effects. In a mouse model for IgA nephropathy, Mizoribine was documented to influence the prolifer

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

GMP synthase [glutamine-hydrolyzing] inhibitor

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504756582
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504756582
• Canonical Smiles: C1=NC(=C(N1C2C(C(C(O2)CO)O)O)O)C(=O)N
• IUPAC Name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxyimidazole-4-carboxamide
• InChIKey: HZQDCMWJEBCWBR-UUOKFMHZSA-N
• INCHI: 1S/C9H13N3O6/c10-7(16)4-8(17)12(2-11-4)9-6(15)5(14)3(1-13)18-9/h2-3,5-6,9,13-15,17H,1H2,(H2,10,16)/t3-,5-,6-,9-/m1/s1
• Isomeric SMILES: C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)N
• WGK Germany: 3
• RTECS: NI3980000
• Molecular Weight: 259.22
• Reaxy-Rn: 4151712
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4151712&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Imidazole ribonucleosides and ribonucleotides
      • Subclass 1-ribosyl-imidazolecarboxamides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Imidazole ribonucleosides and ribonucleotides
• Subclass: 1-ribosyl-imidazolecarboxamides
• Intermediate Tree Nodes: Not available
• Direct Parent: 1-ribosyl-imidazolecarboxamides
• Alternative Parents: Glycosylamines Pentoses 2-heteroaryl carboxamides Carbonylimidazoles N-substituted imidazoles Vinylogous amides Vinylogous acids Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Primary carboxylic acid amides Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives Primary alcohols Organic oxides Organonitrogen compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: 1-ribosyl-imidazolecarboxamide - Glycosyl compound - N-glycosyl compound - Pentose monosaccharide - 2-heteroaryl carboxamide - Imidazole-4-carbonyl group - N-substituted imidazole - Monosaccharide - Azole - Tetrahydrofuran - Vinylogous acid - Imidazole - Heteroaromatic compound - Vinylogous amide - Secondary alcohol - Carboxamide group - Primary carboxylic acid amide - Carboxylic acid derivative - Oxacycle - Azacycle - Organoheterocyclic compound - Alcohol - Hydrocarbon derivative - Organic nitrogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Primary alcohol - Organonitrogen compound - Organooxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

Discover Target: ESR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

Discover Target: NR3C1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PGR Tclin Progesterone receptor (8562 Activities)

Discover Target: PGR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

Discover Target: ADRB2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

Discover Target: CHRM2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

Discover Target: ADRB1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

Discover Target: HTR1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

Discover Target: ADRA2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AR Tclin Androgen Receptor (11781 Activities)

Discover Target: AR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

Discover Target: CHRM1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD2 Tclin Dopamine D2 receptor (23596 Activities)

Discover Target: DRD2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

Discover Target: GABRA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOA Tclin Monoamine oxidase A (11911 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

Discover Target: DRD1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

Discover Target: PTGS1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

Discover Target: SLC6A2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH2 Tclin Histamine H2 receptor (5428 Activities)

Discover Target: HRH2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

Discover Target: HTR2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

Discover Target: HTR2C

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)

Discover Target: AVPR2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

Discover Target: ADORA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

Discover Target: AGTR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A4 Tclin Serotonin transporter (12625 Activities)

Discover Target: SLC6A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

Discover Target: ADRA1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH1 Tclin Histamine H1 receptor (7573 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRM1 Tclin Mu opioid receptor (19785 Activities)

Discover Target: OPRM1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD3 Tclin Dopamine D3 receptor (14368 Activities)

Discover Target: DRD3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

Discover Target: PPARG

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

Discover Target: AVPR1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRD1 Tclin Delta opioid receptor (15096 Activities)

Discover Target: OPRD1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRK1 Tclin Kappa opioid receptor (16155 Activities)

Discover Target: OPRK1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

Discover Target: HTR3A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A3 Tclin Dopamine transporter (10535 Activities)

Discover Target: SLC6A3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTH1R Tclin Parathyroid hormone receptor (47172 Activities)

Discover Target: PTH1R

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GRIN1 Tclin Glutamate (NMDA) receptor subunit zeta 1 (122 Activities)

Discover Target: GRIN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

Discover Target: PDE3A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC29A1 Tclin Equilibrative nucleoside transporter 1 (1711 Activities)

Discover Target: SLC29A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)

Discover Target: ADRA2B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)

Discover Target: ADRA2C

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)

Discover Target: CHRM3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

Discover Target: HTR2B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EDNRA Tclin Endothelin receptor ET-A (5008 Activities)

Discover Target: EDNRA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA2A Tclin Adenosine A2a receptor (16305 Activities)

Discover Target: ADORA2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

Discover Target: ADORA3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BDKRB2 Tclin Bradykinin B2 receptor (3970 Activities)

Discover Target: BDKRB2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH3 Tclin Histamine H3 receptor (10389 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRNA4 Tclin Neuronal acetylcholine receptor protein alpha-4 subunit (1265 Activities)

Discover Target: CHRNA4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Npy1r Neuropeptide Y receptor type 1 (8 Activities)

Discover Target: Npy1r

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cckar Cholecystokinin A receptor (90 Activities)

Discover Target: Cckar

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Pde4d Phosphodiesterase 4D (4 Activities)

Discover Target: Pde4d

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Hdac6 Histone deacetylase 6 (222 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Vero (26788 Activities)

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GCN5 Histone acetyltransferase GCN5 (89 Activities)

Discover Target: GCN5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

pfk 6-phospho-1-fructokinase (7870 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SARS-CoV-2 (38078 Activities)

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SARS-CoV (424 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (52 mg/ml), DMSO (52 mg/ml), ethanol (<1 mg/ml), and methanol
• Sensitivity: Heat sensitive
• Specific Rotation[α]: -26° (C=2,H2O)
• Melt Point(°C): 198 °C(dec.)
• Molecular Weight: 259.220 g/mol
• XLogP3: -1.900
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 259.08 Da
• Monoisotopic Mass: 259.08 Da
• Topological Polar Surface Area: 151.000 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 329.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Zhanding Cui, Dengliang Li, Yinli Xie, Kai Wang, Ying Zhang, Guohua Li, Qian Zhang, Xiaoxueying Chen, Yue Teng, Shihui Zhao, Jiang Shao, Fan Xingmeng, Yanli Zhao, Dongju Du, Yanbing Guo, Hailong Huang, Hao Dong, Guixue Hu, Shuang Zhang, Yongkun Zhao.  (2020)  Nitazoxanide protects cats from feline calicivirus infection and acts synergistically with mizoribine in vitro.  ANTIVIRAL RESEARCH,      [PMID:32579897] [10.1016/j.antiviral.2020.104827]

2. Zhanding Cui, Jinlong Liu, Jinlong Wang, Jing Zhang, Yimei Cao, Kun Li, Zhixun Zhao, Hong Yuan, Xingwen Bai, Xueqing Ma, Pinghua Li, Yuanfang Fu, Huifang Bao, Dong Li, Qiang Zhang, Zaixin Liu, Kai Li, Tong Xu, Zengjun Lu.  (2025)  Formononetin and mizoribine inhibit Porcine Reproductive and Respiratory Syndrome Virus replication in vitro.  Frontiers in Nutrition,      [PMID:40196742] [10.3389/fnut.2024.1501685]