Higromicina B - ≥60%(HPLC), Polvo , CAS No.31282-04-9

CAS: 31282-04-9 Cat. No.: H113147 Peso molecular: 527.52 Número EC: 250-545-5

GRADE & PURITY ≥60%(HPLC), Powder

Synonyms

SMP1_000163 | BCBcMAP01_000235 | O-6-Amino-6-deoxi-L-glicero-D-galacto-heptopiranosilideno-(1-2-3)-O-beta-D-talopiranosil(1-5)-2-deoxi-N3-metil-D-estreptamina | Higromicina B, de Streptomyces hygroscopicus | GS-5543 | (2S,3R,3A'S,4S,4'S,5R,6R,6'R,7'S,7a'

Storage

Conservar a 2-8°C

Shipped In

Hielo húmedo

Descripción general

Antibiótico utilizado a menudo para la selección de células transfectadas con el gen de resistencia a la higromicina de E. coli.

Aplicación：

Un antibiótico aminoglucósido que mata a las bacterias mediante la inhibición de la síntesis de proteínasLa higromicina B se utiliza para la selección y el mantenimiento de células procariotas y eucariotas que contienen el gen de resistencia a la higromicina. Este gen se utiliza con frecuencia como marcador seleccionable en la investigación sobre plantas. Estabiliza el sitio aceptor del ácido ribonucleico de transferencia (ARNt)-ribosómico, inhibiendo así la translocación. Además, actúa como antibiótico aminoglucósido que inhibe la síntesis de proteínas.

Specifications

Sinónimos

SMP1_000163 | BCBcMAP01_000235 | O-6-Amino-6-deoxi-L-glicero-D-galacto-heptopiranosilideno-(1-2-3)-O-beta-D-talopiranosil(1-5)-2-deoxi-N3-metil-D-estreptamina | Higromicina B, de Streptomyces hygroscopicus | GS-5543 | (2S, 3R, 3A'S, 4S, 4'S, 5R, 6R, 6'R, 7'S, 7a'

Especificaciones y pureza

≥60%(HPLC), Polvo

Mecanismos bioquímicos y fisiológicos

Antibiótico aminoglucósido. Activo contra células procariotas y eucariotas. Inhibe la síntesis de proteínas al unirse a la subunidad 30S e inhibir el paso de translocación ribosómica de la elongación.

Condiciones de almacenamiento de almacenamiento

Conservar a 2-8°C

Enviado en

Hielo húmedo

Pureza

≥60%(HPLC)

Nombres e identificadores

• Sonrisas canónicas: CNC1CC(C(C(C1O)OC2C3C(C(C(O2)CO)O)OC4(O3)C(C(C(C(O4)C(CO)N)O)O)O)O)N
• IUPAC Name: (2S,3'R,3aS,4S,4'S,5'R,6R,6'R,7S,7aS)-4-[(1R,2S,3R,5S,6R)-3-amino-2,6-dihydroxy-5-(methylamino)cyclohexyl]oxy-6'-[(1R)-1-amino-2-hydroxyethyl]-6-(hydroxymethyl)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,2'-oxane]-3',4',5',7-tetrol
• InChIKey: GRRNUXAQVGOGFE-XKIAHZFYSA-N
• INCHI: 1S/C20H37N3O13/c1-23-7-2-5(21)9(26)15(10(7)27)33-19-17-16(11(28)8(4-25)32-19)35-20(36-17)18(31)13(30)12(29)14(34-20)6(22)3-24/h5-19,23-31H,2-4,21-22H2,1H3/t5-,6-,7+,8-,9+,10-,11+,12-,13+,14-,15-,16+,17+,18-,19+,20+/m1/s1
• Isómeros SMILES: CN[C@H]1C[C@H]([C@@H]([C@H]([C@@H]1O)O[C@H]2[C@@H]3[C@H]([C@H]([C@H](O2)CO)O)O[C@]4(O3)[C@@H]([C@H]([C@H]([C@H](O4)[C@@H](CO)N)O)O)O)O)N
• Número ONU: 3462
• Grupo de embalaje: I
• Peso molecular: 527.52
• Reaxy-Rn: 1335986
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1335986&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Clase Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Aminosaccharides
          • Level6 Aminoglycosides
            • Level7 Aminocyclitol glycosides
              • Level8 2-deoxystreptamine aminoglycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Clase: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Aminosaccharides - Aminoglycosides - Aminocyclitol glycosides
• Direct Parent: 2-deoxystreptamine aminoglycosides
• Alternative Parents: O-glycosyl compounds Disaccharides Dioxolopyrans Aminocyclitols and derivatives Ortho esters Cyclohexylamines Cyclohexanols Carboxylic acid orthoesters Oxanes 1,3-dioxolanes 1,2-aminoalcohols Polyols Oxacyclic compounds Dialkylamines Acetals Primary alcohols Organopnictogen compounds Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: 2-deoxystreptamine aminoglycoside - O-glycosyl compound - Glycosyl compound - Disaccharide - Dioxolopyran - Aminocyclitol or derivatives - Ortho ester - Cyclohexylamine - Cyclohexanol - Carboxylic acid orthoester - Oxane - Cyclitol or derivatives - Cyclic alcohol - Meta-dioxolane - Secondary alcohol - Orthocarboxylic acid derivative - 1,2-aminoalcohol - Oxacycle - Organoheterocyclic compound - Secondary amine - Polyol - Secondary aliphatic amine - Acetal - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Primary alcohol - Organonitrogen compound - Primary aliphatic amine - Amine - Alcohol - Aliphatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as 2-deoxystreptamine aminoglycosides. These are aminoglycosides containing the 2-deoxystreptamine (1,3-diaminocyclohexane-4,5,6-triol) core.
• 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

Objetivos asociados (no humanos)

Saccharomyces cerevisiae (19171 Activities)

Explore this target

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

Ustilago maydis (75 Activities)

Explore this target

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

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Miscible with water, methanol, buffer solution and ethanol. Immiscible with less polar solvents.
• Sensibilidad: Heat Sensitive
• Rotación específica [α]: 20° (C=1,H2O)
• Punto de fusión (°C): 160-180°C
• Peso molecular: 527.500 g/mol
• XLogP3: -6.600
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 6
• Exact Mass: 527.233 Da
• Monoisotopic Mass: 527.233 Da
• Topological Polar Surface Area: 272.000 Ų
• Heavy Atom Count: 36
• Formal Charge: 0
• Complexity: 756.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 16
• 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

Referencias

1. Hao Zhou, Jiangbo Huang, Fang Wang.  (2023)  Increased transcription of hsa_circ_0000644 upon RUNX family transcription factor 3 downregulation participates in the malignant development of bladder cancer.  CELLULAR SIGNALLING,      [PMID:36627006] [10.1016/j.cellsig.2023.110590]

2. Yong Sun, Tingting Guo, Dawei Guo, Li Guo, Li Chen, Yu Zhang, Liping Wang.  (2016)  Establishment and characterization of an MDCK cell line stably-transfected with chicken Abcb1 encoding P-glycoprotein.  RESEARCH IN VETERINARY SCIENCE,      [PMID:27234533] [10.1016/j.rvsc.2016.03.004]

3. Wang Zhengwei, Lin Jiani, Tan Guisen, Pan Tingzheng, Zhang Hongtian, Liu Jiangang.  (2025)  miR-1270 suppresses glioblastoma development by transcriptional inhibition of nuclear factor IX.  MOLECULAR BIOLOGY REPORTS,  52  (1): (1-10).  [PMID:40815328] [10.1007/s11033-025-10915-3]

4. Daoyan Tang, Minggui Wang, Dan Wang, Danni Yang, Yi Cai, Tao Luo, Jianqing He, Qinglan Wang.  (2025)  Ultra-high field strength electroporation enables efficient DNA transformation and genome editing in nontuberculous mycobacteria.  Microbiology Spectrum,  13  (10):   [PMID:40920009] [10.1128/spectrum.01944-25]

5. Mengjun Yun, Yu Xiong, Zhuobing Wang, Lianjie Xie, Hanwen Ye, Xiaofang Yuan, Weiyi He, Binqing Chen, Zhanjun Lu, Wei Chen.  (2025)  Insect Oral Secretion Protein and Its Related Core Peptide Induce the Host Plant’s Endogenous Abscisic Acid to Enhance Resistance against Insect.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:40270364] [10.1021/acs.jafc.4c12912]

6. Haobo Xing, Qingming Hou, Zhenhua Wang, Shanfei Zhang, Shangxia Song, Lulu Du, Chenghua Gao, Yunfei Li, Fubao Sun.  (2026)  Enhanced Monensin Biosynthesis in Streptomyces cinnamonensis with Multigene Integration and Overexpression of Newly Identified Genes.  BIOCHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.bej.2026.110118]