3-AP - ≥98%(HPLC) , CAS No.143621-35-6

CAS: 143621-35-6 Cat. No.: A167286 Molecular Weight: 195.24 EC Number: 802-845-8

GRADE & PURITY ≥98%(HPLC)

Synonyms

[(E)-(3-amino-2-pyridyl)methyleneamino]thiourea | PAN-811;NSC# 663249;OCX191 | (e)-2-((3-aminopyridin-2-yl)methylene)hydrazine-1-carbothioamide | 5,6-dimethyl-2-aminobenzimidazole | SCHEMBL29370 | 3-AP | AS-16679 | NSC-663249 | Pan 811 | U4XIL4091C | DTXS

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

[(E)-(3-amino-2-pyridyl)methyleneamino]thiourea | PAN-811;NSC# 663249;OCX191 | (e)-2-((3-aminopyridin-2-yl)methylene)hydrazine-1-carbothioamide | 5, 6-dimethyl-2-aminobenzimidazole | SCHEMBL29370 | 3-AP | AS-16679 | NSC-663249 | Pan 811 | U4XIL4091C | DTXS

Specifications & Purity

≥98%(HPLC)

Biochemical and Physiological Mechanisms

Ribonucleotide reductase inhibitor. Also an iron chelator. Inhibits leukemia cell growth and acts in synergy withcisplatin. Activein vivo. 3-aminopyridine carboxaldehyde thiosemicarbazone (3-AP) has a IC50 value of 0.3μM. It exhibits anti-proliferative a

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Action Type

INHIBITOR

Purity

≥98%(HPLC)

Product Properties

• ALogP: -0.2

Names and Identifiers

• Pubchem Sid: 504764828
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504764828
• Canonical Smiles: C1=CC(=C(N=C1)C=NNC(=S)N)N
• IUPAC Name: [(E)-(3-aminopyridin-2-yl)methylideneamino]thiourea
• InChIKey: XMYKNCNAZKMVQN-NYYWCZLTSA-N
• INCHI: 1S/C7H9N5S/c8-5-2-1-3-10-6(5)4-11-12-7(9)13/h1-4H,8H2,(H3,9,12,13)/b11-4+
• Isomeric SMILES: C1=CC(=C(N=C1)/C=N/NC(=S)N)N
• WGK Germany: 3
• Molecular Weight: 195.24
• Reaxy-Rn: 5811939
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=5811939&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pyridines and derivatives
      • Subclass Aminopyridines and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pyridines and derivatives
• Subclass: Aminopyridines and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Aminopyridines and derivatives
• Alternative Parents: Thiosemicarbazones Heteroaromatic compounds Azacyclic compounds Primary amines Organosulfur compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Aminopyridine - Thiosemicarbazone - Heteroaromatic compound - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Primary amine - Organosulfur compound - Organonitrogen compound - Amine - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as aminopyridines and derivatives. These are organic heterocyclic compounds containing an amino group attached to a pyridine ring.
• 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)

RRM2 Tclin Ribonucleoside-diphosphate reductase subunit M2 (1 Activities)

Discover Target: RRM2

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CISD1 Tchem CDGSH iron-sulfur domain-containing protein 1 (1 Activities)

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RRM2 Tclin Ribonucleoside-diphosphate reductase M2 chain (14 Activities)

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A498 (42825 Activities)

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ACHN (49357 Activities)

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BGC-823 (3035 Activities)

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CAKI-1 (44928 Activities)

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CCRF-CEM (65223 Activities)

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COLO 205 (50209 Activities)

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DU-145 (51482 Activities)

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HL-60 (67320 Activities)

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HT-29 (80576 Activities)

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K562 (73714 Activities)

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KB 3-1 (1143 Activities)

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KM12 (47707 Activities)

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M14 (47487 Activities)

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MCF7 (126967 Activities)

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MES-SA (905 Activities)

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MES-SA/Dx5 (643 Activities)

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MOLT-4 (49676 Activities)

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MRC5 (9203 Activities)

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OVCAR-3 (48710 Activities)

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OVCAR-4 (44535 Activities)

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OVCAR-5 (45555 Activities)

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OVCAR-8 (47708 Activities)

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PC-3 (62116 Activities)

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RPMI-8226 (44974 Activities)

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RXF 393 (41971 Activities)

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SF-295 (48000 Activities)

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SGC-7901 (2773 Activities)

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SK-MEL-2 (46422 Activities)

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SK-MEL-28 (48833 Activities)

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SK-MEL-5 (47095 Activities)

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SK-N-MC (815 Activities)

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SK-OV-3 (52876 Activities)

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SN12C (47755 Activities)

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SNB-19 (46794 Activities)

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SW480 (6023 Activities)

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TK-10 (45540 Activities)

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U-251 (51189 Activities)

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UACC-257 (46019 Activities)

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UACC-62 (47335 Activities)

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UO-31 (46270 Activities)

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WI-38 (2654 Activities)

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786-0 (47912 Activities)

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A549 (127892 Activities)

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NCI/ADR-RES (33767 Activities)

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T47D (39041 Activities)

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ECa-109 cell line (1254 Activities)

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EKVX (44102 Activities)

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NCI-H322M (45589 Activities)

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HCC 2998 (41480 Activities)

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Canis familiaris (36305 Activities)

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Mus musculus (284745 Activities)

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L1210 (27553 Activities)

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M109 (194 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solvent:DMSO, Max Conc. mg/mL: 19.52, Max Conc. mM: 100
• Sensitivity: Heat Sensitive
• Melt Point(°C): 234 °C
• Molecular Weight: 195.250 g/mol
• XLogP3: -0.200
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 195.058 Da
• Monoisotopic Mass: 195.058 Da
• Topological Polar Surface Area: 121.000 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 205.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Xin-Xin Fu, Jian-Peng Li, Zhuo-Qian Li, Yan Liu, Chen-Xiao Feng, Hai-Yang Wang, Zhi-Peng Zhao, Qiao-Yun Liu, Zhong-Yi Liu, Zhi-Kun Peng.  (2022)  Selective conversion of 2-methylfuran to 3-acetyl-1-propanol in water over Pd@HZSM-5 catalyst with balanced metal-acid cooperation.  JOURNAL OF CATALYSIS,      [PMID:] [10.1016/j.jcat.2022.07.020]

2. Li Zishuai, Cheng Simin, Lin Qiaohong, Cao Wenbo, Yang Jing, Zhang Minmin, Shen Aijun, Zhang Wenpeng, Xia Yu, Ma Xiaoxiao, Ouyang Zheng.  (2021)  Single-cell lipidomics with high structural specificity by mass spectrometry.  Nature Communications,  12  (1): (1-10).  [PMID:34001877] [10.1038/s41467-021-23161-5]

3. Sen Liu, Hao Ling, Juan Lv, Hongxia Gao, Yanqing Na, Zhiwu Liang.  (2019)  New Insights and Assessment of Primary Alkanolamine/Sulfolane Biphasic Solutions for Post-combustion CO2 Capture: Absorption, Desorption, Phase Separation, and Technological Process.  INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH,      [PMID:] [10.1021/acs.iecr.9b03670]

4. Jing Luo, Jiaojiao Cong, Jie Liu, Yahan Gao, Xiaoya Liu.  (2015)  A facile approach for synthesizing molecularly imprinted graphene for ultrasensitive and selective electrochemical detecting 4-nitrophenol.  ANALYTICA CHIMICA ACTA,      [PMID:25732429] [10.1016/j.aca.2015.01.037]

5. Run Li, Xiandong Hao, Bo Wang, Ning Zhao, Zhiyong Xu, Wenbo Zhao.  (2024)  Highly efficient CO2 capture by a non-aqueous amine-based absorbent of 3 aminopropanol/polyethylene glycol 200: Experimental and computational simulation.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2024.126377]

6. Di Wu, Yi Wang, Wenjing Qi, Jianyang Xu, Kanglin Pei, Lingyan Ma, Lin Qi.  (2024)  Long-lasting chemiluminescence of lucigenin/p-aminophenol system for detection of p-aminophenol in environmental water.  DYES AND PIGMENTS,      [PMID:] [10.1016/j.dyepig.2024.111959]