Kartogenin - Moligand™, ≥98%(HPLC) , CAS No.4727-31-5

CAS: 4727-31-5 Cat. No.: K134657 Molecular Weight: 317.34 EC Number: 803-978-4

GRADE & PURITY Moligand™, ≥98%(HPLC)

Synonyms

KGN | 2-[[1,1'-Biphenyl]-4-ylcarbamoyl]benzoic Acid | 2-[(Biphenyl-4-yl)carbamoyl]benzoic acid | 4'-Phenyl-phthalanilic acid (8CI)

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Kartogenin is an activator of the smad4/smad5 pathway, and promotes the selective differentiation of multipotent mesenchymal stem cells into chondrocytes.
An inducing factor of mesenchymal stem cells into chondrocytes

Specifications

Synonyms

KGN | 2-[[1, 1'-Biphenyl]-4-ylcarbamoyl]benzoic Acid | 2-[(Biphenyl-4-yl)carbamoyl]benzoic acid | 4'-Phenyl-phthalanilic acid (8CI)

Specifications & Purity

Moligand™, ≥98%(HPLC)

Biochemical and Physiological Mechanisms

Kartogenin induces the selective differentiation of multipotent mesenchymal stem cells (MSCs) into chondrocytes. Kartogenin binds to filamin A, and disrupts the specific interaction between filamin A and CBFβ (core-binding factor β subunit). Apparently, k

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

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

Grade

Moligand™

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%(HPLC)

Names and Identifiers

• Pubchem Sid: 504762218
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504762218
• Canonical Smiles: C1=CC=C(C=C1)C2=CC=C(C=C2)NC(=O)C3=CC=CC=C3C(=O)O
• IUPAC Name: 2-[(4-phenylphenyl)carbamoyl]benzoic acid
• InChIKey: SLUINPGXGFUMLL-UHFFFAOYSA-N
• INCHI: 1S/C20H15NO3/c22-19(17-8-4-5-9-18(17)20(23)24)21-16-12-10-15(11-13-16)14-6-2-1-3-7-14/h1-13H,(H,21,22)(H,23,24)
• Isomeric SMILES: C1=CC=C(C=C1)C2=CC=C(C=C2)NC(=O)C3=CC=CC=C3C(=O)O
• WGK Germany: 3
• Molecular Weight: 317.34
• Reaxy-Rn: 14165011
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=14165011&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Anilides
        • Level5 Aromatic anilides
          • Level6 Benzanilides

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Anilides
• Intermediate Tree Nodes: Aromatic anilides
• Direct Parent: Benzanilides
• Alternative Parents: Biphenyls and derivatives Benzoic acids Benzamides Benzoyl derivatives Secondary carboxylic acid amides Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzanilide - Biphenyl - Benzamide - Benzoic acid or derivatives - Benzoic acid - Benzoyl - Secondary carboxylic acid amide - Carboxamide group - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.
• 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(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO: >15 mg/mL
• Sensitivity: Air sensitive，Heat sensitive
• Melt Point(°C): 278 °C
• Molecular Weight: 317.300 g/mol
• XLogP3: 4.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 317.105 Da
• Monoisotopic Mass: 317.105 Da
• Topological Polar Surface Area: 66.400 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 436.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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. Lang Bai, Qibin Han, Zeyu Han, Xiaoyu Zhang, Jingwen Zhao, Huitong Ruan, Junliang Wang, Feng Lin, Wenguo Cui, Xing Yang, Yuefeng Hao.  (2023)  Stem Cells Expansion Vector via Bioadhesive Porous Microspheres for Accelerating Articular Cartilage Regeneration.  Advanced Healthcare Materials,      [PMID:37947298] [10.1002/adhm.202302327]

2. Gang Wei, Yubin Yao, Hongbo Zhang, Wenguo Cui, Yong Lu.  (2023)  Cage-shaped silsesquioxane with multiactive sites for impeding aggregation of small insoluble organic molecule.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2023.144330]

3. Zhang Hanyuan, Fang Weijun, Zhao Tingting, Zhang Huabing, Gao Liang, Li Jingya, Wang Rujing, Xu Weiping.  (2022)  Real-Time MRI Monitoring of GelMA-Based Hydrogel-Loaded Kartogenin for In Situ Cartilage Regeneration.  Frontiers in Bioengineering and Biotechnology,      [PMID:35935481] [10.3389/fbioe.2022.940735]

4. Kaiwen Yang, Yifan Zhao, Chuyao Wang, Yeke Yu, Xiaoyu Zhang, Jie Liu, Chuan Lu, Luxiang Zou, Xiaohui Wei, Dongmei He.  (2024)  Dual-targeted lipid nanoparticles system for synergistic anti-inflammation and cartilage repair in the treatment of temporomandibular joint osteoarthritis.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.148769]

5. Xiaoyu Zhang, Lang Bai, Jing Zhou, Hua Gao, Qi Chen, Wenguo Cui, Xing Yang, Yuefeng Hao.  (2024)  Injectable microspheres adhering to the cartilage matrix promote rapid reconstruction of partial-thickness cartilage defects.  Acta Biomaterialia,      [PMID:38554890] [10.1016/j.actbio.2024.03.021]

6. Hui Yao, Ronghua Tan, Yuchen Zhang, Congcong Wang, Ying Wan, Qing Min.  (2024)  Multi-crosslinked hydrogels composed of hyaluronic acid, silk fibroin and chitosan nanoparticles with capacity of bioactive molecule delivery and degradation tolerance for cartilage tissue engineering.  EUROPEAN POLYMER JOURNAL,      [PMID:] [10.1016/j.eurpolymj.2024.113449]

7. Liang Yu, Meng Chang, Miaolan Zhang, Yuting Yang, Ken Chen, Tao Jiang, Dean Shi, Qunchao Zhang, Jou You.  (2024)  Nanoarchitectonics of 3D-networked bio-based binders for silicon anodes in lithium-ion batteries based on dynamic hydrogen bonding.  Sustainable Energy & Fuels,      [PMID:] [10.1039/D3SE01323E]

8. Yize Zhao, Xing Li, Chengkun Zhao, Yujiang Fan, Ganjun Feng, Yong Sun.  (2025)  Injectable Co-assembled microgels for programmed endogenous regeneration of nucleus pulposus.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.168613]

9. Junqi Dai, Li Ni, Chenyang Jin, Xin Tian, Yujie Shen, Yan Miao, Yong Xu, Fan He, Huilin Yang.  (2025)  Esterase-responsive kartogenin composite hydrogel microspheres boost nucleus pulposus regeneration in intervertebral disc degeneration.  Acta Biomaterialia,      [PMID:40180005] [10.1016/j.actbio.2025.04.001]

10. Guanrong Li, Renhao Ni, Zheyuan Shi, Haijiao Mao, Yang Luo, Xu Cao, Chi Zhang, Yuetian Liu, Zhanping Jin, Jun Chen, Jun Fu, Hua Zhang, Yingchun Zhu.  (2025)  Enhancing BMSC chondrogenesis with a dynamic viscoelastic hyaluronan hydrogel loaded with kartogenin for cartilage repair.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:40345284] [10.1016/j.ijbiomac.2025.144042]

11. Xin Li, Lei Wang, Jing Wang, Honghui Fan, Fei Pang, Wei He, Chao Jiang, Yu Jin, Yihang Shen, Yefeng Wang, Huilong Zeng, Zhangsheng Dai, Ping Zhou, Xujun Hu, Xuanyuan Lu.  (2025)  Enhanced osteoarthritis treatment using an injectable pH-responsive and cartilage-targeted liposome-anchored kartogenin-incorporated methacrylated gelatin hydrogel microspheres.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:40379185] [10.1016/j.ijbiomac.2025.144198]

12. Xin Gan, Jianwen Li, Song Li, Xiaohui Wang, Qianqiu Wang, Xin Chen, Yiwan Huang, Mingbo Nie, Hao Kang, Heshuang Dai.  (2025)  Integrating superlubricative nanomaterials with precision drug delivery for advanced osteoarthritis therapy.  Materials Today Bio,      [PMID:41104046] [10.1016/j.mtbio.2025.102359]

13. Qi Zhu, Luwen Zhu, Jialu Lang, Jiawen Zhu, Di Chen, Yuanyan Huang, Jucong Zhang, Xiaochuan Wu, Jiahao Hu, Jiansong Ji, Qining Yang, Yongzhong Du.  (2025)  Dopamine-functionalized bioinspired pre-chondrogenic hydrogel for cell-free cartilage regeneration.  JOURNAL OF CONTROLLED RELEASE,      [PMID:41237861] [10.1016/j.jconrel.2025.114407]

14. Kai Zhou, Xinlong He, Kun Shi, Danrong Hu, Chenli Yang, Mei Gao, Yiling Wang, Yue Liu, Qian Yang, Binyang Chu, Jinrong Peng, Zhiyong Qian.  (2025)  A dual responsive nanohydrogel system for sustained drug delivery and cartilage penetration in osteoarthritis therapy.  JOURNAL OF CONTROLLED RELEASE,      [PMID:41344484] [10.1016/j.jconrel.2025.114494]

15. Yiming Li, Wei Song, Lei Luo, Zhijie Ma, Haiyan Li, Yaohua He.  (2025)  Advanced Hydrogel/Electrospun Nanofiber Composite Scaffold With Sequential Bioactive Factor Release for Rotator Cuff Repair.  Advanced Healthcare Materials,      [PMID:41451438] [10.1002/adhm.202503563]

16. Xing Li, Yize Zhao, Peiyang Gu, Chengkun Zhao, Yujiang Fan, Xingdong Zhang, Chao Zhao, Peter X. Ma, Ganjun Feng, Yong Sun.  (2026)  Dynamic adaptive coassembled sericin protein orchestrating stem cell development for nucleus pulposus regeneration.  Science Advances,  12  (1):   [PMID:41477862] [10.1126/sciadv.adx2768]

17. Haohua Lai, Li Dong, Dongdong Jiang, Chen Shi, Wenbo Zhong, Chengxiang Sha, Junwei Yan, Xiao Wang, Jing Zhang, Ziyi Yu, Zhaowei Yin, Bin Liang.  (2026)  Multifunctional Bilayer Scaffolds Integrating Melt Electrowriting Fibers and Drug-Loaded Microspheres Promote Osteochondral Regeneration through PI3K–AKT–Mediated Chondro-Osteogenic Signaling.  Materials Today Bio,      [PMID:41624540] [10.1016/j.mtbio.2026.102807]