Kartogenin - 10mM in DMSO , CAS No.4727-31-5

CAS: 4727-31-5 Cat. No.: K424115 Molecular Weight: 317.34 EC Number: 803-978-4

GRADE & PURITY 10mM in DMSO

Synonyms

2-([1,1'-Biphenyl]-4-ylcarbamoyl)benzoic acid | Maybridge3_004725 | SMR004703559 | 2-((4-Biphenylylamino)carbonyl)benzoic acid | Kartogenin | SCHEMBL1336628 | 2-((1,1'-Biphenyl)-4-ylcarbamoyl)benzoic acid | AC-31406 | Q27287128 | 2-((Biphenyl-4-yl)carbamo

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

2-([1, 1'-Biphenyl]-4-ylcarbamoyl)benzoic acid | Maybridge3_004725 | SMR004703559 | 2-((4-Biphenylylamino)carbonyl)benzoic acid | Kartogenin | SCHEMBL1336628 | 2-((1, 1'-Biphenyl)-4-ylcarbamoyl)benzoic acid | AC-31406 | Q27287128 | 2-((Biphenyl-4-yl)carbamo

Specifications & Purity

10mM in DMSO

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 -80°C

Shipped In

Dry ice packs + Cold packs

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

Action Type

ACTIVATOR

Names and Identifiers

• 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

• 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

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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]

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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]