Dicoumarol - Moligand™, ≥98% , Inhibitor of vitamin K epoxide reductase complex subunit 1, CAS No.66-76-2, Inhibitor of vitamin K epoxide reductase complex subunit 1

CAS: 66-76-2 Cat. No.: D155113 Molecular Weight: 336.3 EC Number: 200-632-9

GRADE & PURITY Moligand™, ≥98%

Synonyms

2H-1-Benzopyran-2-one, 3,3'-methylenebis(4-hydroxy- | Di-4-hydroxy-3,3'-methylenedicoumarin | Temparin | 3,3'-Methylenebis[4-hydroxy-1,2-benzopyrone] | Kumoran | Acadyl | NSC41834 | NSC-41834 | 2H-1-Benzopyran-2-one, 3,3'-methylenebis(4-hydroxy)- | BB 021

Storage

Room temperature

Shipped In

Normal

Overview

Prototype of the 4-hydroxycoumarin class of anticoagulants, which act as vitamin K antagonists, preventing formation of prothrombin. There are many reports that dicumarol also inhibits NADPH:quinone oxidoreductase (NQO(1)). In one, it inhibited NQO(1) in a pancreatic cancer cell line, causing increased formation of superoxide and inhibiting cell growth.

Specifications

Synonyms

2H-1-Benzopyran-2-one, 3, 3'-methylenebis(4-hydroxy- | Di-4-hydroxy-3, 3'-methylenedicoumarin | Temparin | 3, 3'-Methylenebis[4-hydroxy-1, 2-benzopyrone] | Kumoran | Acadyl | NSC41834 | NSC-41834 | 2H-1-Benzopyran-2-one, 3, 3'-methylenebis(4-hydroxy)- | BB 021

Specifications & Purity

Moligand™, ≥98%

Storage

Room temperature

Shipped In

Normal

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Inhibitor of vitamin K epoxide reductase complex subunit 1

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488201684
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488201684
• Canonical Smiles: C1=CC=C2C(=C1)C(=C(C(=O)O2)CC3=C(C4=CC=CC=C4OC3=O)O)O
• IUPAC Name: 4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)methyl]chromen-2-one
• InChIKey: DOBMPNYZJYQDGZ-UHFFFAOYSA-N
• INCHI: 1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2
• Isomeric SMILES: C1=CC=C2C(=C1)C(=C(C(=O)O2)CC3=C(C4=CC=CC=C4OC3=O)O)O
• UN Number: 3077
• Packing Group: III
• Molecular Weight: 336.3
• Reaxy-Rn: 335444
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=335444&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Coumarins and derivatives
      • Subclass Hydroxycoumarins

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Coumarins and derivatives
• Subclass: Hydroxycoumarins
• Intermediate Tree Nodes: Not available
• Direct Parent: 4-hydroxycoumarins
• Alternative Parents: 1-benzopyrans Pyranones and derivatives Benzenoids Vinylogous acids Heteroaromatic compounds Lactones Oxacyclic compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 4-hydroxycoumarin - Benzopyran - 1-benzopyran - Pyranone - Pyran - Benzenoid - Heteroaromatic compound - Vinylogous acid - Lactone - Oxacycle - Organoheterocyclic compound - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.
• External Descriptors: coumarins

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)

GPR35 Tchem G-protein coupled receptor 35 (1 Activities)

Discover Target: GPR35

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CYP2C9 Tchem Cytochrome P450 2C9 (3 Activities)

Discover Target: CYP2C9

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

VKORC1 Tclin Vitamin K epoxide reductase complex subunit 1 (0 Activities)

Discover Target: VKORC1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

NQO1 Tchem NAD(P)H dehydrogenase [quinone] 1 (6 Activities)

Discover Target: NQO1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Chemical and Physical Properties

• Molecular Weight: 336.300 g/mol
• XLogP3: 2.600
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 336.063 Da
• Monoisotopic Mass: 336.063 Da
• Topological Polar Surface Area: 93.100 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 605.000
• 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. Yamei Ma, Zhen Zhang, Shengchao Gao, Yue Zhan, Zihao Wei, Ying Liu.  (2023)  The efficient Congo red decolorization coupled with electricity generation via G. sulfurreducens based on microbial fuel cells.  Journal of Environmental Chemical Engineering,      [PMID:] [10.1016/j.jece.2023.111296]

2. Xing Yan, Ming-Jun Zhu.  (2023)  Enhanced bioelectricity generation in thermophilic microbial fuel cell with lignocellulose as an electron donor by resazurin-mediated electron transfer.  BIORESOURCE TECHNOLOGY,      [PMID:37722540] [10.1016/j.biortech.2023.129764]

3. Yanhao Li, Chengfang Hu, Bo Hu, Jian Tian, Gang Zhao, Chuandong Cai, Yuange Li, Zhenyu Sun, Shuo Wang, Sa Pang, Rong Bao, Zaijing Tao, Huajiang Chen, Jinglei Wu, Shen Liu.  (2023)  Sustained Release of Dicumarol via Novel Grafted Polymer in Electrospun Nanofiber Membrane for Treatment of Peritendinous Adhesion.  Advanced Healthcare Materials,  12  (15): (2203078).  [PMID:36864645] [10.1002/adhm.202203078]

4. Yi-Xuan Fu, Wu-Yingzheng Guo, Nan Wang, Yi-Jie Dai, Zi-Ye Zhang, Xin-Lin Sun, Wen-Chao Yang, Guang-Fu Yang.  (2022)  Diagnosis of Bacterial Plant Diseases via a Nitroreductase-Activated Fluorescent Sensor.  ANALYTICAL CHEMISTRY,      [PMID:36469707] [10.1021/acs.analchem.2c04614]

5. Xianghan Zhang, Zhiqing Gao, Yuqiong Xia, Qunyan Dong, Yutian Cao, Qian Jia, Fang Sun, Zheng Li, Chu Tang, Jie Yu.  (2022)  Insight into the spatial interaction of D-π-A bridge derived cyanines and nitroreductase for fluorescent cancer hypoxia detection.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:35189489] [10.1016/j.saa.2022.121031]

6. Bingfeng Liang, Dangxia Zhou.  (2021)  ROS-Activated homodimeric podophyllotoxin nanomedicine with self-accelerating drug release for efficient cancer eradication.  DRUG DELIVERY,      [PMID:34747277] [10.1080/10717544.2021.1995076]

7. Wenjie Ge, Xian Zhang, Qing Wang, Jianjie Mao, Pengfei Jia, Jianping Cai.  (2024)  Dicoumarol attenuates NLRP3 inflammasome activation to inhibit inflammation and fibrosis in knee osteoarthritis.  Molecular Medicine Reports,  29  (6): (1-11).  [PMID:38639180] [10.3892/mmr.2024.13224]

8. Linna Chang, Yan Qin, Zhou Shen, Di Wu, Xiaoping Yin, Leyong Zeng.  (2025)  A photothermal-promoted cascade nanozyme to enhance hydroxyl radical/nitric oxide generation for reactive oxygen species-modulated catalytic/gas therapy.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:40784152] [10.1016/j.jcis.2025.138653]

9. Xiaomin Tan, Yanjuan Huang, Yong Luo, Zijun Lin, Xianmin Shi, Zishan Zeng, Jie Chen, Chunshun Zhao.  (2025)  A molecular-size sieve-inspired metal-organic cage-based hydrogen sulfide probe for colon cancer diagnosis.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.164859]

10. Yanjing Yun, Weitao Yang, Yan Xu, Kexin Bian, Dinghua Liu, Hui Wang, Chang Liu, Shuang Wu, Bingbo Zhang.  (2025)  Ferric Ion-Release Nanoprobes for Hypoxia Magnetic Resonance Imaging and Radiotherapy Stratification in Solid Tumors.  ACS Nano,      [PMID:41292311] [10.1021/acsnano.5c15463]