NP-MRD: Showing NP-Card for Rosiglitazone (NP0334570)

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Record Information

Version

2.0

Created at

2024-09-10 18:57:01 UTC

Updated at

2024-09-10 18:57:01 UTC

NP-MRD ID

NP0334570

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rosiglitazone

Description

Rosiglitazone belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. Rosiglitazone was first documented in 2024 (PMID: 39307787). Based on a literature review a small amount of articles have been published on Rosiglitazone (PMID: 39304103) (PMID: 39301639) (PMID: 39299820) (PMID: 39289148).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05252321292D          

 25 27  0  0  0  0            999 V2000
    7.2598    0.4956    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6012    0.0785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0988    2.4586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4024   -0.4296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4577    0.4910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4793    1.0385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287    0.4910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1736    1.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4591    1.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7447    1.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9273    1.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1722    0.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7447    0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0302    1.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867    0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156    0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0301    0.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156    1.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0668    0.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7433    0.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4577    1.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7432   -0.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287   -1.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6857    0.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6857   -0.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 19  1  0  0  0  0
  2 15  1  0  0  0  0
  2 16  1  0  0  0  0
  3 11  2  0  0  0  0
  4 19  2  0  0  0  0
  5 12  1  0  0  0  0
  5 20  1  0  0  0  0
  5 21  1  0  0  0  0
  6 11  1  0  0  0  0
  6 19  1  0  0  0  0
  7 20  1  0  0  0  0
  7 24  2  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  2  0  0  0  0
 10 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 25  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334570

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1

> <INCHI_IDENTIFIER>
InChI=1/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23)

> <INCHI_KEY>
YASAKCUCGLMORW-UHFFFAOYNA-N

> <FORMULA>
C18H19N3O3S

> <MOLECULAR_WEIGHT>
357.43

> <EXACT_MASS>
357.114712658

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
37.80262614287465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione

> <JCHEM_LOGP>
2.8007741445548446

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.285022667826004

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.370447214503765

> <JCHEM_PKA_STRONGEST_BASIC>
6.402495732811076

> <JCHEM_POLAR_SURFACE_AREA>
71.53

> <JCHEM_REFRACTIVITY>
97.78990000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
rosiglitazone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  S   UNK     0      13.552   0.925   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       6.722   0.147   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      15.118   4.589   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      15.684  -0.802   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       2.721   0.917   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      15.828   1.939   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       0.054   0.917   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      13.391   2.457   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.057   3.227   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.723   2.457   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.798   3.083   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.055   0.147   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.723   0.917   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.390   3.227   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.389   0.917   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.056   0.917   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.390   0.147   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.056   2.457   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.058   0.605   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.387   0.147   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.721   2.457   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.387  -1.393   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.054  -2.163   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.280   0.147   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.280  -1.393   0.000  0.00  0.00           C+0
CONECT    1    8   19                                                       
CONECT    2   15   16                                                       
CONECT    3   11                                                            
CONECT    4   19                                                            
CONECT    5   12   20   21                                                  
CONECT    6   11   19                                                       
CONECT    7   20   24                                                       
CONECT    8    1    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9   13   14                                                  
CONECT   11    3    6    8                                                  
CONECT   12    5   15                                                       
CONECT   13   10   17                                                       
CONECT   14   10   18                                                       
CONECT   15    2   12                                                       
CONECT   16    2   17   18                                                  
CONECT   17   13   16                                                       
CONECT   18   14   16                                                       
CONECT   19    1    4    6                                                  
CONECT   20    5    7   22                                                  
CONECT   21    5                                                            
CONECT   22   20   23                                                       
CONECT   23   22   25                                                       
CONECT   24    7   25                                                       
CONECT   25   23   24                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₉N₃O₃S

Average Mass

357.4300 Da

Monoisotopic Mass

357.11471 Da

IUPAC Name

5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione

Traditional Name

rosiglitazone

CAS Registry Number

Not Available

SMILES

CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1

InChI Identifier

InChI=1/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23)

InChI Key

YASAKCUCGLMORW-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol ethers

Sub Class

Not Available

Direct Parent

Phenol ethers

Alternative Parents

Substituents

Phenoxy compound
Phenol ether
Dialkylarylamine
Alkyl aryl ether
Aminopyridine
Monocyclic benzene moiety
Pyridine
Imidolactam
Heteroaromatic compound
Meta-thiazoline
Carbonic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Azacycle
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aminopyridine (CHEBI:50122 )
thiazolidenediones (CHEBI:50122 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.8	ChemAxon
pKa (Strongest Acidic)	7.37	ChemAxon
pKa (Strongest Basic)	6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	97.79 m³·mol⁻¹	ChemAxon
Polarizability	37.8 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rosiglitazone

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li H, Xie JZ, Fan RX, Yang L, Zhou QY, Zhou NN: [Effect of Sijunzi Decoction on intestinal barrier of type 2 diabetic mice]. Zhongguo Zhong Yao Za Zhi. 2024 Aug;49(16):4510-4520. doi: 10.19540/j.cnki.cjcmm.20240429.401. [PubMed:39307787 ]
Wu Q, Jiao Y, Li J, Ma Y, Wang J, Luo M, Wang Y, Fan X, Liu C: Flavokawain B is an effective natural peroxisome proliferator-activated receptor gamma-selective agonist with a strong glucose-lowering effect. Biochem Pharmacol. 2024 Sep 18;229:116548. doi: 10.1016/j.bcp.2024.116548. [PubMed:39304103 ]
Sun Y, Lian Y, Mei X, Xia J, Feng L, Gao J, Xu H, Zhang X, Yang H, Hao X, Feng Y: Cinobufagin inhibits M2‑like tumor‑associated macrophage polarization to attenuate the invasion and migration of lung cancer cells. Int J Oncol. 2024 Nov;65(5):102. doi: 10.3892/ijo.2024.5690. Epub 2024 Sep 20. [PubMed:39301639 ]
Cuzzocrea S, Pisano B, Dugo L, Ianaro A, Maffia P, Patel NSA, Di Paola R, Ialenti A, Genovese T, Chatterjee PK, Di Rosa M, Caputi AP, Thiemermann C: Retraction notice to "Rosiglitazone, a ligand of the peroxisome proliferator-activated receptor-gamma, reduces acute inflammation" [Eur. J. Pharmacol 483 (1) (2024) 79-93]. Eur J Pharmacol. 2024 Sep 18:177006. doi: 10.1016/j.ejphar.2024.177006. [PubMed:39299820 ]
Li H, Liao X, Lan M, He J, Gao J, Fan Z, Huang J, Wu X, Chen J, Sun G: Arctigenin Modulates Adipogenic-Osteogenic Balance in the Bone Marrow Microenvironment of Ovariectomized Rats via the MEK1/PPARgamma/Wnt/beta-Catenin Pathway. Chem Biol Drug Des. 2024 Sep;104(3):e14625. doi: 10.1111/cbdd.14625. [PubMed:39289148 ]

Showing NP-Card for Rosiglitazone (NP0334570)

MOL for NP0334570 (Rosiglitazone)

3D MOL for NP0334570 (Rosiglitazone)

3D SDF for NP0334570 (Rosiglitazone)

3D-SDF for NP0334570 (Rosiglitazone)

PDB for NP0334570 (Rosiglitazone)

3D PDB for NP0334570 (Rosiglitazone)

SMILES for NP0334570 (Rosiglitazone)

INCHI for NP0334570 (Rosiglitazone)

Structure for NP0334570 (Rosiglitazone)

3D Structure for NP0334570 (Rosiglitazone)