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Luteolin 7-O-glucuronide

CAT: 0804-HY-N1463-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N1463-01Size:1 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Luteolin 7-O-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 17.63, 7.99, 11.42, 12.85, 0.03 μM for MMP-1, MMP-3, MMP-8, MMP-9, MMP-13, respectively[1].
CAS Number
29741-10-4
Product Name Alternative
Luteolin 7-glucuronide
UNSPSC
12352005
Hazard Statement
H302, H315, H319
Target
MMP
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Field of Research
Inflammation/Immunology; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/Luteolin_7-O-glucuronide.html
Purity
99.98
Solubility
DMSO : 125 mg/mL (ultrasonic)
Smiles
O[C@H]([C@H]([C@@H]([C@@H](C(O)=O)O1)O)O)[C@@H]1OC2=CC(O)=C3C(C=C(C4=CC=C(O)C(O)=C4)OC3=C2)=O
Molecular Formula
C21H18O12
Molecular Weight
462.36
Precautions
H302, H315, H319
References & Citations
[1]Crascì L, et al. Correlating In Vitro Target-Oriented Screening and Docking: Inhibition of Matrix Metalloproteinases Activities by Flavonoids. Planta Med. 2017 Jul;83 (11) :901-911.|[2]Cho YC, et al. Anti-Inflammatory and Anti-Oxidative Effects of luteolin-7-O-glucuronide in LPS-Stimulated Murine Macrophages through TAK1 Inhibition and Nrf2 Activation. Int J Mol Sci. 2020 Mar 16;21 (6) :2007. |[3]Ryu D, et al. Luteolin-7-O-Glucuronide Improves Depression-like and Stress Coping Behaviors in Sleep Deprivation Stress Model by Activation of the BDNF Signaling. Nutrients. 2022 Aug 12;14 (16) :3314.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
MMP-1; MMP-13; MMP-3; MMP-8; MMP-9

Chemical Information

Luteolin 7-glucuronide

Luteolin 7-O-beta-D-glucosiduronic acid is a luteolin glucosiduronic acid consisting of luteolin having a beta-D-glucosiduronic acid residue attached at the 7-position. It has a role as a metabolite. It is a luteolin O-glucuronoside, a trihydroxyflavone, a glycosyloxyflavone and a monosaccharide derivative. It is a conjugate acid of a luteolin 7-O-beta-D-glucosiduronate and a luteolin 7-O-beta-D-glucosiduronate(2-).

CAS Number29741-10-4
PubChem CID5280601
IUPAC Name(2S,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
Molecular FormulaC21H18O12
Molecular Weight462.4
XLogP0.8
Topological Polar Surface Area203
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count12
Rotatable Bond Count4
Heavy Atom Count33
Formal Charge0
Complexity785
SMILES
C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)O)O)O
InChI
InChI=1S/C21H18O12/c22-9-2-1-7(3-10(9)23)13-6-12(25)15-11(24)4-8(5-14(15)32-13)31-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-24,26-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1
InChIKey
VSUOKLTVXQRUSG-ZFORQUDYSA-N
Chemical Structure
2D Structure
2D structure of Luteolin 7-glucuronide
CAS: 29741-10-4
CID: 5280601
Formula: C21H18O12
MW: 462.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight462.4
XLogP30.8
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count12
Rotatable Bond Count4
Exact Mass462.07982601
Monoisotopic Mass462.07982601
Topological Polar Surface Area203 Ų
Heavy Atom Count33
Formal Charge0
Complexity785
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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