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Harpagoside

CAT: 0013-GTR19159928-02Size: 500 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19159928-02Size:500 mg
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Description
Harpagoside is an anti-inflammatory small molecule natural product originally isolated from the Harpagophytum procumbens (Devil ’s Claw) root, but can be isolated from other plants such as Crophularia ningpoensis Hemsl (Figwort) . Treatment of HepG2 cells with Harpagoside demonstrated suppression of NF-κB nuclear translocation and degradation of IκB-α, blocking NF-κB activation. Multiple anti-inflammatory cellular effects were correlated with this blockade, as Harpagoside was observed to inhibit the expression of inflammation-mediating enzymes cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS), and to reduce lipopolysaccharide-induced mRNA levels. The suppression of NF-κB activation is indicated as the mechanism beneath the anti-inflammatory effects of Harpagoside.
CAS Number
19210-12-9
Product Name Alternative
SMR001233395 | Eharpagoside
Purity
>98% (HPLC)
Solubility
In Vitro: DMSO : 62.5 mg/mL (126.39 mM)
Smiles
CC1 (CC (C2 (C1C (OC=C2) OC3C (C (C (C (O3) CO) O) O) O) O) O) OC (=O) C=CC4=CC=CC=C4
Molecular Formula
C24H30O11
Molecular Weight
494.49
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
[ (1S,4aS,5R,7S,7aS) -4a,5-dihydroxy-7-methyl-1-[ (2S,3R,4S,5S,6R) -3,4,5-trihydroxy-6- (hydroxymethyl) oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] (E) -3-phenylprop-2-enoate

Chemical Information

Harpagoside

Harpagoside is a terpene glycoside.

CAS Number19210-12-9
PubChem CID5281542
IUPAC Name[(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] (E)-3-phenylprop-2-enoate
Molecular FormulaC24H30O11
Molecular Weight494.5
XLogP-0.6
Topological Polar Surface Area175
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count11
Rotatable Bond Count7
Heavy Atom Count35
Formal Charge0
Complexity811
SMILES
C[C@@]1(C[C@H]([C@]2([C@@H]1[C@@H](OC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)OC(=O)/C=C/C4=CC=CC=C4
InChI
InChI=1S/C24H30O11/c1-23(35-16(27)8-7-13-5-3-2-4-6-13)11-15(26)24(31)9-10-32-22(20(23)24)34-21-19(30)18(29)17(28)14(12-25)33-21/h2-10,14-15,17-22,25-26,28-31H,11-12H2,1H3/b8-7+/t14-,15-,17-,18+,19-,20-,21+,22+,23+,24-/m1/s1
InChIKey
KVRQGMOSZKPBNS-FMHLWDFHSA-N
Chemical Structure
2D Structure
2D structure of Harpagoside
CAS: 19210-12-9
CID: 5281542
Formula: C24H30O11
MW: 494.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight494.5
XLogP3-0.6
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count11
Rotatable Bond Count7
Exact Mass494.17881177
Monoisotopic Mass494.17881177
Topological Polar Surface Area175 Ų
Heavy Atom Count35
Formal Charge0
Complexity811
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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