Structure Database (LMSD)

Common Name
Rhodojaponin III
Systematic Name
2β,3β-epoxy-grayanotpxane-5β,6β,10α,14β,16β-pentol
Synonyms
LM ID
LMPR0104180003
Formula
Exact Mass
Calculate m/z
368.219891
Status
Curated

Classification

Biological Context

Rhodojaponin III is a diterpenoid that has been found in R. molle and has insecticidal and antinociceptive activities.1,2 It reduces pupation and the number of Colorado potato beetle (L. decemlineata) larvae on, and damage to, potato plants when applied at concentrations of 75 and 150 ppm.1 It also induces mortality in adult confused flour beetles (T. confusum). Rhodojaponin III has antinociceptive effects in mouse models of chemical, inflammatory, and neuropathic pain.2 It reduces acetic acid-induced writhing in mice (ID50 = 0.0469 mg/kg) and increases the paw withdrawal threshold for mechanical stimuli in a mouse model of diabetic peripheral neuropathic pain when administered at doses of 0.04 and 0.08 mg/kg. Rhodojaponin III is toxic to mice with an LD50 value of 0.271 mg/kg.

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Rhododendron molle (#49168)
Magnoliopsida (#3398)
Grayanoid diterpene insect antifeedants and insecticides from Rhododendron molle,
Phytochemistry, 1991

String Representations

InChiKey (Click to copy)
VUMZHZYKXUYIHM-GLHQSWFFSA-N
InChi (Click to copy)
InChI=1S/C20H32O6/c1-16(2)15-12(26-15)13-18(4,24)10-6-5-9-14(22)19(10,8-17(9,3)23)7-11(21)20(13,16)25/h9-15,21-25H,5-8H2,1-4H3/t9-,10+,11-,12+,13+,14-,15+,17-,18-,19+,20-/m1/s1
SMILES (Click to copy)
[C@@H]12[C@@](O)(C)C[C@]3(C[C@@H](O)[C@]4(O)C(C)(C)[C@H]5O[C@H]5[C@@]4([H])[C@@](O)(C)[C@]3([H])CC1)[C@@H]2O

Other Databases

PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 26
Rings 5
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 345.50
Topological Polar Surface Area 113.68
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 6
logP 2.19
Molar Refractivity 95.61

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Created at
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Updated at
7th Jan 2025