Structure Database (LMSD)

Common Name
ingenol mebutate
Systematic Name
(1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[E][10]annulen-6-yl (2Z)-2-methylbut-2-enoate
Synonyms
  • 3-Angeloylingenol
  • 3-Ingenyl angelate
  • Ingenol 3-angelate
  • PEP-005
LM ID
LMFA07010911
Formula
C25H34O6
Exact Mass
Calculate m/z
430.23554
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Level 4 Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C20 isoprenoids (diterpenes) [PR0104]
Tigliane and ingenane diterpenoids [PR010433]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Euphorbia peplus (#38846)
Magnoliopsida (#3398)
No citation found

String Representations

InChiKey (Click to copy)
VDJHFHXMUKFKET-UXMMOKKRSA-N
InChi (Click to copy)
InChI=1S/C25H34O6/c1-7-12(2)22(29)31-21-13(3)10-24-14(4)8-17-18(23(17,5)6)16(20(24)28)9-15(11-26)19(27)25(21,24)30/h7,9-10,14,16-19,21,26-27,30H,8,11H2,1-6H3/b12-7-/t14-,16-,17-,18+,19-,21+,24+,25+/m1/s1
SMILES (Click to copy)
[C@@]123C=C(C)[C@H](OC(=O)/C(/C)=C\C)[C@@]1(O)[C@H](O)C(CO)=C[C@]([H])([C@]1([H])C(C)(C)[C@]1([H])C[C@H]2C)C3=O

Other Databases

Wikipedia
ingenol mebutate
CHEBI ID
66913
PubChem CID
46174141

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 4
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 431.16
Topological Polar Surface Area 104.06
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 3.48
Molar Refractivity 116.69

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Created at
-
Updated at
22nd Nov 2024