ingenol mebutate   Click here for help

GtoPdb Ligand ID: 7443

Synonyms: PEP-005 | Picato®
Approved drug PDB Ligand
ingenol mebutate is an approved drug (FDA & EMA (2012))
Comment: Ingenol mebutate is extracted from the plant Euphorbia peplus.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 104.06
Molecular weight 430.24
XLogP 3.21
No. Lipinski's rules broken 0
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Canonical SMILES CC=C(C(=O)OC1C(=CC23C1(O)C(O)C(=CC(C3=O)C1C(CC2C)C1(C)C)CO)C)C
Isomeric SMILES C/C=C(\C(=O)O[C@H]1C(=C[C@]23[C@]1(O)[C@H](O)C(=C[C@H](C3=O)[C@H]1[C@@H](C[C@H]2C)C1(C)C)CO)C)/C
InChI 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
1. Challacombe JM, Suhrbier A, Parsons PG, Jones B, Hampson P, Kavanagh D, Rainger GE, Morris M, Lord JM, Le TT et al.. (2006)
Neutrophils are a key component of the antitumor efficacy of topical chemotherapy with ingenol-3-angelate.
J Immunol, 177 (11): 8123-32. [PMID:17114487]
2. Kedei N, Lundberg DJ, Toth A, Welburn P, Garfield SH, Blumberg PM. (2004)
Characterization of the interaction of ingenol 3-angelate with protein kinase C.
Cancer Res, 64 (9): 3243-55. [PMID:15126366]
3. Lebwohl M, Swanson N, Anderson LL, Melgaard A, Xu Z, Berman B. (2012)
Ingenol mebutate gel for actinic keratosis.
N Engl J Med, 366 (11): 1010-9. [PMID:22417254]
4. Siller G, Gebauer K, Welburn P, Katsamas J, Ogbourne SM. (2009)
PEP005 (ingenol mebutate) gel, a novel agent for the treatment of actinic keratosis: results of a randomized, double-blind, vehicle-controlled, multicentre, phase IIa study.
Australas J Dermatol, 50 (1): 16-22. [PMID:19178487]