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Ingenol 3-Angelate

CAT: 0572-TRC-I655800-1MGSize: 1 mgDry Ice: NoHazardous: No
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CAT#:0572-TRC-I655800-1MGSize:1 mg
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CAS Number
75567-37-2
Synonyms
2-Butenoic acid, 2-methyl-, (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-1a,2,5,5a,6,9,10,10a-octahydro-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1H-2,8a-methanocyclopenta[a]cyclopropa[e]cyclodecen-6-yl ester, (2Z)-; 2-Butenoic acid, 2-methyl-, 1a,2,5,5a,6,9,10,10a-octahydro-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1H-2,8a-methanocyclopenta[a]cyclopropa[e]cyclodecen-6-yl ester, [1aR-[1aα,2β,5β,5aβ,6β(Z),8aα,9α,10aα]]-; 1H-2,8a-Methanocyclopenta[a]cyclopropa[e]cyclodecene, 2-butenoic acid deriv.; 3-Angeloylingenol; 3-Ingenyl angelate; Euphorbia factor An1; Euphorbia factor H1; Ingenol 3-angelate; Ingenol 3-mebutate; Ingenol mebutate; PEP 005; Picato
Hazard Statement
Not a hazardous substance according to GHS.
Purity
>95% (HPLC)
Smiles
C\C=C(\C)/C(=O)O[C@H]1C(=C[C@@]23[C@H](C)C[C@@H]4[C@H]([C@H](C=C(CO)[C@@H](O)[C@]12O)C3=O)C4(C)C)C
Molecular Formula
C25 H34 O6
Molecular Weight
430.53
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
Shipping Conditions
Room Temperature
Storage Conditions
+4°C

Chemical Information

Ingenol Mebutate

Ingenol mebutate is a tetracyclic diterpenoid ester obtained by formal condensation of the carboxy group of (2Z)-2-methylbut-2-enoic (angelic) acid with the 3-hydroxy group of ingenol. Used for the topical treatment of actinic keratosis. It has a role as an antineoplastic agent. It is a carboxylic ester, a cyclic terpene ketone and a tetracyclic diterpenoid. It is functionally related to an angelic acid and an ingenol.

CAS Number75567-37-2
PubChem CID6918670
IUPAC Name[(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxo-4-tetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dienyl] (Z)-2-methylbut-2-enoate
Molecular FormulaC25H34O6
Molecular Weight430.5
XLogP2
Topological Polar Surface Area104
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Heavy Atom Count31
Formal Charge0
Complexity926
SMILES
C/C=C(/C)\C(=O)O[C@H]1C(=C[C@@]23[C@@]1([C@@H](C(=C[C@H](C2=O)[C@H]4[C@H](C4(C)C)C[C@H]3C)CO)O)O)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
InChIKey
VDJHFHXMUKFKET-WDUFCVPESA-N
Chemical Structure
2D Structure
2D structure of Ingenol Mebutate
CAS: 75567-37-2
CID: 6918670
Formula: C25H34O6
MW: 430.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight430.5
XLogP32
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass430.23553880
Monoisotopic Mass430.23553880
Topological Polar Surface Area104 Ų
Heavy Atom Count31
Formal Charge0
Complexity926
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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