ChemSpider 2D Image | Ingenol mebutate | C25H34O6

Ingenol mebutate

  • Molecular FormulaC25H34O6
  • Average mass430.534 Da
  • Monoisotopic mass430.235535 Da
  • ChemSpider ID21171549
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 8 of 8 defined stereocentres


More details:






Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-Dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-4-yl (2Z)-2-methyl-2-butenoate [ACD/IUPAC Name]
(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-Dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-4-yl-(2Z)-2-methyl-2-butenoat [German] [ACD/IUPAC Name]
(2Z)-2-Méthyl-2-buténoate de (1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxyméthyl)-3,11,11,14-tétraméthyl-15-oxotétracyclo[7.5.1.01,5.010,12]pentadéca-2,7-dién-4-yle [French] [ACD/IUPAC Name]
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]cyclodece n-6-yl ester, (2Z)- [ACD/Index Name]
7686S50JAH
9006
(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-e
(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 (Z)-2-methylbut-2-enoate
(2Z)-(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 2-methyl-2-butenoic acid
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CCRIS 4693 [DBID]
I0659_SIGMA [DBID]
PEP-005 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      D06BX02 Wikidata Q426386
    • Bio Activity:

      Activator of protein kinase C (PKC). Exhibits antileukemic activity; induces nuclear translocation of PKC?, and induces apoptosis in acute myeloid leukemia (AML) cell lines and primary AML blast cells . Also displays antiproliferative effects and induces apoptosis in Colo205 cells. Tocris Bioscience 4054
      Activator of protein kinase C (PKC). Exhibits antileukemic activity; induces nuclear translocation of PKC?, and induces apoptosis in acute myeloid leukemia (AML) cell lines and primary AML blast cells. Also displays antiproliferative effects and induces apoptosis in Colo205 cells. Tocris Bioscience 4054
      Activator of protein kinase C (PKC). Exhibits antileukemic activity; induces nuclear translocation of PKC?, and induces apoptosis in acute myeloid leukemia (AML) cell lines and primary AML blast cells. Also displays antiproliferative effects and induces apoptosis in Colo205 cells. Reactivates latent HIV in cell culture. Also acts as a substrate for multidrug transporter. Tocris Bioscience 4054
      Activator of protein kinase C (PKC). Exhibits antileukemic activity; induces nuclear translocation of PKCdelta, and induces apoptosis in acute myeloid leukemia (AML) cell lines and primary AML blast cells. Also displays antiproliferative effects and induces apoptosis in Colo205 cells. Reactivates latent HIV in cell culture. Also acts as a substrate for multidrug transporter. Tocris Bioscience 4054
      Enzymes Tocris Bioscience 4054
      Ingenol Mebutate (PEP 005) is a substance found in the sap of the plant Euphorbia peplus and an inducer of cell death. MedChem Express
      Ingenol Mebutate (PEP 005) is a substance found in the sap of the plant Euphorbia peplus and an inducer of cell death.; Target: PKC; Ingenol mebutate gel applied topically for 2 to 3 days is effective for field treatment of actinic keratoses [1]. MedChem Express HY-B0719
      Ingenol Mebutate (PEP 005) is a substance found in the sap of the plant Euphorbia peplus and an inducer of cell death.;Target: PKC;Ingenol mebutate gel applied topically for 2 to 3 days is effective for field treatment of actinic keratoses [1]. In phase III trials, ingenol mebutate gel applied topically once daily at 0.015% for 3 days or 0.05% for 2 days, respectively, significantly reduced head and non-head actinic keratosis lesions. Adverse events were mostly mild or moderate [2]. MedChem Express HY-B0719
      Kinases Tocris Bioscience 4054
      PKC MedChem Express HY-B0719
      Protein Kinase C Tocris Bioscience 4054
      Protein kinase C activator Tocris Bioscience 4054
      TGF-beta/Smad MedChem Express HY-B0719
      TGF-beta/Smad; MedChem Express HY-B0719

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.3±0.1 g/cm3
Boiling Point: 576.9±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.6 mmHg at 25°C
Enthalpy of Vaporization: 99.2±6.0 kJ/mol
Flash Point: 191.4±23.6 °C
Index of Refraction: 1.594
Molar Refractivity: 115.2±0.4 cm3
#H bond acceptors: 6
#H bond donors: 3
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 1
ACD/LogP: 5.18
ACD/LogD (pH 5.5): 4.96
ACD/BCF (pH 5.5): 3447.19
ACD/KOC (pH 5.5): 11849.82
ACD/LogD (pH 7.4): 4.96
ACD/BCF (pH 7.4): 3446.93
ACD/KOC (pH 7.4): 11848.93
Polar Surface Area: 104 Å2
Polarizability: 45.6±0.5 10-24cm3
Surface Tension: 54.7±5.0 dyne/cm
Molar Volume: 339.5±5.0 cm3

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