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Details

Stereochemistry ACHIRAL
Molecular Formula C30H28O8
Molecular Weight 516.5385
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ROTTLERIN

SMILES

CC(=O)C1=C(O)C(CC2=C(O)C(C(=O)\C=C\C3=CC=CC=C3)=C4OC(C)(C)C=CC4=C2O)=C(O)C(C)=C1O

InChI

InChIKey=DEZFNHCVIZBHBI-ZHACJKMWSA-N
InChI=1S/C30H28O8/c1-15-24(33)19(27(36)22(16(2)31)25(15)34)14-20-26(35)18-12-13-30(3,4)38-29(18)23(28(20)37)21(32)11-10-17-8-6-5-7-9-17/h5-13,33-37H,14H2,1-4H3/b11-10+

HIDE SMILES / InChI

Molecular Formula C30H28O8
Molecular Weight 516.5385
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Rottlerin is a principal phenolic compound of the Kamala plant Mallotus philippinensis. It was thought to be a selective inhibitor of PKCδ (protein kinase Cδ) (IC50=3-6 uM). It also inhibits PKCα, PKCβ, PKCγ, PKCε, PKCη, PKCζ and eEF2K (CaMK III) (IC50 = 5.3 uM). In HT1080 human fibrosarcoma cells, rottlerin induces apoptosis and autophagy via a PKCδ-independent pathway. When tested on HERG channels, rottlerin increased both step and tail HERG current by leftward shifting the voltage and dependence of HERG activation and slowing channel deactivation. Rottlerin is an inhibitor of Chk2, MAPKAPK-2, Pim-3, PKCλ, PKCθ, Plk, PRAK, SRPK1 and an activator of AMPK and HERG. There have been a number of studies published with evidence against the role of Rotterlin as a specific PKCδ inhibitor.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.34 µM [EC50]
3.0 µM [IC50]
1.9 µM [IC50]
5.4 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Xenograft tumor model in nude mice: mice were randomized into 4 treatment groups (control, DMSO, rottlerin 4 mg/kg, and rottlerin 2 mg/kg) with 5 mice per group. All the mice were injected intraperitoneally daily for 4 weeks. Tumors were smaller in the experimental groups than the control and DSMO groups, and tumors were smaller in the rottlerin 4 mg/kg group than the rottlerin 2 mg/kg group.
Route of Administration: Intraperitoneal
In Vitro Use Guide
To inhibit the activity of PKCdelta, either the natural compound rottlerin was transiently applied to the culture medium of high density cell cultures (HDC) in 2.5, 5 or 10 uM concentrations.
Substance Class Chemical
Record UNII
E29LP3ZMUH
Record Status Validated (UNII)
Record Version