Prostratin

Category	Human immunodeficiency Virus (HIV)
CAS	60857-08-1
Description	Prostratin is an activator of protein kinase C (PKC) and also an activator of nuclear factor KB (NF-KB) mediated through activation of the IKKs (IKB kinases). It is an unusual non-tumorigenic phorbol ester and is found in the bark of the mamala tree of Samoa, Homalanthus nutans (Euphorbiaceae). It has potential to be useful in the treatment of HIV as it could flush viral reservoirs in latently infected CD4+ T-cells. It exhibits promising therapeutic potential against other diseases such as cancer and Alzheimer's disease. It inhibits growth and induces differentiation of AML cell lines. It inhibits tumorigenesis in KRAS mutant pancreatic cancer cells and reduces tumor growth in mouse pancreatic tumor models.

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Product Information

Synonyms	Prostratin;60857-08-1;12-Deoxyphorbol-13-acetate;12-Deoxyphorbol 13-acetate;CHEBI:69818;(1aR,1bS,4aR,7aS,7bR,8R,9aS)-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-9aH-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl acetate;Stillingia Factor S7;KO94U6DIQ6;[dihydroxy-(hydroxymethyl)-tetramethyl-oxo-[?]yl] acetate;NSC-623310;NSC 623310; SA 101A; Stillingia factor S7;SCHEMBL344837;CHEMBL170518;Prostratin, >=98% (HPLC);SA-101A;BOJKFRKNLSCGHY-HXGSDTCMSA-N;GLXC-02539;HMS3648K03;BDBM50368315;K-101A;13-O-ACETYL-12-DEOXYPHORBOL;AKOS027250797;CCG-208192;SMP2_000144;12-deoxyphorbol-13-acetate (prostratin);DA-66943;MS-26507;HY-107421;CS-0028449;C20197;SR-01000946228;Q3270742;SR-01000946228-1;BRD-K91145395-001-01-9;(1AR,1BS,4AR,7AS,7BR,8R,9AS)-9A-(ACETYLOXY)-1,1A,1B,4,4A,7A,7B,8,9,9A-DECAHYDRO-4A,7B-DIHYDROXY-3-(HYDROXYMETHYL)-1,1,6,8-TETRAMETHYL-5H-CYCLOPROPA(3,4)BENZ(1,2-E)AZULEN-5-ONE;4a,7b-Dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-9aH-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl acetate;5H-CYCLOPROPA(3,4)BENZ(1,2-E)AZULEN-5-ONE, 9A-(ACETYLOXY)-1,1A,1B,4,4A,7A,7B,8,9,9A-DECAHYDRO-4A,7B-DIHYDROXY-3-(HYDROXYMETHYL)-1,1,6,8-TETRAMETHYL-, (1AR,1BS,4AR,7AS,7BR,8R,9AS)-;5H-CYCLOPROPA(3,4)BENZ(1,2-E)AZULEN-5-ONE, 9A-(ACETYLOXY)-1,1A,1B,4,4A,7A,7B,8,9,9A-DECAHYDRO-4A,7B-DIHYDROXY-3-(HYDROXYMETHYL)-1,1,6,8-TETRAMETHYL-, (1AR-(1A.ALPHA.,1B.BETA.,4A.BETA.,7A.ALPHA.,7B.ALPHA.,8.ALPHA.,9A.ALPHA.))-;
IUPAC Name	[(1R,2S,6R,10S,11R,13S,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] acetate
Molecular Weight	364.5
Molecular Formula	C22H36O4
Canonical SMILES	CCCCC(C)(C)[C@@H](/C=C/[C@H]1C=CC(=O)[C@@H]1CCCCCCC(=O)O)O
InChI	InChI=1S/C22H30O6/c1-11-6-16-20(26,18(11)25)9-14(10-23)7-15-17-19(4,5)21(17,28-13(3)24)8-12(2)22(15,16)27/h6-7,12,15-17,23,26-27H,8-10H2,1-5H3/t12-,15+,16-,17-,20-,21+,22-/m1/s1
InChIKey	BOJKFRKNLSCGHY-HXGSDTCMSA-N
Boiling Point	550.5±50.0 °C \| Condition: Press: 760 Torr
Purity	95%
Density	1.31±0.1 g/cm3 \| Condition: Temp: 20 °C Press: 760 Torr
Solubility	DMSO: soluble10 mg/mL, clear
Appearance	Solid
Application	Prostratin has potential to be useful in the treatment of HIV. It exhibits promising therapeutic potential against other diseases such as cancer and Alzheimer's disease.
Storage	4°C, protect from light *In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)