[(6R,10S)-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
Basic information
- CAS
60857-08-1- Standard SMILES
CC(=O)OC12CC(C)C3(O)C4C=C(C)C(=O)[C@@]4(O)CC(CO)=C[C@H]3C1C2(C)C- InChIKey
BOJKFRKNLSCGHY-UMJKPZNRSA-N- Molecular formula
- C22H30O6
- Average molar mass
- 390.5 g/mol
- Monoisotopic mass
- 390.20423867
Overview
13-O-Acetylphorbol has been reported in Euphorbia fischeriana with data available.
Names & identifiers
- Preferred name
- [(6R,10S)-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
- IUPAC
- [(6R,10S)-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
- English name
- Prostratin, PKC activator
- Molecular formula
- C22H30O6
- Molecular weight
- 390.47
Names & synonyms
NSC623310[(6R,10S)-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] acetate13-O-AcetylphorbolSCHEMBL29565915NCI60_0069515H-Cyclopropa[3,2-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)-PROSTRATINSA 101ANSC 623310CCRIS 6292Prostatin >99%Stillingia Facto
Show more names
Prostratin[P0077]Prostratin, PKC activator12-DEOXYPHORBOL 13-ACETATE
Database identifiers
- CAS
60857-08-1
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 104 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 825
Physicochemical properties
- Melting point
- 216 · 216-219℃
- Boiling point
- 550.5 · 550.5±50.0 °C(Predicted)
- Density
- 1.31 · 1.31
- storage temp.
- -20 °C · -20°C
- solubility
- 30 mg/ml · Soluble in DMSO at 30mg/ml
- form
- white powder
- pka
- 11.4 · 11.40±0.70(Predicted)
- color
- Off-white
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
- InChIKey
- BOJKFRKNLSCGHY-HXGSDTCMSA-N
- SMILES
- C[C@@H]1C[C@]2(OC(C)=O)[C@H]([C@@H]3C=C(CO)C[C@@]4(O)[C@@H](C=C(C)C4=O)[C@@]13O)C2(C)C
- FDA UNII
- 94 U6DIQ6 · KO94U6DIQ6
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- WGK Germany
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 2916200090
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
DescriptionActivation of latent reservoirs of HIV-infected cells is a treatment strategy designed to reduce viral load and eliminate the perpetuation of retroviral infection. Prostratin is a non-tumor promoting phorbol ester that potently induces HIV-1 reactivation in latent reservoirs of infected Jurkat-LAT-GFP cells with an IC50 value of ~0.5 μM. Originally, prostratin was isolated from plant sources including P. prostrata, E. cornigera, and H. nutans. The effects of prostratin are mediated through activation of NF-κB via protein kinase C and by downregulation of HIV-1 receptor CD4 expression and its co-receptors CXCR4 and CCR5.
UsesActivation of latent reservoirs of HIV-infected cells is a treatment strategy designed to reduce viral load and eliminate the perpetuation of retroviral infection. Prostratin is a non-tumor promoting phorbol ester that potently induces HIV-1 reactivation in latent reservoirs of infected Jurkat-LAT-GFP cells . [Cayman Chemical]
Additional notes
DefinitionChEBI: A natural product found in Euphorbia fischeriana.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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