13-Acetylphorbol

Identification

Name
13-Acetylphorbol
Accession Number
DB04376  (EXPT02656)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 406.4694
Monoisotopic: 406.199153314
Chemical Formula
C22H30O7
InChI Key
SDSVJYOOAPRSDA-RPCQODIISA-N
InChI
InChI=1S/C22H30O7/c1-10-6-15-20(27,17(10)25)8-13(9-23)7-14-16-19(4,5)22(16,29-12(3)24)18(26)11(2)21(14,15)28/h6-7,11,14-16,18,23,26-28H,8-9H2,1-5H3/t11-,14+,15-,16-,18-,20-,21-,22-/m1/s1
IUPAC Name
(1S,2S,6R,10S,11R,13S,14R,15R)-1,6,14-trihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl acetate
SMILES
[H][[email protected]]12[[email protected]]3([H])C=C(CO)C[[email protected]]4(O)C(=O)C(C)=C[[email protected]@]4([H])[[email protected]@]3(O)[[email protected]]([H])(C)[[email protected]@]([H])(O)[[email protected]@]1(OC(C)=O)C2(C)C

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UProtein kinase C delta typeNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
499953
PubChem Substance
46507195
ChemSpider
437370
ChEBI
45127
ChEMBL
CHEMBL1235429
HET
PRB
PDB Entries
1ptr

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.44 mg/mLALOGPS
logP0.63ALOGPS
logP-0.34ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)12.54ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity104.93 m3·mol-1ChemAxon
Polarizability43.05 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9046
Blood Brain Barrier+0.633
Caco-2 permeable-0.6839
P-glycoprotein substrateSubstrate0.7052
P-glycoprotein inhibitor INon-inhibitor0.7109
P-glycoprotein inhibitor IINon-inhibitor0.9293
Renal organic cation transporterNon-inhibitor0.906
CYP450 2C9 substrateNon-substrate0.8371
CYP450 2D6 substrateNon-substrate0.8803
CYP450 3A4 substrateSubstrate0.6857
CYP450 1A2 substrateNon-inhibitor0.8571
CYP450 2C9 inhibitorNon-inhibitor0.6084
CYP450 2D6 inhibitorNon-inhibitor0.9221
CYP450 2C19 inhibitorNon-inhibitor0.8804
CYP450 3A4 inhibitorNon-inhibitor0.8718
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8095
Ames testAMES toxic0.5277
CarcinogenicityNon-carcinogens0.933
BiodegradationNot ready biodegradable0.9148
Rat acute toxicity2.7826 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9958
hERG inhibition (predictor II)Non-inhibitor0.8528
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Diterpenoids
Direct Parent
Phorbol esters
Alternative Parents
Tertiary alcohols / Secondary alcohols / Ketones / Cyclic alcohols and derivatives / Carboxylic acid esters / Polyols / Monocarboxylic acids and derivatives / Primary alcohols / Organic oxides / Hydrocarbon derivatives
Substituents
Phorbol ester / Cyclic alcohol / Tertiary alcohol / Carboxylic acid ester / Ketone / Secondary alcohol / Polyol / Monocarboxylic acid or derivatives / Carboxylic acid derivative / Organic oxide
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
phorbol ester (CHEBI:45127) / Tigliane and ingenane diterpenoids (LMPR0104330003)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein serine/threonine kinase activity
Specific Function
Calcium-independent, phospholipid- and diacylglycerol (DAG)-dependent serine/threonine-protein kinase that plays contrasting roles in cell death and cell survival by functioning as a pro-apoptotic ...
Gene Name
PRKCD
Uniprot ID
Q05655
Uniprot Name
Protein kinase C delta type
Molecular Weight
77504.445 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:27