PHORBOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H28O6
Molecular Weight	364.4327
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12[C@]3([H])C=C(CO)C[C@]4(O)C(=O)C(C)=C[C@@]4([H])[C@@]3(O)[C@H](C)[C@@H](O)[C@@]1(O)C2(C)C

InChI

InChIKey=QGVLYPPODPLXMB-UBTYZVCOSA-N

InChI=1S/C20H28O6/c1-9-5-13-18(24,15(9)22)7-11(8-21)6-12-14-17(3,4)20(14,26)16(23)10(2)19(12,13)25/h5-6,10,12-14,16,21,23-26H,7-8H2,1-4H3/t10-,12+,13-,14-,16-,18-,19-,20-/m1/s1

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
Induced cytoskeletal changes in bovine pulmonary artery endothelial cells by resveratrol and the accompanying modified responses to arterial shear stress.	2001	11178103
Protein kinase C-alpha coordinately regulates cytosolic phospholipase A(2) activity and the expression of cyclooxygenase-2 through different mechanisms in mouse keratinocytes.	2001 Apr	11259631
Regulation of acute cortisol synthesis by cAMP-dependent protein kinase and protein kinase C in a teleost species, the rainbow trout (Oncorhynchus mykiss).	2001 Apr	11250648
TH1/TH2 and TC1/TC2 profiles in peripheral blood and bronchoalveolar lavage fluid cells in pulmonary sarcoidosis.	2001 Feb	11174202
Oxidative stress during hemodialysis: effect of heparin.	2001 Feb	11169003
Matrix metalloproteinases and TIMP-1 production by peripheral blood granulocytes from COPD patients and asthmatics.	2001 Feb	11167375
Induction of c-fos and c-jun messenger ribonucleic acid expression by prostaglandin F2alpha is mediated by a protein kinase C-dependent extracellular signal-regulated kinase mitogen-activated protein kinase pathway in bovine luteal cells.	2001 Feb	11159862
Hyperphosphorylation of Na-pump contributes to defective renal dopamine response in old rats.	2001 Feb	11158212
Cell cycle-dependent expression of cyclooxygenase-2 in human fibroblasts.	2001 Feb	11156939
Heterologous activation of protein kinase C stimulates phosphorylation of delta-opioid receptor at serine 344, resulting in beta-arrestin- and clathrin-mediated receptor internalization.	2001 Feb 16	11085981
Vascular endothelial growth factor KDR receptor signaling potentiates tumor necrosis factor-induced tissue factor expression in endothelial cells.	2001 Feb 16	11058594
Protein kinase C phosphorylates RGS2 and modulates its capacity for negative regulation of Galpha 11 signaling.	2001 Feb 23	11063746
Low level Pb(2+) exposure affects hippocampal protein kinase C gamma gene and protein expression in rats.	2001 Feb 9	11165444
Protein kinase C suppresses spontaneous, transient, outwards K+ currents through modulation of the Na/Ca exchanger in guinea-pig gastric myocytes.	2001 Jan	11214600
Involvement of peripheral polymorphonuclear leukocytes in oxidative stress and inflammation in type 2 diabetic patients.	2001 Jan	11194213
Mice lacking tartrate-resistant acid phosphatase (Acp 5) have disordered macrophage inflammatory responses and reduced clearance of the pathogen, Staphylococcus aureus.	2001 Jan	11168643
The immune dysregulatory compound mercuric chloride induces integrin-mediated T-lymphocyte adhesion.	2001 Jan	11168634
Reduced neuritic outgrowth and cell adhesion in neuronal cells transfected with human alpha-synuclein.	2001 Jan	11161475
Effects of PKC isozyme inhibitors on constrictor responses in the feline pulmonary vascular bed.	2001 Jan	11133494
Modulation of inducible nitric oxide synthase expression in rat intestinal cells by colon tumor promoters.	2001 Jan	11115551
Up-regulation of nucleolin mRNA and protein in peripheral blood mononuclear cells by extracellular-regulated kinase.	2001 Jan 12	11042220
Cognitive impairment in Coffin-Lowry syndrome correlates with reduced RSK2 activation.	2001 Jan 23	11160957
Effect of interferon-alpha on production of reactive oxygen species by human neutrophils.	2001 Jan-Feb	11180657
Molecular characterization of bovine prostaglandin G/H synthase-2 and regulation in uterine stromal cells.	2001 Mar	11207216
Signal transduction of flumazenil-induced preconditioning in myocytes.	2001 Mar	11179070
Amplification effect and mechanism of action of ET-1 in U-46619-induced vasoconstriction in pig skin.	2001 Mar	11171649
Modulation of GABA(A) receptors by benzodiazepines and barbiturates is autonomous of PKC activation.	2001 Mar	11166325
Induction of the respiratory burst in turtle peritoneal macrophages by Salmonella muenchen.	2001 Mar	11113285
Corticosterone-induced rapid phosphorylation of p38 and JNK mitogen-activated protein kinases in PC12 cells.	2001 Mar 16	11257496
Capsaicin suppresses phorbol ester-induced activation of NF-kappaB/Rel and AP-1 transcription factors in mouse epidermis.	2001 Mar 26	11179825
CD45 negatively regulates monocytic cell differentiation by inhibiting phorbol 12-myristate 13-acetate-dependent activation and tyrosine phosphorylation of protein kinase Cdelta.	2001 Mar 30	11124968

Patents

Name

Type

Language

PHORBOL

Common Name

English

NSC-154778

Code

English

PHORBOL [MI]

Common Name

English

PHORBOL [HSDB]

Common Name

English

(1AR,1BS,4AR,7AS,7BS,8R,9R,9AS)-1,1A,1B,4,4A,7A,7B,8,9,9A-DECAHYDRO-4A,7B,9,9A-TETRAHYDROXY-3-(HYDROXYMETHYL)-1,1,6,8-TETRAMETHYL-5H-CYCLOPROPA(3,4)BENZ(1,2-E)AZULEN-5-ONE

Common Name

English

Code System Code Type Description

WIKIPEDIA

PHORBOL