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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 of PHORBOL

SMILES

C[C@@H]1[C@@H](O)[C@]2(O)[C@H]([C@@H]3C=C(CO)C[C@@]4(O)[C@@H](C=C(C)C4=O)[C@@]13O)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
Molecular Formula C20H28O6
Molecular Weight 364.4327
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
149124
PubMed

PubMed

TitleDatePubMed
The epithelium-specific ETS protein EHF/ESE-3 is a context-dependent transcriptional repressor downstream of MAPK signaling cascades.
2001-06-08
Protein kinase C-alpha coordinately regulates cytosolic phospholipase A(2) activity and the expression of cyclooxygenase-2 through different mechanisms in mouse keratinocytes.
2001-04
Regulation of acute cortisol synthesis by cAMP-dependent protein kinase and protein kinase C in a teleost species, the rainbow trout (Oncorhynchus mykiss).
2001-04
PKD in intestinal epithelial cells: rapid activation by phorbol esters, LPA, and angiotensin through PKC.
2001-04
Insulin increases the turnover rate of Na+-K+-ATPase in human fibroblasts.
2001-04
K+ channels and the microglial respiratory burst.
2001-04
IL-1beta enhances beta2-adrenergic receptor expression in human airway epithelial cells by activating PKC.
2001-04
Capsaicin suppresses phorbol ester-induced activation of NF-kappaB/Rel and AP-1 transcription factors in mouse epidermis.
2001-03-26
Corticosterone-induced rapid phosphorylation of p38 and JNK mitogen-activated protein kinases in PC12 cells.
2001-03-16
Glycated serum albumin-induced vascular smooth muscle cell proliferation through activation of the mitogen-activated protein kinase/extracellular signal-regulated kinase pathway by protein kinase C.
2001-03-09
Expression of matrix metalloproteinases and tissue inhibitors of metalloproteinases in human optic nerve head astrocytes.
2001-03-01
Ceramide-induced cell death in the prostate cancer cell line LNCaP has both necrotic and apoptotic features.
2001-03-01
Regulation of Smad signaling by protein kinase C.
2001-03
Inhibitory effect of 2,3-butanedione monoxime (BDM) on Na(+)/Ca(2+) exchange current in guinea-pig cardiac ventricular myocytes.
2001-03
Constitutive alpha-secretase cleavage of the beta-amyloid precursor protein in the furin-deficient LoVo cell line: involvement of the pro-hormone convertase 7 and the disintegrin metalloprotease ADAM10.
2001-03
Octreotide potentiates PKC-dependent vasoconstrictors in portal-hypertensive and control rats.
2001-03
Phosphoinositide fatty acids regulate phosphatidylinositol 5-kinase, phospholipase C and protein kinase C activities.
2001-03
Signalling mechanisms underlying the myogenic response in human subcutaneous resistance arteries.
2001-03
Pharmacological differences between the human and rat vanilloid receptor 1 (VR1).
2001-03
Evidence for direct involvement of beta-catenin in phorbol ester-induced neurite outgrowth in GT1-1 hypothalamic neurones.
2001-03
Molecular characterization of bovine prostaglandin G/H synthase-2 and regulation in uterine stromal cells.
2001-03
Interferon-tau suppresses prostaglandin F2alpha secretion independently of the mitogen-activated protein kinase and nuclear factor kappa B pathways.
2001-03
Synaptotagmin I expression in mast cells of normal human tissues, systemic mast cell disease, and a human mast cell leukemia cell line.
2001-03
Effects of different durations of exercise on macrophage functions in mice.
2001-03
Signal transduction of flumazenil-induced preconditioning in myocytes.
2001-03
Amplification effect and mechanism of action of ET-1 in U-46619-induced vasoconstriction in pig skin.
2001-03
Enhancer regions of ovine interferon-tau gene that confer PMA response or cell type specific transcription.
2001-02-28
An essential role for calmodulin in regulating human T cell aggregation.
2001-02-23
Inhibition of depolarisation-evoked [(3)H]noradrenaline release from SH-SYFY human neuroblastoma cells by muscarinic (M1) receptors is not mediated by changes in [Ca(2+)].
2001-02-19
Effect of interferon-alpha on production of reactive oxygen species by human neutrophils.
2001-02-17
Phorbol esters modulate the Ras exchange factor RasGRP3.
2001-02-01
Characterization of metabolites of the chemopreventive agent curcumin in human and rat hepatocytes and in the rat in vivo, and evaluation of their ability to inhibit phorbol ester-induced prostaglandin E2 production.
2001-02-01
Phosphorylation and desensitization of alpha1d-adrenergic receptors.
2001-02-01
Tephrosia purpurea alleviates phorbol ester-induced tumor promotion response in murine skin.
2001-02
Cytokine-induced restoration of differentiation and cell cycle arrest in v-Myc transformed U-937 monoblasts correlates with reduced Myc activity.
2001-02
Oxidized-LDL enhances coronary vasoconstriction by increasing the activity of protein kinase C isoforms alpha and epsilon.
2001-02
Endothelin-1 enhances eicosanoids-induced coronary smooth muscle contraction by activating specific protein kinase C isoforms.
2001-02
Influence of breast-feeding on the production of cytokines.
2001-02
Ischemia-induced ventricular fibrillation in isolated perfused rat heart: role of alpha1A-adrenoceptor mediated activation of protein kinase C.
2001-02
Regulation of MAP kinase by calcium-sensing receptor in bovine parathyroid and CaR-transfected HEK293 cells.
2001-02
Na+/K+ATPase activity inhibition and isoform-specific translocation of protein kinase C following angiotensin II administration in isolated eel enterocytes.
2001-02
TH1/TH2 and TC1/TC2 profiles in peripheral blood and bronchoalveolar lavage fluid cells in pulmonary sarcoidosis.
2001-02
Synthesis of 7,8-disubstituted benzolactam-V8 and its binding to protein kinase C.
2001-01-22
Expression of thrombospondin-1 in human hepatocarcinoma cell lines and its regulation by transcription factor Jun/AP-1.
2001-01
Protein kinase C suppresses spontaneous, transient, outwards K+ currents through modulation of the Na/Ca exchanger in guinea-pig gastric myocytes.
2001-01
Modulation of H2 histamine receptor-mediated cAMP generation and granulocytic differentiation by extracellular nucleotides via activation of protein kinase C.
2001-01
Involvement of peripheral polymorphonuclear leukocytes in oxidative stress and inflammation in type 2 diabetic patients.
2001-01
Inhibition of carcinogen induced c-Ha-ras and c-fos proto-oncogenes expression by dietary curcumin.
2001
Induced cytoskeletal changes in bovine pulmonary artery endothelial cells by resveratrol and the accompanying modified responses to arterial shear stress.
2001
Down-regulation of particulate protein kinase Cepsilon and up-regulation of nuclear activator protein-1 DNA binding in liver following in vivo exposure of B6C3F1 male mice to heptachlor epoxide.
2001
Patents

Patents

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1
JPH00272866A
1
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1
JPH01157384A
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1
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1
JPH01291796A
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JPH0163378A
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1
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1
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:52:32 GMT 2025
Edited
by admin
on Mon Mar 31 18:52:32 GMT 2025
Record UNII
XUZ76S9127
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-154778
Preferred Name English
PHORBOL
HSDB   MI  
Common Name 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
Created by admin on Mon Mar 31 18:52:32 GMT 2025 , Edited by admin on Mon Mar 31 18:52:32 GMT 2025
PRIMARY
MERCK INDEX
m8714
Created by admin on Mon Mar 31 18:52:32 GMT 2025 , Edited by admin on Mon Mar 31 18:52:32 GMT 2025
PRIMARY Merck Index
CHEBI
8116
Created by admin on Mon Mar 31 18:52:32 GMT 2025 , Edited by admin on Mon Mar 31 18:52:32 GMT 2025
PRIMARY
MESH
C033085
Created by admin on Mon Mar 31 18:52:32 GMT 2025 , Edited by admin on Mon Mar 31 18:52:32 GMT 2025
PRIMARY
CAS
17673-25-5
Created by admin on Mon Mar 31 18:52:32 GMT 2025 , Edited by admin on Mon Mar 31 18:52:32 GMT 2025
PRIMARY
NSC
154778
Created by admin on Mon Mar 31 18:52:32 GMT 2025 , Edited by admin on Mon Mar 31 18:52:32 GMT 2025
PRIMARY
EPA CompTox
DTXSID2021155
Created by admin on Mon Mar 31 18:52:32 GMT 2025 , Edited by admin on Mon Mar 31 18:52:32 GMT 2025
PRIMARY
FDA UNII
XUZ76S9127
Created by admin on Mon Mar 31 18:52:32 GMT 2025 , Edited by admin on Mon Mar 31 18:52:32 GMT 2025
PRIMARY
PUBCHEM
442070
Created by admin on Mon Mar 31 18:52:32 GMT 2025 , Edited by admin on Mon Mar 31 18:52:32 GMT 2025
PRIMARY
HSDB
4328
Created by admin on Mon Mar 31 18:52:32 GMT 2025 , Edited by admin on Mon Mar 31 18:52:32 GMT 2025
PRIMARY
NIH
NCATS
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