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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H40O8
Molecular Weight 504.6124
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHORBOL 12,13-DIBUTYRATE

SMILES

CCCC(=O)O[C@@H]1[C@@H](C)[C@]2(O)[C@@H]3C=C(C)C(=O)[C@@]3(O)CC(CO)=C[C@H]2[C@@H]4C(C)(C)[C@]14OC(=O)CCC

InChI

InChIKey=BQJRUJTZSGYBEZ-YVQNUNKESA-N
InChI=1S/C28H40O8/c1-7-9-20(30)35-24-16(4)27(34)18(22-25(5,6)28(22,24)36-21(31)10-8-2)12-17(14-29)13-26(33)19(27)11-15(3)23(26)32/h11-12,16,18-19,22,24,29,33-34H,7-10,13-14H2,1-6H3/t16-,18+,19-,22-,24-,26-,27-,28-/m1/s1

HIDE SMILES / InChI

Molecular Formula C28H40O8
Molecular Weight 504.6124
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Ionizing radiation alters myofilament calcium sensitivity in vascular smooth muscle: potential role of protein kinase C.
2005-09
Freezing without surrounding cryomedium preserves the endothelium and its function in human internal mammary arteries.
2005-08
Modulation of Ca(2+)-dependent and Ca(2+)-independent miniature endplate potentials by phorbol ester and adenosine in frog.
2005-08
Protein kinase C delta and epsilon mediate positive inotropy in adult ventricular myocytes.
2005-05
EBV infection induces expression of the transcription factors ATF-2/c-Jun in B lymphocytes but not in B-CLL cells.
2005-05
Signaling of short- and long-term regulation of intestinal epithelial type 1 Na+/H+ exchanger by interferon-gamma.
2005-05
Identification of plasma membrane macro- and microdomains from wavelet analysis of FRET microscopy.
2005-05
Identification of a novel splice variant of human PD-L1 mRNA encoding an isoform-lacking Igv-like domain.
2005-04
Regulation of intracellular Cl- concentration through volume-regulated ClC-3 chloride channels in A10 vascular smooth muscle cells.
2005-02-25
Investigation of PKC isoform-specific translocation and targeting of the current of the late afterhyperpolarizing potential of myenteric AH neurons.
2005-02
Endothelin-1 acts via protein kinase C to block KATP channels in rabbit coronary and pulmonary arterial smooth muscle cells.
2005-02
Stimulation of beta-adrenoceptors inhibits store-operated channel currents via a cAMP-dependent protein kinase mechanism in rabbit portal vein myocytes.
2005-01-15
Anti-Plasmodium activity of ceramide analogs.
2004-12-10
Adenosine inhibits GABAergic and glycinergic transmission in adult rat substantia gelatinosa neurons.
2004-11
Coregulation of glutamate uptake and long-term sensitization in Aplysia.
2004-10-06
Mechanisms of arginine-vasopressin-induced Ca2+ oscillations in beta-cells (HIT-T15): a role for oscillating protein kinase C.
2004-10
Partial bladder outlet obstruction abolishes the receptor- and G protein-dependent increase in calcium sensitivity in rabbit bladder smooth muscle.
2004-10
Evidence for protein kinase involvement in long-term postsynaptic excitation of intrinsic primary afferent neurons in the intestine.
2004-09-30
Mechanisms underlying postjunctional synergism between responses of the vas deferens to noradrenaline and ATP.
2004-09-13
Functional and molecular characterization of a volume-activated chloride channel in rabbit corneal epithelial cells.
2004-09-01
Expression of matrix metalloproteinase-9 in human platelets: regulation of platelet activation in in vitro and in vivo studies.
2004-09
Intestinal Na+-K+-ATPase activity and molecular events downstream of interferon-gamma receptor stimulation.
2004-08
Novel phosphospecific antibodies for monitoring phosphorylation of proteins encoded by the myosin light chain kinase genetic locus.
2004-07
Amyloid beta peptide directly inhibits PKC activation.
2004-06
Noncompetitive metabotropic glutamate5 receptor antagonist (E)-2-methyl-6-styryl-pyridine (SIB1893) depresses glutamate release through inhibition of voltage-dependent Ca2+ entry in rat cerebrocortical nerve terminals (synaptosomes).
2004-06
Characterization of phorbol esters activity on individual mammalian protein kinase C isoforms, using the yeast phenotypic assay.
2004-05-03
Cisplatin resistance is associated with deregulation in protein kinase C-delta.
2004-04-16
Heat-shock response is associated with enhanced contractility of vascular smooth muscle in isolated rat aorta.
2004-04
Dopamine acutely decreases type 3 Na(+)/H(+) exchanger activity in renal OK cells through the activation of protein kinases A and C signalling cascades.
2004-03-19
Properties of the basal calcium influx in human red blood cells.
2004-03-09
Abrogation of p21 expression by flavopiridol enhances depsipeptide-mediated apoptosis in malignant pleural mesothelioma cells.
2004-03-01
Protein kinase C regulates functional coupling of beta1-adrenergic receptors to Gi/o-mediated responses in cardiac myocytes.
2004-02
Actin cytoskeleton remodelling via local inhibition of contractility at discrete microdomains.
2004-01-15
Quercetin inhibits the invasion of murine melanoma B16-BL6 cells by decreasing pro-MMP-9 via the PKC pathway.
2004-01
Expression and regulation of interleukin-23 subunits in human peripheral blood mononuclear cells and hematopoietic cell lines in response to various inducers.
2004
N-methyl-D-aspartate receptors enhance mechanical responses and voltage-dependent Ca2+ channels in rat dorsal root ganglia neurons through protein kinase C.
2004
Mechanisms involved in the antiplatelet activity of ketamine in human platelets.
2003-12-03
Comparison of the effects of phorbol dibutyrate and low-frequency stimulation of synaptic inputs on the excitability of myenteric AH neurons.
2003-12
[Changes in the contractility of the NIH3T3 fibroblast induced by the over-expression of CPI-17].
2003-11
T cell receptor-independent basal signaling via Erk and Abl kinases suppresses RAG gene expression.
2003-11
Intracellular mechanism of mitochondrial adenosine triphosphate-sensitive potassium channel activation with isoflurane.
2003-10
Pregabalin and gabapentin reduce release of substance P and CGRP from rat spinal tissues only after inflammation or activation of protein kinase C.
2003-09
Phorbol ester induces CYP2E1 in astrocytes, through a protein kinase C- and tyrosine kinase-dependent mechanism.
2003-08
Prolactin regulates adenylyl cyclase and insulin secretion in rat pancreatic islets.
2003-06-30
Bombesin, lysophosphatidic acid, and epidermal growth factor rapidly stimulate focal adhesion kinase phosphorylation at Ser-910: requirement for ERK activation.
2003-06-20
15-deoxy-delta12,14 prostaglandin J2 synergizes with phorbol ester to induce proliferation in Swiss 3T3 cells independently of peroxisome proliferator-activated receptor gamma and PGD2 receptors.
2003-06
Heat induced HSP20 phosphorylation without increased cyclic nucleotide levels in swine carotid media.
2003-04-25
Pharmacological characteristics of bombesin receptor mediating hypothermia in the central nervous system of rats.
2003-04-18
Involvement of the antiplatelet activity of magnesium sulfate in suppression of protein kinase C and the Na+/H+ exchanger.
2003-03-10
The forskolin-induced opening of tight junctions in Xenopus gallbladder epithelium is mediated by protein kinase C.
2003-02
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:52:00 GMT 2025
Edited
by admin
on Mon Mar 31 19:52:00 GMT 2025
Record UNII
67MX82CL58
Record Status Validated (UNII)
Record Version
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Name Type Language
PHORBOL 12,13-DIBUTYRATE
Common Name English
NSC-622507
Preferred Name English
PDBU
Common Name English
PHORBOL DIBUTYRATE
Common Name English
PHORBOL 12,13-DIBUTANOATE
Common Name English
Code System Code Type Description
CHEBI
17598
Created by admin on Mon Mar 31 19:52:00 GMT 2025 , Edited by admin on Mon Mar 31 19:52:00 GMT 2025
PRIMARY
PUBCHEM
37783
Created by admin on Mon Mar 31 19:52:00 GMT 2025 , Edited by admin on Mon Mar 31 19:52:00 GMT 2025
PRIMARY
WIKIPEDIA
PHORBOL 12,13-DIBUTYRATE
Created by admin on Mon Mar 31 19:52:00 GMT 2025 , Edited by admin on Mon Mar 31 19:52:00 GMT 2025
PRIMARY
CAS
37558-16-0
Created by admin on Mon Mar 31 19:52:00 GMT 2025 , Edited by admin on Mon Mar 31 19:52:00 GMT 2025
PRIMARY
NSC
622507
Created by admin on Mon Mar 31 19:52:00 GMT 2025 , Edited by admin on Mon Mar 31 19:52:00 GMT 2025
PRIMARY
FDA UNII
67MX82CL58
Created by admin on Mon Mar 31 19:52:00 GMT 2025 , Edited by admin on Mon Mar 31 19:52:00 GMT 2025
PRIMARY
EPA CompTox
DTXSID50958628
Created by admin on Mon Mar 31 19:52:00 GMT 2025 , Edited by admin on Mon Mar 31 19:52:00 GMT 2025
PRIMARY