CYTOCHALASIN D

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H37NO6
Molecular Weight	507.6179
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1[C@H]2[C@H](CC3=CC=CC=C3)NC(=O)[C@@]24[C@@H](\C=C\C[C@H](C)C(=O)[C@](C)(O)\C=C\[C@H]4OC(C)=O)[C@H](O)C1=C

InChI

InChIKey=SDZRWUKZFQQKKV-JHADDHBZSA-N

InChI=1S/C30H37NO6/c1-17-10-9-13-22-26(33)19(3)18(2)25-23(16-21-11-7-6-8-12-21)31-28(35)30(22,25)24(37-20(4)32)14-15-29(5,36)27(17)34/h6-9,11-15,17-18,22-26,33,36H,3,10,16H2,1-2,4-5H3,(H,31,35)/b13-9+,15-14+/t17-,18+,22-,23-,24+,25-,26+,29+,30+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C30H37NO6
Molecular Weight	507.6179
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=22305779

Cytochalasin D, a tropical fungal metabolite, is a disruptor of actin filament function, resulting in multinucleated cell formation, reversible inhibition of cell movement, and the induction of cellular extrusion. It was shown that cytochalasin D inhibits murine CT26 colorectal carcinoma cells growth and angiogenesis.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
actin polymerization or depolymerization 1 Target ID: GO:0008154 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9688570	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Colorectal cancer 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22305779	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Oxidative stress and endocytosis are involved in upregulation of interleukin-8 expression in airway cells exposed to PM2.5.	2016-12	26303504
The role of Rho-kinases in IL-1β release through phagocytosis of fibrous particles in human monocytes.	2015-01	24760326
Nickel induces interleukin-1β secretion via the NLRP3-ASC-caspase-1 pathway.	2014-04	24158569
Comparison of wood smoke PM2.5 obtained from the combustion of FIR and beech pellets on inflammation and DNA damage in A549 and THP-1 human cell lines.	2013-12	23670201
Increased nuclear thioredoxin-1 potentiates cadmium-induced cytotoxicity.	2013-01	22961094
Role of zinc metallothionein-3 (ZnMt3) in epidermal growth factor (EGF)-induced c-Abl protein activation and actin polymerization in cultured astrocytes.	2011-11-25	21900236
Resveratrol inhibits the epidermal growth factor-induced epithelial mesenchymal transition in MCF-7 cells.	2011-11-01	21794976
Regulation of retinoschisin secretion in Weri-Rb1 cells by the F-actin and microtubule cytoskeleton.	2011	21738583
Silica crystals and aluminum salts activate the NALP3 inflammasome through phagosomal destabilization.	2008-08	18604214
Simvastatin inhibits TNFalpha-induced invasion of human cardiac myofibroblasts via both MMP-9-dependent and -independent mechanisms.	2007-08	17560598
Zinc and the cytoskeleton in the neuronal modulation of transcription factor NFAT.	2007-01	17044076
The internalization and degradation of human copper transporter 1 following cisplatin exposure.	2006-11-15	17108132
Microtubules are required for NF-kappaB nuclear translocation in neuroblastoma IMR-32 cells: modulation by zinc.	2006-10	17029595
Cytoskeletal architecture differentially controls post-transcriptional processing of IL-6 and IL-8 mRNA in airway epithelial-like cells.	2006-05-15	16499908
Chemokine gene activation in human bone marrow-derived osteoblasts following exposure to particulate wear debris.	2006-04	16392133
A role for cytoskeletal elements in the light-driven translocation of proteins in rod photoreceptors.	2005-11	16249472
PDX-1 protein is internalized by lipid raft-dependent macropinocytosis.	2005	16405074
Protective role of Nd1 in doxorubicin-induced cardiotoxicity.	2004-11-01	15485691
The role of the cytoskeleton in cellular adhesion molecule expression in tumor necrosis factor-stimulated endothelial cells.	2004-04-01	15034928
Rho protein-mediated changes in the structure of the actin cytoskeleton regulate human inducible NO synthase gene expression.	2003-07-01	12799187
Role of the cytoskeleton in secretion of chloride by shark rectal gland.	2002-12	12444471
Simvastatin increases fibrinolytic activity in human peritoneal mesothelial cells independent of cholesterol lowering.	2002-11	12371961
Zinc has an insulin-like effect on glucose transport mediated by phosphoinositol-3-kinase and Akt in 3T3-L1 fibroblasts and adipocytes.	2001-05	11340092
Actin filaments are involved in the regulation of trafficking of two closely related chemokine receptors, CXCR1 and CXCR2.	2001-01-15	11145710
Phagocytic uptake of Encephalitozoon cuniculi by nonprofessional phagocytes.	2000-12	11083817
Microtubules, but not actin filaments, drive daughter cell budding and cell division in Toxoplasma gondii.	2000-04	10704375
Mechanisms of GM-CSF increase by diesel exhaust particles in human airway epithelial cells.	2000-01	10645887
Cadmium inhibits albumin endocytosis in opossum kidney epithelial cells.	1999-12-01	10581208
Inhibition of sandfly fever Sicilian virus (Phlebovirus) replication in vitro by antiviral compounds.	1997-12-24	9403935
Mycobacterium tuberculosis invades and replicates within type II alveolar cells.	1996-04	8606107
Cytochalasin D inhibits lipopolysaccharide-induced tumor necrosis factor production in macrophages.	1993-10	8409756
Glutathione status and the incidence of neural tube defects elicited by direct acting teratogens in vitro.	1988-06	3135633

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Latrunculin B (LatB) and cytochalasin D (CytoD) at 0.5μM profoundly altered F-actin structures in a Rho kinase-dependent manner, but only CytoD strongly induced the pro-fibrotic factor CTGF (connective tissue growth factor) in primary human renal epithelial cells. Preincubation with CytoD but not LatB synergistically enhanced the TGFβ-1-stimulated synthesis of CTGF. CytoD had no direct effect on the phosphorylation of Smad2/3, but facilitated their phosphorylation and thus activation by TGFβ-1.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:52:52 GMT 2025` Edited by `admin` on `Mon Mar 31 19:52:52 GMT 2025`
Record UNII	SY9F0FZ3TO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CYTOCHALASIN D

Common Name

English

NSC-209835

Preferred Name

English

(-)-CYTOCHALASIN D

Common Name

English

CYTOCHALASIN D [HSDB]

Common Name

English

1H-CYCLOUNDEC(D)ISOINDOLE-1,11(2H)-DIONE, 15-(ACETYLOXY)-3,3A,4,5,6,6A,9,10,12,15-DECAHYDRO-6,12-DIHYDROXY-4,10,12-TRIMETHYL-5-METHYLENE-3-(PHENYLMETHYL)-, (3S,3AR,4S,6S,6AR,7E,10S,12R,13E,15R,15AR)-

Common Name

English

(11)CYTOCHALASA-6(12),13,19-TRIENE-1,17-DIONE, 21-(ACETYLOXY)-7,18-DIHYDROXY-16,18-DIMETHYL-10-PHENYL-, (7S,13E,16S,18R,19E,21R)-

Common Name

English

ZYGOSPORIN A

Common Name

English

Code System Code Type Description

MESH

D015638