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Substance Name: Cytochalasin D
RN: 22144-77-0
UNII: SY9F0FZ3TO
InChIKey: SDZRWUKZFQQKKV-JHADDHBZSA-N

Note

  • A fungal metabolite that blocks cytoplasmic cleavage by blocking formation of contractile microfilament structures resulting in multinucleated cell formation, reversible inhibition of cell movement, and the induction of cellular extrusion. Additional reported effects include the inhibition of actin polymerization, DNA synthesis, sperm motility, glucose transport, thyroid secretion, and growth hormone release.

Molecular Formula

  • C30-H37-N-O6

Molecular Weight

  • 507.6233
 

Classification Codes

  • Enzyme Inhibitors
  • Mutation Data
  • Natural Product
  • Nucleic Acid Synthesis Inhibitors
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Cytochalasin D

MeSH Heading

  • Cytochalasin D

Synonyms

  • (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)-
  • 1H-Cycloundec(d)isoindole-1,11(2H)-dione, 3-benzyl-3,3-alpha4,5,6,6-alpha,9,10,12,15-decahydro-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylene-, 15-acetate
  • 7,18-Dihydroxy-10-phenyl-5,16,18-trimethyl-(11)cytochalas-21-acetoxy-6(12),13,19-trien-17-one
  • Cytochalasin D
  • Cytohalasin D
  • EINECS 244-804-1
  • HSDB 3549
  • Lygosporin A
  • NSC 209835
  • UNII-SY9F0FZ3TO
  • Zygosporin A

Systematic Names

  • (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)-
  • 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)-
  • 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-(3R*,3aS*,4R*,6R*,6aS*,7E,10R*,12S*,13E,15S*,15aS*))-
  • 1H-Cycloundec(d)isoindole-1,11(2H)-dione, 3-benzyl-3,3-alpha,4,5,6,6-alpha,9,10,12,15-decahydro-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylene-, 15-acetate
  • 7(S),18(R)-Dihydroxy-16(S),18-dimethyl-10-phenyl(11)cytochalasa-6(12),13(E),19(E)-triene-1,17-dione 21(R)-acetate

Registry Numbers

CAS Registry Number

  • 22144-77-0

FDA UNII

  • SY9F0FZ3TO

System Generated Number

  • 0022144770

Structure Descriptors

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

InChIKey

SDZRWUKZFQQKKV-JHADDHBZSA-N

Smiles

[C@]123[C@H]([C@@H](NC3=O)Cc3ccccc3)[C@@H](C(=C)[C@H]([C@@H]1C=CC[C@@H](C(=O)[C@](C=C[C@H]2OC(=O)C)(C)O)C)O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 2mg/kg (2mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: EXCITEMENT
Teratology, The International Journal of Abnormal Development. Vol. 25, Pg. 11, 1982.
mouse LD50 oral 36mg/kg (36mg/kg)   Journal of Antibiotics. Vol. 21, Pg. 523, 1968.
mouse LD50 subcutaneous 1850ug/kg (1.85mg/kg)   Journal of Antibiotics. Vol. 21, Pg. 523, 1968.
rat LD50 intraperitoneal 900ug/kg (0.9mg/kg)   Teratology, The International Journal of Abnormal Development. Vol. 15, Pg. 27A, 1977.