(9R,13S,15S,15aS,16S,18aS,18bS)-16-benzyl-13-hydroxy-9,15-dimethyl-14-methylidene-2H,5H,6H,7H,8H,9H,10H,13H,14H,15H,15aH,16H,17H,18H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,5,18-trione

• ChemBase ID: 138649
• Molecular Formular: C29H35NO5
• Molecular Mass: 477.5919
• Monoisotopic Mass: 477.25152323
• SMILES: C[C@@H]1CCCC(=O)/C=C\C(=O)O[C@]23[C@@H](/C=C/C1)[C@@H](C(=C)[C@H]([C@H]2[C@@H](NC3=O)Cc1ccccc1)C)O
• Canonical SMILES: C[C@@H]1CCCC(=O)/C=C\C(=O)O[C@@]23[C@@H](/C=C/C1)[C@H](O)C(=C)[C@H]([C@H]3[C@@H](NC2=O)Cc1ccccc1)C
• InChI: InChI=1S/C29H35NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18-19,23-24,26-27,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/t18-,19-,23+,24+,26+,27-,29-/m1/s1
• InChIKey: ZMAODHOXRBLOQO-WDEFJXGESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9R,13S,15S,15aS,16S,18aS,18bS)-16-benzyl-13-hydroxy-9,15-dimethyl-14-methylidene-2H,5H,6H,7H,8H,9H,10H,13H,14H,15H,15aH,16H,17H,18H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,5,18-trione
• IUPAC Traditional name: cytochalasin A
• Synonyms: Cytochalasin A from Helminthosporium dematioideum; Cytochalasin A from Drechslera dematioidea; 细胞松弛素 A 来源于长蠕孢菌; 细胞松弛素 A 来源于Drechslera dematioidea

Database IDs

• CAS Number: 14110-64-6
• EC Number: 237-964-9
• MDL Number: MFCD00005935
• Beilstein Number: 949521
• PubChem SID: 24892882; 162232900
• PubChem CID: 57431204

CALCULATED PROPERTIES

• Acid pKa: 13.067214
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.4936953
• LogD (pH = 7.4): 4.4936943
• Log P: 4.4936953
• Molar Refractivity: 135.5196 cm^3
• Polarizability: 52.439987 Å^3
• Polar Surface Area: 92.7 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: soluble20 mg/mL, clear, colorless
• Melting Point: 190-191 °C

Safety Information

• European Hazard Symbols: Highly toxic (T+)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 63-26/27/28
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330-H361
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥99.0% (TLC)
• Empirical Formula (Hill Notation): C29H35NO5

DETAILS

Sigma Aldrich - C6637

Other Notes
Oxidized analog of cytochalasin B.
Biochem/physiol Actions
Cytochalasin A reacts with sulfhydryls, and inhibits growth and glucose transport in Saccharomyces. Cytochalasin A is an oxidizing analog of cytochalsin B.

Sigma Aldrich - 857793

Features and Benefits
The cytochalasins are fungal metabolites which exhibit interesting effects on cell activity. They are important tools for cytological research.

Sigma Aldrich - 30375

Other Notes
Inhibits polymerization of tubulin1
Biochem/physiol Actions
Cytochalasin A reacts with sulfhydryls, and inhibits growth and glucose transport in Saccharomyces. Cytochalasin A is an oxidizing analog of cytochalsin B.