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14930-96-2 molecular structure
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(5R,9R,13S,15S,15aS,16S,18aS,18bS)-16-benzyl-5,13-dihydroxy-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-2,18-dione

ChemBase ID: 133759
Molecular Formular: C29H37NO5
Molecular Mass: 479.60778
Monoisotopic Mass: 479.26717329
SMILES and InChIs

SMILES:
C[C@@H]1CCC[C@H](/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)O
Canonical SMILES:
C[C@@H]1CCC[C@@H](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/C29H37NO5/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/h4-6,8,11-12,14-16,18-19,22-24,26-27,31,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8-,16-15-/t18-,19-,22-,23+,24+,26+,27-,29-/m1/s1
InChIKey:
GBOGMAARMMDZGR-WIPIJLBNSA-N

Cite this record

CBID:133759 http://www.chembase.cn/molecule-133759.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(5R,9R,13S,15S,15aS,16S,18aS,18bS)-16-benzyl-5,13-dihydroxy-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-2,18-dione
IUPAC Traditional name
cytochalasin B
Synonyms
Phomin
Cytochalasin B from Drechslera dematioidea
细胞松弛素 B 来源于Drechslera dematioidea
CAS Number
14930-96-2
EC Number
239-000-2
MDL Number
MFCD00077704
Beilstein Number
1096207
PubChem SID
24892890
162228036
PubChem CID
24870911

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
C6762 external link Add to cart Please log in.
Data Source Data ID
PubChem 24870911 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.110297  H Acceptors
H Donor LogD (pH = 5.5) 4.082357 
LogD (pH = 7.4) 4.082356  Log P 4.082357 
Molar Refractivity 136.417 cm3 Polarizability 52.98627 Å3
Polar Surface Area 95.86 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO: soluble10 mg/mL expand Show data source
Apperance
white powder expand Show data source
RTECS
RO0205000 expand Show data source
European Hazard Symbols
Highly toxic Highly toxic (T+) expand Show data source
UN Number
1544 expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
2 expand Show data source
Risk Statements
63-26/27/28 expand Show data source
Safety Statements
28-36/37-45 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H300-H310-H330-H361 expand Show data source
GHS Precautionary statements
P260-P264-P280-P284-P301 + P310-P302 + P350 expand Show data source
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 expand Show data source
RID/ADR
UN 1544 6.1/PG 2 expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
≥98% (HPLC) expand Show data source
Quality Level
PREMIUM expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - C6762 external link
Biochem/physiol Actions
One of a group of fungal metabolites that interfere with a wide variety of cellular movements. Useful tool for characterizing some of the polymerization properties of actin,1 and in studies on cytokinesis.2 Probe for the two hexose-transport systems in rat L6 myoblasts.3
Cell permeable fungal toxin that disrupts contractile microfilaments by inhibiting actin polymerization. This, in turn, induces DNA fragmentation, inhibits cell division, and disrupts many cell processes. Inhibits glucose transport.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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