Cyclo(L-alanyl-2-mercapto-L-tryptophanyl-4,5-dihydroxy-L-leucyl-L-valyl-erythro-3-hydroxy-D-alpha-aspartyl-L-cysteinyl-cis-4-hydroxy-L-prolyl, cyclic (2, 6)-sulfide
Basic information
- CAS
26645-35-2- Standard SMILES
CC(C)C1NC(=O)[C@H](C[C@](C)(O)CO)NC(=O)[C@@H]2Cc3c([nH]c4ccccc34)SC[C@H](NC(=O)[C@@H](C(=O)O)NC1=O)C(=O)N1CC(O)C[C@H]1C(=O)N[C@@H](C)C(=O)N2- InChIKey
WFTPZVCBTJDQRQ-RIENQSPCSA-N- Molecular formula
- C36H48N8O12S
- Average molar mass
- 816.9 g/mol
- Monoisotopic mass
- 816.31124017
Names & identifiers
- Preferred name
- Cyclo(L-alanyl-2-mercapto-L-tryptophanyl-4,5-dihydroxy-L-leucyl-L-valyl-erythro-3-hydroxy-D-alpha-aspartyl-L-cysteinyl-cis-4-hydroxy-L-prolyl, cyclic (2, 6)-sulfide
- IUPAC
- (1S,14R,20S,23S,28S,34S)-28-[(2S)-2,3-dihydroxy-2-methylpropyl]-18-hydroxy-23-methyl-15,21,24,26,29,32,35-heptaoxo-31-propan-2-yl-12-thia-10,16,22,25,27,30,33,36-octazapentacyclo[12.11.11.03,11.04,9.016,20]hexatriaconta-3(11),4,6,8-tetraene-34-carboxylic acid
- English name
- Phallacidin
- Molecular formula
- C37H50N8O13S
- Molecular weight
- 846.91
Names & synonyms
[(2S)-2,3-dihydroxy-2-methyl-propyl]-hydroxy-isopropyl-methyl-heptaoxo-[?]carboxylic acidCyclo(L-alanyl-2-mercapto-L-tryptophanyl-4,5-dihydroxy-L-leucyl-L-valyl-erythro-3-hydroxy-D-.alpha.-aspartyl-L-cysteinyl-cis-4-hydroxy-L-prolyl, cyclic (2, 6)-sulfidePHALLICIDINPhallacidinPhallacidin DISCONTINUEDCYCLO(ALA-2-MERCAPTO-TRP-4phallacidin from amanita phalloidesPhallacidin from Amanita phalloidesCyclo(Ala-2-Mercapto-Trp-45-DIHYDROXY-LEU-VAL-ERYTHRO-3-HYDROXY-D-ASP-CYS-CIS-4-HYDROXY-PRO)-3-hydroxy-d-alpha-aspartyl-l-cysteinyl-cis-4-hydroxy-l-prolyl)cyclic(2-6)-scyclic(l-alanyl-2-mercapto-l-tryptophyl-4,5-dihydroxy-l-leucyl-l-valyl-erythro
Database identifiers
- CAS
26645-35-2- PubChem CID
- 72380
Properties
Computed structural properties
- XLogP
- -0.7
- Topological polar surface area
- 334 Ų
- Hydrogen bond donors
- 11
- Hydrogen bond acceptors
- 13
- Rotatable bonds
- 5
- Heavy atoms
- 57
- Formal charge
- 0
- Complexity
- 1,600
Physicochemical properties
- Boiling point
- 1435.246 · 1435.246±65.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.1678 · 1.1678 (rough estimate)
- refractive index
- 1.74 · 1.7400 (estimate)
- solubility
- DMF: Soluble; DMSO: Soluble; Methanol: Soluble; Water: Soluble
- form
- White to off-white powder.
- pka
- 3.129 · 3.129±0.11(predicted)
- color
- White to off-white
- Appearance
- Solid Powder
- biological source
- Amanita phalloides
- Sequence
- Ala-Trp-Leu-Val-{D-Asp}-Cys-{Hyp} (Sulfide bridge: Trp2- Cys6)
- InChIKey
- KUBDTFZQCYLLGC-UHFFFAOYSA-N
- SMILES
- CC(C)C1NC(=O)C(CC(C)(O)CO)NC(=O)C2Cc3c(SCC(NC(=O)C(NC1=O)C(O)C(O)=O)C(=O)N4CC(O)CC4C(=O)NC(C)C(=O)N2)[nH]c5ccccc35
- UNSPSC Code
- 12352202 · 12352202
- NACRES
- 56 · NA.56
- Symbol(GHS)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- GT8943000
- ridadr
- 1544
- hs_code
- 2934999090
- risk_code
- 26/27/28
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T+
- safety_code
- 22-36/37/39-45
- hazard_class
- 6.1(a)
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- I
- Hazard statements
- H300+H310+H330
- Hazard Classifications
- Acute Tox. 1 InhalationAcute Tox. 2 DermalAcute Tox. 2 Oral
- Precautionary statements
- P260-P262-P264-P280-P302+P352+P310-P304+P340+P310
Chemistry & industry
Applications
DescriptionPhallacidin is a natural mycotoxin first isolated from the death cap mushroom, A. phalloides. It binds filamentous actin (F-actin) like phalloidin , but contains a carboxyl group for coupling reactions.
UsesToxin Phallacidin is a weak fluorescent bicyclic peptide probe in aquous solution, Which is isolated from Amanita phalloides mushroom and could be used for blocking F-actin staining by labeled phallotoxins, which promotes actin polymerization.
UsesPhallacidin is a natural mycotoxin first isolated from the death cap mushroom. It binds filamentous actin like phalloidin.
Additional notes
DefinitionChEBI: A homodetic bicyclic heptapeptide having a sulfide bridge.
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