Basic information
- CAS
17466-45-4- Standard SMILES
CC1NC(=O)C(CC(C)(O)CO)NC(=O)C2Cc3c([nH]c4ccccc34)SCC(NC(=O)C(C(C)O)NC1=O)C(=O)N1CC(O)CC1C(=O)NC(C)C(=O)N2- InChIKey
KPKZJLCSROULON-UHFFFAOYSA-N- Molecular formula
- C35H48N8O11S
- Average molar mass
- 788.9 g/mol
- Monoisotopic mass
- 788.31632536
Overview
See also: Phalloidin (annotation moved to).
Names & identifiers
- Preferred name
- Phalloidin from Amanita phalloides
- IUPAC
- 28-(2,3-dihydroxy-2-methylpropyl)-18-hydroxy-34-(1-hydroxyethyl)-23,31-dimethyl-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-15,21,24,26,29,32,35-heptone
- English name
- PHALLOIDIN
- Molecular formula
- C35H48N8O11S
- Molecular weight
- 788.87
Names & synonyms
Phalloidin from Amanita phalloidesC35H48N8O11S28-(2,3-Dihydroxy-2-methylpropyl)-18-hydroxy-34-(1-hydroxyethyl)-23,31-dimethyl-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-15,21,24,26,29,32,35-heptoneSCHEMBL39329GTPL4736orb1706102MSK7217KPKZJLCSROULON-UHFFFAOYSA-NNSC523214SMP1_000234DA-65261LS-15367
Show more names
PHALLOIDINphalloidineGlycerol Formal Impurity 5Phalloidin *CAS#: 17466-45-4*PHALLOIDIN, AMANITA PHALLOIDESPhalloidin trifluoroacetate saltPhalloidin, 90%, from Amanita phalloides
Phalloidin from Amanita phalloides, >=90%NS00015477T19512(2,3-dihydroxy-2-methyl-propyl)-hydroxy-(1-hydroxyethyl)-dimethyl-[?]heptone28-(2,3-dihydroxy-2-methyl-propyl)-18-hydroxy-34-(1-hydroxyethyl)-23,31-dimethyl-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-15,21,24,26,29,32,35-heptone29-(2,3-Dihydroxy-2-methylpropyl)-2-hydroxy-23-(1-hydroxyethyl)-6,26-dimethyl-1,2,3,3a,5,6,8,9,10,15-decahydro-17H-18,9-(epiminoethanoiminoethanoiminoethanoiminomethano)pyrrolo[1',2':5,6][1,5,8,11]thiatriazacyclopentadecino[15,14-b]indole-4,7,19,22,25,28,31(18H)-heptoneCyclic(L-alanyl-D-threonyl-L-cysteinyl-cis-4-hydroxy-L-prolyl-L-alanyl-2-mercapto-L-tryptophyl-4, cyclic (3.fwdarw.6)-sulfideCyclo(L-alanyl-2-mercapto-L-tryptophanyl-4,5-dihydroxy-L-leucyl-L-alanyl-threonyl-cysteinyl-L-cis-4-hydroxy-L-prolyl, cyclic (2, 6)-sulfide
Properties
Computed structural properties
- XLogP
- -1.7
- Topological polar surface area
- 317 Ų
- Hydrogen bond donors
- 11
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 4
- Heavy atoms
- 55
- Formal charge
- 0
- Complexity
- 1,510
Physicochemical properties
- Melting point
- 280 · 280-282°
- alpha
- 55.7 ° · +55.7°(D/20℃)(c=0.5,メタノール)
- Density
- 1.1612 · 1.1612 (rough estimate)
- refractive index
- 1.74 · 1.7400 (estimate)
- storage temp.
- 2 C · +2C to +8C
- solubility
- 10 mg/ml; · DMF: 10 mg/ml; DMSO: 10 mg/ml; Ethanol: 10 mg/ml; Water: 0.5 mg/ml (warm)
- form
- White crystalline solid
- Boiling point
- 1370.5 · 1370.5±65.0 °C(Predicted)
- pka
- 13.03 · 13.03±0.70(Predicted)
- color
- Hexahydrate, needles or crystals from water
- biological source
- Amanita phalloides
- optical activity
- 62.3 · +62.3 (Ethanol)
- Water Solubility
- 1 mg/ml · Soluble to 1 mg/ml in water
- Merck
- 13 · 13,7273
- BRN
- 4347460 · 4347460
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
- F
- 18
- wgk
- 3
- rtecs
- SE9800000
- ridadr
- UN 3462 6.1/PG 2
- hs_code
- 2934999090
- Toxicity
- LD50 i.m. in albino mice: 3.3 mg/g (Vogt); LD50 i.p. in mice: 2 mg/kg (Wieland, Wieland)
- risk_code
- 26/27/28
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T+
- safety_code
- 22-28-36/37-45
- 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. 2 Oral
- Precautionary statements
- P260-P262-P264-P280-P302+P352+P310-P304+P340+P310
- Hazardous Substances Data
- 17466-45-4(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionPhalloidin is a natural mycotoxin first isolated from the death cap mushroom, A. phalloides. It binds F-actin and stabilizes actin fibers. Fluorescently labeled phalloidin is commonly used to stain F-actin in cells.
UsesPhalloidin has been used: As a supplement in PEM buffer and dimethyl sulfoxide (DMSO).As a drug.In immunohistochemistry to stain F-actin.
General DescriptionPhalloidin is a phallotoxin produced by death cap mushroom Amanita phalloides. It is a cyclic peptide, which interacts with actin, and this was first identified in phalloidin-poisoned rats. It is a heptapeptide, cyclic in nature, with a crosslink between tryptophan at position 6 and cysteine at position 3. The side chain of amino acid 7 (γ-δ-dihydroxyleucine) in phalloidin, is accessible to modifications, through which fluorescently labeled phalloidin compounds can be produced.
Suppliers65 total
阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司0731-88532326 13319508186 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
上海鸿肽生物科技有限公司
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…