2-[(3S,6R,12S,15S,18S,21S,24S,27S)-18,21-bis(2-aminoethyl)-12-benzyl-3-[(1S)-2-chloro-1-hydroxyethyl]-15-{3-[(diaminomethylidene)amino]propyl}-24-(hydroxymethyl)-27-(3-hydroxyundecanamido)-2,5,8,11,14,17,20,23,26-nonaoxo-9-propylidene-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosan-6-yl]-2-hydroxyacetic acid

• ChemBase ID: 154036
• Molecular Formular: C53H85ClN14O17
• Molecular Mass: 1225.7786
• Monoisotopic Mass: 1224.59056501
• SMILES: CCCCCCCCC(CC(=O)N[C@@H]1COC(=O)[C@H](NC(=O)[C@H](NC(=O)/C(=C/CC)/NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC1=O)CO)CCN)CCN)CCCN=C(N)N)Cc1ccccc1)C(C(=O)O)O)[C@@H](CCl)O)O
• Canonical SMILES: CCCCCCCCC(CC(=O)N[C@@H]1COC(=O)[C@H](NC(=O)[C@H](NC(=O)/C(=C/CC)/NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC1=O)CO)CCN)CCN)CCCN=C(N)N)C(C(=O)O)O)[C@@H](CCl)O)O
• InChI: InChI=1S/C53H85ClN14O17/c1-3-5-6-7-8-12-17-30(70)25-39(72)60-37-28-85-52(84)40(38(71)26-54)67-50(81)41(42(73)51(82)83)68-46(77)31(14-4-2)61-47(78)35(24-29-15-10-9-11-16-29)65-43(74)32(18-13-23-59-53(57)58)62-44(75)33(19-21-55)63-45(76)34(20-22-56)64-48(79)36(27-69)66-49(37)80/h9-11,14-16,30,32-38,40-42,69-71,73H,3-8,12-13,17-28,55-56H2,1-2H3,(H,60,72)(H,61,78)(H,62,75)(H,63,76)(H,64,79)(H,65,74)(H,66,80)(H,67,81)(H,68,77)(H,82,83)(H4,57,58,59)/t30?,32-,33-,34-,35-,36-,37-,38+,40-,41+,42?/m0/s1
• InChIKey: YMFYPHGOLKNWQN-MADLOLTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3S,6R,12S,15S,18S,21S,24S,27S)-18,21-bis(2-aminoethyl)-12-benzyl-3-[(1S)-2-chloro-1-hydroxyethyl]-15-{3-[(diaminomethylidene)amino]propyl}-24-(hydroxymethyl)-27-(3-hydroxyundecanamido)-2,5,8,11,14,17,20,23,26-nonaoxo-9-propylidene-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosan-6-yl]-2-hydroxyacetic acid
• IUPAC Traditional name: [(3S,6R,12S,15S,18S,21S,24S,27S)-18,21-bis(2-aminoethyl)-12-benzyl-3-[(1S)-2-chloro-1-hydroxyethyl]-15-{3-[(diaminomethylidene)amino]propyl}-24-(hydroxymethyl)-27-(3-hydroxyundecanamido)-2,5,8,11,14,17,20,23,26-nonaoxo-9-propylidene-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosan-6-yl](hydroxy)acetic acid
• Synonyms: SR-E; Syringomycin E

Database IDs

• CAS Number: 124888-22-8
• EC Number: 231-791-2
• PubChem SID: 162248175; 24899726
• PubChem CID: 16219978

CALCULATED PROPERTIES

• Acid pKa: 3.2335577
• H Acceptors: 21
• H Donor: 18
• LogD (pH = 5.5): -13.47504
• LogD (pH = 7.4): -11.668355
• Log P: -7.859971
• Molar Refractivity: 303.3754 cm^3
• Polarizability: 118.93655 Å^3
• Polar Surface Area: 522.86 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solution

Safety Information

• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: -20°C

Product Information

• Purity: >95% (HPLC)
• Biological Source: from Pseudomonas syringae B-301D
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C53H85ClN14O17

DETAILS

Sigma Aldrich - S6946

Physical form
Supplied as a 0.5 mg/mL solution in 1 mM hydrochloric acid.
Biochem/physiol Actions
Syringomycin E (SR-E) is a phytotoxin of the cyclic lipodepsinonapeptides class composed of a 3-hydroxy fatty acid tail attached to a polar peptide head that contains nine amino acid residues. SR-E is a potent biosurfactant, which is toxic to many plants and fungi and is implicated as a virulence factor in several major plant diseases such as holcus spot disease of maize and bacterial canker of stone fruits. Syringomycin E inhibits the growth of several yeast strains including Rhodotorula pilimanae and Saccharomyces cerevisiae and is also effective against human pathogenic fungi. Syringomycin E targets the plant and fungal plasma membrane altering several of its functions such as membrane potential, protein phosphorylation, H+-ATPase activity, and ion fluxes. All of these effects are related to SR-E pore formation in the host membrane. At least six molecules of syringomycin E compose a channel with a radius of ~1 nm and individual channels can become aggregated into clusters that exhibit synchronous opening and closing. Remarkably, the host membrane composition influences the sensitivity to syringomycin E and membrane lipids directly participate in the channel gating. Syringomycin E is reported to cause lysis of erythrocytes of different origin.
Specifications
2-[(3S,6S,12S,15S,18S,21S,24S,27S)-18,21-Bis(2-aminoethyl)-12-benzyl-3-[(1R)-2-chloro-1-hydroxy-ethyl]-15-[3-(diaminomethylideneamino)propyl]-24-(hydroxymethyl)-27-(3-hydroxyundecanoylamino)-2,5,8,11,14,17,20,23,26-nonaoxo-9-propylidene-1-oxa-4,7,10,13,16,19,22,25-octazacyclooctacos-6-yl]-2-hydroxy-acetic acid