3-(3-bromo-4-hydroxyphenyl)-N-[2-({2-[3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-2-(N-hydroxyimino)propanamide

• ChemBase ID: 153164
• Molecular Formular: C22H24Br2N4O6S2
• Molecular Mass: 664.38716
• Monoisotopic Mass: 661.95040051
• SMILES: c1c(cc(c(c1)O)Br)C/C(=N/O)/C(=O)NCCSSCCNC(=O)/C(=N\O)/Cc1cc(c(cc1)O)Br
• Canonical SMILES: O/N=C(\C(=O)NCCSSCCNC(=O)/C(=N\O)/Cc1ccc(c(c1)Br)O)/Cc1ccc(c(c1)Br)O
• InChI: InChI=1S/C22H24Br2N4O6S2/c23-15-9-13(1-3-19(15)29)11-17(27-33)21(31)25-5-7-35-36-8-6-26-22(32)18(28-34)12-14-2-4-20(30)16(24)10-14/h1-4,9-10,29-30,33-34H,5-8,11-12H2,(H,25,31)(H,26,32)
• InChIKey: LMAFSGDNHVBIHU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(3-bromo-4-hydroxyphenyl)-N-[2-({2-[3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-2-(N-hydroxyimino)propanamide
• IUPAC Traditional name: 3-(3-bromo-4-hydroxyphenyl)-N-[2-({2-[3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-2-(N-hydroxyimino)propanamide
• Synonyms: Bisprasin, N,N"-(dithiodi-2,1-ethanediyl)bis[3-bromo-4-hydroxy-a-(hydroxyimino)-benzenepropanamide; Psammaplin A

Database IDs

• CAS Number: 110659-91-1
• PubChem SID: 162247303
• PubChem CID: 6399893

CALCULATED PROPERTIES

• Acid pKa: 6.273931
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): 4.0113583
• LogD (pH = 7.4): 2.2065783
• Log P: 4.081383
• Molar Refractivity: 149.0862 cm^3
• Polarizability: 56.860638 Å^3
• Polar Surface Area: 163.84 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble
• Apperance: solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C22H24Br2N4O6S2

DETAILS

Sigma Aldrich - P8749

Biochem/physiol Actions
Psammaplin A is an antibiotic, anti-tumor, DNA methyltransferase inhibitor. It is a bromotyrosine-derived, symmetrical conjugate of cystamine, which was first isolated from the Psammaplinaplysilla sponge. Psammaplin A impedes angiogenesis as well as bacterial and tumor cell growth. Psammaplin A inhibits the activities of several key enzymes in prokaryotic and eukaryotic systems including those involved in epigenetic control of gene expression, DNA replication, angiogensis, and microbial detoxification.