(2E,10E,12E,16E,18E)-17-ethyl-6-hydroxy-9-(hydroxymethyl)-3,5,7,11,15-pentamethyl-19-(3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-oxononadeca-2,10,12,16,18-pentaenoic acid

• ChemBase ID: 131740
• Molecular Formular: C33H48O7
• Molecular Mass: 556.73002
• Monoisotopic Mass: 556.34000388
• SMILES: CC/C(=C\C(C)C/C=C/C(=C/C(CO)C(=O)C(C)C(C(C)C/C(=C/C(=O)O)/C)O)/C)/C=C/C1C(C=CC(=O)O1)C
• Canonical SMILES: OCC(C(=O)C(C(C(C/C(=C/C(=O)O)/C)C)O)C)/C=C(/C=C/CC(/C=C(/C=C/C1OC(=O)C=CC1C)\CC)C)\C
• InChI: InChI=1S/C33H48O7/c1-8-27(13-14-29-24(5)12-15-31(37)40-29)17-21(2)10-9-11-22(3)18-28(20-34)33(39)26(7)32(38)25(6)16-23(4)19-30(35)36/h9,11-15,17-19,21,24-26,28-29,32,34,38H,8,10,16,20H2,1-7H3,(H,35,36)/b11-9+,14-13+,22-18+,23-19+,27-17+
• InChIKey: KZMHNEBMQDBQND-MRBODPGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,10E,12E,16E,18E)-17-ethyl-6-hydroxy-9-(hydroxymethyl)-3,5,7,11,15-pentamethyl-19-(3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-oxononadeca-2,10,12,16,18-pentaenoic acid
• IUPAC Traditional name: (2E,10E,12E,16E,18E)-17-ethyl-6-hydroxy-9-(hydroxymethyl)-3,5,7,11,15-pentamethyl-19-(3-methyl-6-oxo-2,3-dihydropyran-2-yl)-8-oxononadeca-2,10,12,16,18-pentaenoic acid
• Synonyms: Kazusamycin A

Database IDs

• CAS Number: 92090-94-3
• MDL Number: MFCD03265635
• PubChem SID: 162226017
• PubChem CID: 5477877

CALCULATED PROPERTIES

• Acid pKa: 4.568904
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 5.316503
• LogD (pH = 7.4): 3.5421696
• Log P: 6.294634
• Molar Refractivity: 164.2527 cm^3
• Polarizability: 61.916958 Å^3
• Polar Surface Area: 121.13 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: chloroform: soluble; DMSO: soluble; ethanol: soluble; H2O: insoluble; hexane: insoluble; methanol: soluble; methanol: water: soluble7:3
• Apperance: aqueous methanol solution
• Flash Point: 15 °C; 59 °F

Safety Information

• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: 1230
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H301-H311-H331-H370
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1230 3/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Biological Source: from Streptomyces sp.
• Shipped in: dry ice

DETAILS

Sigma Aldrich - K1764

Biochem/physiol Actions
Kazusamycin A, an unsaturated branched chain fatty acid with a terminal lactone ring, is a hydroxy analog of Leptomycin B. It has significant in vitro cytotoxic activity against various human and mouse tumor lines encompassing a wide range of tissue types. Kazusamycin A exhibits in vivo antitumor activity against experimental murine tumors. It inhibits nuclear export and Rev translocation, a regulatory gene product in the HIV genome, at nanomolar concentrations.
Physical form
70% methanol solution.