(1S,3S,5R,8S,10S,11S,13R,16R,17R)-10-hydroxy-8-[(2S,3R)-3-methoxy-4,8-dimethyl-9-(2-methyl-1,3-oxazol-4-yl)nona-4,6,8-trien-2-yl]-11,16-dimethyl-4,7,12,18-tetraoxatetracyclo[15.3.1.03,5.011,13]henicos-14-ene-6,19-dione

• ChemBase ID: 153536
• Molecular Formular: C35H47NO9
• Molecular Mass: 625.74898
• Monoisotopic Mass: 625.32508209
• SMILES: Cc1nc(co1)/C=C(\C)/C=C/C=C(\C)/[C@@H]([C@@H](C)[C@@H]1C[C@@H]([C@]2([C@H](O2)C=C[C@H]([C@H]2C[C@@H](C[C@H]3[C@H](O3)C(=O)O1)CC(=O)O2)C)C)O)OC
• Canonical SMILES: CO[C@H]([C@H]([C@H]1OC(=O)[C@H]2O[C@H]2C[C@H]2CC(=O)O[C@H](C2)[C@@H](C=C[C@@H]2[C@@]([C@H](C1)O)(C)O2)C)C)/C(=C/C=C/C(=C/c1coc(n1)C)/C)/C
• InChI: InChI=1S/C35H47NO9/c1-19(13-25-18-41-23(5)36-25)9-8-10-21(3)32(40-7)22(4)27-17-29(37)35(6)30(45-35)12-11-20(2)26-14-24(16-31(38)42-26)15-28-33(43-28)34(39)44-27/h8-13,18,20,22,24,26-30,32-33,37H,14-17H2,1-7H3/t20-,22+,24+,26-,27+,28+,29+,30-,32+,33-,35+/m1/s1
• InChIKey: OWPCHSCAPHNHAV-DZGWBSNCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3S,5R,8S,10S,11S,13R,16R,17R)-10-hydroxy-8-[(2S,3R)-3-methoxy-4,8-dimethyl-9-(2-methyl-1,3-oxazol-4-yl)nona-4,6,8-trien-2-yl]-11,16-dimethyl-4,7,12,18-tetraoxatetracyclo[15.3.1.0^3,^5.0^1^1,^1^3]henicos-14-ene-6,19-dione
• IUPAC Traditional name: (1S,3S,5R,8S,10S,11S,13R,16R,17R)-10-hydroxy-8-[(2S,3R)-3-methoxy-4,8-dimethyl-9-(2-methyl-1,3-oxazol-4-yl)nona-4,6,8-trien-2-yl]-11,16-dimethyl-4,7,12,18-tetraoxatetracyclo[15.3.1.0^3,^5.0^1^1,^1^3]henicos-14-ene-6,19-dione
• Synonyms: Rhizoxin from Rhizopus sp.

Database IDs

• CAS Number: 90996-54-6
• MDL Number: MFCD01939948
• PubChem SID: 24899405; 162247675
• PubChem CID: 71308262

CALCULATED PROPERTIES

• Acid pKa: 13.824323
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 3.7225552
• LogD (pH = 7.4): 3.72256
• Log P: 3.7225602
• Molar Refractivity: 168.6673 cm^3
• Polarizability: 65.63601 Å^3
• Polar Surface Area: 133.15 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: VI1800000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: >95% (HPLC)

DETAILS

Sigma Aldrich - R8149

Biochem/physiol Actions
An antitumor agent, rhizoxin is a 16-member ring lactone having an oxazole ring in its structure. This macrolide inhibits microtubule assembly and also depolymerizes pre-formed microtubles. Rhizoxin binds to β-tubulin in most eucaryotic cells including animals, plants and fungi. It completely prevents formation of an intrachain cross-link in β-tubulin by N,N′-ethylene-bis-(iodo-acetamide). Due to its antimitotic activity it is used as an antitumor agent e.g., in human small cell lung cancer cell lines.