(1R,4R,5R,6R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadeca-10(16),11-diene-3,7-dione

• ChemBase ID: 165656
• Molecular Formular: C16H21NO6
• Molecular Mass: 323.34104
• Monoisotopic Mass: 323.1368874
• SMILES: c12ccn3c1[C@@H](CC3)OC(=O)[C@@H]([C@]([C@](C(=O)OC2)(O)C)(O)C)C
• Canonical SMILES: O=C1O[C@@H]2CCn3c2c(COC(=O)[C@]([C@]([C@H]1C)(C)O)(C)O)cc3
• InChI: InChI=1S/C16H21NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,6,9,11,20-21H,5,7-8H2,1-3H3/t9-,11+,15+,16-/m0/s1
• InChIKey: ZONSVLURFASOJK-LLAGZRPASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4R,5R,6R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0^1^3,^1^6]hexadeca-10(16),11-diene-3,7-dione
• IUPAC Traditional name: (1R,4R,5R,6R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0^1^3,^1^6]hexadeca-10(16),11-diene-3,7-dione
• Synonyms: (3R,4R,5R,13aR)-4,5,8,12,13,13a-Hexahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione; Monocrotaline Pyrrole, 3,8-Didehydromonocrotaline; Dehydro Monocrotaline, 90%

Database IDs

• CAS Number: 23291-96-5
• PubChem SID: 162259789
• PubChem CID: 104764

CALCULATED PROPERTIES

• Acid pKa: 11.494031
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.4516037
• LogD (pH = 7.4): 0.45156923
• Log P: 0.45160416
• Molar Refractivity: 79.5687 cm^3
• Polarizability: 31.551207 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Beige Solid
• Melting Point: 77-79°C (dec.)

Safety Information

• Storage Condition: -86°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D229750

A metabolite of the potent hepatotoxin Monocrotaline.

REFERENCES

• Mattocks, A.R.: J.C.S., 8, 1155 (1969)
• Tepe, J.J. and Williams, R.M.: JACS, 121, 13, 2951 (1999)