| Identification | Back Directory | [Name]
NISTC15503874 | [CAS]
15503-87-4 | [Synonyms]
Usaramin
Usaramine
Mucronatine
NISTC15503874
(15E)-Retrorsine
trans-Retrorsine
(15E)-12,18-Dihydroxysenecionan-11,16-dione
[1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione,3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-,(3E,5R,6S,14aR,14bR)- | [Molecular Formula]
C18H25NO6 | [MDL Number]
MFCD01684242 | [MOL File]
15503-87-4.mol | [Molecular Weight]
351.39 |
| Chemical Properties | Back Directory | [Melting point ]
178-180℃ | [Boiling point ]
583.2±50.0 °C(Predicted) | [density ]
1.32±0.1 g/cm3 (20 ºC 760 Torr) | [solubility ]
DMF: insol; DMSO: 1 mg/ml; Ethanol: insol; PBS (pH 7.2): 5 mg/ml | [form ]
A solid | [pka]
12.00±0.40(Predicted) | [color ]
White to off-white | [InChI]
InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3+/t11-,14-,15-,18-/m1/s1 | [InChIKey]
BCJMNZRQJAVDLD-FXGRWVCYSA-N | [SMILES]
N12CC=C3COC(=O)[C@@](O)(CO)[C@H](C)C/C(=C\C)/C(=O)O[C@@]([H])([C@]13[H])CC2 | [CAS DataBase Reference]
15503-87-4 |
| Hazard Information | Back Directory | [Hazard]
A poison. | [Description]
A pyrrolizidine alkaloid first isolated from Crotalaria usararnoensis E. G. Baker,
this base has more recently been found in C. brevifolia and C. rnucronata. The
alkaloid has [α]20D + 6.1° (c 0.38, EtOH) or + 7.1° (c 1.83, EtOH). It yields a
picrate, m.p. 230- 2°C (dec.); picrolonate, m.p. 148-150°C (dec.); reineckate,
m.p. 190-2°C (dec.) and methiodide, m.p. 229-230°C (dec.). Alkaline
hydrolysis furnishes retronecine and retronecic acid, m.p. 177-9°C. It has been
suggested that the base may be identical with Mucronatine (q.v.). | [Uses]
Usaramine is a pyrrolizidine alkaloid isolated from seeds of Crolatalaria pallida. Usaramine demonstrates a highlighted antibiofilm activity against Staphylococcus epidermidis by reducing more than 50% of biofilm formation without killing the bacteria[1]. | [Definition]
ChEBI: LSM-2938 is a macrolide. | [References]
Culvenor, Smith., Austral. J. Chern., 19,2127 (1966)
Sawhney et al., Ind. J. Chern., 5, 655 (1967) |
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