Shurimycin A

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Category Antibiotics
Catalog number BBF-02907
CAS 143906-47-2
Molecular Weight 1082.36
Molecular Formula C56H95N3O17

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Description

It is produced by the strain of Str. hygroscopicus A1491. It has anti-gram-positive bacteria and fungi effects.

Specification

Synonyms Scopafungin, 2,3-didehydro-35-de[11-[[imino(methylamino)methyl]amino]-1,3-dimethyl-7-undecenyl]-2-demethyl-3-deoxy-35-[9-[[imino(methylamino)methyl]amino]-1-methyl-5-nonenyl]-30-methyl-; MBA 028-24A; Antibiotic MBA 028-24A
IUPAC Name 3-[[(10E,12E,18Z,20E)-5,7,9,23,25,27,31,33,34,35-decahydroxy-8,10,14,22,26,30-hexamethyl-15-[(E)-10-[(N'-methylcarbamimidoyl)amino]dec-6-en-2-yl]-17-oxo-16,37-dioxabicyclo[31.3.1]heptatriaconta-10,12,18,20-tetraen-3-yl]oxy]-3-oxopropanoic acid
Canonical SMILES CC1CCC(C(C(CC(C(C=CC=CC(=O)OC(C(C=CC=C(C(C(C(CC(CC(CC2CC(C(C(O2)(CC1O)O)O)O)OC(=O)CC(=O)O)O)O)C)O)C)C)C(C)CCCC=CCCCNC(=NC)N)C)O)O)C)O
InChI InChI=1S/C56H95N3O17/c1-33-18-14-15-22-50(69)75-53(36(4)19-13-11-9-10-12-16-25-59-55(57)58-8)37(5)21-17-20-35(3)52(71)39(7)45(63)27-40(60)26-41(74-51(70)31-49(67)68)28-42-29-47(65)54(72)56(73,76-42)32-48(66)34(2)23-24-43(61)38(6)46(64)30-44(33)62/h9-10,14-15,17-18,20-22,33-34,36-48,52-54,60-66,71-73H,11-13,16,19,23-32H2,1-8H3,(H,67,68)(H3,57,58,59)/b10-9+,18-14+,21-17+,22-15-,35-20+
InChI Key LTUWJYTYKHHVPU-RNIVMLCHSA-N

Properties

Appearance Colorless Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Fungi
Boiling Point 1137.8±75.0°C (Predicted)
Melting Point 130°C (dec.)
Density 1.26±0.1 g/cm3 (Predicted)
Solubility Soluble in Methanol, Acetone

Reference Reading

1. Structural studies of new macrolide antibiotics, shurimycins A and B
S Kumazawa, Y Asami, K Awane, H Ohtani, C Fukuchi, T Mikawa, T Hayase J Antibiot (Tokyo). 1994 Jun;47(6):688-96. doi: 10.7164/antibiotics.47.688.
The structures of new antibiotics, shurimycins A and B produced by Streptomyces hygroscopicus A1491, were elucidated from the physico-chemical properties, 2D NMR techniques and chemical degradation experiments to be 36-membered macrolides related to azalomycins, scopafungin and guanidylfungins. Shurimycins were active against fungi and Gram-positive bacteria.

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