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Ikarugamycin

CAT: 0931-T15556-01Size: 500 µgDry Ice: NoHazardous: No
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CAT#:0931-T15556-01Size:500 µg
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CAS Number
36531-78-9
Target
Others, Apoptosis, Caspase, Antibiotic
Related Pathways
Apoptosis, Others, Proteases/Proteasome, Microbiology/Virology
Bioactivity
Ikarugamycin is a macrolide antibiotic discovered in Streptomyces, exhibiting antiprotozoal activity, inducing apoptosis and activating caspases, and also acting as a CME (clathrin-mediated endocytosis) inhibitor.
Smiles
C(C)[C@H]1[C@]2([C@@]([C@@]3([C@@]([C@@]4([C@@](C3)(/C=C/C(=O)C5=C(O)[C@@](NC5=O)(CCCNC(=O)/C=C\C4)[H])[H])[H])(C=C2)[H])[H])(C[C@H]1C)[H])[H]
Molecular Formula
C29H38N2O4
Molecular Weight
478.62
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Ikarugamycin

Ikarugamycin is a polyketide macrolactam containing a tetramic acid (pyrrolidine-2,4-dione) ring system. It is isolated from Streptomyces as an antibiotic with antiprotozoal and cytotoxic activities. It has a role as an antimicrobial agent, an antineoplastic agent, an antiprotozoal drug, an apoptosis inducer and a bacterial metabolite. It is a lactam, a polyketide, an organic heteropentacyclic compound, an enone and an azamacrocycle.

CAS Number36531-78-9
PubChem CID54680304
IUPAC Name(1Z,3E,5S,7R,8R,10R,11R,12S,15R,16S,18Z,25S)-11-ethyl-2-hydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.05,16.07,15.08,12]octacosa-1,3,13,18-tetraene-20,27,28-trione
Molecular FormulaC29H38N2O4
Molecular Weight478.6
XLogP5
Topological Polar Surface Area95.5
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count1
Heavy Atom Count35
Formal Charge0
Complexity1010
SMILES
CC[C@@H]1[C@@H](C[C@H]2[C@H]1C=C[C@H]3[C@@H]2C[C@@H]/4[C@@H]3C/C=C\C(=O)NCCC[C@H]5C(=O)/C(=C(\C=C4)/O)/C(=O)N5)C
InChI
InChI=1S/C29H38N2O4/c1-3-18-16(2)14-22-20(18)10-11-21-19-6-4-8-26(33)30-13-5-7-24-28(34)27(29(35)31-24)25(32)12-9-17(19)15-23(21)22/h4,8-12,16-24,32H,3,5-7,13-15H2,1-2H3,(H,30,33)(H,31,35)/b8-4-,12-9+,27-25-/t16-,17-,18-,19+,20+,21-,22+,23+,24+/m1/s1
InChIKey
GHXZHWYUSAWISC-KZRBWAKNSA-N
Chemical Structure
2D Structure
2D structure of Ikarugamycin
CAS: 36531-78-9
CID: 54680304
Formula: C29H38N2O4
MW: 478.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight478.6
XLogP35
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count1
Exact Mass478.28315770
Monoisotopic Mass478.28315770
Topological Polar Surface Area95.5 Ų
Heavy Atom Count35
Formal Charge0
Complexity1010
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
LBA53178-01Ikarugamycin
A18973-1Ikarugamycin 1mg
A18973-0.5Ikarugamycin 0.5mg
452207-01Ikarugamycin discontinued, see I2300-20

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