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A 83586C

CAT: 0931-T26456-02Size: 500 mgDry Ice: NoHazardous: No
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CAT#:0931-T26456-02Size:500 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
116364-81-9
Target
Others, Antibacterial, Antibiotic
Related Pathways
Others, Microbiology/Virology
Bioactivity
A-83586C is a depsipeptide antibiotic from Streptomyces karnatakensis with potent against Gram-positive activity in vitro. A-83586C acts as a highly potent inhibitor of beta-catenin/TCF4 signaling within cancer cells, while simultaneously downregulating osteopontin (Opn) expression. A-83586C also inhibits E2F-mediated transcription by downregulating E2F1 expression and inducing dephosphorylation of the oncogenic hyperphosphorylated retinoblastoma protein (pRb) .
Smiles
[C@@](C(N[C@H]1[C@H](C(C)C)OC(=O)[C@@]([C@H](C)O)(NC(=O)[C@]2(N(C(=O)[C@@H](C)N(C)C(=O)[C@H](C)N(O)C(=O)[C@@]3(N(C1=O)NCCC3)[H])NCCC2)[H])[H])=O)(CC)(O)[C@]4(O)O[C@H](\C(=C\[C@@H](C(/C(=C/C)/C)=O)C)\C)[C@@H](C)CC4
Molecular Formula
C47H76N8O14
Molecular Weight
977.15
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

A 83586C

from Streptomyces karnatakensis; cyclic hexadepsipeptide; structure given in first source

CAS Number116364-81-9
PubChem CID6449925
IUPAC Name(2S)-2-[(2R,5S,6S)-6-[(2E,4S,6E)-4,6-dimethyl-5-oxoocta-2,6-dien-2-yl]-2-hydroxy-5-methyloxan-2-yl]-2-hydroxy-N-[(3R,6S,9R,16S,17S,20R,23S)-7-hydroxy-20-[(1S)-1-hydroxyethyl]-3,4,6-trimethyl-2,5,8,15,19,22-hexaoxo-17-propan-2-yl-18-oxa-1,4,7,13,14,21,27-heptazatricyclo[21.4.0.09,14]heptacosan-16-yl]butanamide
Molecular FormulaC47H76N8O14
Molecular Weight977.2
XLogP3
Topological Polar Surface Area297
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count16
Rotatable Bond Count10
Heavy Atom Count69
Formal Charge0
Complexity2020
SMILES
CC[C@@](C(=O)N[C@H]1[C@@H](OC(=O)[C@H](NC(=O)[C@@H]2CCCNN2C(=O)[C@H](N(C(=O)[C@@H](N(C(=O)[C@H]3CCCNN3C1=O)O)C)C)C)[C@H](C)O)C(C)C)([C@]4(CC[C@@H]([C@H](O4)/C(=C/[C@H](C)C(=O)/C(=C/C)/C)/C)C)O)O
InChI
InChI=1S/C47H76N8O14/c1-13-25(5)36(57)27(7)23-28(8)38-26(6)19-20-47(66,69-38)46(65,14-2)45(64)51-35-37(24(3)4)68-44(63)34(31(11)56)50-39(58)32-17-15-21-48-53(32)41(60)29(9)52(12)40(59)30(10)55(67)42(61)33-18-16-22-49-54(33)43(35)62/h13,23-24,26-27,29-35,37-38,48-49,56,65-67H,14-22H2,1-12H3,(H,50,58)(H,51,64)/b25-13+,28-23+/t26-,27-,29+,30-,31-,32-,33+,34+,35-,37-,38-,46+,47+/m0/s1
InChIKey
BJRNAAQGIMGUML-IYSUCPQHSA-N
Chemical Structure
2D Structure
2D structure of A 83586C
CAS: 116364-81-9
CID: 6449925
Formula: C47H76N8O14
MW: 977.2
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight977.2
XLogP33
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count16
Rotatable Bond Count10
Exact Mass976.54809913
Monoisotopic Mass976.54809913
Topological Polar Surface Area297 Ų
Heavy Atom Count69
Formal Charge0
Complexity2020
Isotope Atom Count0
Defined Atom Stereocenter Count13
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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