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Thiocoraline

CAT: 0931-T36096Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0931-T36096Size:1 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
173046-02-1
Target
Others, Antibacterial
Related Pathways
Others, Microbiology/Virology
Bioactivity
Thiocoraline is a depsipeptide and DNAbis-intercalator originally isolated fromMicromonosporawith antibacterial and anticancer activities.1,2It is active against the Gram-positive bacteriaS. aureus, B. subtilis, andM. luteus (MICs = 0.05, 0.05, and 0.03 μg/ml, respectively) but not Gram-negativeE. coli, K. pneumoniae, orP. aeruginosa (MICs = >100 μg/ml for all) .1Thiocoraline inhibits RNA and DNA polymerase and thymidylate synthase (IC50s = 6, 6, and 15 μg/ml, respectively), as well as RNA and DNA synthesisin vitro (IC50s = 0.008 and 0.4 μg/ml, respectively) . It is cytotoxic to P388, A549, HT-29, and MEL-28 cancer cells (IC50s = 0.002, 0.002, 0.01, and 0.002 μg/ml, respectively) .
Smiles
CSCC1N(C)C(=O)C2CSSCC(N(C)C(=O)CNC(=O)C(CSC1=O)NC(=O)c1nc3ccccc3cc1O)C(=O)N(C)C(CSC)C(=O)SCC(NC(=O)c1nc3ccccc3cc1O)C(=O)NCC(=O)N2C
Molecular Formula
C48H56N10O12S6
Molecular Weight
1157.39
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Thiocoraline

Thiocoraline has been reported in Micromonospora marina, Micromonospora, and Streptomyces albus with data available.

CAS Number173046-02-1
PubChem CID485475
IUPAC Name3-hydroxy-N-[20-[(3-hydroxyquinoline-2-carbonyl)amino]-2,12,15,25-tetramethyl-11,24-bis(methylsulfanylmethyl)-3,6,10,13,16,19,23,26-octaoxo-9,22,28,29-tetrathia-2,5,12,15,18,25-hexazabicyclo[12.12.4]triacontan-7-yl]quinoline-2-carboxamide
Molecular FormulaC48H56N10O12S6
Molecular Weight1157.4
XLogP3.2
Topological Polar Surface Area450
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count20
Rotatable Bond Count8
Heavy Atom Count76
Formal Charge0
Complexity2000
SMILES
CN1C2CSSCC(C(=O)N(C(C(=O)SCC(C(=O)NCC1=O)NC(=O)C3=NC4=CC=CC=C4C=C3O)CSC)C)N(C(=O)CNC(=O)C(CSC(=O)C(N(C2=O)C)CSC)NC(=O)C5=NC6=CC=CC=C6C=C5O)C
InChI
InChI=1S/C48H56N10O12S6/c1-55-31-23-75-76-24-32(46(68)58(4)34(22-72-6)48(70)74-19-29(41(63)49-17-37(55)61)53-43(65)39-35(59)15-25-11-7-9-13-27(25)51-39)56(2)38(62)18-50-42(64)30(20-73-47(69)33(21-71-5)57(3)45(31)67)54-44(66)40-36(60)16-26-12-8-10-14-28(26)52-40/h7-16,29-34,59-60H,17-24H2,1-6H3,(H,49,63)(H,50,64)(H,53,65)(H,54,66)
InChIKey
UPGGKUQISSWRJJ-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Thiocoraline
CAS: 173046-02-1
CID: 485475
Formula: C48H56N10O12S6
MW: 1157.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1157.4
XLogP33.2
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count20
Rotatable Bond Count8
Exact Mass1156.24034430
Monoisotopic Mass1156.24034430
Topological Polar Surface Area450 Ų
Heavy Atom Count76
Formal Charge0
Complexity2000
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count6
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
HY-P3116Thiocoraline

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