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Calicheamicin

CAT: 0931-T14858-02Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0931-T14858-02Size:1 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
108212-75-5
Target
DNA Alkylator/Crosslinker, Apoptosis, ADC Cytotoxin, Antibacterial, Antibiotic
Related Pathways
Microbiology/Virology, Apoptosis, Antibody-drug Conjugate/ADC Related, DNA Damage/DNA Repair
Purity
0.9878
Bioactivity
Calicheamicin (Calicheamicin γ1) is an antitumor antibiotic and is a DNA synthesis inhibitor. It also is a cytotoxic agent that causes double-strand DNA breaks.
Smiles
[H][C@@]1(C[C@H](OC)[C@H](CO1)NCC)O[C@@H]1[C@@H](O)[C@H](NO[C@H]2C[C@H](O)[C@H](SC(=O)c3c(C)c(I)c(O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](OC)[C@H]4O)c(OC)c3OC)[C@@H](C)O2)[C@@H](C)O[C@@]1([H])O[C@H]1C#C\C=C/C#C[C@]2(O)CC(=O)C(NC(=O)OC)=C1\C2=C\CSSSC
Molecular Formula
C55H74IN3O21S4
Molecular Weight
1368.35
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Calicheamicin gamma1I

structure given in first source; isolated from Micromonospora echinospora sp. calichensis; acts as a DNA double-stranded cleaving agent

CAS Number108212-75-5
PubChem CID10953353
IUPAC NameS-[(2R,3S,4S,6S)-6-[[(2R,3S,4S,5R,6R)-5-[(2S,4S,5S)-5-(ethylamino)-4-methoxyoxan-2-yl]oxy-4-hydroxy-6-[[(2S,5Z,9R,13E)-9-hydroxy-12-(methoxycarbonylamino)-13-[2-(methyltrisulfanyl)ethylidene]-11-oxo-2-bicyclo[7.3.1]trideca-1(12),5-dien-3,7-diynyl]oxy]-2-methyloxan-3-yl]amino]oxy-4-hydroxy-2-methyloxan-3-yl] 4-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5-iodo-2,3-dimethoxy-6-methylbenzenecarbothioate
Molecular FormulaC55H74IN3O21S4
Molecular Weight1368.4
XLogP2
Topological Polar Surface Area410
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count27
Rotatable Bond Count24
Heavy Atom Count84
Formal Charge0
Complexity2500
SMILES
CCN[C@H]1CO[C@H](C[C@@H]1OC)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@H]3C#C/C=C\C#C[C@@]\4(CC(=O)C(=C3/C4=C\CSSSC)NC(=O)OC)O)C)NO[C@H]5C[C@@H]([C@@H]([C@H](O5)C)SC(=O)C6=C(C(=C(C(=C6OC)OC)O[C@H]7[C@@H]([C@@H]([C@H]([C@@H](O7)C)O)OC)O)I)C)O)O
InChI
InChI=1S/C55H74IN3O21S4/c1-12-57-30-24-73-35(22-34(30)68-6)78-48-43(63)40(26(3)75-53(48)77-33-17-15-13-14-16-19-55(67)23-32(61)41(58-54(66)72-10)38(33)29(55)18-20-82-84-81-11)59-80-36-21-31(60)50(28(5)74-36)83-51(65)37-25(2)39(56)46(49(71-9)45(37)69-7)79-52-44(64)47(70-8)42(62)27(4)76-52/h13-14,18,26-28,30-31,33-36,40,42-44,47-48,50,52-53,57,59-60,62-64,67H,12,20-24H2,1-11H3,(H,58,66)/b14-13-,29-18+/t26-,27+,28-,30+,31+,33+,34+,35+,36+,40-,42+,43+,44-,47-,48-,50-,52+,53+,55+/m1/s1
InChIKey
HXCHCVDVKSCDHU-PJKCJEBCSA-N
Chemical Structure
2D Structure
2D structure of Calicheamicin gamma1I
CAS: 108212-75-5
CID: 10953353
Formula: C55H74IN3O21S4
MW: 1368.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1368.4
XLogP32
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count27
Rotatable Bond Count24
Exact Mass1367.27424
Monoisotopic Mass1367.27424
Topological Polar Surface Area410 Ų
Heavy Atom Count84
Formal Charge0
Complexity2500
Isotope Atom Count0
Defined Atom Stereocenter Count19
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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