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Calicheamicin

Calicheamicin

Synopsis, Chemistry

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Also known as: Calicheamicin, 108212-75-5, Calicheamicin gamma1, Calicheamicin y1, Ex-a2429, Cs-5320

Molecular Formula

C₅₅H₇₄IN₃O₂₁S₄

Molecular Weight

1368.4 g/mol

InChI Key

HXCHCVDVKSCDHU-GPCZLZLMSA-N

Enediyne aminoglycosides derived from the bacterium MICROMONOSPORA ECHINOSPORA that are used as antineoplastic antibiotics. They bind to DNA in both healthy and tumor cells, resulting in strand scission and cell death.

1 2D Structure

Calicheamicin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

S-[(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,13Z)-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

2.1.2 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

2.1.3 InChI Key

HXCHCVDVKSCDHU-GPCZLZLMSA-N

2.1.4 Canonical SMILES

CCNC1COC(CC1OC)OC2C(C(C(OC2OC3C#CC=CC#CC4(CC(=O)C(=C3C4=CCSSSC)NC(=O)OC)O)C)NOC5CC(C(C(O5)C)SC(=O)C6=C(C(=C(C(=C6OC)OC)OC7C(C(C(C(O7)C)O)OC)O)I)C)O)O

2.1.5 Isomeric 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

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Calicheamicin

2. Calicheamicins

3. Calicheamicin Gamma(1)i

4. Calichemicin Gamma1

2.2.2 Depositor-Supplied Synonyms

1. Calicheamicin

2. 108212-75-5

3. Calicheamicin Gamma1

4. Calicheamicin Y1

5. Ex-a2429

6. Cs-5320

7. Ac-31931

8. Hy-19609

2.3 Create Date

2015-12-18

3 Chemical and Physical Properties

Molecular Formula	C₅₅H₇₄IN₃O₂₁S₄
Molecular Weight	1368.4 g/mol
XLogP3	2
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	27
Rotatable Bond Count	24
Exact Mass	1367.27424 g/mol
Monoisotopic Mass	1367.27424 g/mol
Topological Polar Surface Area	410 Å²
Heavy Atom Count	84
Formal Charge	0
Complexity	2500
Isotope Atom Count	0
Defined Atom Stereocenter Count	19
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

Mutagens

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes. (See all compounds classified as Mutagens.)