(2S,3S,4S)-6-{[(2S,3S,4S)-6-{[(2R,3R,4R)-6-{[(2S,3S)-6-{[(4S,5R,6S)-5-(acetyloxy)-4-{[(4S,5S,6S)-4-hydroxy-5-methoxy-6-methyloxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-3-[(1R,3S,4S)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-8,9-dihydroxy-7-methyl-1-oxo-1,2,3,4-tetrahydroanthracen-2-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl acetate

• ChemBase ID: 155131
• Molecular Formular: C57H82O26
• Molecular Mass: 1183.24538
• Monoisotopic Mass: 1182.50943274
• SMILES: Cc1c(cc2cc3c(c(c2c1O)O)C(=O)[C@H]([C@@H](C3)[C@H](C(=O)[C@H]([C@H](C)O)O)OC)OC1C[C@H]([C@@H]([C@H](O1)C)O)OC1C[C@@H]([C@H]([C@@H](O1)C)O)OC1C[C@]([C@H]([C@@H](O1)C)OC(=O)C)(C)O)OC1C[C@@H]([C@@H]([C@@H](O1)C)OC(=O)C)OC1C[C@@H]([C@@H]([C@@H](O1)C)OC)O
• Canonical SMILES: CO[C@H]([C@@H]1Cc2cc3cc(OC4C[C@H](OC5C[C@H](O)[C@@H]([C@@H](O5)C)OC)[C@@H]([C@@H](O4)C)OC(=O)C)c(c(c3c(c2C(=O)[C@H]1OC1C[C@@H](OC2C[C@H](OC3O[C@@H](C)[C@@H]([C@@](C3)(C)O)OC(=O)C)[C@H]([C@@H](O2)C)O)[C@@H]([C@H](O1)C)O)O)O)C)C(=O)[C@H]([C@@H](O)C)O
• InChI: InChI=1S/C57H82O26/c1-21-34(79-40-19-37(53(26(6)75-40)77-28(8)59)82-38-16-33(61)52(70-11)25(5)74-38)15-31-13-30-14-32(54(71-12)51(68)46(63)22(2)58)55(50(67)44(30)49(66)43(31)45(21)62)83-41-18-35(47(64)24(4)73-41)80-39-17-36(48(65)23(3)72-39)81-42-20-57(10,69)56(27(7)76-42)78-29(9)60/h13,15,22-27,32-33,35-42,46-48,52-56,58,61-66,69H,14,16-20H2,1-12H3/t22-,23-,24+,25-,26-,27-,32-,33-,35+,36-,37-,38?,39?,40?,41?,42?,46-,47+,48-,52+,53+,54+,55-,56-,57-/m0/s1
• InChIKey: ZYVSOIYQKUDENJ-MTPXVABGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S)-6-{[(2S,3S,4S)-6-{[(2R,3R,4R)-6-{[(2S,3S)-6-{[(4S,5R,6S)-5-(acetyloxy)-4-{[(4S,5S,6S)-4-hydroxy-5-methoxy-6-methyloxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-3-[(1R,3S,4S)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-8,9-dihydroxy-7-methyl-1-oxo-1,2,3,4-tetrahydroanthracen-2-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl acetate
• IUPAC Traditional name: (2S,3S,4S)-6-{[(2S,3S,4S)-6-{[(2R,3R,4R)-6-{[(2S,3S)-6-{[(4S,5R,6S)-5-(acetyloxy)-4-{[(4S,5S,6S)-4-hydroxy-5-methoxy-6-methyloxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-3-[(1R,3S,4S)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-8,9-dihydroxy-7-methyl-1-oxo-3,4-dihydro-2H-anthracen-2-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]oxy}-3-hydroxy-2-methyloxan-4-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl acetate
• Synonyms: Chromomycin A3 from Streptomyces griseus

Database IDs

• CAS Number: 7059-24-7
• EC Number: 230-348-0
• MDL Number: MFCD00043151
• PubChem SID: 24856424; 162249269; 24892514
• PubChem CID: 15953908

CALCULATED PROPERTIES

• Acid pKa: 8.491728
• H Acceptors: 24
• H Donor: 8
• LogD (pH = 5.5): 3.5978289
• LogD (pH = 7.4): 3.564568
• Log P: 3.5982683
• Molar Refractivity: 280.0633 cm^3
• Polarizability: 115.29123 Å^3
• Polar Surface Area: 359.34 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: GB7875000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 61-28
• Safety Statements: 53-28-36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H360
• GHS Precautionary statements: P201-P264-P301 + P310-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 1
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ~95% (HPLC); ≥95% (HPLC)
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C57H82O26

DETAILS

Sigma Aldrich - C2659

Biochem/physiol Actions
An antibiotic exhibiting anti-bacterial, anti-fungal and antitumor activities. Serves as a fluorescent DNA stain. Useful for the detection of protamine deficiency in sperm chromatin. The compound blocks macromolecule synthesis by a specific, reversible interaction with DNA in the presence of bivalent metal ions. Binding to DNA minor groove mediates an efficient competitive inhibition of DNA gyrase and significantly affects topoisomerase II activity.

Sigma Aldrich - 27100

Other Notes
Review: As inhibitor of DNA and RNA polymerase1; Fluorescent staining of DNA for flow cytometry2