5,21-dichloro-23-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1(16),2(10),4,6,8,11(15),17(22),18,20-nonaene-12,14-dione

• ChemBase ID: 155075
• Molecular Formular: C27H21Cl2N3O7
• Molecular Mass: 570.37754
• Monoisotopic Mass: 569.07565539
• SMILES: CO[C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O)n1c2c(cccc2Cl)c2c1c1c(c3cccc(c3[nH]1)Cl)c1c2c(=O)[nH]c1=O)CO
• Canonical SMILES: CO[C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)n1c2c(Cl)cccc2c2c1c1[nH]c3c(c1c1c2c(=O)[nH]c1=O)cccc3Cl
• InChI: InChI=1S/C27H21Cl2N3O7/c1-38-24-13(8-33)39-27(23(35)22(24)34)32-20-10(5-3-7-12(20)29)15-17-16(25(36)31-26(17)37)14-9-4-2-6-11(28)18(9)30-19(14)21(15)32/h2-7,13,22-24,27,30,33-35H,8H2,1H3,(H,31,36,37)/t13-,22-,23-,24-,27-/m1/s1
• InChIKey: QEHOIJJIZXRMAN-QZQSLCQPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,21-dichloro-23-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0^2,^1^0.0^4,^9.0^1^1,^1^5.0^1^7,^2^2]tricosa-1(16),2(10),4,6,8,11(15),17(22),18,20-nonaene-12,14-dione
• IUPAC Traditional name: rebeccamycin
• Synonyms: Rebeccamycin

Database IDs

• CAS Number: 93908-02-2
• MDL Number: MFCD01718312
• PubChem SID: 162249213; 24899375
• PubChem CID: 73110

CALCULATED PROPERTIES

• Acid pKa: 8.051588
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 2.5884032
• LogD (pH = 7.4): 2.5032644
• Log P: 2.5896325
• Molar Refractivity: 141.0628 cm^3
• Polarizability: 58.73478 Å^3
• Polar Surface Area: 146.04 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥3 mg/mL; THF: soluble
• Apperance: yellow solid

Safety Information

• Storage Condition: protect from light
• German water hazard class: -
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... TOP1(7150)mouse ... Prkca(18750)rat ... Prkca(24680)

Product Information

• Purity: ≥98% (HPLC)
• Biological Source: from Saccharothrix aerocolonigenes
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C27H21Cl2N3O7

DETAILS

Sigma Aldrich - R4900

Biochem/physiol Actions
Rebeccamycin is an antibiotic composed of a halogenated indolocarbazole chromophore linked via N-glycosidic bond to a glucose derivative. As an antitumor agent,1 it is cytotoxic to tumor cell lines such as human lung adenocarcinoma, colon carcinoma and nasopharyngeal carcinoma, etc.2 Rebeccamycin intercalates into the DNA and is an inhibitor of topoisomerase I. It stabilizes the covalent topoisomerase I-DNA intermediate (the cleavable complex) resulting in increased DNA strand breaks.3