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Rebeccamycin

CAT: 0931-T16726-02Size: 2500 μgDry Ice: NoHazardous: No
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CAT#:0931-T16726-02Size:2500 μg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
93908-02-2
Target
ADC Cytotoxin, Antibiotic, Topoisomerase
Related Pathways
Microbiology/Virology, DNA Damage/DNA Repair, Antibody-drug Conjugate/ADC Related
Bioactivity
Rebeccamycin is an antitumor antibiotic+ inhibits DNA topoisomerase I. Rebeccamycin appears to exert its primary antineoplastic effect by poisoning topoisomerase I. It also has a negligible effect on protein kinase C and topoisomerase II.
Smiles
O=C1C2=C3C(N(C=4C3=CC=CC4Cl)[C@@]5(O[C@H](CO)[C@@H](OC)[C@H](O)[C@H]5O)[H])=C6C(=C2C(=O)N1)C=7C(N6)=C(Cl)C=CC7
Molecular Formula
C27H21Cl2N3O7
Molecular Weight
570.38
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Rebeccamycin

Rebeccamycin is a N-glycosyl compound, an organochlorine compound, an organic heterohexacyclic compound and an indolocarbazole.

CAS Number93908-02-2
PubChem CID73110
IUPAC Name5,21-dichloro-3-[(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-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione
Molecular FormulaC27H21Cl2N3O7
Molecular Weight570.4
XLogP2.6
Topological Polar Surface Area146
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count7
Rotatable Bond Count3
Heavy Atom Count39
Formal Charge0
Complexity1010
SMILES
CO[C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O)N2C3=C(C=CC=C3Cl)C4=C5C(=C6C7=C(C(=CC=C7)Cl)NC6=C42)C(=O)NC5=O)CO
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
Chemical Structure
2D Structure
2D structure of Rebeccamycin
CAS: 93908-02-2
CID: 73110
Formula: C27H21Cl2N3O7
MW: 570.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight570.4
XLogP32.6
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count7
Rotatable Bond Count3
Exact Mass569.0756554
Monoisotopic Mass569.0756554
Topological Polar Surface Area146 Ų
Heavy Atom Count39
Formal Charge0
Complexity1010
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
HY-19825Rebeccamycin
GA2054-1mgRebeccamycin solid
207378-01Rebeccamycin (NSC 359079, BRN 4732638)
MBS1478150-01Recombinant Lechevalieria aerocolonigenes Rebeccamycin O-methyltransferase (rebM)
207087-01Becatecarin (6-N-[2- (Diethylamino) ethyl]rebeccamycin, NSC 655649, BMY-27557-14, BMS-181176, XL119)

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