Basic information
- CAS
151276-95-8- Standard SMILES
CCCCCCCCC/C=C/C=C/C(=O)NCC(=O)N[C@@H]1[C@@H](O)[C@@H](O)[C@@H](Nc2ncnc3nc[nH]c23)O[C@H]1[C@@H](O)CO- InChIKey
LQIPDFIUPOYMPR-BKYURJJWSA-N- Molecular formula
- C28H43N7O7
- Average molar mass
- 589.7 g/mol
- Monoisotopic mass
- 589.32239674
Overview
KRN-5500 is under investigation in clinical trial NCT00002923 (KRN5500 in Treating Patients With Metastatic Solid Tumors).
Names & identifiers
- Preferred name
- Krn-5500
- IUPAC
- (2E,4E)-N-[2-[[(2R,3R,4R,5R,6S)-2-[(1S)-1,2-dihydroxyethyl]-4,5-dihydroxy-6-(7H-purin-6-ylamino)oxan-3-yl]amino]-2-oxoethyl]tetradeca-2,4-dienamide
- English name
- KRN-5500
- Molecular formula
- C28H43N7O7
- Molecular weight
- 589.68
Names & synonyms
Krn 5500KRN-5500151276-95-8KRN5500SPK-2418VH13L5K20DTXSID608733336-(4-Deoxy-4-((2E,4E)-tetradecadienoylglycyl)amino-L-glycero-b-L-mannoheptopyranosyl)amino-9H-purineNSC-650426RefChem:151469DTXCID10820837(2E,4E)-N-((((2R,3R,4R,5R,6S)-2-((1S)-1,2-dihydroxyethyl)-4,5-dihydroxy-6-((9H-purin-6-yl)amino)oxan-3-yl)carbamoyl)methyl)tetradeca-2,4-dienamide
Show more names
NSC650426L-glycero-β-L-manno-Heptopyranosylamine, 4-deoxy-4-[[2-[[(2E,4E)-1-oxo-2,4-tetradecadien-1-yl]amino]acetyl]amino]-N-1H-purin-6-yl-(2E,4E)-N-[2-[[(2R,3R,4R,5R,6S)-2-[(1S)-1,2-dihydroxyethyl]-4,5-dihydroxy-6-(7H-purin-6-ylamino)oxan-3-yl]amino]-2-oxoethyl]tetradeca-2,4-dienamide
UNII-8VH13L5K20orb1700223SCHEMBL2357505CHEMBL4296683SCHEMBL30626129SCHEMBL31060330AKOS040748681DB15215
Database identifiers
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 215 Ų
- Hydrogen bond donors
- 8
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 17
- Heavy atoms
- 42
- Formal charge
- 0
- Complexity
- 880
Physicochemical properties
- Density
- 1.4 · 1.40±0.1 g/cm3(Predicted)
- pka
- 12.95 · 12.95±0.46(Predicted)
- NCI Dictionary of Cancer Terms
- 5500 · KRN5500
- FDA UNII
- 8 VH13L5K20 · 8VH13L5K20
- NCI Drug Dictionary
- 5500 · KRN5500
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.
Applications
UsesKRN5500 (NSC 650426), a Spicamycin (HY-127130) derivative and a nucleoside-like antibiotic with anti-tumor activity. KRN5500 also induces apoptosis via the down-regulation of Bcl-2 expression. KRN5500 shows a significant efficacy in the human tumor xenograft model in mice[1][2].
Suppliers4 total
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
BOC Sciences+1-631-485-4226 · [email protected]
济南思考化学有限公司0531-0000 · [email protected]
TargetMol中国（陶术生物）15002134094 · [email protected]
Related reactions
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Compound notes
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