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PZ0182

Pactamycin

≥95% (HPLC)

Synonym(s):

2-Hydroxy-6-methylbenzoic acid [(1S,2R,3R,4S,5S)-5-[(3-acetylphenyl)amino]-4-amino-3-[[(dimethylamino)carbonyl]amino]-1,2-dihydroxy-3-[(1S)-1-hydroxyethyl]-2-methylcyclopentyl]methyl ester, PNU-0015800, U-15800

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About This Item

Empirical Formula (Hill Notation):
C28H38N4O8
CAS Number:
23668-11-3
Molecular Weight:
558.62
UNSPSC Code:
51101500
PubChem Substance ID:
329823756
MDL number:
MFCD00158126
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assay

≥95% (HPLC)

form

powder

optical activity

[α]/D +20 to +30° in 95% ethanol

color

white to tan

solubility

DMSO: ≥12 mg/mL

storage temp.

2-8°C

SMILES string

C[C@H](O)[C@]1(NC(=O)N(C)C)[C@@H](N)[C@H](Nc2cccc(c2)C(C)=O)[C@](O)(COC(=O)c3c(C)cccc3O)[C@]1(C)O

InChI

1S/C28H38N4O8/c1-15-9-7-12-20(35)21(15)24(36)40-14-27(39)23(30-19-11-8-10-18(13-19)16(2)33)22(29)28(17(3)34,26(27,4)38)31-25(37)32(5)6/h7-13,17,22-23,30,34-35,38-39H,14,29H2,1-6H3,(H,31,37)/t17-,22-,23-,26-,27+,28-/m0/s1

InChI key

WVIUOSJLUCTGFK-JUJPXXQGSA-N

Biochem/physiol Actions

Antitumor antibiotic
Pactamycin is a potent protein synthesis inhibitor, inhibiting protein synthesis at the translocation step on the 70S ribosome. It has activity against Gram-positive and Gram-negative bacteria, and broad antitumor, antiviral, and antiplasmodial activity. Cytotoxicity limits it clinical use.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
081M4701V

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J Cao et al.
RNA (New York, N.Y.), 4(2), 181-188 (1998-05-07)
A 22-codon upstream open reading frame (uORF2) in the human cytomegalovirus UL4 transcript leader inhibits downstream translation in cis. Previous studies revealed that the peptide product of uORF2 mediates this inhibitory effect by interfering with translation termination at its own
Hai P Nguyen et al.
Biochemistry, 58(25), 2804-2808 (2019-06-13)
Mitomycins make up a group of antitumor natural products that are biosynthesized from aminohydroxybenzoic acid (AHBA) and N-acetylglucosamine (GlcNAc). While the biosynthetic gene cluster was reported two decades ago, the mechanism by which the two building blocks, AHBA and GlcNAc
S Chiaberge et al.
The Journal of biological chemistry, 273(42), 27070-27075 (1998-10-09)
AC914 mRNA, a pre-spore-specific mRNA that accumulates only in the post-aggregation stage of development, is transcribed constitutively as shown by nuclear run-off experiments and by fusing its promoter to the luciferase reporter gene. The same mRNA disappears quickly from disaggregated
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