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Identification
NamePuromycin
Accession NumberDB08437
TypeSmall Molecule
GroupsExperimental
Description

Puromycin is an antibiotic that is a protein synthesis inhibitor by inhibiting translation. Puromycin is used in cell biology as selective agent in cell culture systems. It is toxic to prokaryotic and eukaryotic cells.

Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII4A6ZS6Q2CL
CAS number53-79-2
WeightAverage: 471.5096
Monoisotopic: 471.223017073
Chemical FormulaC22H29N7O5
InChI KeyInChIKey=RXWNCPJZOCPEPQ-NVWDDTSBSA-N
InChI
InChI=1S/C22H29N7O5/c1-28(2)19-17-20(25-10-24-19)29(11-26-17)22-18(31)16(15(9-30)34-22)27-21(32)14(23)8-12-4-6-13(33-3)7-5-12/h4-7,10-11,14-16,18,22,30-31H,8-9,23H2,1-3H3,(H,27,32)/t14-,15+,16+,18+,22+/m0/s1
IUPAC Name
(2S)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-methoxyphenyl)propanamide
SMILES
[H][C@](N)(CC1=CC=C(OC)C=C1)C(=O)N[C@]1([H])[C@@]([H])(CO)O[C@@]([H])(N2C=NC3=C(N=CN=C23)N(C)C)[C@]1([H])O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • 6-alkylaminopurine
  • N-glycosyl compound
  • Glycosyl compound
  • Phenylpropylamine
  • Amphetamine or derivatives
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Methoxybenzene
  • Dialkylarylamine
  • Phenol ether
  • Anisole
  • Aralkylamine
  • Aminopyrimidine
  • Alkyl aryl ether
  • Fatty acyl
  • Imidolactam
  • Benzenoid
  • Pyrimidine
  • N-substituted imidazole
  • Monosaccharide
  • Fatty amide
  • Saccharide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9747
Blood Brain Barrier-0.8691
Caco-2 permeable-0.7728
P-glycoprotein substrateSubstrate0.737
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.9243
CYP450 2C9 substrateNon-substrate0.8029
CYP450 2D6 substrateNon-substrate0.8107
CYP450 3A4 substrateSubstrate0.7097
CYP450 1A2 substrateNon-inhibitor0.9058
CYP450 2C9 inhibitorNon-inhibitor0.9133
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9393
CYP450 3A4 inhibitorNon-inhibitor0.724
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8922
Ames testNon AMES toxic0.8607
CarcinogenicityNon-carcinogens0.8681
BiodegradationNot ready biodegradable0.9882
Rat acute toxicity2.2651 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9903
hERG inhibition (predictor II)Non-inhibitor0.5719
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point168°C-182°Chttp://www.fermentek.co.il/puromycin.htm
water solubility50mg/mlhttp://www.fermentek.co.il/puromycin.htm
Predicted Properties
PropertyValueSource
Water Solubility1.01 mg/mLALOGPS
logP-0.1ALOGPS
logP-0.3ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)12.35ChemAxon
pKa (Strongest Basic)8.03ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area160.88 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity122.96 m3·mol-1ChemAxon
Polarizability49.46 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0z20c00000-347a5da10b8c2c85e6c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0z10000000-4a2ce92d6902f4ad8eaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-4z00000000-039465e4b89c78bd0b11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0k81z00000-37dea53aac093ce884f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0z50400000-f60802f57acd3074b4c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-6z10000000-d2fbe55b0731a8cf001fView in MoNA
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Structural constituent of ribosome
Specific Function:
May play a role in compensating for the inactivated X-linked gene during spermatogenesis.
Gene Name:
RPL10L
Uniprot ID:
Q96L21
Molecular Weight:
24518.595 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Structural constituent of ribosome
Specific Function:
Associated with ribosomes but is not required for canonical ribosome function and has extra-ribosomal functions. Component of the GAIT (gamma interferon-activated inhibitor of translation) complex which mediates interferon-gamma-induced transcript-selective translation inhibition in inflammation processes. Upon interferon-gamma activation and subsequent phosphorylation dissociates from the ribo...
Gene Name:
RPL13A
Uniprot ID:
P40429
Molecular Weight:
23577.11 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Structural constituent of ribosome
Specific Function:
Not Available
Gene Name:
RPL23
Uniprot ID:
P62829
Molecular Weight:
14865.335 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Structural constituent of ribosome
Specific Function:
Not Available
Gene Name:
RPL15
Uniprot ID:
P61313
Molecular Weight:
24145.945 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Structural constituent of ribosome
Specific Function:
Not Available
Gene Name:
RPL19
Uniprot ID:
P84098
Molecular Weight:
23465.775 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Structural constituent of ribosome
Specific Function:
This protein binds to a specific region on the 26S rRNA.
Gene Name:
RPL23A
Uniprot ID:
P62750
Molecular Weight:
17694.885 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Structural constituent of ribosome
Specific Function:
Involved in the biogenesis of the 60S ribosomal subunit. Ensures the docking of GTPBP4/NOG1 to pre-60S particles (By similarity).
Gene Name:
RSL24D1
Uniprot ID:
Q9UHA3
Molecular Weight:
19621.02 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Structural constituent of ribosome
Specific Function:
Not Available
Gene Name:
RPL26L1
Uniprot ID:
Q9UNX3
Molecular Weight:
17256.2 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Structural constituent of ribosome
Specific Function:
Not Available
Gene Name:
RPL8
Uniprot ID:
P62917
Molecular Weight:
28024.52 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Structural constituent of ribosome
Specific Function:
Binds to the 23S rRNA.
Gene Name:
RPL37
Uniprot ID:
P61927
Molecular Weight:
11077.81 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Structural constituent of ribosome
Specific Function:
The L3 protein is a component of the large subunit of cytoplasmic ribosomes.
Gene Name:
RPL3
Uniprot ID:
P39023
Molecular Weight:
46108.72 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Structural constituent of ribosome
Specific Function:
Binds to 5S ribosomal RNA (By similarity). Required for rRNA maturation and formation of the 60S ribosomal subunits. Promotes nucleolar location of PML (By similarity).
Gene Name:
RPL11
Uniprot ID:
P62913
Molecular Weight:
20252.235 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Transferase activity, transferring amino-acyl groups
Specific Function:
Functions in the N-end rule pathway of protein degradation where it conjugates Leu, Phe and, less efficiently, Met from aminoacyl-tRNAs to the N-termini of proteins containing an N-terminal arginine or lysine.
Gene Name:
aat
Uniprot ID:
P0A8P1
Molecular Weight:
26618.275 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
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Drug created on September 15, 2010 15:31 / Updated on July 27, 2015 10:36