Puromycin

Identification

Name
Puromycin
Accession Number
DB08437
Type
Small Molecule
Groups
Experimental
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
Synonyms
  • puromicina
External IDs
3123-L / 3123L / CL-13900 / P-638
Categories
UNII
4A6ZS6Q2CL
CAS number
53-79-2
Weight
Average: 471.5096
Monoisotopic: 471.223017073
Chemical Formula
C22H29N7O5
InChI Key
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U60S ribosomal protein L10-likeNot AvailableHuman
U60S ribosomal protein L13aNot AvailableHuman
U60S ribosomal protein L23Not AvailableHuman
U60S ribosomal protein L15Not AvailableHuman
U60S ribosomal protein L19Not AvailableHuman
U60S ribosomal protein L23aNot AvailableHuman
UProbable ribosome biogenesis protein RLP24Not AvailableHuman
U60S ribosomal protein L26-like 1Not AvailableHuman
U60S ribosomal protein L8Not AvailableHuman
U60S ribosomal protein L37Not AvailableHuman
U60S ribosomal protein L3Not AvailableHuman
U60S ribosomal protein L11Not AvailableHuman
ULeucyl/phenylalanyl-tRNA--protein transferaseNot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Puromycin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Puromycin is combined with (S)-Warfarin.
1,10-PhenanthrolineThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Puromycin.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Puromycin is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Puromycin.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Puromycin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Puromycin is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Puromycin.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Puromycin is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Puromycin.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C01610
PubChem Compound
439530
PubChem Substance
99444908
ChemSpider
388623
ChEBI
17939
ChEMBL
CHEMBL469912
HET
PUY
Wikipedia
Puromycin
PDB Entries
1q7y / 2dpt / 3q3d / 4tva / 5nc5

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)168°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 RuleNoChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0900300000-347a5da10b8c2c85e6c0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dj-0900000000-4a2ce92d6902f4ad8eaa
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dj-1900000000-039465e4b89c78bd0b11
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0229-0520900000-37dea53aac093ce884f6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0910100000-f60802f57acd3074b4c1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03xs-1900000000-d2fbe55b0731a8cf001f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-0000900000-f82e7526c7ebd78049d9
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03k9-0900500000-0d48aed0c9497b5ab8f3
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-0900000000-af8be24075f803a58153
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-0900000000-571b6483dc540c02d098
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-0900000000-08775f201fb11e558b53
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0000900000-6133e2c60106f3437756
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-05fr-0005900000-a760a4943250cd5405b9
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0809000000-eb619283ee6c689551e3
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0w29-0900000000-ca39c6d95b7bd8fba81b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0900000000-253fadebaa39d03e1cd1
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-0a4i-0219000000-6595a051c26ce2ee007b

Taxonomy

Description
This compound belongs to the class of organic compounds known as purine 3'-deoxyribonucleosides. These are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 3.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleosides
Sub Class
Purine 3'-deoxyribonucleosides
Direct Parent
Purine 3'-deoxyribonucleosides
Alternative Parents
Phenylalanine and derivatives / Alpha amino acid amides / 6-alkylaminopurines / Glycosylamines / Pentoses / Amphetamines and derivatives / Phenoxy compounds / Anisoles / Dialkylarylamines / Methoxybenzenes
show 18 more
Substituents
Purine 3'-deoxyribonucleoside / Phenylalanine or derivatives / Alpha-amino acid amide / N-glycosyl compound / Glycosyl compound / 6-alkylaminopurine / 6-aminopurine / Alpha-amino acid or derivatives / Pentose monosaccharide / Amphetamine or derivatives
show 45 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
puromycins (CHEBI:17939)

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
Uniprot Name
60S ribosomal protein L10-like
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 ...
Gene Name
RPL13A
Uniprot ID
P40429
Uniprot Name
60S ribosomal protein L13a
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
Uniprot Name
60S ribosomal protein L23
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
Uniprot Name
60S ribosomal protein L15
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
Uniprot Name
60S ribosomal protein L19
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
Uniprot Name
60S ribosomal protein L23a
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
Uniprot Name
Probable ribosome biogenesis protein RLP24
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
Uniprot Name
60S ribosomal protein L26-like 1
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
Uniprot Name
60S ribosomal protein L8
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
Uniprot Name
60S ribosomal protein L37
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
Uniprot Name
60S ribosomal protein L3
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
Uniprot Name
60S ribosomal protein L11
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 arginin...
Gene Name
aat
Uniprot ID
P0A8P1
Uniprot Name
Leucyl/phenylalanyl-tRNA--protein transferase
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]

Drug created on September 15, 2010 15:31 / Updated on November 02, 2018 06:49