Details of the Drug

General Information of Drug (ID: DMDKLB5)

Drug Name
Puromycin
Synonyms
puromycin; Stylomycin; Puromycinum; Puromycine; Puromicina; UNII-4A6ZS6Q2CL; P-638; Stillomycin; CL 13900; 3123L; 4A6ZS6Q2CL; 3'-(L-alpha-Amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyladenosine; (S)-3'-((2-Amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3'-deoxy-N,N-dimethyladenosine; GNF-PF-2016; Puromycinum [INN-Latin]; Puromycine [INN-French]; Puromicina [INN-Spanish]; 9-{3-deoxy-3-[(O-methyl-L-tyrosyl)amino]-beta-D-xylofuranosyl}-N,N-dimethyl-9H-purin-6-amine; Bacterenomycin
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 471.5
Logarithm of the Partition Coefficient (xlogp) 0
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 10
Chemical Identifiers
Formula
C22H29N7O5
IUPAC Name
(2S)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-methoxyphenyl)propanamide
Canonical SMILES
CN(C)C1=NC=NC2=C1N=CN2C3C(C(C(O3)CO)NC(=O)C(CC4=CC=C(C=C4)OC)N)O
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
InChIKey
RXWNCPJZOCPEPQ-NVWDDTSBSA-N
Cross-matching ID
PubChem CID
439530
ChEBI ID
CHEBI:17939
CAS Number
53-79-2
DrugBank ID
DB08437
VARIDT ID
DR01525

Molecular Interaction Atlas of This Drug


Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [1]
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Protein Interaction/Cellular Processes [3]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [4]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Regulation of Drug Effects [5]
Bcl-2-like protein 1 (BCL2L1) OTRC5K9O B2CL1_HUMAN Gene/Protein Processing [4]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [6]
C-C motif chemokine 4 (CCL4) OT6B8P25 CCL4_HUMAN Gene/Protein Processing [6]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [4]
Cytochrome P450 1A1 (CYP1A1) OTE4EFH8 CP1A1_HUMAN Gene/Protein Processing [7]
Differentially expressed in FDCP 6 homolog (DEF6) OTIRBYVK DEFI6_HUMAN Protein Interaction/Cellular Processes [8]
Heme oxygenase 1 (HMOX1) OTC1W6UX HMOX1_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 A prediction model of substrates and non-substrates of breast cancer resistance protein (BCRP) developed by GA-CG-SVM method. Comput Biol Med. 2011 Nov;41(11):1006-13.
2 ATP-binding cassette transporters as pitfalls in selection of transgenic cells. Anal Biochem. 2010 Apr 15;399(2):246-50.
3 Melatonin antagonizes the intrinsic pathway of apoptosis via mitochondrial targeting of Bcl-2. J Pineal Res. 2008 Apr;44(3):316-25. doi: 10.1111/j.1600-079X.2007.00532.x.
4 Melatonin promotes puromycin-induced apoptosis with activation of caspase-3 and 5'-adenosine monophosphate-activated kinase-alpha in human leukemia HL-60 cells. J Pineal Res. 2011 May;50(4):367-73. doi: 10.1111/j.1600-079X.2010.00852.x. Epub 2011 Jan 18.
5 ATP-binding cassette transporters as pitfalls in selection of transgenic cells. Anal Biochem. 2010 Apr 15;399(2):246-50. doi: 10.1016/j.ab.2009.12.014. Epub 2009 Dec 14.
6 Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents. Leuk Res. 2010 Jul;34(7):917-24. doi: 10.1016/j.leukres.2009.12.002. Epub 2010 Feb 8.
7 Superinduction of CYP1A1 in MCF10A cultures by cycloheximide, anisomycin, and puromycin: a process independent of effects on protein translation and unrelated to suppression of aryl hydrocarbon receptor proteolysis by the proteasome. Mol Pharmacol. 2004 Oct;66(4):936-47.
8 DEF6, a novel substrate for the Tec kinase ITK, contains a glutamine-rich aggregation-prone region and forms cytoplasmic granules that co-localize with P-bodies. J Biol Chem. 2012 Sep 7;287(37):31073-84. doi: 10.1074/jbc.M112.346767. Epub 2012 Jul 24.
9 A Quantitative Approach to Screen for Nephrotoxic Compounds In Vitro. J Am Soc Nephrol. 2016 Apr;27(4):1015-28. doi: 10.1681/ASN.2015010060. Epub 2015 Aug 10.