Puromycin

Details

• Internal ID: 0474a959-a45f-4752-bb7e-d2332f4fa67e
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleosides > Purine 3-deoxyribonucleosides
• 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
• SMILES (Canonical): CN(C)C1=NC=NC2=C1N=CN2C3C(C(C(O3)CO)NC(=O)C(CC4=CC=C(C=C4)OC)N)O
• SMILES (Isomeric): CN(C)C1=NC=NC2=C1N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)CO)NC(=O)[C@H](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
• InChI Key: RXWNCPJZOCPEPQ-NVWDDTSBSA-N
• Popularity: 18,544 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₉N₇O₅
• Molecular Weight: 471.50 g/mol
• Exact Mass: 471.22301705 g/mol
• Topological Polar Surface Area (TPSA): 161.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.79
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

• 53-79-2
• Stylomycin
• Puromicina
• Puromycine
• Puromycinum
• Stillomycin
• P-638
• 3123L
• GNF-PF-2016
• CL 13,900
• CHEBI:17939
• CL-13900
• 4A6ZS6Q2CL
• 3'-(L-alpha-Amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyladenosine
• CL 13900
• (S)-3'-((2-Amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3'-deoxy-N,N-dimethyladenosine
• DTXSID8036788
• P 638
• 3123-L
• 3'-deoxy-N,N-dimethyl-3'-(O-methyl-L-tyrosinamido)adenosine
• Adenosine, 3'-((2-amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3'-deoxy-N,N-dimethyl-, (S)-
• CL 16536
• (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
• Adenosine, 3'-(alpha-amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyl-, L-
• NSC3055
• CL13900
• (S)-3'-[[2-Amino-3-(4-methoxyphenyl)-1-oxopropyl]amino]-3'-deoxy-N,N-dimethyladenosine
• (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
• RefChem:177304
• DTXCID6016788
• L-3'-(alpha-amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyladenosine
• P638
• Puromycin (USAN)
• PUROMYCIN [USAN]
• Adenosine, 3'-(((2S)-2-amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3'-deoxy-N,N-dimethyl-
• (S)-2-amino-N-((2S,3S,4R,5R)-5-(6-(dimethylamino)-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl)-3-(4-methoxyphenyl)propanamide
• Achromycin (purine derivative)
• TCMDC-123493
• 3'-deoxy-N,N-dimethyl-3'-[(O-methyl-L-tyrosyl)amino]adenosine
• (2S)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl]-3-(4-methoxyphenyl)propanamide
• 9-{3-deoxy-3-[(O-methyl-L-tyrosyl)amino]-beta-D-xylofuranosyl}-N,N-dimethyl-9H-purin-6-amine
• NSC 3055
• Puromycine [INN-French]
• Puromycinum [INN-Latin]
• Puromicina [INN-Spanish]
• UNII-4A6ZS6Q2CL
• Bacterenomycin
• Puromycin [USAN:INN:BAN]
• Achromycin;
• Stillomycin;
• Stylomycin;
• C22H29N7O5
• Adenosine, 3'-[[(2S)-2-amino-3-(4-methoxyphenyl)-1-oxopropyl]amino]-3'-deoxy-N,N-dimethyl-
• PUY
• Antibiotic 3123L;
• Antibiotic P 638;
• PUROMYCIN [INN]
• PUROMYCIN [MI]
• Prestwick3_000480
• Epitope ID:140945
• Antibiotic CL 13900;
• PUROMYCIN [WHO-DD]
• SCHEMBL4570
• BSPBio_000620
• BPBio1_000682
• CHEMBL469912
• orb1705876
• SCHEMBL29355751
• GTPL13311
• 3'-(L-.alpha.-Amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyladenosine
• RXWNCPJZOCPEPQ-NVWDDTSBSA-N
• HMS2089F18
• AAA05379
• HY-B1743
• CL 16,536 (*Dihydrochloride*)
• BDBM50277158
• EX-A13431
• AKOS030485964
• CCG-208505
• CS-6500
• DB08437
• 6-Dimethylamino-9-(3'-(p-methoxy-L-phenylalanylamino)-beta-D-ribofuranosyl)-purine
• NCGC00179500-01
• NCGC00179500-07
• NCGC00179500-14
• AB00514661
• NS00011702
• C01610
• D05653
• G85883
• AB00514661-07
• Q424696
• BRD-K36007650-001-01-9
• BRD-K36007650-300-02-3
• Q27167243
• 3'-[[(2S)-2-amino-3-(4-methoxyphenyl)-1-oxopropyl]amino]-3'-deoxy-N,N-diemthyladenosine
• (2S)-2-amino-N-[(2S,3S,4R,5R)-5-(6-dimethylaminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-methoxyphenyl)propanamide
• 2-amino-N-[5-[6-(dimethylamino)-9-purinyl]-4-hydroxy-2-(hydroxymethyl)-3-oxolanyl]-3-(4-methoxyphenyl)propanamide
• Adenosine, 3'-(-amino-p-methoxyhydrocinnamamido)-3'-deoxy-N, N-dimethyl-, dihydrochloride, L-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8649	86.49%
Caco-2	-	0.8596	85.96%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Lysosomes	0.4061	40.61%
OATP2B1 inhibitior	-	0.7148	71.48%
OATP1B1 inhibitior	+	0.9101	91.01%
OATP1B3 inhibitior	+	0.9462	94.62%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9279	92.79%
BSEP inhibitior	+	0.6599	65.99%
P-glycoprotein inhibitior	-	0.9167	91.67%
P-glycoprotein substrate	+	0.9344	93.44%
CYP3A4 substrate	+	0.6472	64.72%
CYP2C9 substrate	-	0.8022	80.22%
CYP2D6 substrate	-	0.7799	77.99%
CYP3A4 inhibition	-	0.7240	72.40%
CYP2C9 inhibition	-	0.9133	91.33%
CYP2C19 inhibition	-	0.9393	93.93%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9058	90.58%
CYP2C8 inhibition	+	0.4671	46.71%
CYP inhibitory promiscuity	-	0.8922	89.22%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5662	56.62%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9545	95.45%
Skin irritation	-	0.7861	78.61%
Skin corrosion	-	0.9350	93.50%
Ames mutagenesis	-	0.5837	58.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7488	74.88%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	+	0.8305	83.05%
skin sensitisation	-	0.8711	87.11%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.7765	77.65%
Acute Oral Toxicity (c)	III	0.7259	72.59%
Estrogen receptor binding	+	0.8905	89.05%
Androgen receptor binding	+	0.6339	63.39%
Thyroid receptor binding	+	0.5637	56.37%
Glucocorticoid receptor binding	+	0.8970	89.70%
Aromatase binding	+	0.5889	58.89%
PPAR gamma	+	0.5577	55.77%
Honey bee toxicity	-	0.7903	79.03%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	-	0.7982	79.82%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293232	Q16637	Survival motor neuron protein	891.3 nM; 794.3 nM	Potency; Potency	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.81%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.55%	99.17%
CHEMBL2581	P07339	Cathepsin D	96.45%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.23%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	92.80%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.91%	91.11%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	89.97%	93.10%
CHEMBL4040	P28482	MAP kinase ERK2	88.52%	83.82%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.55%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.23%	95.56%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	86.06%	92.29%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.06%	95.89%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	85.89%	82.86%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.30%	94.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.48%	95.50%
CHEMBL2535	P11166	Glucose transporter	84.04%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	83.68%	94.73%
CHEMBL3492	P49721	Proteasome Macropain subunit	82.79%	90.24%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.74%	95.83%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	81.47%	95.64%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.24%	96.00%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	80.99%	100.00%

Plants that contains it

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Cross-Links

• PubChem: 439530
• LOTUS: LTS0046853
• wikiData: Q424696