Penicillin V

Details

• Internal ID: 192fa1f4-19a5-4492-9c84-1e27b8502fd1
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Dipeptides
• IUPAC Name: (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• SMILES (Canonical): CC1(C(N2C(S1)C(C2=O)NC(=O)COC3=CC=CC=C3)C(=O)O)C
• SMILES (Isomeric): CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)COC3=CC=CC=C3)C(=O)O)C
• InChI: InChI=1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1
• InChI Key: BPLBGHOLXOTWMN-MBNYWOFBSA-N
• Popularity: 5,433 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₈N₂O₅S
• Molecular Weight: 350.40 g/mol
• Exact Mass: 350.09364285 g/mol
• Topological Polar Surface Area (TPSA): 121.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 0.70
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• Phenoxymethylpenicillin
• 87-08-1
• Oracillin
• Vebecillin
• Penicillin phenoxymethyl
• Phenopenicillin
• Distaquaine V
• Meropenin
• Phenomycilline
• V-Cillin
• Fenospen
• Beromycin
• Fenacilin
• Stabicillin
• Apopen
• Oratren
• Ospen
• Eskacillin V
• Phenoxymethyl penicillin
• Pen-V
• Pen-vee
• Pen-Oral
• Phenocillin
• Phenoxymethylenepenicillinic acid
• phenoxymethylpenicillinic acid
• Rocilin
• Compocillin V
• Eskacillian V
• Fenoximetilpenicilina
• Crystapen V
• V-Cil
• V-Tablopen
• Acipen V
• V-Cylina
• V-Cyline
• Phenoxymethylpenicilline
• Phenoxymethylpenicillinum
• P-Mega-Tablinen
• 6-Phenoxyacetamidopenicillanic acid
• Fenossimetilpenicillina
• phenoxomethylpenicillin
• (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CHEBI:27446
• Z61I075U2W
• (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
• (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• DTXSID3023429
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenoxyacetyl)amino)-, (2S-(2alpha,5alpha,6beta))-
• Phenoxymethylpenicillinum calcium
• Fenoxymethylpenicillin
• Beromycin, Penicillin
• Berromycin, Penicillin
• Penicillin, Phenoxymethyl
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenoxyacetyl)amino)-, (2S,5R,6R)-
• (2S,5R,6R)-3,3-dimethyl-7-oxo-6-((2-phenoxyacetyl)amino)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
• (2S,5R,6R)-3,3-dimethyl-7-oxo-6-((phenoxyacetyl)amino)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
• Penicillin Beromycin
• Penicillin Berromycin
• Sodium, Penicillin V
• V Sodium, Penicillin
• RefChem:6106
• DTXCID303429
• J01CE02
• 201-722-0
• Fenoxypen
• Phenoximethylpenicillinum
• Fenossimetilpenicillina [DCIT]
• Fenoximetilpenicilina [INN-Spanish]
• Calcipen
• Phenoxymethylpenicillin (INN)
• Phenoxymethylpenicillin [INN]
• (2S,5R,6R)-3,3-DIMETHYL-7-OXO-6-(2-PHENOXYACETAMIDO)-4-THIA-1- AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
• PNV
• Penicillin V [USAN]
• Phenoxymethylpenicillin 100 microg/mL in Acetonitrile
• Penicillanic acid, 6-phenoxyacetamido-
• Phenoxymethylpenicilline [INN-French]
• Phenoxymethylpenicillinum [INN-Latin]
• CCRIS 752
• V-Cillin (TN)
• Penicillin V (USP)
• HSDB 6314
• EINECS 201-722-0
• BRN 0096259
• Penicillin V [USAN:USP]
• UNII-Z61I075U2W
• Fenacillin;
• Phenocillin;
• Stabicillin;
• Fenoxypen;
• Meropenin;
• Oracillin;
• Penicillin-V
• Fenospen;
• Fenocin;
• Oratren;
• Apopen;
• Ospen;
• Pen-Vee;
• penicillin-v-potassium
• 3,3-Dimethyl-7-oxo-6-((phenyloxyacetyl)amino)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
• PC Pen VK
• Spectrum_001007
• Spectrum2_000495
• Spectrum3_000543
• Spectrum4_000472
• Spectrum5_001409
• Phenoxymethylpenicillin RS
• Phenoxymethylpenicillin CRS
• CHEMBL615
• Epitope ID:115011
• Epitope ID:116056
• PENICILLIN V [MI]
• PENICILLIN V [HSDB]
• SCHEMBL49223
• BSPBio_002185
• KBioGR_000944
• KBioSS_001487
• 4-27-00-05884 (Beilstein Handbook Reference)
• MLS001304105
• phenoxymethylpenicillanyl group
• DivK1c_000779
• SPBio_000389
• PENICILLIN V [USP-RS]
• orb1983600
• CHEBI:53706
• GTPL10920
• HY-B0975A
• KBio1_000779
• KBio2_001487
• KBio2_004055
• KBio2_006623
• KBio3_001685
• MSK5619
• NINDS_000779
• GLXC-25717
• PENICILLIN V [ORANGE BOOK]
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenoxyacetyl)amino)-, (2S-(2.alpha.,5.alpha.,6.beta.))-
• 2,2-dimethyl-6beta-[(phenoxyacetyl)amino]penam-3alpha-carboxylic acid
• BDBM50370584
• EBC-26689
• PENICILLIN V [USP MONOGRAPH]
• 3,3-dimethyl-6beta-[(phenoxyacetyl)amino]penam-2alpha-carboxylic acid (PIN)
• AKOS015969737
• DB00417
• PHENOXYMETHYLPENICILLIN [MART.]
• IDI1_000779
• PHENOXYMETHYLPENICILLIN [WHO-DD]
• PHENOXYMETHYLPENICILLIN [WHO-IP]
• phenoxymethyl penicillinic acid*free acid
• (2S,5R,6R)-3,3-dimethyl-7-oxo-6-{[(phenyloxy)acetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• DA-76706
• SMR000539431
• SBI-0051477.P003
• AB00514745
• CS-0013728
• NS00078894
• PHENOXYMETHYLPENICILLIN [EP MONOGRAPH]
• Phenoxymethylpenicillin for system suitability
• C08126
• D05411
• G77824
• PHENOXYMETHYLPENICILLINUM [WHO-IP LATIN]
• EN300-19735891
• Phenoxymethylpenicillin for system suitability CRS
• Q422215
• BRD-K43966364-237-02-2
• BRD-K43966364-237-03-0
• BRD-K43966364-237-04-8
• 6beta-Phenoxyacetamido-2,2-dimethylpenam-3alpha-carboxylic acid
• Penicillin V, United States Pharmacopeia (USP) Reference Standard
• Phenoxymethylpenicillin, European Pharmacopoeia (EP) Reference Standard

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7272	72.72%
Caco-2	-	0.9372	93.72%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.4391	43.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9336	93.36%
OATP1B3 inhibitior	+	0.9417	94.17%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5173	51.73%
P-glycoprotein inhibitior	-	0.9024	90.24%
P-glycoprotein substrate	-	0.9118	91.18%
CYP3A4 substrate	+	0.6081	60.81%
CYP2C9 substrate	-	0.8075	80.75%
CYP2D6 substrate	-	0.8549	85.49%
CYP3A4 inhibition	-	0.8257	82.57%
CYP2C9 inhibition	-	0.8501	85.01%
CYP2C19 inhibition	-	0.8361	83.61%
CYP2D6 inhibition	-	0.8725	87.25%
CYP1A2 inhibition	-	0.8802	88.02%
CYP2C8 inhibition	-	0.9343	93.43%
CYP inhibitory promiscuity	-	0.8785	87.85%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6500	65.00%
Carcinogenicity (trinary)	Non-required	0.6952	69.52%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9802	98.02%
Skin irritation	-	0.7582	75.82%
Skin corrosion	-	0.9251	92.51%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5615	56.15%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.5188	51.88%
skin sensitisation	+	0.5677	56.77%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.7241	72.41%
Acute Oral Toxicity (c)	III	0.4535	45.35%
Estrogen receptor binding	-	0.5287	52.87%
Androgen receptor binding	-	0.7780	77.80%
Thyroid receptor binding	-	0.7375	73.75%
Glucocorticoid receptor binding	-	0.6089	60.89%
Aromatase binding	-	0.5971	59.71%
PPAR gamma	-	0.6296	62.96%
Honey bee toxicity	-	0.8144	81.44%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8291	82.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.55%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.60%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	93.90%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.04%	91.11%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.73%	94.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.65%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.50%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.59%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.87%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.12%	99.17%
CHEMBL4208	P20618	Proteasome component C5	83.90%	90.00%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	83.03%	92.67%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.36%	93.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6869
• LOTUS: LTS0139640
• wikiData: Q422215