Piperacillin

Details

• Internal ID: 687871d3-ddd9-484d-9f61-6653b27f2d52
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides
• IUPAC Name: (2S,5R,6R)-6-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• SMILES (Canonical): CCN1CCN(C(=O)C1=O)C(=O)NC(C2=CC=CC=C2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
• SMILES (Isomeric): CCN1CCN(C(=O)C1=O)C(=O)N[C@H](C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
• InChI: InChI=1S/C23H27N5O7S/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34)/t13-,14-,15+,20-/m1/s1
• InChI Key: IVBHGBMCVLDMKU-GXNBUGAJSA-N
• Popularity: 4,020 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₇N₅O₇S
• Molecular Weight: 517.60 g/mol
• Exact Mass: 517.16311939 g/mol
• Topological Polar Surface Area (TPSA): 182.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -0.24
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• 61477-96-1
• Piperacillin anhydrous
• Piperacilline
• Pipercillin
• Piperacilina
• Peracin
• Piperacillina
• Piperacillinum
• PIPC
• CHEBI:8232
• (2S,5R,6R)-6-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• (2S,5R,6R)-6-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 9I628532GX
• DTXSID2023482
• AB Piperacillin
• (2S,5R,6R)-6-[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-6-(((((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)phenylacetyl)amino)-7-oxo-, (2S-(2-alpha,5-alpha,6-beta(S*)))-
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)phenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta(S*)))-
• (2S,5R,6R)-6-((R)-2-(4-Ethyl-2,3-dioxo-1-piperazinecarboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid monohydrate
• Pipera hameln
• (2S,5R,6R)-6-(((2R)-2-(((4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl)amino)-2-phenylacetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
• (2S,5R,6R)-6-(((2R)-2-((4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino)-2-phenylacetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
• (2S,5R,6R)-6-((2R)-2-(((4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl)amino)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
• Piperacillin curasan
• Curasan, Piperacillin
• Piperacillin ratiopharm
• RefChem:929312
• DTXCID303482
• J01CA12
• 262-811-8
• X00B0D5O0E
• Piperacillin [INN]
• MFCD00865043
• Piperacillin hydrate
• Piperacillin (INN)
• CHEMBL702
• PIPERACILLIN, ANHYDROUS
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(2R)-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
• (2S,5R,6R)-6-[[(2R)-2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)amino]-2-phenyl-acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 6beta-{(2R)-2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-2-phenylacetamido}-2,2-dimethylpenam-3alpha-carboxylic acid
• Peperacillin
• Pipracil, Piper
• (2S,5R,6R)-6-((R)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Peracin (TN)
• CCRIS 7362
• EINECS 262-811-8
• Piperacilina [INN-Spanish]
• Piperacilline [INN-French]
• Piperacillinum [INN-Latin]
• Piperacillin?
• UNII-9I628532GX
• Piperacillin CRS
• WPP
• Prestwick0_000755
• Prestwick1_000755
• Prestwick2_000755
• Prestwick3_000755
• PIPERACILLIN [MI]
• PIPERACILLIN [JAN]
• Epitope ID:116652
• 6-(D-(-)-alpha-(4-Ethyl-2,3-dioxo-1-piperazinecarboxamido)phenylacetamido)penicillanic acid
• SCHEMBL33894
• BSPBio_000770
• PIPERACILLIN [MART.]
• (2S-(2alpha,5alpha,6beta(S*)))-6-(((((4-Ethyl-2,3-dioxopiperazin-1-yl)carbonyl)amino)phenylacetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
• BIDD:GT0167
• PIPERACILLIN [WHO-DD]
• SPBio_002709
• BPBio1_000848
• GTPL10921
• MSK5644
• GLXC-22993
• HMS2090H19
• HY-B1923
• Tazocin (piperacillin + tazobactam)
• BDBM50240426
• EBC-12090
• AKOS016007827
• DB00319
• FE27060
• (2S,5R,6R)-6-[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• AS-13671
• SY240046
• CS-0013978
• NS00009682
• D08380
• AB01275515-01
• EN300-6733491
• 477P961
• Q423787
• BRD-K86873305-236-03-0
• BRD-K86873305-236-14-7
• BRD-K86873305-236-15-4
• BRD-K86873305-236-16-2
• Z2587996977
• (2S,5R,6R)-6-((R)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8192	81.92%
Caco-2	-	0.8397	83.97%
Blood Brain Barrier	-	0.9750	97.50%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Lysosomes	0.5689	56.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8997	89.97%
OATP1B3 inhibitior	+	0.9424	94.24%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9294	92.94%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6411	64.11%
CYP2C9 substrate	-	0.8148	81.48%
CYP2D6 substrate	-	0.8744	87.44%
CYP3A4 inhibition	-	0.8856	88.56%
CYP2C9 inhibition	-	0.7568	75.68%
CYP2C19 inhibition	-	0.7289	72.89%
CYP2D6 inhibition	-	0.9002	90.02%
CYP1A2 inhibition	-	0.8597	85.97%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.9480	94.80%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.6259	62.59%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.9625	96.25%
Skin irritation	-	0.7542	75.42%
Skin corrosion	-	0.9175	91.75%
Ames mutagenesis	-	0.9700	97.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5842	58.42%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	0.8000	80.00%
skin sensitisation	-	0.8191	81.91%
Respiratory toxicity	+	1.0000	100.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8269	82.69%
Acute Oral Toxicity (c)	III	0.6105	61.05%
Estrogen receptor binding	+	0.5417	54.17%
Androgen receptor binding	-	0.5841	58.41%
Thyroid receptor binding	-	0.5215	52.15%
Glucocorticoid receptor binding	+	0.5831	58.31%
Aromatase binding	+	0.5494	54.94%
PPAR gamma	+	0.6260	62.60%
Honey bee toxicity	-	0.8384	83.84%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9745	97.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	99.06%	90.17%
CHEMBL2581	P07339	Cathepsin D	98.94%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.07%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.66%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.97%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.89%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.48%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.25%	82.69%
CHEMBL4208	P20618	Proteasome component C5	87.72%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.70%	91.19%
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	84.35%	88.81%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.73%	86.33%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.53%	96.61%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.28%	93.00%
CHEMBL5028	O14672	ADAM10	80.20%	97.50%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.12%	97.50%

Plants that contains it

• Chrozophora oblongifolia
• Croton laevigatus

Cross-Links

• PubChem: 43672
• LOTUS: LTS0103460
• wikiData: Q104908398