Piperacillin

C23H27N5O7S — CID 43672

IUPAC(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

SMILESCCN1CCN(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

InChIInChI=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

InChIKeyIVBHGBMCVLDMKU-GXNBUGAJSA-N

MW517.60 g/mol

LogP0.50

Rot. Bonds6

About Piperacillin

Piperacillin (PubChem CID 43672) has the molecular formula C23H27N5O7S and a molecular weight of 517.60 g/mol. Its IUPAC name is (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.

Molecular Properties

Compound Name	Piperacillin
PubChem CID	43672
Molecular Formula	C23H27N5O7S
Molecular Weight	517.60 g/mol
Exact Mass	517.16
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	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
InChIKey	IVBHGBMCVLDMKU-GXNBUGAJSA-N
XLogP	0.50
TPSA	182.00 Å²
H-Bond Donors	3
H-Bond Acceptors	8
Rotatable Bonds	6
Heavy Atoms	36
Complexity	982

Lipinski Rule of Five

1 violation

Rule	Value
MW ≤ 500	517.60
LogP ≤ 5	0.50
H-Bond Donors ≤ 5	3
H-Bond Acceptors ≤ 10	8

Computed Properties (RDKit)

Structural Alerts	{'alert_name': 'diketo_group', 'substructure': 'N/A'}

Frequently Asked Questions

What is the IUPAC name of Piperacillin?

The IUPAC name of Piperacillin (CID 43672) is (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.

What is the SMILES notation for Piperacillin?

The canonical SMILES for Piperacillin is 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.

What is the InChIKey of Piperacillin?

The InChIKey is IVBHGBMCVLDMKU-GXNBUGAJSA-N. The full InChI is 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.

What are the key properties of Piperacillin?

Piperacillin has a molecular weight of 517.60 g/mol, XLogP of 0.50, 6 rotatable bonds, 3 hydrogen bond donors, and 8 hydrogen bond acceptors.

Where does this data come from?

All data for Piperacillin is sourced from PubChem (CID 43672), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).