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64817-22-7 molecular structure
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(2R,4S)-2-[(R)-carboxy[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetamido]methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

ChemBase ID: 176754
Molecular Formular: C23H29N5O8S
Molecular Mass: 535.57006
Monoisotopic Mass: 535.17368391
SMILES and InChIs

SMILES:
N(C(=O)[C@H](NC(=O)N1C(=O)C(=O)N(CC1)CC)c1ccccc1)[C@@H]([C@@H]1N[C@H](C(S1)(C)C)C(=O)O)C(=O)O
Canonical SMILES:
CCN1CCN(C(=O)C1=O)C(=O)N[C@H](c1ccccc1)C(=O)N[C@@H]([C@@H]1N[C@H](C(S1)(C)C)C(=O)O)C(=O)O
InChI:
InChI=1S/C23H29N5O8S/c1-4-27-10-11-28(19(31)18(27)30)22(36)25-13(12-8-6-5-7-9-12)16(29)24-14(20(32)33)17-26-15(21(34)35)23(2,3)37-17/h5-9,13-15,17,26H,4,10-11H2,1-3H3,(H,24,29)(H,25,36)(H,32,33)(H,34,35)/t13-,14+,15+,17-/m1/s1
InChIKey:
OKSUEATVFIVTFV-WBTNSWJXSA-N

Cite this record

CBID:176754 http://www.chembase.cn/molecule-176754.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R,4S)-2-[(R)-carboxy[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetamido]methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
IUPAC Traditional name
(2R,4S)-2-[(R)-carboxy[(2R)-2-(4-ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-phenylacetamido]methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid
Synonyms
[2R-[2α[R*(R*)],4β]]-4-Carboxy-α-[[[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-5,5-dimethyl-2-thiazolidineacetic Acid
α-(4-Ethyl-2,3-dioxo-1-piperazinecarboxamido)benzylpenicilloic Acid (T 1220 B)
Piperacillin EP Impurity B
Piperacilloic Acid
CAS Number
64817-22-7
PubChem SID
164232664
PubChem CID
54669584

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC P479970 external link Add to cart
PubChem 54669584 external link
Data Source Data ID Price
TRC
P479970 external link Add to cart Please log in.
Data Source Data ID
PubChem 54669584 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 2.6392198  H Acceptors
H Donor LogD (pH = 5.5) -4.4267683 
LogD (pH = 7.4) -6.5168524  Log P -2.5868757 
Molar Refractivity 129.3745 cm3 Polarizability 50.877766 Å3
Polar Surface Area 185.45 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
MSDS Link
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Certificate of Analysis
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DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - P479970 external link
A degradation product of Piperacillin (P479950), a new β-lactam antibiotic.

REFERENCES

REFERENCES

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  • • Waxman, D.J., et al.: J. Biol. Chem., 255, 3964 (1980)
  • • Waley, S.G., et al.: Biochem. J., et al.: 205, 631 (1980)
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PATENTS

PATENTS

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INTERNET

INTERNET

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