Nafcillin (CED0004782)

Record Information

Version

1.0

Creation Date

2016-05-25 18:21:32 UTC

Update Date

2026-08-21 18:47:56 UTC

Accession Number

CHEM022143

Identification

Common Name

Nafcillin

Class

Small Molecule

Description

Nafcillin is an organic compound with the chemical formula C21H22N2O5S and an average molecular weight of 414.48 g/mol. Nafcillin belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. This compound is found in or released from two recorded sources: healthcare, pharmaceuticals, and veterinary products, specifically within the categories of penicillins and antibiotics. Recorded exposure routes for nafcillin include oral, intravenous, intramuscular, and inhalation. In terms of its biological activity, there are five recorded protein targets for nafcillin. It acts as an inhibitor of Penicillin-binding protein 1b (pbp1b), Penicillin-binding protein 2B (penA), Penicillin-binding protein 2a (pbp2a), and serine-type D-Ala-D-Ala carboxypeptidase (pbp3), as well as one other protein.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2-Ethoxy-1-naphthalenyl)penicillin	ChEBI
(2-Ethoxy-1-naphthyl)penicillin	ChEBI
(2S,5R,6R)-6-[(2-Ethoxy-1-naphthoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
(2S,5R,6R)-6-[(2-Ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
(2S,5R,6R)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
6-(2-Ethoxy-1-naphthamido)penicillanic acid	ChEBI
Nafcilina	ChEBI
Nafcilline	ChEBI
Nafcillinum	ChEBI
Naphcillin	ChEBI
(2S,5R,6R)-6-[(2-Ethoxy-1-naphthoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
(2S,5R,6R)-6-[(2-Ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
(2S,5R,6R)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
6-(2-Ethoxy-1-naphthamido)penicillanate	Generator
Nafcillin sodium salt	HMDB
Nafcil	HMDB
Nafcillin, monosodium salt, anhydrous	HMDB
Nafcillin sodium	HMDB
Nafcillin, sodium	HMDB
Naphthamidopenicillin	HMDB
Sodium nafcillin	HMDB
Sodium, nafcillin	HMDB

Chemical Formula

C₂₁H₂₂N₂O₅S

Average Molecular Mass

414.475 g/mol

Monoisotopic Mass

414.125 g/mol

CAS Registry Number

985-16-0

IUPAC Name

(2S,5R,6R)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Traditional Name

nafcillin

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(OCC)C=CC2=CC=CC=C12)C(O)=O

InChI Identifier

InChI=1S/C21H22N2O5S/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27)/t15-,16+,19-/m1/s1

InChI Key

GPXLMGHLHQJAGZ-JTDSTZFVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Penicillin
1-naphthalenecarboxylic acid or derivatives
N-acyl-alpha amino acid or derivatives
1-naphthalenecarboxamide
Alpha-amino acid or derivatives
Naphthalene
Penam
Alkyl aryl ether
Benzenoid
Beta-lactam
Tertiary carboxylic acid amide
Thiazolidine
Azetidine
Secondary carboxylic acid amide
Carboxamide group
Lactam
Carboxylic acid
Ether
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Dialkylthioether
Hemithioaminal
Thioether
Organic oxygen compound
Organopnictogen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

penicillin (CHEBI:7447 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.017 g/L	ALOGPS
logP	3.21	ALOGPS
logP	2.29	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.94 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	108.14 m³·mol⁻¹	ChemAxon
Polarizability	42.22 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00dv-6559000000-476ab0db07d5480232f4	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00di-9423600000-8e41142db1f7e5fa26c3	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0090000000-65901bf6905f35a84f24	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-006x-0090000000-517308aedcbe6210d46e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00dl-8390000000-c3d759b208856f69cc83	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-9210000000-3431effabf1bb94e4b20	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-9200000000-8d4bae5167cd78d8f059	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-9200000000-00cc24f858c63f2e6ac5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-9500000000-d447304de567843fa59a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00xr-9500000000-fbdf096e0285a04fc391	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0600-9300000000-976ae9913f6b5bc3f293	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-80966e1fb91b5e682c61	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0910000000-04c58a908553834f1db1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00dj-0900000000-9ab759b60ea1b1ccb0a7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0900000000-1e9b29becf8d78e99cfa	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00xu-0900000000-dbba294d0a77e44851ed	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0900000000-9ac2c1b4dcbf3f1421d9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-1900000000-46b494a78d0ebbbc8079	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-7900000000-dc8fdcb9afe3b064db85	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-02ti-9300000000-847a94b299fb6ea1ddca	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0090000000-c9457bba69de43e462e3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-006x-0090000000-13c61e4d442524a4f12e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-9210000000-811024a6a573f4bc2026	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00dl-8290000000-22d79112c5be56c1103d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00dj-0900000000-7779626e4ff6f62cabba	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0900000000-5e6debfa979f8e04ed4f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0900000000-ced334fa586756dcbd5b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0910000000-79fabf069078ab82b4d6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0900-0972300000-2fcf6e422525f1825413	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-08fr-1950000000-56d3b44eb26e98206983	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-08mi-2910000000-89a6a7cdc5521d4da995	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0091000000-e9e7c7093646248dfa76	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0293000000-58fe940779036ea82755	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00bc-9751000000-54d52028a568bb18dd96	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0200900000-1e947daffd07f20b52be	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00or-0691400000-5a3b18691b058adff272	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0910000000-333d1c0f30302cde4260	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0233900000-5fa9295c5ec09282ae99	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000f-9754100000-a2c68186dd411241b587	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000f-3911000000-2fd90e315bfcd737de8c	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
5512.0	Log mg/kg	[3100:9800]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
306	Antibiotics	Healthcare, pharmaceuticals & veterinary products	Not Available
340	Penicillins	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

1 pathway

Nafcillin Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Beta-lactamase ACC-4	A4ZYU9	Escherichia coli	Predicted (SEA)	0.0778492
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	110.079
Click to view 3D structure	Efflux transporter	Q3S5C3	Salmonella newport	Predicted (SEA)	0.233548
Click to view 3D structure	Class C beta-lactamase CMY-36	Q48435	Klebsiella pneumoniae	Predicted (SEA)	0.233548
Click to view 3D structure	Speckle-type POZ protein	O43791	Humans	Predicted (SEA)	1.24559
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	64.9263
Click to view 3D structure	Trans-cinnamate 4-monooxygenase	Q04468	Helianthus tuberosus	Predicted (SEA)	9.10836
Click to view 3D structure	Beta-lactamase	P00811	Escherichia coli (strain K12)	Predicted (SEA)	5.83869
Click to view 3D structure	Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2	Q9UL51	Humans	Predicted (SEA)	18.9952
Click to view 3D structure	Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1	Q9GZU7	Humans	Predicted (SEA)	361.532
Click to view 3D structure	ATP-dependent molecular chaperone HSP82	C4YTQ8	Candida albicans (strain WO-1) (Yeast)	Predicted (SEA)	615.709
Click to view 3D structure	Listeriolysin regulatory protein	P22262	Listeria monocytogenes serovar 1/2a (strain ATCC BAA-679 / EGD-e)	Predicted (SEA)	9.809
Click to view 3D structure	Fe(3+)-Zn(2+) purple acid phosphatase	P80366	Phaseolus vulgaris	Predicted (SEA)	60.6445
Click to view 3D structure	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820	Humans	Predicted (SEA)	1033.53
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	5051.48
Click to view 3D structure	72 kDa type IV collagenase	P08253	Humans	Predicted (SEA)	1753.16
Click to view 3D structure	Disintegrin and metalloproteinase domain-containing protein 17	O77636	Sus scrofa	Predicted (SEA)	219.379
Click to view 3D structure	Mitochondrial import inner membrane translocase subunit TIM10	P87108	Saccharomyces cerevisiae S288c	Predicted (SEA)	348.92
Click to view 3D structure	PER-2 beta-lactamase	A2RP81	Citrobacter freundii	Predicted (SEA)	0.544945
Click to view 3D structure	Serine/threonine-protein kinase pim-1	P11309	Humans	Predicted (SEA)	4013.98
Click to view 3D structure	Caspase-3	P42574	Humans	Predicted (SEA)	832.753
Click to view 3D structure	Chaperone protein dnaK	C3TRK2	Escherichia coli	Predicted (SEA)	68.1959
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	2352.45
Click to view 3D structure	DNA (cytosine-5)-methyltransferase 1	P26358	Humans	Predicted (SEA)	585.893
Click to view 3D structure	Mitogen-activated protein kinase 9	P45984	Humans	Predicted (SEA)	3900.56