Athanor by arbastro
download
Library

Nafcillin

Athanor · official

C21H22N2O5S · 414.5 g/mol

IUPAC name: 6-[(2-ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Also called Unipen, penicillinase-resistant

Drugs
Open in Athanor
The structure of Nafcillin
Drawn from its SMILES with RDKit

Names and identifiers

IUPAC name
6-[(2-ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Synonyms
Unipen, penicillinase-resistant, SCHEMBL6462735
+ 4 more

GPXLMGHLHQJAGZ-UHFFFAOYSA-N, NS00009701, 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2-ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, [2S-(2.alpha.,5.alpha.,6.beta.)]-, 6-[(2-Ethoxy-1-naphthoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid #

Molecular formula
C21H22N2O5S
Empirical formula
C21H22N2O5S
Molecular weight
414.5 g/mol
Exact mass
414.12494
CAS number
147-52-4
PubChem CID
23568
Canonical SMILES
CCOC1=C(C2=CC=CC=C2C=C1)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
Isomeric SMILES
CCOC1=C(C2=CC=CC=C2C=C1)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
InChI
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)
InChIKey
GPXLMGHLHQJAGZ-UHFFFAOYSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms
29
Rings
4
Aromatic rings
2
Fraction sp³ carbons (Fsp3)
0.38
H-bond donors
2
H-bond acceptors
5 computed here · PubChem 6
Rotatable bonds
5
TPSA (Ų)
95.9 computed here · PubChem 121
Formal charge
0
XLogP3
2.9 PubChem
Complexity
699 PubChem
Stereocenters
0 defined, 3 undefinedCIP: C17: undefined · C21: undefined · C29: undefined
Double-bond geometry
None specified
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C60.85%
  • H5.35%
  • N6.76%
  • O19.30%
  • S7.74%

Isotope pattern

100%414.12525%415.1288.5%416.1251.6%417.127418.128

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
2.48 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-3.9 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
3.4 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 414.48
  • log P ≤ 5 (Crippen): 2.48
  • H-bond donors ≤ 5: 2
  • H-bond acceptors ≤ 10: 5

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

No GHS hazard classification was found in the sources.

Safety data sheets on the supplier’s page: Hairui Chemical, MolCore, Mcule.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
  2. [2]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  3. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  4. ·Literature on PubChem

Data last updated 2026-10-14.