6-[[(2-ETHOXY-1-NAPHTHALENYL)CARBONYL]AMINO]-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLATE|(2S,5R,6R)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2....

General Information

Structure

Molecular Formula

C₂₁H₂₁N₂O₅S-

Molecular Mass

413.46684

Exact Mass

413.11711778

Charge

-1

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)/p-1/t15-,16+,19-/m1/s1

InChIKey

GPXLMGHLHQJAGZ-JTDSTZFVSA-M

Canonic Smiles

CCOc1ccc2c(c1C(=O)N[C@@H]1C(=O)N3[C@@H]1SC([C@@H]3C(=O)[O-])(C)C)cccc2

Isomeric Smiles

O(c1ccc2c(c1C(=O)N[C@@H]1C(=O)N3[C@@H](C(=O)[O-])C(C)(C)S[C@H]13)cccc2)CC

Calculated Properties

JChem

LogD (pH = 7.4)

-1.13

LogD (pH = 5.5)

0.12

Log P

2.29

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

3.31

Polar Surface Area

98.77

Polarizability

41.69

Molar Refractivity

118.98

LOG S

-7.05

Data Source

Academic Data

Data Source

Names and Identifiers

IUPAC Traditional name

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

IUPAC name

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

Synonyms

6-[[(2-ETHOXY-1-NAPHTHALENYL)CARBONYL]AMINO]-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLATE(2S,5R,6R)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylatenafcillin(1-)

Names and Identifiers

Registration numbers

PubChem CID

PubChem SID

Beilstein Number

CHEBI ID

Protein Data Bank