CAS 40957-90-2|tabtoxin|(<i>S</i>)-γ-(3-Hydroxy-2-oxo-3-azetidinyl)-L-α-aminobutyryl-L-threonine|(2S,3R)-2-[(2S)-2-amino-4-[(3S)-3-hydroxy-2-oxoazetidin-3-yl]butanamido]-3-hydroxybutanoic acid|Tab...

General Information

Structure

Molecular Formula

C₁₁H₁₉N₃O₆

Molecular Mass

289.28506

Exact Mass

289.12738534

Charge

InChI

InChI=1S/C11H19N3O6/c1-5(15)7(9(17)18)14-8(16)6(12)2-3-11(20)4-13-10(11)19/h5-7,15,20H,2-4,12H2,1H3,(H,13,19)(H,14,16)(H,17,18)/t5-,6+,7+,11+/m1/s1

InChIKey

BFSBNVPBVGFFCF-WDOVLDDZSA-N

Canonic Smiles

O=C([C@H](CC[C@]1(O)CNC1=O)N)N[C@H](C(=O)O)[C@H](O)C

Isomeric Smiles

O=C(O)[C@@H](NC(=O)[C@@H](N)CC[C@@]1(O)C(=O)NC1)[C@H](O)C

Calculated Properties

JChem

LogD (pH = 7.4)

-5.59

LogD (pH = 5.5)

-5.47

Log P

-5.47

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

3.32

Polar Surface Area

161.98

Polarizability

27.73

Molar Refractivity

65.36

LOG S

-0.61

Data Source

Academic Data

Data Source

Names and Identifiers

IUPAC Traditional name

tabtoxin

Synonyms

(S)-γ-(3-Hydroxy-2-oxo-3-azetidinyl)-L-α-aminobutyryl-L-threonineTabtoxinN-[(2S)-2-Amino-4-[(3S)-3-hydroxy-2-oxo-3-azetidinyl]-1-oxobutyl]-L-threoninetabtoxinN-((2S)-2-amino-4-((3S)-3-hydroxy-2-oxo-3-azetidinyl)-1-oxobutyl)-L-threoninewildfire toxin(2S,3R)-2-({(2S)-2-amino-4-[(3S)-3-hydroxy-2-oxoazetidin-3-yl]butanoyl}amino)-3-hydroxybutanoic acid

IUPAC name

(2S,3R)-2-[(2S)-2-amino-4-[(3S)-3-hydroxy-2-oxoazetidin-3-yl]butanamido]-3-hydroxybutanoic acid

Names and Identifiers

Registration numbers

CAS Number

PubChem CID

Wikipedia Title

Chemspider ID