SID90341304

ID: ALA1201213

Cas Number: 530-08-5

PubChem CID: 3762

Product Number: I611181, Order Now?

Max Phase: Approved

First Approval: 1979

Molecular Formula: C13H21NO3

Molecular Weight: 239.31

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Dilabron | Etyprenaline | Isoetharine | Neoisuprel | WIN 3406 | WIN-3046 | WIN-3406 | WIN3406 | isoetharine|Isoetarine|Isoetarin|530-08-5|Isoetarinum [INN-Latin]|Isoetarina [INN-Spanish]|Dilabron|Etyprenaline|Win 3406|Neoisuprel|4-[1-hydroxy-2-(propan-2-ylamino)butyl]benzene-1,2-diol|Win-3406|CHEBI:6005|Isoetarina|Isoetharine (USP)|Isoetarinum|4-{1-hydroxy-2-[(propan-2-yl)amino]butyl}benzene-1,2-diol|EINECS 208-472-1|Bronkometer; Dilabron; Etyprenaline; Isoctarine|1,2-Benzenediol, 4-(1-hydroxy-2Show More⌵

Synonyms from Alternative Forms(15): Isoetarine hydrochloride | Asthmalitan | Dl-isoetharine hydrochloride | Isoetharine hcl | Isoetharine hydrochloride | Beta-2 | Bronkosol | Isoetharine hydrochloride s/f | Numotac | Isoetharine mesylate | Isoetarine mesilate | Isoetharine mesilate | NSC-759286 | Bronchilator | Bronkometer

Canonical SMILES:  CCC(NC(C)C)C(O)c1ccc(O)c(O)c1

Standard InChI:  InChI=1S/C13H21NO3/c1-4-10(14-8(2)3)13(17)9-5-6-11(15)12(16)7-9/h5-8,10,13-17H,4H2,1-3H3

Standard InChI Key:  HUYWAWARQUIQLE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    0.0625    1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    2.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917   -0.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9333    2.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042   -1.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042    1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833    1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833   -0.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9333   -0.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833    3.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917    2.2458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9250    1.0833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667   -2.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042   -0.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792   -3.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250   -2.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  6  1  0
  4  2  1  0
  5  3  1  0
  6  1  1  0
  7  9  1  0
  8  1  1  0
  9  8  2  0
 10  4  1  0
 11  6  1  0
 12  7  1  0
 13  5  1  0
 14  3  1  0
 15 13  1  0
 16 13  1  0
 17 14  1  0
  4  7  2  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA1201213

   Isoetharine Hydrochloride
2. 

   ALA1201213

   Isoetharine mesylate salt

3. Parent:

   

   ALA1201213

   isoetarine

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: Yes

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 239.31

Molecular Weight (Monoisotopic): 239.1521

AlogP: 1.91

#Rotatable Bonds: 5

Polar Surface Area: 72.72

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.01

CX Basic pKa: 9.01

CX LogP: 1.05

CX LogD: -0.22

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.59

Np Likeness Score: 0.58

References

1. PubChem BioAssay data set, 

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

3. Peterson YK, Cameron RB, Wills LP, Trager RE, Lindsey CC, Beeson CC, Schnellmann RG..  (2013)  β2-Adrenoceptor agonists in the regulation of mitochondrial biogenesis.,  23  (19): [PMID:23954364] [10.1016/j.bmcl.2013.07.052]

4. WHO Anatomical Therapeutic Chemical Classification, 

5. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]

6. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson.  (2020)  Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2,  [10.1101/2020.04.21.054387]

7. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

8. Gebauer L, Jensen O, Brockmöller J, Dücker C..  (2022)  Substrates and Inhibitors of the Organic Cation Transporter 3 and Comparison with OCT1 and OCT2.,  65  (18.0): [PMID:36067397] [10.1021/acs.jmedchem.2c01075]

9. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(6):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6