[2-Hydroxy-3-(4-hydroxy-phenoxy)-propyl]-isopropyl-ammonium (prenalterol)

ID: ALA1160714

Cas Number: 57526-81-5

PubChem CID: 42396

Product Number: P612920, Order Now?

Max Phase: Phase

Molecular Formula: C12H19NO3

Molecular Weight: 225.29

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Phenol metabolite | Prenalterol|57526-81-5|(S)-4-(2-Hydroxy-3-(isopropylamino)propoxy)phenol|Prenalterolum|Prenalterol [INN:BAN]|CGP 7760B|Prenalterolum [INN-Latin]|EINECS 260-791-5|4-[(2S)-2-hydroxy-3-(propan-2-ylamino)propoxy]phenol|PHENOL METABOLITE|CHEBI:8391|M4G34404CX|Hyprenan|Phenol, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-, (S)-|BRN 5740338|(-)-(S)-1-(p-Hydroxyphenoxy)-3-(isopropylamino)-2-propanol|UNII-M4G34404CX|(S)-4-(2-Hydroxy-3-((1-methylethyl)amino)propoxy)phenol|PRENALTEROL Show More⌵

Synonyms from Alternative Forms(5): Prenalterol hcl | Prenalterol hydrochloride | CGP 7760B | CGP-7760B | H 133/22

Canonical SMILES:  CC(C)NC[C@H](O)COc1ccc(O)cc1

Standard InChI:  InChI=1S/C12H19NO3/c1-9(2)13-7-11(15)8-16-12-5-3-10(14)4-6-12/h3-6,9,11,13-15H,7-8H2,1-2H3/t11-/m0/s1

Standard InChI Key:  ADUKCCWBEDSMEB-NSHDSACASA-N

Molfile:  

     RDKit          2D

 17 17  0  0  1  0  0  0  0  0999 V2000
   -7.3955   -3.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1100   -3.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1100   -4.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3955   -5.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6810   -4.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6810   -3.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8245   -5.1268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9666   -3.4768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2521   -3.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5376   -3.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8232   -3.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5376   -2.6518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1087   -3.4768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3942   -3.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6797   -3.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3942   -4.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8231   -3.0643    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  2  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  3  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 10 17  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1160714

   prenalterol

2. Alternative Forms:

   

   ALA1160714

   PRENALTEROL HYDROCHLORIDE

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 225.29

Molecular Weight (Monoisotopic): 225.1365

AlogP: 1.13

#Rotatable Bonds: 6

Polar Surface Area: 61.72

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.11

CX Basic pKa: 9.47

CX LogP: 0.80

CX LogD: -0.92

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.68

Np Likeness Score: -0.13

References

1. Donné-Op den Kelder GM, Bultsma T, Timmerman H, Rademaker B..  (1988)  Mapping of the beta 2-adrenoceptor on Chang liver cells. Differences between high- and low-affinity receptor states.,  31  (6): [PMID:2836587] [10.1021/jm00401a004]

2. IJzerman AP, Aué GH, Bultsma T, Linschoten MR, Timmerman H..  (1985)  Quantitative evaluation of the beta 2-adrenoceptor affinity of phenoxypropanolamines and phenylethanolamines.,  28  (9): [PMID:2993621] [10.1021/jm00147a037]

3. Howe R, Rao BS, Holloway BR, Stribling D..  (1992)  Selective beta 3-adrenergic agonists of brown adipose tissue and thermogenesis. 1. [4-[2-[(2-Hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetates.,  35  (10): [PMID:1350309] [10.1021/jm00088a009]

4. Erhardt PW..  (1987)  In search of the digitalis replacement.,  30  (2): [PMID:3027335] [10.1021/jm00385a001]

5. Yoshida F, Topliss JG..  (2000)  QSAR model for drug human oral bioavailability.,  43  (13): [PMID:10891117] [10.1021/jm0000564]

6. Linschoten MR, Bultsma T, IJzerman AP, Timmerman H..  (1986)  Mapping the turkey erythrocyte beta receptor: a distance geometry approach.,  29  (2): [PMID:3005570] [10.1021/jm00152a017]

7. Barlow JJ, Main BG, Snow HM..  (1981)  Beta-adrenoceptor stimulant properties of amidoalkylamino-substituted 1-aryl-2-ethanols and 1-(aryloxy)-2-propanols.,  24  (3): [PMID:6115058] [10.1021/jm00135a015]

8. Lövgren K, Hedberg A, Nilsson JL..  (1980)  Adrenergic receptor agonists. Benzofuranylethanolamines.,  23  (6): [PMID:6104731] [10.1021/jm00180a008]

9. Kruhlak NL, Choi SS, Contrera JF, Weaver JL, Willard JM, Hastings KL, Sancilio LF..  (2008)  Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.,  18  (2): [PMID:20020916] [10.1080/15376510701857262]

10. WHO Anatomical Therapeutic Chemical Classification, 

11. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

12. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

13. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

14. Jensen O, Brockmöller J, Dücker C..  (2021)  Identification of Novel High-Affinity Substrates of OCT1 Using Machine Learning-Guided Virtual Screening and Experimental Validation.,  64  (5.0): [PMID:33606526] [10.1021/acs.jmedchem.0c02047]

15. 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(4):

• Scientific Literature
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data