2-tert-Butylamino-1-(2,5-dimethoxy-phenyl)-propan-1-ol (Butoxamine)

ID: ALA289093

Cas Number: 2922-20-5

PubChem CID: 18026

Max Phase: Unknown

Molecular Formula: C15H25NO3

Molecular Weight: 267.37

Molecule Type: Small molecule

Names and Identifiers

Synonyms from Alternative Forms(7): Butaxamine hydrochloride | Butoxamine hydrochloride | BW 64 9 | BW 64-9 | BW- 64-9 | BW-64-9 | NSC-106565

Canonical SMILES:  COc1ccc(OC)c(C(O)C(C)NC(C)(C)C)c1

Standard InChI:  InChI=1S/C15H25NO3/c1-10(16-15(2,3)4)14(17)12-9-11(18-5)7-8-13(12)19-6/h7-10,14,16-17H,1-6H3

Standard InChI Key:  TWUSDDMONZULSC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -0.4064   -0.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4064    0.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3101    1.5051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3011    0.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3101   -0.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1168   -0.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3853    1.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3101   -1.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1168   -1.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1168    0.6743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4064   -2.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0295   -0.5449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333   -2.2156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0115    0.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716    2.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8128    1.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0301    2.5978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7370   -0.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5437   -1.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  4  3  1  0
  4  2  1  0
  5  1  1  0
  6  1  2  0
  7  3  1  0
  8  5  2  0
  9  6  1  0
  2 10  1  0
 11  9  2  0
 12  5  1  0
 13  9  1  0
 14  4  1  0
 15  7  1  0
 16  7  1  0
 17  7  1  0
 18 12  1  0
 19 13  1  0
  8 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA289093

   BUTOXAMINE

2. Alternative Forms:

   

   ALA289093

   Butoxamine hydrochloride

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 267.37

Molecular Weight (Monoisotopic): 267.1834

AlogP: 2.51

#Rotatable Bonds: 5

Polar Surface Area: 50.72

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.60

CX Basic pKa: 9.58

CX LogP: 2.06

CX LogD: -0.09

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.86

Np Likeness Score: -0.15

References

1. Macchia B, Balsamo A, Lapucci A, Martinelli A, Macchia F, Breschi MC, Fantoni B, Martinotti E..  (1985)  An interdisciplinary approach to the design of new structures active at the beta-adrenergic receptor. Aliphatic oxime ether derivatives.,  28  (2): [PMID:2857200] [10.1021/jm00380a001]

2. McNeal ET, Lewandowski GA, Daly JW, Creveling CR..  (1985)  [3H]Batrachotoxinin A 20 alpha-benzoate binding to voltage-sensitive sodium channels: a rapid and quantitative assay for local anesthetic activity in a variety of drugs.,  28  (3): [PMID:2579237] [10.1021/jm00381a019]

3. Macchia B, Balsamo A, Lapucci A, Macchia F, Martinelli A, Ammon HL, Prasad SM, Breschi MC, Ducci M, Martinotti E..  (1987)  Role of the (acyloxy)methyl moiety in eliciting the adrenergic beta-blocking activity of 3-(acyloxy)propanolamines.,  30  (4): [PMID:2882026] [10.1021/jm00387a006]

4. Leclerc G, Mann A, Wermuth CG, Bieth N, Schwartz J..  (1977)  Synthesis and beta-adrenergic blocking activity of a novel class of aromatic oxime ethers.,  20  (12): [PMID:22751] [10.1021/jm00222a023]

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

Source

Source(2):

• Scientific Literature
• IMI-CARE SARS-CoV-2 Data