4-(2-Hydroxy-3-isopropylamino-propoxy)-naphthalen-1-ol

ID: ALA1137

Cas Number: 69499-28-1

PubChem CID: 91565

Max Phase: Preclinical

Molecular Formula: C16H21NO3

Molecular Weight: 275.35

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4-Hydroxy Propranolol | 4-Hydroxypropranolol|10476-53-6|4'-hydroxypropanolol|4-[2-hydroxy-3-(propan-2-ylamino)propoxy]naphthalen-1-ol|(+/-)-4-HYDROXYPROPRANOLOL, HYDROCHLORIDE|2449QP4SVP|4-(2-Hydroxy-3-(isopropylamino)propoxy)naphthalen-1-ol|4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}naphthalen-1-ol|UNII-2449QP4SVP|CHEMBL1137|1-(4-Hydroxynaphth-1-yloxy)-3-isopropylamino-2-propanol|DTXSID70893062|CHEBI:168939|CWEPACWBWIOYID-UHFFFAOYSA-N|4-(2-Hydroxy-3-((1-methylethyl)amino)propoxy)-1-naphthalenolShow More⌵

Canonical SMILES:  CC(C)NCC(O)COc1ccc(O)c2ccccc12

Standard InChI:  InChI=1S/C16H21NO3/c1-11(2)17-9-12(18)10-20-16-8-7-15(19)13-5-3-4-6-14(13)16/h3-8,11-12,17-19H,9-10H2,1-2H3

Standard InChI Key:  CWEPACWBWIOYID-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2907    2.9981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8717    7.5123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812    5.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870    3.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8775    6.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2928   -2.6973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    5.8509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1681    8.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1634    9.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2098    7.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  3  2  0
  7  6  1  0
  8 11  1  0
  9 10  1  0
 10  5  1  0
 11  9  1  0
 12  4  1  0
 13  9  1  0
 14  1  2  0
 15  2  2  0
 16  8  1  0
 17 16  1  0
 18 16  1  0
 19 14  1  0
 20 19  2  0
 15 20  1  0
  7  4  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1137

   4-HYDROXYPROPRANOLOL SULFATE

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: 275.35

Molecular Weight (Monoisotopic): 275.1521

AlogP: 2.28

#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: 9.30

CX Basic pKa: 9.91

CX LogP: 1.57

CX LogD: 0.08

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.76

Np Likeness Score: -0.07

References

1. Oatis JE, Russell MP, Knapp DR, Walle T..  (1981)  Ring-hydroxylated propranolol: synthesis and beta-receptor antagonist and vasodilating activities of the seven isomers.,  24  (3): [PMID:6115057] [10.1021/jm00135a014]

2. Oatis JE, Walle T, Daniell HB, Gaffney TE, Knapp DR..  (1985)  Synthesis of 4'-hydroxypropranolol sulfate, a major non-beta-blocking propranolol metabolite in man.,  28  (6): [PMID:2861287] [10.1021/jm00383a023]

3. Nelson WL, Bartels MJ, Bednarski PJ, Zhang S, Messick K, Horng JS, Ruffolo RR..  (1984)  The 3,4-catechol derivative of propranolol, a minor dihydroxylated metabolite.,  27  (7): [PMID:6330358] [10.1021/jm00373a008]

4. Rauls DO, Baker JK..  (1979)  Relationship of nonspecific antiarrhythmic and negative inotropic activity with physicochemical parameters of propranolol analogues.,  22  (1): [PMID:423187] [10.1021/jm00187a018]

5. Loi CM, Smith DA, Dalvie D..  (2013)  Which metabolites circulate?,  41  (5): [PMID:23454828] [10.1124/dmd.112.050278]

6. Drug metabolism data, 

Source

Source(2):

• Scientific Literature
• Curated Drug Metabolism Pathways