(2R,3S)-5-(3-(butylamino)-2-hydroxypropoxy)-1,2,3,4-tetrahydronaphthalene-2,3-diol

ID: ALA3246789

PubChem CID: 90672694

Max Phase: Preclinical

Molecular Formula: C17H27NO4

Molecular Weight: 309.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCNCC(O)COc1cccc2c1C[C@H](O)[C@H](O)C2

Standard InChI:  InChI=1S/C17H27NO4/c1-2-3-7-18-10-13(19)11-22-17-6-4-5-12-8-15(20)16(21)9-14(12)17/h4-6,13,15-16,18-21H,2-3,7-11H2,1H3/t13?,15-,16+/m1/s1

Standard InChI Key:  VSMUQFAEQWNNML-CZVYVAOFSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    5.3637   -9.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0747  -10.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0786  -10.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3735  -11.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6646  -10.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9595  -11.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2485  -10.9594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2425  -10.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9476   -9.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6586  -10.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3577   -8.9015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0624   -8.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7730   -8.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4777   -8.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7790   -9.7083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1884   -8.8808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5435  -11.3725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5320   -9.7373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8931   -8.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6038   -8.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3085   -8.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0192   -8.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  1 10  2  0
  5 10  1  0
  1 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 14 16  1  0
  7 17  1  1
  8 18  1  1
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3246789

   (2R,3S)-5-[3-(butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol

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: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 309.41

Molecular Weight (Monoisotopic): 309.1940

AlogP: 0.64

#Rotatable Bonds: 8

Polar Surface Area: 81.95

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.59

CX Basic pKa: 9.76

CX LogP: 1.14

CX LogD: -1.17

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.53

Np Likeness Score: 0.28

References

1. Condon ME, Cimarusti CM, Fox R, Narayanan VL, Reid J, Sundeen JE, Hauck FP..  (1978)  Nondepressant beta-adrenergic blocking agents. 1. Substituted 3-amino-1-(5,6,7,8-tetrahydro-1-naphthoxy)-2-propanols.,  21  (9): [PMID:31485] [10.1021/jm00207a014]

Source

Source(1):

• Scientific Literature