(2R,3S)-5-(2-hydroxy-3-(2,4,4-trimethylpentan-2-ylamino)propoxy)-1,2,3,4-tetrahydronaphthalene-2,3-diol

ID: ALA3246790

PubChem CID: 90672695

Max Phase: Preclinical

Molecular Formula: C21H35NO4

Molecular Weight: 365.51

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H35NO4/c1-20(2,3)13-21(4,5)22-11-15(23)12-26-19-8-6-7-14-9-17(24)18(25)10-16(14)19/h6-8,15,17-18,22-25H,9-13H2,1-5H3/t15?,17-,18+/m1/s1

Standard InChI Key:  KFGVTGYQHZQTHM-KVJCIMDZSA-N

Molfile:  

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    6.2315  -15.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2354  -16.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304  -17.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8214  -16.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1164  -17.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4053  -16.7746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3994  -15.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1044  -15.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8154  -15.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5145  -14.7168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2192  -14.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9299  -14.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6346  -14.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9359  -15.5236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3453  -14.6961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7003  -17.1878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888  -15.5526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0500  -14.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7606  -14.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6342  -13.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4514  -13.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4653  -14.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1760  -14.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4594  -13.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2508  -14.0532    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
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 13 15  1  0
 14 16  1  0
  7 17  1  1
  8 18  1  1
 16 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3246790

   (2R,3S)-5-[2-hydroxy-3-(2,4,4-trimethylpentan-2-ylamino)propoxy]-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: 365.51

Molecular Weight (Monoisotopic): 365.2566

AlogP: 2.05

#Rotatable Bonds: 7

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: 9.99

CX LogP: 2.42

CX LogD: -0.09

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.59

Np Likeness Score: -0.08

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