2,5-Dihydroxy-N-[2-(2-hydroxy-3-phenoxy-propylamino)-ethyl]-benzamide; compound with oxalic acid

ID: ALA3392275

PubChem CID: 13030894

Max Phase: Preclinical

Molecular Formula: C20H24N2O9

Molecular Weight: 346.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCNCC(O)COc1ccccc1)c1cc(O)ccc1O.O=C(O)C(=O)O

Standard InChI:  InChI=1S/C18H22N2O5.C2H2O4/c21-13-6-7-17(23)16(10-13)18(24)20-9-8-19-11-14(22)12-25-15-4-2-1-3-5-15;3-1(4)2(5)6/h1-7,10,14,19,21-23H,8-9,11-12H2,(H,20,24);(H,3,4)(H,5,6)

Standard InChI Key:  PCALMSVAVAACCF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
    5.0384   -6.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8634   -6.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2759   -7.0198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2759   -5.5909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6259   -5.5909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6259   -7.0198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3073   -3.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5943   -2.7188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0204   -2.7188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2990   -3.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5943   -1.8932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8812   -3.1317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7335   -3.1400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8773   -2.7021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0121   -4.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034   -2.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903   -3.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7335   -3.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7337   -2.7063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0204   -1.8932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1559   -3.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3076   -1.8807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0079   -5.1958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0165   -3.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1681   -2.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4468   -3.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4428   -2.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1559   -3.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7381   -3.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4428   -4.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7381   -3.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  1  5  2  0
  1  6  1  0
  8  7  1  0
  9  7  2  0
 10  7  1  0
 11  8  2  0
 12  8  1  0
 13  9  1  0
 14 17  1  0
 15 10  2  0
 16 24  1  0
 17 16  1  0
 18 15  1  0
 19 26  1  0
 20  9  1  0
 21 14  1  0
 22 16  1  0
 23 15  1  0
 24 19  1  0
 25 12  1  0
 26 25  1  0
 27 21  1  0
 28 21  2  0
 29 27  2  0
 30 28  1  0
 31 30  2  0
 18 13  2  0
 31 29  1  0
M  END

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: 346.38

Molecular Weight (Monoisotopic): 346.1529

AlogP: 0.86

#Rotatable Bonds: 9

Polar Surface Area: 111.05

Molecular Species: BASE

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.37

CX Basic pKa: 8.99

CX LogP: 1.02

CX LogD: 0.36

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.34

Np Likeness Score: -0.44

References

1. Lare MS, Smith LH..  (1982)  Beta-adrenergic blocking agents. 22. 1-Phenoxy-3-[[(substituted-amido) alkyl]amino]-2-propanols.,  25  (11): [PMID:6128420] [10.1021/jm00353a004]

Source

Source(1):

• Scientific Literature