1-(3,5-Diiodo-4-methoxy-benzyl)-1,2,3,4-tetrahydro-isoquinoline-6,7-diol

ID: ALA308351

PubChem CID: 9871887

Max Phase: Preclinical

Molecular Formula: C17H17I2NO3

Molecular Weight: 537.13

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(I)cc(CC2NCCc3cc(O)c(O)cc32)cc1I

Standard InChI:  InChI=1S/C17H17I2NO3/c1-23-17-12(18)4-9(5-13(17)19)6-14-11-8-16(22)15(21)7-10(11)2-3-20-14/h4-5,7-8,14,20-22H,2-3,6H2,1H3

Standard InChI Key:  CCQIDZRURGYWNQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    5.5542   -5.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6292   -7.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0375   -6.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -6.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -5.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1042   -7.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6292   -7.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -5.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5917   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0375   -4.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -5.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -5.8125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5917   -7.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1125   -6.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0750   -6.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1500   -6.7042    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    7.1042   -8.5125    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    8.1500   -7.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000   -6.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -5.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000   -4.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -4.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1500   -8.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  0
  3  1  2  0
  4  1  1  0
  5  1  1  0
  6 13  1  0
  7 14  2  0
  8  3  1  0
  9 15  1  0
 10  5  2  0
 11 10  1  0
 12  4  1  0
 13  9  2  0
 14  9  1  0
 15  4  1  0
 16  7  1  0
 17  6  1  0
 18  2  1  0
 19  8  1  0
 20 22  1  0
 21 11  1  0
 22  5  1  0
 23 18  1  0
 20 12  1  0
  8 11  2  0
  2  6  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA308351

   TMQ, 3',5'-Diiodo

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: 537.13

Molecular Weight (Monoisotopic): 536.9298

AlogP: 3.75

#Rotatable Bonds: 3

Polar Surface Area: 61.72

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.52

CX Basic pKa: 8.50

CX LogP: 4.42

CX LogD: 3.50

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.41

Np Likeness Score: 1.22

References

1. Zheng W, Nikulin VI, Konkar AA, Vansal SS, Shams G, Feller DR, Miller DD..  (1999)  2-Amino-4-benzyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridines: novel selective beta3-adrenoceptor agonists.,  42  (12): [PMID:10377236] [10.1021/jm990012z]

2. De Los Angeles JE, Nikulin VI, Shams G, Konkar AA, Mehta R, Feller DR, Miller DD..  (1996)  Iodinated analogs of trimetoquinol as highly potent and selective beta 2-adrenoceptor ligands.,  39  (19): [PMID:8809159] [10.1021/jm960208o]

3. He Y, Nikulin VI, Vansal SS, Feller DR, Miller DD..  (2000)  Synthesis and human beta-adrenoceptor activity of 1-(3,5-diiodo-4- methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-6-ol derivatives in vitro.,  43  (4): [PMID:10691685] [10.1021/jm990463j]

4. Christoff JJ, Bradley L, Miller DD, Lei L, Rodriguez F, Fraundorfer P, Romstedt K, Shams G, Feller DR..  (1997)  Synthesis and evaluation of trimetoquinol derivatives: novel thromboxane A2/prostaglandin H2 antagonists with diminished beta-adrenergic agonist activity.,  40  (1): [PMID:9016331] [10.1021/jm950896w]

Source

Source(1):

• Scientific Literature