N-{1-[4-(6-Bromobenzo[1,3]dioxol-5-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-8-yl]ethylidene}-N'-(5-iodo(125)-pyridin-2-yl)-hydrazine

ID: ALA566570

PubChem CID: 45486411

Max Phase: Preclinical

Molecular Formula: C26H22BrIN4O2

Molecular Weight: 629.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=N\Nc1ccc([125I])cn1)c1ccc2c(c1)[C@@H]1C=CC[C@@H]1[C@H](c1cc3c(cc1Br)OCO3)N2

Standard InChI:  InChI=1S/C26H22BrIN4O2/c1-14(31-32-25-8-6-16(28)12-29-25)15-5-7-22-19(9-15)17-3-2-4-18(17)26(30-22)20-10-23-24(11-21(20)27)34-13-33-23/h2-3,5-12,17-18,26,30H,4,13H2,1H3,(H,29,32)/b31-14+/t17-,18+,26-/m1/s1/i28-2

Standard InChI Key:  ZADIWYPHRKHAFC-ZNXJKJKRSA-N

Molfile:  

     RDKit          2D

 36 41  0  0  0  0  0  0  0  0999 V2000
    9.9833  -14.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6954  -15.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4074  -14.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4058  -14.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1167  -15.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8298  -14.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8274  -14.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1158  -13.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2704  -15.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5551  -14.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5625  -16.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2730  -16.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9892  -16.5535    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.8424  -16.1479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8404  -15.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0544  -15.0687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5705  -15.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0576  -16.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9810  -14.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6954  -13.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5236  -12.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7030  -12.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3678  -13.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4042  -13.2500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2625  -14.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5405  -13.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2563  -14.0759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5379  -12.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9695  -13.6612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6852  -14.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6832  -14.8969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3981  -15.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1123  -14.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1070  -14.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3915  -13.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8286  -15.3015    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 19 20  1  0
  8  3  1  0
 19  1  1  0
  3  4  2  0
  9 10  2  0
 10 15  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  1  0
  1  2  1  0
 20 24  1  6
 14 11  1  0
 19 25  1  6
  4  5  1  0
  7 26  1  0
 11 12  2  0
 26 27  2  0
 12  9  1  0
 26 28  1  0
  1  9  1  1
 27 29  1  0
  2  4  1  0
 29 30  1  0
 12 13  1  0
 30 31  2  0
 14 15  2  0
 31 32  1  0
  5  6  2  0
 32 33  2  0
  3 20  1  0
 33 34  1  0
  6  7  1  0
 34 35  2  0
 35 30  1  0
 33 36  1  0
M  ISO  1  36 125
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: 629.30

Molecular Weight (Monoisotopic): 627.9971

AlogP: 6.84

#Rotatable Bonds: 4

Polar Surface Area: 67.77

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 5.19

CX LogP: 6.36

CX LogD: 6.35

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.14

Np Likeness Score: -0.91

References

1. Ramesh C, Nayak TK, Burai R, Dennis MK, Hathaway HJ, Sklar LA, Prossnitz ER, Arterburn JB..  (2010)  Synthesis and characterization of iodinated tetrahydroquinolines targeting the G protein-coupled estrogen receptor GPR30.,  53  (3): [PMID:20041667] [10.1021/jm9011802]

Source

Source(1):

• Scientific Literature