1-{2-[4-(6-bromobenzo[1,3]dioxol-5-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-8-yl]ethyl}-3-(3-iodo(125)-phenyl)urea

ID: ALA569278

PubChem CID: 45486406

Max Phase: Preclinical

Molecular Formula: C28H25BrIN3O3

Molecular Weight: 658.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCc1ccc2c(c1)[C@@H]1C=CC[C@@H]1[C@H](c1cc3c(cc1Br)OCO3)N2)Nc1cccc([125I])c1

Standard InChI:  InChI=1S/C28H25BrIN3O3/c29-23-14-26-25(35-15-36-26)13-22(23)27-20-6-2-5-19(20)21-11-16(7-8-24(21)33-27)9-10-31-28(34)32-18-4-1-3-17(30)12-18/h1-5,7-8,11-14,19-20,27,33H,6,9-10,15H2,(H2,31,32,34)/t19-,20+,27-/m1/s1/i30-2

Standard InChI Key:  ZAKNBQXENRAVAB-DBBOMHGISA-N

Molfile:  

     RDKit          2D

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   -2.6338  -15.5292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9218  -14.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9234  -15.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125  -15.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4994  -15.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0587  -15.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3400  -16.7660    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9250  -13.4625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2114  -13.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9271  -14.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6403  -13.8737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3561  -14.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7850  -14.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7832  -15.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4981  -15.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2123  -15.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2070  -14.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4915  -13.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9187  -13.8540    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
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  8  3  1  0
 19  1  1  0
  3  4  2  0
  9 10  2  0
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 20 21  1  0
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  1  2  1  0
 20 24  1  6
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  4  5  1  0
  7 26  1  0
 11 12  2  0
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  1  9  1  1
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  2  4  1  0
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  5  6  2  0
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  3 20  1  0
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  6  7  1  0
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  7  8  2  0
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M  ISO  1  38 125
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: 658.33

Molecular Weight (Monoisotopic): 657.0124

AlogP: 6.97

#Rotatable Bonds: 5

Polar Surface Area: 71.62

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.33

CX Basic pKa: 3.03

CX LogP: 6.45

CX LogD: 6.45

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.20

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