4-(1-Benzo[1,3]dioxol-5-ylmethyl-piperidin-4-ylamino)-6-chloro-chromen-2-one

ID: ALA194564

Cas Number: 638191-35-2

PubChem CID: 10047339

Max Phase: Preclinical

Molecular Formula: C22H21ClN2O4

Molecular Weight: 412.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1cc(NC2CCN(Cc3ccc4c(c3)OCO4)CC2)c2cc(Cl)ccc2o1

Standard InChI:  InChI=1S/C22H21ClN2O4/c23-15-2-4-19-17(10-15)18(11-22(26)29-19)24-16-5-7-25(8-6-16)12-14-1-3-20-21(9-14)28-13-27-20/h1-4,9-11,16,24H,5-8,12-13H2

Standard InChI Key:  FBKMRPXQTLKWBJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.5667   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2875   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2875   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7125   -1.6417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167    0.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4292    1.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000    1.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625    2.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375    2.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167    0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -5.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4292   -0.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4292   -1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417    0.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9917   -2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7125   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9917   -1.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417    0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -3.7125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  5  1  0
  7  1  1  0
  8 24  1  0
  9 15  2  0
 10 21  2  0
 11  9  1  0
 12  3  2  0
 13 10  1  0
 14 11  1  0
 15 17  1  0
 16  4  2  0
 17 19  1  0
 18  5  2  0
 19  8  1  0
 20  7  1  0
 21 27  1  0
 22 20  1  0
 23 20  1  0
 24 23  1  0
 25 22  1  0
 26 12  1  0
 27 17  2  0
 28 26  2  0
 29 26  1  0
  4  6  1  0
  8 25  1  0
 28 18  1  0
 10  9  1  0
 14 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA194564

   4-[[1-(1,3-Benzodioxol-5-ylmethyl)-4-piperidinyl]amino]-6-chloro-2H-1-benzopyran-2-one

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: 412.87

Molecular Weight (Monoisotopic): 412.1190

AlogP: 4.25

#Rotatable Bonds: 4

Polar Surface Area: 63.94

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.93

CX LogP: 2.80

CX LogD: 2.16

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.65

Np Likeness Score: -0.82

References

1. Kym PR, Iyengar R, Souers AJ, Lynch JK, Judd AS, Gao J, Freeman J, Mulhern M, Zhao G, Vasudevan A, Wodka D, Blackburn C, Brown J, Che JL, Cullis C, Lai SJ, LaMarche MJ, Marsilje T, Roses J, Sells T, Geddes B, Govek E, Patane M, Fry D, Dayton BD, Brodjian S, Falls D, Brune M, Bush E, Shapiro R, Knourek-Segel V, Fey T, McDowell C, Reinhart GA, Preusser LC, Marsh K, Hernandez L, Sham HL, Collins CA..  (2005)  Discovery and characterization of aminopiperidinecoumarin melanin concentrating hormone receptor 1 antagonists.,  48  (19): [PMID:16161992] [10.1021/jm050598r]

Source

Source(1):

• Scientific Literature