(S)-(-)-2-[[[3-(Morpholinomethyl)-2H-chromen-8-yl]oxy]-methyl]morpholine Hydrochloride

ID: ALA1202783

PubChem CID: 49860422

Max Phase: Preclinical

Molecular Formula: C19H27ClN2O4

Molecular Weight: 346.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C1=C(CN2CCOCC2)COc2c1cccc2OC[C@@H]1CNCCO1.Cl

Standard InChI:  InChI=1S/C19H26N2O4.ClH/c1-2-16-10-15(12-21-5-8-22-9-6-21)13-25-19(16)18(3-1)24-14-17-11-20-4-7-23-17;/h1-3,10,17,20H,4-9,11-14H2;1H/t17-;/m0./s1

Standard InChI Key:  YJXRBQIKJUJCPY-LMOVPXPDSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   10.2910    3.3790    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870    3.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2907    2.9981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942   -1.4964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929   -0.7441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4946   -1.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7910   -0.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7858    0.7649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4842    1.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1877    0.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812    5.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8758    6.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8669    7.5130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5634    8.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2688    7.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2777    5.9976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 12  1  0
 10 18  1  0
 18 19  1  0
 19 20  1  0
 20  4  1  0
 20  8  2  0
 21  2  1  6
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 21  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: 346.43

Molecular Weight (Monoisotopic): 346.1893

AlogP: 1.16

#Rotatable Bonds: 5

Polar Surface Area: 52.19

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.20

CX LogP: 0.95

CX LogD: 0.06

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.86

Np Likeness Score: -0.42

References

1. Berg S, Larsson LG, Rényi L, Ross SB, Thorberg SO, Thorell-Svantesson G..  (1998)  (R)-(+)-2-[[[3-(Morpholinomethyl)-2H-chromen-8-yl]oxy]methyl] morpholine methanesulfonate: a new selective rat 5-hydroxytryptamine1B receptor antagonist.,  41  (11): [PMID:9599242] [10.1021/jm970806i]

Source

Source(1):

• Scientific Literature