Pyrrobutamine

ID: ALA1697849

Cas Number: 91-82-7

PubChem CID: 5284614

Max Phase: Unknown

Molecular Formula: C20H22ClN

Molecular Weight: 311.86

Molecule Type: Small molecule

Names and Identifiers

Synonyms from Alternative Forms(2): Pyrrobutamine diphosphate | Pyrrobutamine phosphate

Canonical SMILES:  Clc1ccc(C/C(=C\CN2CCCC2)c2ccccc2)cc1

Standard InChI:  InChI=1S/C20H22ClN/c21-20-10-8-17(9-11-20)16-19(18-6-2-1-3-7-18)12-15-22-13-4-5-14-22/h1-3,6-12H,4-5,13-16H2/b19-12+

Standard InChI Key:  WDYYVNNRTDZKAZ-XDHOZWIPSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    2.0367    4.4759    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    3.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    3.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7982   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    3.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002   -1.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7028   -2.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5262   -2.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  8 13  1  0
  7 14  2  0
  5 16  1  0
 16 17  2  0
  2 17  1  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 19 15  1  0
 22 15  1  0
 20 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1697849

   PYRROBUTAMINE

2. Alternative Forms:

   

   ALA1697849

   PYRROBUTAMINE PHOSPHATE

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 311.86

Molecular Weight (Monoisotopic): 311.1441

AlogP: 5.06

#Rotatable Bonds: 5

Polar Surface Area: 3.24

Molecular Species: BASE

HBA: 1

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.91

CX LogP: 5.41

CX LogD: 3.89

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.75

Np Likeness Score: -0.78

References

1. Kruhlak NL, Choi SS, Contrera JF, Weaver JL, Willard JM, Hastings KL, Sancilio LF..  (2008)  Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.,  18  (2): [PMID:20020916] [10.1080/15376510701857262]

2. WHO Anatomical Therapeutic Chemical Classification, 

Source

Source(2):

• Scientific Literature
• WHO Anatomical Therapeutic Chemical Classification