3-((2-hydroxyethyl)((3-oxo-2,3-dihydrochromeno[4,3,2-de]phthalazin-10-yl)methyl)amino)propanoic acid

ID: ALA3527001

PubChem CID: 118753214

Max Phase: Preclinical

Molecular Formula: C20H19N3O5

Molecular Weight: 381.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCN(CCO)Cc1ccc2c(c1)-c1n[nH]c(=O)c3cccc(c13)O2

Standard InChI:  InChI=1S/C20H19N3O5/c24-9-8-23(7-6-17(25)26)11-12-4-5-15-14(10-12)19-18-13(20(27)22-21-19)2-1-3-16(18)28-15/h1-5,10,24H,6-9,11H2,(H,22,27)(H,25,26)

Standard InChI Key:  SGCSKXTWDWVPQP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    4.8316   -4.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8304   -5.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5385   -5.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2441   -5.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9542   -5.4468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5367   -3.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2483   -4.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9536   -3.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9534   -2.9833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -2.5753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5303   -2.9870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6712   -4.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6682   -5.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3791   -5.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0977   -5.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1007   -4.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3852   -3.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8103   -3.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5161   -4.2241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5059   -5.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2076   -5.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9254   -4.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2192   -3.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8208   -2.5815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6368   -3.8343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2018   -6.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4937   -6.6787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9091   -6.6887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  6  1  1  0
  7  4  1  0
  4  5  1  0
  5 13  1  0
 12  8  1  0
  6  7  2  0
  6 11  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 12 13  2  0
 12 17  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 23  1  0
 20 21  1  0
 22 23  1  0
 11 24  2  0
 22 25  1  0
 21 26  1  0
 26 27  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3527001

   ---

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: 381.39

Molecular Weight (Monoisotopic): 381.1325

AlogP: 1.96

#Rotatable Bonds: 7

Polar Surface Area: 115.75

Molecular Species: ZWITTERION

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.81

CX Basic pKa: 8.54

CX LogP: -1.50

CX LogD: -1.52

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.45

Np Likeness Score: -0.90

References

1. Lai WG, Farah N, Moniz GA, Wong YN..  (2011)  A Baeyer-Villiger oxidation specifically catalyzed by human flavin-containing monooxygenase 5.,  39  (1): [PMID:20947616] [10.1124/dmd.110.035360]

Source

Source(1):

• Scientific Literature