4-((3,4-Dihydropyrano[4,3-b]indol-5(1H)-yl)methyl)-N-hydroxybenzamide

ID: ALA4531802

PubChem CID: 155546486

Max Phase: Preclinical

Molecular Formula: C19H18N2O3

Molecular Weight: 322.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NO)c1ccc(Cn2c3c(c4ccccc42)COCC3)cc1

Standard InChI:  InChI=1S/C19H18N2O3/c22-19(20-23)14-7-5-13(6-8-14)11-21-17-4-2-1-3-15(17)16-12-24-10-9-18(16)21/h1-8,23H,9-12H2,(H,20,22)

Standard InChI Key:  PLXSOPIGQFDAJE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   20.1353  -28.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1342  -29.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8422  -29.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5519  -29.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5491  -28.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8404  -27.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2602  -29.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2615  -30.2616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9673  -29.0347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.6757  -29.4422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4275  -27.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4273  -26.9922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8351  -25.7348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0863  -26.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8782  -26.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4246  -26.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1734  -25.3007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3758  -25.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7656  -26.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0188  -25.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4762  -25.1352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6803  -25.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4300  -26.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9743  -26.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  1 11  1  0
 11 12  1  0
 12 14  1  0
 13 20  1  0
 19 12  1  0
 13 14  2  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4531802

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 322.36

Molecular Weight (Monoisotopic): 322.1317

AlogP: 2.88

#Rotatable Bonds: 3

Polar Surface Area: 63.49

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.20

CX Basic pKa: ┄

CX LogP: 2.47

CX LogD: 2.47

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.58

Np Likeness Score: -0.75

References

1. Géraldy M, Morgen M, Sehr P, Steimbach RR, Moi D, Ridinger J, Oehme I, Witt O, Malz M, Nogueira MS, Koch O, Gunkel N, Miller AK..  (2019)  Selective Inhibition of Histone Deacetylase 10: Hydrogen Bonding to the Gatekeeper Residue is Implicated.,  62  (9): [PMID:30964290] [10.1021/acs.jmedchem.8b01936]

Source

Source(1):

• Scientific Literature