3,11-Dihydro-3-oxopyrano[3,2-a]carbazole-2-carboxylic acid

ID: ALA2414995

PubChem CID: 71770035

Max Phase: Preclinical

Molecular Formula: C16H9NO4

Molecular Weight: 279.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc2c(ccc3c4ccccc4[nH]c23)oc1=O

Standard InChI:  InChI=1S/C16H9NO4/c18-15(19)11-7-10-13(21-16(11)20)6-5-9-8-3-1-2-4-12(8)17-14(9)10/h1-7,17H,(H,18,19)

Standard InChI Key:  IVSBKPZOUQONEV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
   16.7020  -15.4112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7903  -14.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2194  -14.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1689  -13.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9446  -15.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0000  -14.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3239  -13.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5920  -14.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5404  -15.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2173  -15.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0296  -14.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4561  -15.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2644  -15.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6444  -14.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4116  -14.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2123  -14.0134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9887  -13.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4609  -14.6614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6973  -16.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3136  -16.8259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5140  -16.0760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  5  1  1  0
  1  3  1  0
  2  3  2  0
  3 11  1  0
 17  4  2  0
  4  2  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 15 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 16  1  0
 15 16  1  0
 17 15  1  0
 14 18  2  0
 13 19  1  0
 19 20  1  0
 19 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2414995

   3-oxo-11H-pyrano[3,2-a]carbazole-2-carboxylic acid

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: 279.25

Molecular Weight (Monoisotopic): 279.0532

AlogP: 3.13

#Rotatable Bonds: 1

Polar Surface Area: 83.30

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.46

CX Basic pKa: ┄

CX LogP: 2.49

CX LogD: -0.90

Aromatic Rings: 4

Heavy Atoms: 21

QED Weighted: 0.52

Np Likeness Score: 0.18

References

1. Francisco CS, Rodrigues LR, Cerqueira NM, Oliveira-Campos AM, Rodrigues LM, Esteves AP..  (2013)  Synthesis of novel psoralen analogues and their in vitro antitumor activity.,  21  (17): [PMID:23886808] [10.1016/j.bmc.2013.06.049]

Source

Source(1):

• Scientific Literature