Ethyl 3,11-dihydro-3-oxopyrano[3,2-a]carbazole-2-carboxylate

ID: ALA2414994

PubChem CID: 73346077

Max Phase: Preclinical

Molecular Formula: C18H13NO4

Molecular Weight: 307.31

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H13NO4/c1-2-22-17(20)13-9-12-15(23-18(13)21)8-7-11-10-5-3-4-6-14(10)19-16(11)12/h3-9,19H,2H2,1H3

Standard InChI Key:  AYVGGVRTODEMSB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   15.2709   -3.3069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3605   -1.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7962   -2.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7450   -1.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5018   -2.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5580   -2.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8715   -1.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1283   -2.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0759   -2.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7632   -3.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6189   -2.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0520   -3.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8728   -3.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2587   -2.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0068   -1.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8199   -1.8874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5774   -1.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0878   -2.5454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3125   -4.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9229   -4.7433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1418   -3.9818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0936   -4.7722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7038   -5.5049    0.0000 C   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
 20 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2414994

   ethyl 3-oxo-11H-pyrano[3,2-a]carbazole-2-carboxylate

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: 307.31

Molecular Weight (Monoisotopic): 307.0845

AlogP: 3.60

#Rotatable Bonds: 2

Polar Surface Area: 72.30

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.46

CX Basic pKa: ┄

CX LogP: 3.22

CX LogD: 3.22

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.45

Np Likeness Score: -0.08

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