(E)-N-(6,7-Dihydro-4H-[1,3]dioxolo[4',5':7,8]isoquinolino-[3,2-a][1,3]dioxolo[4,5-g]isoquinolin-4-ylidene)-propionamide

ID: ALA4519983

PubChem CID: 155542144

Max Phase: Preclinical

Molecular Formula: C22H18N2O5

Molecular Weight: 390.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC(=O)/N=c1\c2c3c(ccc2cc2n1CCc1cc4c(cc1-2)OCO4)OCO3

Standard InChI:  InChI=1S/C22H18N2O5/c1-2-19(25)23-22-20-13(3-4-16-21(20)29-11-26-16)7-15-14-9-18-17(27-10-28-18)8-12(14)5-6-24(15)22/h3-4,7-9H,2,5-6,10-11H2,1H3/b23-22+

Standard InChI Key:  PQASMRLZJSXMIA-GHVJWSGMSA-N

Molfile:  

 
     RDKit          2D

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   17.8575   -4.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8609   -4.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2867   -4.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5681   -3.6727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4396   -4.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4408   -4.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6585   -3.8380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   18.5749   -5.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5777   -6.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0081   -5.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0093   -6.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.7372   -7.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5357   -7.6475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0244   -6.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5277   -6.2916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7153   -4.9062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5432   -5.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0873   -4.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7134   -5.9141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8791   -3.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 26 28  2  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4519983

   ---

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: 390.40

Molecular Weight (Monoisotopic): 390.1216

AlogP: 3.16

#Rotatable Bonds: 1

Polar Surface Area: 71.28

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.53

CX LogD: 2.53

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.64

Np Likeness Score: 0.11

References

1. Xie M, Zhang HJ, Deng AJ, Wu LQ, Zhang ZH, Li ZH, Wang WJ, Qin HL..  (2016)  Synthesis and Structure-Activity Relationships of N-Dihydrocoptisine-8-ylidene Aromatic Amines and N-Dihydrocoptisine-8-ylidene Aliphatic Amides as Antiulcerative Colitis Agents Targeting XBP1.,  79  (4): [PMID:26981782] [10.1021/acs.jnatprod.5b00807]

Source

Source(1):

• Scientific Literature