Lycogarubic acid methyl ester

ID: ALA585151

PubChem CID: 11338520

Max Phase: Preclinical

Molecular Formula: C23H17N3O4

Molecular Weight: 399.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Lycogarubicacid Methyl Ester | Lycogarubicacid methyl ester|CHEMBL585151

Canonical SMILES:  COC(=O)c1[nH]c(C(=O)O)c(-c2c[nH]c3ccccc23)c1-c1c[nH]c2ccccc12

Standard InChI:  InChI=1S/C23H17N3O4/c1-30-23(29)21-19(15-11-25-17-9-5-3-7-13(15)17)18(20(26-21)22(27)28)14-10-24-16-8-4-2-6-12(14)16/h2-11,24-26H,1H3,(H,27,28)

Standard InChI Key:  CUKHLCPFGKVMHR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   13.1076    0.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6919   -0.8860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3634   -0.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0232   -0.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2777    0.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7251    0.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9177    0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6659    0.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2202   -0.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5883    1.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4183    1.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6707    1.8516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9980    2.3358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3312    1.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9049    0.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6552   -0.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3273   -0.8674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7282    0.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9853   -0.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7898   -0.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3381    0.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0761    0.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2722    1.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3755    2.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1012    1.8878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3546    3.1056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6096    2.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5973    3.0690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9003    1.8222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8020    2.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 10  2  0
  6  7  2  0
 11 15  1  0
 16 17  1  0
  3  1  2  0
  7  8  1  0
 15 16  2  0
 17 19  1  0
 18 15  1  0
  8  9  2  0
 18 19  2  0
  9  4  1  0
 19 20  1  0
  1  5  1  0
 20 21  2  0
  1 10  1  0
 21 22  1  0
 11 12  2  0
 22 23  2  0
 23 18  1  0
  4  5  2  0
 12 24  1  0
  4  2  1  0
 24 25  1  0
  5  6  1  0
 24 26  2  0
  2  3  1  0
 14 27  1  0
 10 11  1  0
 27 28  2  0
 12 13  1  0
 27 29  1  0
 13 14  1  0
 25 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA585151

   LYCOGARUBICACID METHYL ESTER

Molecule Features

Natural Product: Yes

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: 399.41

Molecular Weight (Monoisotopic): 399.1219

AlogP: 4.80

#Rotatable Bonds: 4

Polar Surface Area: 110.97

Molecular Species: ACID

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.51

CX Basic pKa: ┄

CX LogP: 4.05

CX LogD: 0.70

Aromatic Rings: 5

Heavy Atoms: 30

QED Weighted: 0.33

Np Likeness Score: 0.27

References

1. Arai MA, Masada A, Ohtsuka T, Kageyama R, Ishibashi M..  (2009)  The first Hes1 dimer inhibitors from natural products.,  19  (19): [PMID:19716294] [10.1016/j.bmcl.2009.07.146]

Source

Source(1):

• Scientific Literature