3-(5-Hydroxy-1H-indol-3-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester

ID: ALA439675

PubChem CID: 11441783

Max Phase: Preclinical

Molecular Formula: C24H19N3O5

Molecular Weight: 429.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1[nH]c(C(=O)OC)c(-c2c[nH]c3ccc(O)cc23)c1-c1c[nH]c2ccccc12

Standard InChI:  InChI=1S/C24H19N3O5/c1-31-23(29)21-19(15-10-25-17-6-4-3-5-13(15)17)20(22(27-21)24(30)32-2)16-11-26-18-8-7-12(28)9-14(16)18/h3-11,25-28H,1-2H3

Standard InChI Key:  SZBJDRXMLSSPCV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    5.9642   -5.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9634   -6.7261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4512   -6.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1777   -6.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7465   -5.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7516   -6.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4674   -6.8850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2154   -4.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3065   -5.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8311   -6.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3268   -6.7095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0932   -5.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1022   -6.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8193   -6.8406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5279   -6.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7972   -5.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2191   -5.1701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0413   -4.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2978   -3.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6251   -3.3268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9585   -3.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0026   -3.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7241   -3.7747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9816   -2.5570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2369   -3.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2246   -2.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5277   -3.8403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4288   -3.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8062   -3.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
 17 18  1  0
  8  9  2  0
 18 19  2  0
 19 14  1  0
  9  4  1  0
 18 20  1  0
  1  5  1  0
 11 21  1  0
 21 22  2  0
  1 10  1  0
  4  5  2  0
 12 13  1  0
 10 21  1  0
 22 23  1  0
 23 24  1  0
 24 10  2  0
  4  2  1  0
 22 25  1  0
  5  6  1  0
 25 26  1  0
 11 12  2  0
 25 27  2  0
 13 15  1  0
 24 28  1  0
 14 11  1  0
 28 29  2  0
  2  3  1  0
 28 30  1  0
  6  7  2  0
 26 31  1  0
 14 15  2  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA439675

   LYCOGARUBIN B

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: 429.43

Molecular Weight (Monoisotopic): 429.1325

AlogP: 4.59

#Rotatable Bonds: 4

Polar Surface Area: 120.20

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.29

CX Basic pKa: ┄

CX LogP: 4.09

CX LogD: 3.79

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.31

Np Likeness Score: 0.39

References

1. Hosoya T, Yamamoto Y, Uehara Y, Hayashi M, Komiyama K, Ishibashi M..  (2005)  New cytotoxic bisindole alkaloids with protein tyrosine kinase inhibitory activity from a myxomycete Lycogala epidendrum.,  15  (11): [PMID:15911254] [10.1016/j.bmcl.2005.03.103]

2. 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]

3. Iwai Y, Murakami K, Gomi Y, Hashimoto T, Asakawa Y, Okuno Y, Ishikawa T, Hatakeyama D, Echigo N, Kuzuhara T..  (2011)  Anti-influenza activity of marchantins, macrocyclic bisbibenzyls contained in liverworts.,  6  (5): [PMID:21625478] [10.1371/journal.pone.0019825]

Source

Source(1):

• Scientific Literature