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

ID: ALA371472

Cas Number: 150044-77-2

PubChem CID: 11037060

Max Phase: Preclinical

Molecular Formula: C24H19N3O4

Molecular Weight: 413.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Lycogarubin C | Lycogarubin C|150044-77-2|1H-Pyrrole-2,5-dicarboxylic acid, 3,4-di-1H-indol-3-yl-, dimethyl ester|CHEMBL371472|SCHEMBL12658123|DTXSID80452826

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

Standard InChI:  InChI=1S/C24H19N3O4/c1-30-23(28)21-19(15-11-25-17-9-5-3-7-13(15)17)20(22(27-21)24(29)31-2)16-12-26-18-10-6-4-8-14(16)18/h3-12,25-27H,1-2H3

Standard InChI Key:  DKTWEIRHZXHFQB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   -2.8937    0.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3093   -0.8694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6379   -0.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9782   -0.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7235    0.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2762    1.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0836    0.8419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3354    0.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7810   -0.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4131    1.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5830    1.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3306    1.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033    2.3524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6701    1.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0964    0.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461   -0.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740   -0.8508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2731    0.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0159   -0.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7886   -0.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0748    0.8746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2709    1.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6258    2.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1000    1.9044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6467    3.1222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3917    2.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4040    3.0856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1010    1.8387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8006    2.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8185    2.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 14 10  2  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA371472

   LYCOGARUBIN C

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: 413.43

Molecular Weight (Monoisotopic): 413.1376

AlogP: 4.88

#Rotatable Bonds: 4

Polar Surface Area: 99.97

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.21

CX Basic pKa: ┄

CX LogP: 4.39

CX LogD: 4.06

Aromatic Rings: 5

Heavy Atoms: 31

QED Weighted: 0.37

Np Likeness Score: 0.18

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. McArthur KA, Mitchell SS, Tsueng G, Rheingold A, White DJ, Grodberg J, Lam KS, Potts BC..  (2008)  Lynamicins A-E, chlorinated bisindole pyrrole antibiotics from a novel marine actinomycete.,  71  (10): [PMID:18842058] [10.1021/np800286d]

3. 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