lycogalic acid A

ID: ALA491841

Cas Number: 150044-68-1

PubChem CID: 11326613

Max Phase: Preclinical

Molecular Formula: C22H15N3O4

Molecular Weight: 385.38

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H15N3O4/c26-21(27)19-17(13-9-23-15-7-3-1-5-11(13)15)18(20(25-19)22(28)29)14-10-24-16-8-4-2-6-12(14)16/h1-10,23-25H,(H,26,27)(H,28,29)

Standard InChI Key:  FZDVNXHYGMEEDT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   -1.2210   -0.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6079   -1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7794   -1.9653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5640   -2.2202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1771   -1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0056   -0.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4905   -0.1938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0056    0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210    0.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5536    0.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5536    1.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210    2.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1348    2.8341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9747    1.6780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2311    1.7836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7160    1.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5410    1.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9535    0.4017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9535    1.8306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2311    0.4487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4860   -0.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2706   -0.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9851   -0.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996   -0.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996   -1.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9851   -1.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2706   -1.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4860   -1.6708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0011   -1.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0
  2  1  1  0
  1  9  1  0
  3  2  2  0
  4  3  1  0
  5  4  2  0
  5  6  1  0
  6  7  1  0
  8  7  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 20 10  1  0
 12 11  1  0
 11 15  1  0
 12 13  2  0
 12 14  1  0
 16 15  1  0
 20 16  2  0
 17 16  1  0
 17 18  2  0
 17 19  1  0
 20 21  1  0
 21 22  1  0
 21 29  2  0
 22 23  2  0
 22 27  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 29 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA491841

   LYCOGALIC ACID A

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: 385.38

Molecular Weight (Monoisotopic): 385.1063

AlogP: 4.71

#Rotatable Bonds: 4

Polar Surface Area: 121.97

Molecular Species: ACID

HBA: 2

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.21

CX Basic pKa: ┄

CX LogP: 3.70

CX LogD: -2.99

Aromatic Rings: 5

Heavy Atoms: 29

QED Weighted: 0.31

Np Likeness Score: 0.24

References

1. 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]

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]

Source

Source(1):

• Scientific Literature