Terrelumamide A

ID: ALA4474465

PubChem CID: 139587886

Max Phase: Preclinical

Molecular Formula: C20H20N6O7

Molecular Weight: 456.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccccc1NC(=O)[C@@H](NC(=O)c1cnc2c(n1)c(=O)[nH]c(=O)n2C)[C@@H](C)O

Standard InChI:  InChI=1S/C20H20N6O7/c1-9(27)13(17(29)23-11-7-5-4-6-10(11)19(31)33-3)24-16(28)12-8-21-15-14(22-12)18(30)25-20(32)26(15)2/h4-9,13,27H,1-3H3,(H,23,29)(H,24,28)(H,25,30,32)/t9-,13+/m1/s1

Standard InChI Key:  YVUJATOOBNWJDN-RNCFNFMXSA-N

Molfile:  

 
     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    5.4397  -17.0124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4397  -17.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1450  -18.2341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1450  -16.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8502  -17.0124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8486  -17.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5529  -18.2351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2592  -17.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2568  -17.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5520  -16.6060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7326  -18.2392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1450  -15.7825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9632  -16.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6722  -17.0051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9606  -15.7816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3786  -16.5943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0876  -17.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3760  -15.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0824  -15.3662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6670  -15.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0902  -17.8178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7940  -16.5897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5030  -16.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5012  -17.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2094  -18.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9168  -17.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9115  -16.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2028  -16.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1971  -15.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9019  -15.3549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4865  -15.3648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6125  -15.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1462  -19.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  2 11  2  0
  4 12  2  0
  9 13  1  0
 13 14  1  0
 13 15  2  0
 16 14  1  1
 16 17  1  0
 16 18  1  0
 18 19  1  1
 18 20  1  0
 17 21  2  0
 17 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 30 32  1  0
  3 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474465

   ---

Molecule Features

Natural Product: Yes

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: 456.42

Molecular Weight (Monoisotopic): 456.1393

AlogP: -1.08

#Rotatable Bonds: 6

Polar Surface Area: 185.37

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 13

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.62

CX Basic pKa: ┄

CX LogP: 0.12

CX LogD: 0.10

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: -1.00

References

1. Daniels BJ, Li FF, Furkert DP, Brimble MA..  (2019)  Naturally Occurring Lumazines.,  82  (7): [PMID:31317731] [10.1021/acs.jnatprod.9b00351]

Source

Source(1):

• Scientific Literature