Solitumine A

ID: ALA4476071

PubChem CID: 155537754

Max Phase: Preclinical

Molecular Formula: C20H27N3O4

Molecular Weight: 373.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(C)(C)[C@H]1Nc2ccccc2C(=O)[C@@H]1CNC(=O)CC[C@H](N)C(=O)O

Standard InChI:  InChI=1S/C20H27N3O4/c1-4-20(2,3)18-13(11-22-16(24)10-9-14(21)19(26)27)17(25)12-7-5-6-8-15(12)23-18/h4-8,13-14,18,23H,1,9-11,21H2,2-3H3,(H,22,24)(H,26,27)/t13-,14-,18-/m0/s1

Standard InChI Key:  XWENKFHGXXDYEW-DEYYWGMASA-N

Molfile:  

 
     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    6.4013   -5.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9969   -5.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5879   -5.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4543   -3.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4531   -4.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1612   -5.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1594   -3.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8680   -3.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8668   -4.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5769   -5.0341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2928   -4.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -3.7996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5793   -3.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0027   -3.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7082   -4.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4147   -5.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0047   -2.5755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7134   -2.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7154   -1.3515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4201   -2.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1288   -2.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8355   -2.5825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5442   -2.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2509   -2.5859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5462   -1.3584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8335   -3.3997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5793   -2.5665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  6
 11  2  1  1
  2 15  1  0
 15 16  2  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 22 26  1  1
 13 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476071

   ---

Molecule Features

Natural Product: No

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: 373.45

Molecular Weight (Monoisotopic): 373.2002

AlogP: 1.80

#Rotatable Bonds: 8

Polar Surface Area: 121.52

Molecular Species: ZWITTERION

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.80

CX Basic pKa: 9.11

CX LogP: -0.58

CX LogD: -0.59

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: 0.71

References

1. Rodríguez JPG, Bernardi DI, Gubiani JR, Magalhães de Oliveira J, Morais-Urano RP, Bertonha AF, Bandeira KF, Bulla JIQ, Sette LD, Ferreira AG, Batista JM, Silva TS, Santos RAD, Martins CHG, Lira SP, Cunha MGD, Trivella DBB, Grazzia N, Gomes NES, Gadelha F, Miguel DC, Cauz ACG, Brocchi M, Berlinck RGS..  (2020)  Water-Soluble Glutamic Acid Derivatives Produced in Culture by Penicillium solitum IS1-A from King George Island, Maritime Antarctica.,  83  (1): [PMID:31895573] [10.1021/acs.jnatprod.9b00635]

Source

Source(1):

• Scientific Literature