Epiccocarines B

ID: ALA5269058

Max Phase: Preclinical

Molecular Formula: C23H31NO5

Molecular Weight: 401.50

Names and Identifiers

Canonical SMILES:  CC/C=C(\C)C[C@H](C)C[C@H](C)/C(O)=C1/C(=O)N[C@@H]([C@@H](O)c2ccc(O)cc2)C1=O

Standard InChI:  InChI=1S/C23H31NO5/c1-5-6-13(2)11-14(3)12-15(4)20(26)18-22(28)19(24-23(18)29)21(27)16-7-9-17(25)10-8-16/h6-10,14-15,19,21,25-27H,5,11-12H2,1-4H3,(H,24,29)/b13-6+,20-18-/t14-,15-,19-,21-/m0/s1

Standard InChI Key:  CRZCNQJDEBVYEU-DUQOIEBXSA-N

Molfile:  

 
     RDKit          2D

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   -3.8952   -0.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1832   -0.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1832   -1.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8934   -1.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6098   -1.2655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3244   -1.6781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4686   -0.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4686    0.8011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7539   -0.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0005   -0.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8609   -1.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6677   -1.2569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4485   -2.1427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762   -0.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6132    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8503    0.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2626    1.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0873    1.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4997    2.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3244    2.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8503    2.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6132    1.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885   -1.4283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7870    0.6954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4455   -0.8858    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
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  3  8  1  0
  8  9  1  6
 10  8  1  0
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 11 12  1  0
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 13 14  1  0
 14 10  1  0
 13 15  2  0
 12 16  2  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 22 26  1  0
 20 27  1  1
 16 28  1  0
 11 29  2  0
 10 30  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5269058

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 401.50

Molecular Weight (Monoisotopic): 401.2202

AlogP: 3.71

#Rotatable Bonds: 8

Polar Surface Area: 106.86

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.93

CX Basic pKa: ┄

CX LogP: 3.78

CX LogD: 1.33

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.23

Np Likeness Score: 1.47

References

1. Mishra SK, Tripathi G, Kishore N, Singh RK, Singh A, Tiwari VK..  (2017)  Drug development against tuberculosis: Impact of alkaloids.,  137  [PMID:28628823] [10.1016/j.ejmech.2017.06.005]

Source

Source(1):

• Scientific Literature