Epiccocarines A

ID: ALA5282916

Max Phase: Preclinical

Molecular Formula: C23H31NO4

Molecular Weight: 385.50

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](Cc2ccc(O)cc2)C1=O

Standard InChI:  InChI=1S/C23H31NO4/c1-5-6-14(2)11-15(3)12-16(4)21(26)20-22(27)19(24-23(20)28)13-17-7-9-18(25)10-8-17/h6-10,15-16,19,25-26H,5,11-13H2,1-4H3,(H,24,28)/b14-6+,21-20-/t15-,16-,19-/m0/s1

Standard InChI Key:  KGVANRZKBPUYPV-PWFBFJQWSA-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
   -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
   -0.4484   -0.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
    2.0256    0.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
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  9  8  1  1
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 21 22  2  0
 22 23  1  0
 23 24  1  0
 21 25  1  0
 19 26  1  1
 15 27  1  0
 10 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5282916

   ---

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: 385.50

Molecular Weight (Monoisotopic): 385.2253

AlogP: 4.22

#Rotatable Bonds: 8

Polar Surface Area: 86.63

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.04

CX Basic pKa: ┄

CX LogP: 4.69

CX LogD: 2.36

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.27

Np Likeness Score: 1.45

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