4-desmethyl Englerin A

ID: ALA4103330

PubChem CID: 137657858

Max Phase: Preclinical

Molecular Formula: C25H32O6

Molecular Weight: 428.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@]12C[C@@H](OC(=O)CO)[C@](C)(O1)[C@@H]1CCC[C@H]1[C@@H]2OC(=O)/C=C/c1ccccc1

Standard InChI:  InChI=1S/C25H32O6/c1-16(2)25-14-20(29-22(28)15-26)24(3,31-25)19-11-7-10-18(19)23(25)30-21(27)13-12-17-8-5-4-6-9-17/h4-6,8-9,12-13,16,18-20,23,26H,7,10-11,14-15H2,1-3H3/b13-12+/t18-,19-,20-,23+,24-,25+/m1/s1

Standard InChI Key:  NPVSBJCCCCHRKG-FDPHBAIQSA-N

Molfile:  

     RDKit          2D

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   10.8226   -8.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0008   -9.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.6287   -7.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0040   -8.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3223   -9.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7256   -9.7923    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0590   -9.0131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2663  -10.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8289  -10.4864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.2253   -8.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2878   -6.9468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0905   -7.1067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3807   -6.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3901   -5.8611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5547   -6.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1442   -5.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3191   -5.9657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9137   -5.2492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0895   -5.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6741   -5.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0891   -6.6785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9120   -6.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0
  1  2  1  0
  2  3  1  0
  6  4  1  0
  3  5  1  0
  4  5  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  6  1  0
  7 11  1  6
  6 12  1  1
  4 13  1  0
 13  2  1  0
  4 14  1  6
  5 15  1  1
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
  2 20  1  6
 20 21  1  0
 20 22  1  0
  1 23  1  6
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103330

   ---

Molecule Features

Natural Product: No

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: 428.53

Molecular Weight (Monoisotopic): 428.2199

AlogP: 3.52

#Rotatable Bonds: 6

Polar Surface Area: 82.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.13

CX Basic pKa: ┄

CX LogP: 4.09

CX LogD: 4.09

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.55

Np Likeness Score: 2.15

References

1. Elliott DC, Beutler JA, Parker KA..  (2017)  Importance of a 4-Alkyl Substituent for Activity in the Englerin Series.,  8  (7): [PMID:28740610] [10.1021/acsmedchemlett.7b00161]

Source

Source(1):

• Scientific Literature