berkchaetoazaphilone B

ID: ALA3759602

PubChem CID: 127028675

Max Phase: Preclinical

Molecular Formula: C25H32O7

Molecular Weight: 444.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCC(=O)[C@@]12O[C@@]13C1=COC(C[C@H](C)O)=CC1=CC(=O)[C@]3(C)OC2=O

Standard InChI:  InChI=1S/C25H32O7/c1-4-5-6-7-8-9-10-11-20(27)24-22(29)31-23(3)21(28)14-17-13-18(12-16(2)26)30-15-19(17)25(23,24)32-24/h13-16,26H,4-12H2,1-3H3/t16-,23-,24-,25+/m0/s1

Standard InChI Key:  YEGUZQUADBNQFP-NBQXJWNKSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   -7.4200    3.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4200    1.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8000    3.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1100    4.1600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8000    1.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1100    1.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1100   -0.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8000   -1.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5000   -0.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0600   -0.7900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400    0.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7842   -2.2799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0401    0.4234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1214    2.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3724   -1.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7209    4.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7244    5.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6863    6.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7646    6.2474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5000    1.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1000    1.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1600    2.6100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2906    2.4543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6832    4.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7066    5.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685    6.6931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2918    7.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8537    9.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8770   10.3242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4389   11.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4623   12.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1119   14.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  4  1  0
  2  6  1  0
  5  3  2  0
  3  4  1  0
  5  6  1  0
  5 20  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
 20  9  1  0
  9 10  1  0
 10 11  1  0
 11 21  1  0
  8 12  2  0
 11 13  2  0
 21 14  1  6
  9 15  1  6
  1 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  1
 21 20  1  0
 21 22  1  0
 20 22  1  1
 14 23  2  0
 14 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3759602

   ---

Molecule Features

Natural Product: Yes

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: 444.52

Molecular Weight (Monoisotopic): 444.2148

AlogP: 3.60

#Rotatable Bonds: 11

Polar Surface Area: 102.43

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.62

CX LogD: 3.62

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.22

Np Likeness Score: 1.68

References

1. Stierle AA, Stierle DB, Girtsman T, Mou TC, Antczak C, Djaballah H..  (2015)  Azaphilones from an Acid Mine Extremophile Strain of a Pleurostomophora sp.,  78  (12): [PMID:26641525] [10.1021/acs.jnatprod.5b00519]

Source

Source(1):

• Scientific Literature