Baraphenazine A

ID: ALA4445692

PubChem CID: 145721012

Max Phase: Preclinical

Molecular Formula: C21H18N2O7

Molecular Weight: 410.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)C1(O)O[C@@H]2[C@@H](Cc3nc4c(O)cccc4nc3[C@@H]2O)[C@H]1c1ccc(O)cc1

Standard InChI:  InChI=1S/C21H18N2O7/c24-10-6-4-9(5-7-10)15-11-8-13-17(18(26)19(11)30-21(15,29)20(27)28)22-12-2-1-3-14(25)16(12)23-13/h1-7,11,15,18-19,24-26,29H,8H2,(H,27,28)/t11-,15+,18-,19+,21?/m0/s1

Standard InChI Key:  BFBFPQNRDXCHEY-WNQJUYSBSA-N

Molfile:  

 
     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    2.3585   -4.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3567   -4.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0707   -5.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0721   -3.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7869   -4.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7839   -4.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5029   -5.2706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4943   -3.6190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0684   -2.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2099   -4.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2126   -4.8516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9282   -5.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9229   -3.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6412   -4.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6411   -4.8447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4254   -5.0962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9075   -4.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4230   -3.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6716   -2.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4803   -2.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7329   -2.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1783   -1.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3703   -1.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1194   -2.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4291   -0.6233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7339   -4.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1486   -5.1406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1414   -3.7096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3120   -5.1366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8532   -5.6383    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6318   -3.1949    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9274   -6.0848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7 11  2  0
 10  8  2  0
  8  5  1  0
  4  9  1  0
 10 11  1  0
 10 13  1  0
 11 12  1  0
 12 15  1  0
 14 13  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 18 19  1  1
 22 25  1  0
 17 26  1  0
 26 27  2  0
 26 28  1  0
 17 29  1  0
 15 30  1  6
 14 31  1  6
 12 32  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4445692

   ---

Molecule Features

Natural Product: Yes

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: 410.38

Molecular Weight (Monoisotopic): 410.1114

AlogP: 1.20

#Rotatable Bonds: 2

Polar Surface Area: 153.23

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.82

CX Basic pKa: 1.90

CX LogP: 1.10

CX LogD: -2.04

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.42

Np Likeness Score: 1.11

References

1. Wang X, Abbas M, Zhang Y, Elshahawi SI, Ponomareva LV, Cui Z, Van Lanen SG, Sajid I, Voss SR, Shaaban KA, Thorson JS..  (2019)  Baraphenazines A-G, Divergent Fused Phenazine-Based Metabolites from a Himalayan Streptomyces.,  82  (6): [PMID:31117525] [10.1021/acs.jnatprod.9b00289]

Source

Source(1):

• Scientific Literature