Baraphenazine C

ID: ALA4575651

PubChem CID: 145721014

Max Phase: Preclinical

Molecular Formula: C23H19N3O6

Molecular Weight: 433.42

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]1c1c[nH]c2ccccc12

Standard InChI:  InChI=1S/C23H19N3O6/c27-16-7-3-6-14-18(16)26-15-8-11-17(12-9-24-13-5-2-1-4-10(12)13)23(31,22(29)30)32-21(11)20(28)19(15)25-14/h1-7,9,11,17,20-21,24,27-28,31H,8H2,(H,29,30)/t11-,17-,20+,21+,23?/m0/s1

Standard InChI Key:  NFKKAYYYJYWZMD-XXTYAYNPSA-N

Molfile:  

 
     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
    2.5157  -19.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5139  -20.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2289  -20.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2304  -19.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9462  -19.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9433  -20.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6632  -20.9384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6546  -19.2844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2266  -18.4603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3713  -19.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3739  -20.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0905  -20.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0852  -19.2733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8047  -19.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8045  -20.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5899  -20.7638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0727  -20.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5875  -19.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8365  -18.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9003  -20.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3156  -20.8082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3084  -19.3751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4778  -20.8043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0169  -21.3067    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7952  -18.8597    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0897  -21.7539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8244  -17.3123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3456  -17.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6080  -17.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6093  -18.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3198  -18.7896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0293  -18.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0239  -17.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3129  -17.1496    0.0000 C   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
 18 19  1  1
 17 20  1  0
 20 21  2  0
 20 22  1  0
 17 23  1  0
 15 24  1  6
 14 25  1  6
 12 26  1  6
 19 30  1  0
 29 27  1  0
 27 28  1  0
 28 19  2  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4575651

   ---

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: 433.42

Molecular Weight (Monoisotopic): 433.1274

AlogP: 1.98

#Rotatable Bonds: 2

Polar Surface Area: 148.79

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.03

CX Basic pKa: 1.95

CX LogP: 1.55

CX LogD: -1.61

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.32

Np Likeness Score: 0.88

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