Baraphenazine G

ID: ALA4452016

PubChem CID: 145721018

Max Phase: Preclinical

Molecular Formula: C25H16N4O6

Molecular Weight: 468.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc2c(c3nc4cccc(O)c4nc13)[C@@H]1Cc3nc4cccc(O)c4nc3[C@@](O)(C1)O2

Standard InChI:  InChI=1S/C25H16N4O6/c30-15-5-2-4-13-20(15)28-19-11(24(32)33)8-17-18(22(19)27-13)10-7-14-23(25(34,9-10)35-17)29-21-12(26-14)3-1-6-16(21)31/h1-6,8,10,30-31,34H,7,9H2,(H,32,33)/t10-,25-/m1/s1

Standard InChI Key:  IKZAYRLYTAVSAG-REFGNXHDSA-N

Molfile:  

 
     RDKit          2D

 36 42  0  0  0  0  0  0  0  0999 V2000
   26.4070   -3.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4051   -4.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1216   -4.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1230   -3.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8403   -3.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8373   -4.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5586   -4.8343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5500   -3.1771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1193   -2.3514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2681   -3.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2707   -4.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9888   -4.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9834   -3.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7043   -3.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4151   -4.8165    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   29.9777   -2.3374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6943   -2.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6860   -4.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4053   -3.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4026   -3.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1160   -2.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8260   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8297   -3.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1156   -4.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1128   -5.2137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.5375   -4.3954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.5381   -5.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8223   -5.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8210   -6.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5347   -6.8622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2512   -6.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2490   -5.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5399   -2.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2549   -3.1581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5389   -1.9215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.9628   -5.2110    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 18  1  0
 14 13  1  0
 14 18  1  0
 18 15  1  1
 13 16  1  1
 13 17  1  0
 17 19  1  0
 20 18  1  0
 19 20  2  0
 20 24  1  0
 23 22  1  0
 21 19  1  0
 21 22  2  0
 23 24  1  0
 24 25  2  0
 25 28  1  0
 27 26  1  0
 26 23  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 27  2  0
 22 33  1  0
 33 34  1  0
 33 35  2  0
 32 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4452016

   ---

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: 468.43

Molecular Weight (Monoisotopic): 468.1070

AlogP: 3.10

#Rotatable Bonds: 1

Polar Surface Area: 158.78

Molecular Species: ACID

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.66

CX Basic pKa: 2.00

CX LogP: 3.15

CX LogD: -0.14

Aromatic Rings: 5

Heavy Atoms: 35

QED Weighted: 0.27

Np Likeness Score: 0.67

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