Baraphenazine E

ID: ALA4465010

PubChem CID: 145721016

Max Phase: Preclinical

Molecular Formula: C25H17N5O3

Molecular Weight: 435.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NC(=O)c1cccc2nc3c4c(ccc3nc12)[C@H]1c2nc3c(O)cccc3nc2C[C@@H]4[C@@H]1O

Standard InChI:  InChI=1S/C25H17N5O3/c26-25(33)11-3-1-4-13-20(11)28-15-8-7-10-18(22(15)29-13)12-9-16-23(19(10)24(12)32)30-21-14(27-16)5-2-6-17(21)31/h1-8,12,19,24,31-32H,9H2,(H2,26,33)/t12-,19-,24-/m0/s1

Standard InChI Key:  GXPOPLPOQDCTPY-JGWMJADOSA-N

Molfile:  

 
     RDKit          2D

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   12.8908  -10.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6014  -11.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6028   -9.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3142   -9.7901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3112  -10.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0267  -11.0220    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0181   -9.3785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5991   -8.5595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7303   -9.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7329  -10.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4451  -11.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4398   -9.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1546   -9.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1545  -10.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.9530  -10.6397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8690   -9.2593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2388   -9.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7812  -10.6881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1502  -11.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9767  -11.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4328  -10.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0612  -10.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5118   -9.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3287   -9.4076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1441   -8.6296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8597  -11.0042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.4341   -8.5455    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.4423  -10.1819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  5  4  2  0
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  6  7  1  0
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 16 17  2  0
 16 19  1  0
 17 21  1  0
 20 18  1  0
 18 19  2  0
 20 21  1  0
 21 22  2  0
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 24 23  1  0
 23 20  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 24  2  0
 30 31  1  0
 30 32  2  0
 29 30  1  0
 15 33  1  1
 13 34  1  1
 14 35  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4465010

   ---

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: 435.44

Molecular Weight (Monoisotopic): 435.1331

AlogP: 2.68

#Rotatable Bonds: 1

Polar Surface Area: 135.11

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.40

CX Basic pKa: 2.14

CX LogP: 2.10

CX LogD: 2.06

Aromatic Rings: 5

Heavy Atoms: 33

QED Weighted: 0.34

Np Likeness Score: 0.55

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