(R)-4-allyl-7-oxo-2,3,(S)-3a,4,7,10-hexahydro-1H-5-oxa-10,11,11b-triazacyclopenta[a]anthracene-8-carboxylic acid

ID: ALA377191

PubChem CID: 11843682

Max Phase: Preclinical

Molecular Formula: C17H17N3O4

Molecular Weight: 327.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC[C@H]1Oc2cc3c(O)c(C(=O)O)cnc3nc2N2CCC[C@@H]12

Standard InChI:  InChI=1S/C17H17N3O4/c1-2-4-12-11-5-3-6-20(11)16-13(24-12)7-9-14(21)10(17(22)23)8-18-15(9)19-16/h2,7-8,11-12H,1,3-6H2,(H,22,23)(H,18,19,21)/t11-,12+/m0/s1

Standard InChI Key:  QSIVMIATOWAMAS-NWDGAFQWSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  1  0  0  0  0  0999 V2000
   15.1956  -14.8194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1938  -13.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9091  -13.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9126  -14.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6317  -14.8199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3521  -14.4068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3487  -13.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6249  -13.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0624  -13.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7782  -13.5714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0599  -12.3486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6204  -12.3496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4807  -14.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4803  -13.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7715  -13.1873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0584  -13.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7758  -14.8222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0537  -14.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4407  -14.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7839  -15.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6089  -15.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3465  -13.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6295  -13.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9176  -13.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1398  -14.0062    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  8 12  1  0
 13 14  1  0
  2 14  2  0
  3  4  1  0
  3  8  2  0
  4  5  2  0
 13 17  1  0
 14 15  1  0
 15 16  1  0
 16 18  1  0
 17 18  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
 13  1  2  0
  1  4  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
  9 10  1  0
 16 22  1  1
  9 11  2  0
 22 23  1  0
  7  9  1  0
 23 24  2  0
 18 25  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA377191

   (15S,16R)-4-oxo-16-prop-2-enyl-17-oxa-7,9,11-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),2,5,8-tetraene-5-carboxylic acid

Molecule Features

Natural Product: No

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: 327.34

Molecular Weight (Monoisotopic): 327.1219

AlogP: 2.34

#Rotatable Bonds: 3

Polar Surface Area: 95.78

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.45

CX Basic pKa: 0.70

CX LogP: 3.16

CX LogD: -0.23

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.84

Np Likeness Score: 0.35

References

1. Hinman MM, Rosenberg TA, Balli D, Black-Schaefer C, Chovan LE, Kalvin D, Merta PJ, Nilius AM, Pratt SD, Soni NB, Wagenaar FL, Weitzberg M, Wagner R, Beutel BA..  (2006)  Novel antibacterial class: a series of tetracyclic derivatives.,  49  (16): [PMID:16884296] [10.1021/jm060010w]

Source

Source(1):

• Scientific Literature