2-nitro-alpha-desmotroposantonin

ID: ALA4098029

PubChem CID: 137661585

Max Phase: Preclinical

Molecular Formula: C15H17NO5

Molecular Weight: 291.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(O)c([N+](=O)[O-])c(C)c2c1[C@@H]1OC(=O)[C@@H](C)[C@@H]1CC2

Standard InChI:  InChI=1S/C15H17NO5/c1-6-9-4-5-10-7(2)15(18)21-14(10)11(9)8(3)13(17)12(6)16(19)20/h7,10,14,17H,4-5H2,1-3H3/t7-,10-,14+/m0/s1

Standard InChI Key:  QFCUJYMUVGFDOK-MRCLBUSBSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   17.3363   -9.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6186   -9.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9052   -9.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9052  -10.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1938  -11.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4760  -10.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4760   -9.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1938   -9.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7584  -11.0268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6269  -11.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3363  -10.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9432  -11.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6130  -11.9098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7975  -11.8283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0303  -12.6253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7542  -10.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0491  -10.2029    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.0432  -11.6124    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1954   -8.5540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7640   -9.3757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7653   -8.5527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0505   -9.7860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1954  -11.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  4  5  2  0
  6  5  1  0
  7  6  2  0
  8  7  1  0
  3  8  2  0
  6  9  1  0
  4 10  1  0
 11 10  1  0
 11  1  1  0
 11 12  1  0
 13 12  1  0
 14 13  1  0
 10 14  1  0
 13 15  2  0
 12 16  1  6
 11 17  1  6
 10 18  1  6
  8 19  1  0
  7 20  1  0
 20 21  1  0
 20 22  2  0
  5 23  1  0
M  CHG  2  20   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4098029

   ---

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: 291.30

Molecular Weight (Monoisotopic): 291.1107

AlogP: 2.71

#Rotatable Bonds: 1

Polar Surface Area: 89.67

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.55

CX Basic pKa: ┄

CX LogP: 3.55

CX LogD: 3.32

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.49

Np Likeness Score: 1.20

References

1. Chinthakindi PK, Singh J, Gupta S, Nargotra A, Mahajan P, Kaul A, Ahmed Z, Koul S, Sangwan PL..  (2017)  Synthesis of α-santonin derivatives for diminutive effect on T and B-cell proliferation and their structure activity relationships.,  127  [PMID:27847171] [10.1016/j.ejmech.2016.11.018]

Source

Source(1):

• Scientific Literature