(R)-2-((R)-7-hydroxy-5,8-dimethyl-1,2,3,4-tetrahydronapthalen-2-yl)-N-(4-methyl-3-nitropyridin-2-yl)propanamide

ID: ALA4104415

PubChem CID: 137656953

Max Phase: Preclinical

Molecular Formula: C21H25N3O4

Molecular Weight: 383.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(O)c(C)c2c1CC[C@@H]([C@@H](C)C(=O)Nc1nccc(C)c1[N+](=O)[O-])C2

Standard InChI:  InChI=1S/C21H25N3O4/c1-11-7-8-22-20(19(11)24(27)28)23-21(26)13(3)15-5-6-16-12(2)9-18(25)14(4)17(16)10-15/h7-9,13,15,25H,5-6,10H2,1-4H3,(H,22,23,26)/t13-,15-/m1/s1

Standard InChI Key:  YHSXCCPZVKSSHZ-UKRRQHHQSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   14.4525   -3.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4514   -4.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1661   -4.8443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1643   -3.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8798   -3.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8786   -4.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5954   -4.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3181   -4.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3193   -3.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5979   -3.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0314   -4.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0291   -5.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7470   -4.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4603   -4.8541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7493   -3.6147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1658   -5.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7366   -4.8434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1619   -2.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3122   -5.2583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.1759   -4.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8864   -4.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6015   -4.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6043   -3.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8860   -3.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1738   -3.6232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8818   -5.6860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1652   -6.0947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5941   -6.1025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3146   -4.8662    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
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 13 15  2  0
  3 16  1  0
  2 17  1  0
  4 18  1  0
  8 19  1  6
 14 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 21 26  1  0
 26 27  1  0
 26 28  2  0
 22 29  1  0
M  CHG  2  26   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4104415

   ---

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: 383.45

Molecular Weight (Monoisotopic): 383.1845

AlogP: 4.00

#Rotatable Bonds: 4

Polar Surface Area: 105.36

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.11

CX Basic pKa: 3.07

CX LogP: 5.37

CX LogD: 5.37

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.61

Np Likeness Score: -0.12

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