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

ID: ALA4063595

PubChem CID: 137635529

Max Phase: Preclinical

Molecular Formula: C22H27NO3

Molecular Weight: 353.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(NC(=O)[C@H](C)[C@@H]2CCc3c(C)cc(O)c(C)c3C2)cc1O

Standard InChI:  InChI=1S/C22H27NO3/c1-12-5-7-17(11-20(12)24)23-22(26)14(3)16-6-8-18-13(2)9-21(25)15(4)19(18)10-16/h5,7,9,11,14,16,24-25H,6,8,10H2,1-4H3,(H,23,26)/t14-,16-/m1/s1

Standard InChI Key:  LAXBOMIOHMRCPM-GDBMZVCRSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   15.3317   -4.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3305   -5.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0453   -5.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0435   -3.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7589   -4.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7577   -5.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4745   -5.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1973   -5.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1984   -4.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4770   -3.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9105   -5.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9082   -6.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6262   -5.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3394   -5.4416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6285   -4.2021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0450   -6.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6157   -5.4308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0411   -2.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1914   -5.8457    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.0551   -5.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7655   -5.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4807   -5.0388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4835   -4.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7651   -3.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0530   -4.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1985   -3.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7646   -2.9736    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
  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
 23 26  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4063595

   ---

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: 353.46

Molecular Weight (Monoisotopic): 353.1991

AlogP: 4.40

#Rotatable Bonds: 3

Polar Surface Area: 69.56

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.48

CX Basic pKa: ┄

CX LogP: 5.75

CX LogD: 5.74

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.77

Np Likeness Score: 0.05

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