sodium (2R,3'R,6'S)-7-cyano-3'-hydroxy-2',2',6'-trimethyl-3H-spiro[1-benzofuran-2,1'-cyclohexane]-5-carboxylate

ID: ALA385874

PubChem CID: 44416746

Max Phase: Preclinical

Molecular Formula: C18H20NNaO4

Molecular Weight: 315.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1CC[C@@H](O)C(C)(C)[C@@]12Cc1cc(C(=O)[O-])cc(C#N)c1O2.[Na+]

Standard InChI:  InChI=1S/C18H21NO4.Na/c1-10-4-5-14(20)17(2,3)18(10)8-12-6-11(16(21)22)7-13(9-19)15(12)23-18;/h6-7,10,14,20H,4-5,8H2,1-3H3,(H,21,22);/q;+1/p-1/t10-,14+,18+;/m0./s1

Standard InChI Key:  FWMLMCCWANGMTM-UBNBEPBNSA-M

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -2.7716   -5.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7716   -5.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0604   -6.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3493   -5.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3493   -5.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0604   -4.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2341   -2.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6504   -1.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4784   -1.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8864   -2.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6436   -3.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4746   -3.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7303   -4.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3897   -4.1483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6325   -4.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1881   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8940   -1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7178   -1.2332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4657   -5.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4147   -2.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4091   -2.6348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4815   -6.2874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4850   -0.5101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667   -5.9292    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 12  1  0
 11 12  2  0
 12 13  1  0
  6 13  1  1
  6 14  1  6
 14 11  1  0
  5 15  1  1
  1 16  1  0
 17 18  2  0
  9 17  1  0
  1 19  1  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
 20 21  3  0
  7 20  1  0
  5  6  1  0
 11  7  1  0
  2 22  1  1
 17 23  1  0
M  CHG  2  23  -1  24   1
M  END

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: 315.37

Molecular Weight (Monoisotopic): 315.1471

AlogP: 2.75

#Rotatable Bonds: 1

Polar Surface Area: 90.55

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.16

CX Basic pKa: ┄

CX LogP: 2.97

CX LogD: -0.09

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.83

Np Likeness Score: 1.50

References

1. Useglio M, Castellano PM, Operto MA, Torres R, Kaufman TS..  (2006)  Synthesis of 3H-spiro[benzofuran-2,1'-cyclohexane] derivatives from naturally occurring filifolinol and their classical complement pathway inhibitory activity.,  16  (19): [PMID:16875818] [10.1016/j.bmcl.2006.07.029]

Source

Source(1):

• Scientific Literature