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

ID: ALA386856

PubChem CID: 44416730

Max Phase: Preclinical

Molecular Formula: C17H20BrNaO4

Molecular Weight: 369.25

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(Br)c1O2.[Na+]

Standard InChI:  InChI=1S/C17H21BrO4.Na/c1-9-4-5-13(19)16(2,3)17(9)8-11-6-10(15(20)21)7-12(18)14(11)22-17;/h6-7,9,13,19H,4-5,8H2,1-3H3,(H,20,21);/q;+1/p-1/t9-,13+,17+;/m0./s1

Standard InChI Key:  ZJPFWUFECNIOCY-GWWJNUJNSA-M

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -1.7743   -6.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7743   -6.8305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631   -7.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3519   -6.8305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3519   -6.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631   -5.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2368   -3.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6530   -2.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4811   -2.8930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8890   -3.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6462   -4.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4773   -4.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7330   -5.1035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3924   -5.1050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3648   -5.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1907   -5.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8966   -2.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7205   -2.1899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4684   -6.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871   -3.5980    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877   -1.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4841   -7.2440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667   -5.7750    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
 11  7  1  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  0
  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
  7 20  1  0
  1  2  1  0
  1  6  1  0
 17 21  1  0
  2 22  1  1
M  CHG  2  21  -1  23   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: 369.25

Molecular Weight (Monoisotopic): 368.0623

AlogP: 3.64

#Rotatable Bonds: 1

Polar Surface Area: 66.76

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.21

CX Basic pKa: ┄

CX LogP: 3.88

CX LogD: 0.85

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.79

Np Likeness Score: 1.90

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