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

ID: ALA214077

PubChem CID: 44416728

Max Phase: Preclinical

Molecular Formula: C17H21NaO4

Molecular Weight: 290.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1CC[C@@H](O)C(C)(C)[C@@]12Cc1cc(C(=O)[O-])ccc1O2.[Na+]

Standard InChI:  InChI=1S/C17H22O4.Na/c1-10-4-7-14(18)16(2,3)17(10)9-12-8-11(15(19)20)5-6-13(12)21-17;/h5-6,8,10,14,18H,4,7,9H2,1-3H3,(H,19,20);/q;+1/p-1/t10-,14+,17+;/m0./s1

Standard InChI Key:  HADKAHLVCWHYPD-NKDGEMLNSA-M

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    2.3667   -5.7750    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   -0.0007   -7.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007   -8.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7105   -8.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4217   -8.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4217   -7.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7105   -6.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5368   -4.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1205   -4.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2924   -4.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1155   -4.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1274   -5.6101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2963   -5.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0406   -6.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3813   -6.3966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1383   -6.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -6.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230   -3.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9469   -3.4816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6948   -7.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2859   -2.7585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7105   -8.5357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
 12  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 13  1  0
 12 13  2  0
 13 14  1  0
  7 14  1  0
  7 15  1  6
 15 12  1  0
  6 16  1  1
  2 17  1  0
 18 19  2  0
 10 18  1  0
  2 20  1  0
  2  3  1  0
 18 21  1  0
  3 22  1  1
M  CHG  2   1   1  21  -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: 290.36

Molecular Weight (Monoisotopic): 290.1518

AlogP: 2.88

#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: 4.34

CX Basic pKa: ┄

CX LogP: 3.11

CX LogD: 0.18

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.83

Np Likeness Score: 2.05

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