sodium 2-[(1R,3R,4S)-3,4-dihydroxy-4-methylcyclohexyl]-4-hydroxy-2-methyl-2,3-dihydro-1-benzofuran-7-carboxylate

ID: ALA214520

PubChem CID: 44416645

Max Phase: Preclinical

Molecular Formula: C17H21NaO6

Molecular Weight: 322.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]1(O)CC[C@@H]([C@]2(C)Cc3c(O)ccc(C(=O)[O-])c3O2)C[C@H]1O.[Na+]

Standard InChI:  InChI=1S/C17H22O6.Na/c1-16(22)6-5-9(7-13(16)19)17(2)8-11-12(18)4-3-10(15(20)21)14(11)23-17;/h3-4,9,13,18-19,22H,5-8H2,1-2H3,(H,20,21);/q;+1/p-1/t9-,13-,16+,17+;/m1./s1

Standard InChI Key:  ZIJUTOYEFPEYII-UYEOROLZSA-M

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   -0.0716   -6.0380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7826   -5.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0445   -3.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3738   -2.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1992   -2.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6090   -3.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3675   -4.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1976   -4.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4517   -5.1361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1120   -5.1383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686   -3.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802   -2.9158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4944   -6.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2079   -5.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9164   -6.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176   -6.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2008   -7.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4870   -6.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6326   -5.6221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6332   -7.2710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9325   -7.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4300   -3.6453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2845   -4.3405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3588   -6.5403    0.0000 H   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  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  8  1  0
  7  8  2  0
  8  9  1  0
  2  9  1  0
  2 10  1  0
 10  7  1  0
 11 12  2  0
  3 11  1  0
  2 13  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 15 19  1  6
 16 20  1  6
 16 21  1  0
  2  1  1  1
  6 22  1  0
 11 23  1  0
 13 24  1  1
M  CHG  2  23  -1  25   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: 322.36

Molecular Weight (Monoisotopic): 322.1416

AlogP: 1.70

#Rotatable Bonds: 2

Polar Surface Area: 107.22

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.01

CX Basic pKa: ┄

CX LogP: 1.48

CX LogD: -1.67

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.66

Np Likeness Score: 2.29

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