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

ID: ALA216298

PubChem CID: 16046115

Max Phase: Preclinical

Molecular Formula: C16H22O3

Molecular Weight: 262.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1CC[C@@H](O)C(C)(C)[C@@]12Cc1cc(O)ccc1O2

Standard InChI:  InChI=1S/C16H22O3/c1-10-4-7-14(18)15(2,3)16(10)9-11-8-12(17)5-6-13(11)19-16/h5-6,8,10,14,17-18H,4,7,9H2,1-3H3/t10-,14+,16+/m0/s1

Standard InChI Key:  LCCNGMPSHBOPBJ-DRZCJDIDSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  1  0  0  0  0  0999 V2000
   -1.5171   -7.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5171   -8.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8060   -8.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0949   -8.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0949   -7.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8060   -6.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0202   -4.9106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3960   -4.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2240   -4.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6319   -4.9163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3892   -5.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2202   -5.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4758   -6.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1354   -6.4142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6217   -6.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9335   -6.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2111   -7.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6402   -3.4901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2300   -8.5549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  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  1
  6 14  1  6
 14 11  1  0
  5 15  1  1
  1 16  1  0
  9 18  1  0
  1 17  1  0
  2 19  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA216298

   (1'R,2R,4'S)-2',2',4'-trimethylspiro[3H-1-benzofuran-2,3'-cyclohexane]-1',5-diol

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: 262.35

Molecular Weight (Monoisotopic): 262.1569

AlogP: 2.88

#Rotatable Bonds: ┄

Polar Surface Area: 49.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.96

CX Basic pKa: ┄

CX LogP: 3.15

CX LogD: 3.15

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.76

Np Likeness Score: 2.66

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