1-[(2R,3'R,6'S)-3',5-dihydroxy-2',2',6'-trimethyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-6-yl]ethanone

ID: ALA217674

PubChem CID: 44416601

Max Phase: Preclinical

Molecular Formula: C18H24O4

Molecular Weight: 304.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)c1cc2c(cc1O)C[C@@]1(O2)[C@@H](C)CC[C@@H](O)C1(C)C

Standard InChI:  InChI=1S/C18H24O4/c1-10-5-6-16(21)17(3,4)18(10)9-12-7-14(20)13(11(2)19)8-15(12)22-18/h7-8,10,16,20-21H,5-6,9H2,1-4H3/t10-,16+,18+/m0/s1

Standard InChI Key:  RYEIGWLPNHBHCW-FEMPBKKVSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  1  0  0  0  0  0999 V2000
   -1.8727   -7.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8727   -7.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1616   -8.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4503   -7.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4503   -7.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1616   -6.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3352   -4.7443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7515   -4.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5796   -4.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9875   -4.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7446   -5.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757   -5.4606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8314   -6.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4908   -6.2480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2663   -6.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2892   -6.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5668   -7.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3441   -3.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798   -3.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7604   -2.6012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5856   -8.3889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9956   -3.3236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
 11  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 12  2  0
 11 12  1  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 22  1  0
  1 17  1  0
  8 18  1  0
  1  2  1  0
 18 19  1  0
  1  6  1  0
 18 20  2  0
  2  3  1  0
  2 21  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA217674

   1-[(2R,3'R,6'S)-3',5-dihydroxy-2',2',6'-trimethylspiro[3H-1-benzofuran-2,1'-cyclohexane]-6-yl]ethanone

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: 304.39

Molecular Weight (Monoisotopic): 304.1675

AlogP: 3.09

#Rotatable Bonds: 1

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.56

CX Basic pKa: ┄

CX LogP: 3.36

CX LogD: 3.36

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.78

Np Likeness Score: 2.30

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