(2R,3'R,6'S)-4-acetyl-2',2',6'-trimethyl-3H-spiro[1-benzofuran-2,1'-cyclohexane]-3',5-diol

ID: ALA215790

PubChem CID: 44416602

Max Phase: Preclinical

Molecular Formula: C18H24O4

Molecular Weight: 304.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)c1c(O)ccc2c1C[C@@]1(O2)[C@@H](C)CC[C@@H](O)C1(C)C

Standard InChI:  InChI=1S/C18H24O4/c1-10-5-8-15(21)17(3,4)18(10)9-12-14(22-18)7-6-13(20)16(12)11(2)19/h6-7,10,15,20-21H,5,8-9H2,1-4H3/t10-,15+,18+/m0/s1

Standard InChI Key:  OZFBDEHVMJHKST-WQFPPAFTSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  1  0  0  0  0  0999 V2000
    1.3283  -10.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3283  -11.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0395  -11.4172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507  -11.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507  -10.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0395   -9.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8658   -7.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4496   -7.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6215   -7.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2136   -7.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4564   -8.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6253   -8.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3696   -9.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7102   -9.2859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4674   -9.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9119   -9.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6342  -10.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3897   -7.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0245   -7.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202   -8.5051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2054   -6.3616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6154  -11.4268    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 21  1  0
  1 17  1  0
 10 18  1  0
  1  2  1  0
 18 19  1  0
  1  6  1  0
 18 20  2  0
  2  3  1  0
  2 22  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA215790

   1-[(2R,3'R,6'S)-3',5-dihydroxy-2',2',6'-trimethylspiro[3H-1-benzofuran-2,1'-cyclohexane]-4-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: 9.60

CX Basic pKa: ┄

CX LogP: 3.36

CX LogD: 3.36

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.78

Np Likeness Score: 2.16

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