(4S,5R)-1-(benzyloxymethyl)-4-(hydroxymethyl)spiro[4.5]deca-1,6-dien-8-one

ID: ALA3764226

PubChem CID: 127041221

Max Phase: Preclinical

Molecular Formula: C19H22O3

Molecular Weight: 298.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C=C[C@@]2(CC1)C(COCc1ccccc1)=CC[C@@H]2CO

Standard InChI:  InChI=1S/C19H22O3/c20-12-16-6-7-17(19(16)10-8-18(21)9-11-19)14-22-13-15-4-2-1-3-5-15/h1-5,7-8,10,16,20H,6,9,11-14H2/t16-,19+/m1/s1

Standard InChI Key:  BBHBYVMLXQWNLR-APWZRJJASA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    0.0186    0.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8574   -0.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0186   -1.6401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4351   -1.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4351    0.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3979    1.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5656    2.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3168    3.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0251    3.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1742    1.6588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4377    4.9961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    1.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3557   -0.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    0.6951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1042   -1.7326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6051   -1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3536   -3.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8536   -3.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5991   -4.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8446   -5.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3446   -5.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5991   -4.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6  7  2  0
  6  1  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  1 10  1  1
  8 11  2  0
  5 12  1  1
  2 13  1  0
 12 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3764226

   ---

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: 298.38

Molecular Weight (Monoisotopic): 298.1569

AlogP: 3.05

#Rotatable Bonds: 5

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.40

CX LogD: 2.40

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.85

Np Likeness Score: 1.52

References

1. Ling T, Gautam LN, Griffith E, Das S, Lang W, Shadrick WR, Shelat A, Lee R, Rivas F..  (2016)  Synthesis and evaluation of colletoic acid core derivatives.,  110  [PMID:26820555] [10.1016/j.ejmech.2016.01.027]

Source

Source(1):

• Scientific Literature