((6S,7aR)-6-Allyl-7a-((S)-1-(3-chloro-4-methoxyphenyl)propan-2-yl)-7,7a-dihydrobenzo[d][1,3]dioxol-5(6H)-one)

ID: ALA4537874

PubChem CID: 126509134

Max Phase: Preclinical

Molecular Formula: C20H23ClO4

Molecular Weight: 362.85

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC[C@H]1C[C@]2([C@@H](C)Cc3ccc(OC)c(Cl)c3)OCOC2=CC1=O

Standard InChI:  InChI=1S/C20H23ClO4/c1-4-5-15-11-20(19(10-17(15)22)24-12-25-20)13(2)8-14-6-7-18(23-3)16(21)9-14/h4,6-7,9-10,13,15H,1,5,8,11-12H2,2-3H3/t13-,15-,20+/m0/s1

Standard InChI Key:  STQXFXBYKYRAMV-ZQGRQUNCSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   36.8914  -12.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8914  -13.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6032  -13.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3192  -13.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6032  -11.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3180  -12.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9251  -11.6864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.5933  -10.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7734  -11.0204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6032  -14.3033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.1767  -13.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4561  -13.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7415  -13.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8830  -11.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8786  -10.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1697  -11.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4478  -11.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4480  -10.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7356  -10.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0167  -10.5943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0250  -11.4244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7424  -11.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2991  -10.1891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5887  -10.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7353   -9.3543    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  5  1  0
  2  3  1  0
  3  4  1  0
  4  6  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  5  9  1  6
  3 10  2  0
  2 11  1  1
 11 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  1  6
 14 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
 20 23  1  0
 23 24  1  0
 19 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4537874

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 362.85

Molecular Weight (Monoisotopic): 362.1285

AlogP: 4.32

#Rotatable Bonds: 6

Polar Surface Area: 44.76

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.60

CX LogD: 4.60

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.71

Np Likeness Score: 1.12

References

1. Huang Z, Williams RB, Martin SM, Lawrence JA, Norman VL, O'Neil-Johnson M, Harding J, Mangette JE, Liu S, Guzzo PR, Starks CM, Eldridge GR..  (2018)  Bifidenone: Structure-Activity Relationship and Advanced Preclinical Candidate.,  61  (15): [PMID:29995409] [10.1021/acs.jmedchem.7b01644]

Source

Source(1):

• Scientific Literature