Bifidenone

ID: ALA4083202

PubChem CID: 126508539

Max Phase: Preclinical

Molecular Formula: C21H26O5

Molecular Weight: 358.43

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H26O5/c1-5-6-16-12-21(20(11-17(16)22)25-13-26-21)14(2)9-15-7-8-18(23-3)19(10-15)24-4/h5,7-8,10-11,14,16H,1,6,9,12-13H2,2-4H3/t14-,16-,21+/m0/s1

Standard InChI Key:  BHTLRQBVGVBCSE-WDUKFBBWSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    9.8930  -13.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8930  -13.9913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6024  -14.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3077  -13.9913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6024  -12.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3069  -13.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9159  -12.6202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5852  -11.8725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7719  -11.9574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8847  -12.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8818  -11.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1743  -12.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4611  -12.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1817  -14.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4693  -13.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7581  -14.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6024  -15.2212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4611  -11.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7487  -11.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0373  -11.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0429  -12.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7559  -12.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3339  -12.7764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3235  -11.1281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6192  -12.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3195  -10.3067    0.0000 C   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
  5 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
  2 14  1  1
 14 15  1  0
 15 16  2  0
  3 17  2  0
 13 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 13  1  0
 21 23  1  0
 20 24  1  0
 23 25  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4083202

   ---

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: 358.43

Molecular Weight (Monoisotopic): 358.1780

AlogP: 3.67

#Rotatable Bonds: 7

Polar Surface Area: 53.99

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.84

CX LogD: 3.84

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.70

Np Likeness Score: 1.35

References

1. Williams RB, Martin SM, Lawrence JA, Norman VL, O'Neil-Johnson M, Eldridge GR, Starks CM..  (2017)  Isolation and Identification of the Novel Tubulin Polymerization Inhibitor Bifidenone.,  80  (3): [PMID:28335606] [10.1021/acs.jnatprod.6b00893]

2. 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