Sodium 3-Methoxy-9-(3,4,5-trimethoxyphenyl)-5H-benzo[7]annulen-4-ylphosphate

ID: ALA4557472

PubChem CID: 146373850

Max Phase: Preclinical

Molecular Formula: C21H21Na2O8P

Molecular Weight: 434.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(C2=CC=CCc3c2ccc(OC)c3OP(=O)([O-])[O-])cc(OC)c1OC.[Na+].[Na+]

Standard InChI:  InChI=1S/C21H23O8P.2Na/c1-25-17-10-9-15-14(7-5-6-8-16(15)20(17)29-30(22,23)24)13-11-18(26-2)21(28-4)19(12-13)27-3;;/h5-7,9-12H,8H2,1-4H3,(H2,22,23,24);;/q;2*+1/p-2

Standard InChI Key:  XEDDVBNSCCTTGD-UHFFFAOYSA-L

Molfile:  

     RDKit          2D

 32 32  0  0  0  0  0  0  0  0999 V2000
   38.6763  -29.4106    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   40.9545  -29.0144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.7440  -28.2261    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   40.1666  -28.8026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.3121  -23.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3110  -24.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0190  -24.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7287  -24.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7259  -23.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0173  -23.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0176  -25.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7499  -25.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9337  -26.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4287  -27.2738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6126  -27.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0994  -26.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2814  -25.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6838  -25.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9042  -25.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7254  -26.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3243  -26.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0148  -22.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.7213  -21.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4320  -23.0154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.1413  -23.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6043  -23.0218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.6041  -22.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9457  -26.5716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.3440  -26.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1457  -27.6743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.5269  -27.9837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.4155  -29.4106    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  3  2  1  0
  4  3  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 12  2  0
 12 13  1  0
 11 17  1  0
 13 14  2  0
 14 15  1  0
 16 15  1  0
  7 11  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 10 22  1  0
 22 23  1  0
  9 24  1  0
 24 25  1  0
  5 26  1  0
 26 27  1  0
 20 28  1  0
 28 29  1  0
 21 30  1  0
 30  3  1  0
  3 31  2  0
M  CHG  4   1   1   2  -1   4  -1  32   1
M  END

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: 434.38

Molecular Weight (Monoisotopic): 434.1131

AlogP: 3.74

#Rotatable Bonds: 7

Polar Surface Area: 103.68

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.61

CX Basic pKa: ┄

CX LogP: 3.07

CX LogD: -0.17

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.64

Np Likeness Score: 1.00

References

1. Niu H, Strecker TE, Gerberich JL, Campbell JW, Saha D, Mondal D, Hamel E, Chaplin DJ, Mason RP, Trawick ML, Pinney KG..  (2019)  Structure Guided Design, Synthesis, and Biological Evaluation of Novel Benzosuberene Analogues as Inhibitors of Tubulin Polymerization.,  62  (11): [PMID:31059248] [10.1021/acs.jmedchem.9b00551]

Source

Source(1):

• Scientific Literature