sodium(1R,4S,5R)-1,4,5-trihydroxy-3-(naphthalen-2-ylmethoxy)-2-(naphthalen-2-ylmethyl)cyclohex-2-enecarboxylate

ID: ALA1823566

PubChem CID: 46840608

Max Phase: Preclinical

Molecular Formula: C29H25NaO6

Molecular Weight: 470.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C([O-])[C@@]1(O)C[C@@H](O)[C@H](O)C(OCc2ccc3ccccc3c2)=C1Cc1ccc2ccccc2c1.[Na+]

Standard InChI:  InChI=1S/C29H26O6.Na/c30-25-16-29(34,28(32)33)24(15-18-9-11-20-5-1-3-7-22(20)13-18)27(26(25)31)35-17-19-10-12-21-6-2-4-8-23(21)14-19;/h1-14,25-26,30-31,34H,15-17H2,(H,32,33);/q;+1/p-1/t25-,26+,29-;/m1./s1

Standard InChI Key:  ROVNGCLRNGFXEC-DDLJGEAHSA-M

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
    2.3750    0.9687    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    0.1084    0.4130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5256   -0.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9383    0.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1835   -0.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1835   -1.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5293   -1.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2421   -1.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2421   -0.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7642    0.4180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5233    1.1294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9567   -1.9615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5293   -2.7822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8982   -1.9615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6141   -1.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3286   -1.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9005   -0.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9038    0.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0419   -1.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0345   -3.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3232   -2.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7554   -2.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7556   -1.9663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4690   -1.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1828   -1.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1785   -2.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4646   -3.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1897    0.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6262    1.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6197    0.9176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9102    2.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1925    1.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5218    2.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5197    2.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2027    3.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9141    2.9852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
 16 19  2  0
 19 23  1  0
  4 10  1  0
 22 20  1  0
  3  4  1  1
 20 21  2  0
 21 16  1  0
  4 11  2  0
  5  6  2  0
 22 23  1  0
  8 12  1  1
 23 24  2  0
 24 25  1  0
  7 13  1  6
 25 26  2  0
  5  3  1  0
 26 27  1  0
 27 22  2  0
  6 14  1  0
 18 28  2  0
 28 32  1  0
  6  7  1  0
 31 29  1  0
 14 15  1  0
 29 30  2  0
 30 18  1  0
  7  8  1  0
 15 16  1  0
 31 32  1  0
  8  9  1  0
 32 33  2  0
  5 17  1  0
 33 34  1  0
  9  3  1  0
 34 35  2  0
 17 18  1  0
 35 36  1  0
 36 31  2  0
M  CHG  2   1   1  10  -1
M  END

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: 470.52

Molecular Weight (Monoisotopic): 470.1729

AlogP: 3.95

#Rotatable Bonds: 6

Polar Surface Area: 107.22

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.87

CX Basic pKa: ┄

CX LogP: 3.37

CX LogD: 0.14

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.34

Np Likeness Score: 0.70

References

1. Tizón L, Otero JM, Prazeres VF, Llamas-Saiz AL, Fox GC, van Raaij MJ, Lamb H, Hawkins AR, Ainsa JA, Castedo L, González-Bello C..  (2011)  A prodrug approach for improving antituberculosis activity of potent Mycobacterium tuberculosis type II dehydroquinase inhibitors.,  54  (17): [PMID:21780742] [10.1021/jm2006063]

Source

Source(1):

• Scientific Literature