(4bS,8R,8aR)-8-((R)-1-(2-bromophenylamino)-1-oxo-3-phenylpropan-2-ylcarbamoyl)-2-isopropyl-4b,8-dimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthrene-3-sulfonic acid

ID: ALA4214656

PubChem CID: 145972990

Max Phase: Preclinical

Molecular Formula: C35H41BrN2O5S

Molecular Weight: 681.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1cc2c(cc1S(=O)(=O)O)[C@@]1(C)CCC[C@@](C)(C(=O)N[C@H](Cc3ccccc3)C(=O)Nc3ccccc3Br)[C@@H]1CC2

Standard InChI:  InChI=1S/C35H41BrN2O5S/c1-22(2)25-20-24-15-16-31-34(3,26(24)21-30(25)44(41,42)43)17-10-18-35(31,4)33(40)38-29(19-23-11-6-5-7-12-23)32(39)37-28-14-9-8-13-27(28)36/h5-9,11-14,20-22,29,31H,10,15-19H2,1-4H3,(H,37,39)(H,38,40)(H,41,42,43)/t29-,31-,34-,35-/m1/s1

Standard InChI Key:  FPINEFQCAFQWQM-PEWUYPRLSA-N

Molfile:  

     RDKit          2D

 45 49  0  0  0  0  0  0  0  0999 V2000
    0.9203  -25.4925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6376  -25.9071    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6365  -25.0801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8771  -26.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6999  -25.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8736  -25.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4643  -25.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1091  -25.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6974  -26.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3406  -26.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9299  -25.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9247  -27.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983  -27.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6831  -28.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0858  -28.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9122  -28.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3360  -28.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2710  -27.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1611  -28.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5685  -28.7664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5744  -27.3364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3994  -27.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8169  -26.6306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8111  -28.0565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3935  -28.7698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6361  -28.0600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0436  -28.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4054  -25.9138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8252  -25.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4143  -24.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5884  -24.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1752  -25.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5844  -25.9154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6262  -29.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0331  -30.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8590  -30.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2763  -29.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8630  -28.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2310  -26.6272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4563  -24.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8681  -23.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6313  -24.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7419  -27.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5065  -28.0380    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2728  -28.0654    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  9  2  0
  8  5  2  0
  5  6  1  0
  6  7  2  0
  7  4  1  0
  8  9  1  0
  8 11  1  0
  9 13  1  0
 12 10  1  0
 10 11  1  0
 12 13  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 13 18  1  1
 17 19  1  0
 19 20  2  0
 19 21  1  0
 22 21  1  6
 22 23  1  0
 22 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 23 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
 27 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 27  1  0
  7  2  1  0
  2 39  1  0
  6 40  1  0
 40 41  1  0
 40 42  1  0
 17 43  1  1
 12 44  1  6
 38 45  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4214656

   ---

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: 681.69

Molecular Weight (Monoisotopic): 680.1920

AlogP: 7.20

#Rotatable Bonds: 8

Polar Surface Area: 112.57

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -1.47

CX Basic pKa: 0.23

CX LogP: 6.40

CX LogD: 5.88

Aromatic Rings: 3

Heavy Atoms: 44

QED Weighted: 0.22

Np Likeness Score: 0.39

References

1. Huang RZ, Liang GB, Huang XC, Zhang B, Zhou MM, Liao ZX, Wang HS..  (2017)  Discovery of dehydroabietic acid sulfonamide based derivatives as selective matrix metalloproteinases inactivators that inhibit cell migration and proliferation.,  138  [PMID:28756264] [10.1016/j.ejmech.2017.07.020]

Source

Source(1):

• Scientific Literature