DL-2-[3'-(3''-tert-Butyl-5'',9''-dimethyl-7''-oxo-7H-furo[3,2-g][1]benzopyran-6''-yl)propionylamino]-3-phenylpropionic acid

ID: ALA2322558

PubChem CID: 3377704

Max Phase: Preclinical

Molecular Formula: C29H31NO6

Molecular Weight: 489.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(CCC(=O)NC(Cc2ccccc2)C(=O)O)c(=O)oc2c(C)c3occ(C(C)(C)C)c3cc12

Standard InChI:  InChI=1S/C29H31NO6/c1-16-19(11-12-24(31)30-23(27(32)33)13-18-9-7-6-8-10-18)28(34)36-26-17(2)25-21(14-20(16)26)22(15-35-25)29(3,4)5/h6-10,14-15,23H,11-13H2,1-5H3,(H,30,31)(H,32,33)

Standard InChI Key:  KIEVDFRSMMJDAN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
   13.5577  -30.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5559  -28.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2645  -28.9984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2679  -29.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9803  -30.2310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6938  -29.8177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6904  -28.9925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9735  -28.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8496  -29.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8509  -29.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0703  -28.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5867  -29.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0684  -30.0740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8190  -27.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3667  -27.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0199  -27.7968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6016  -27.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9690  -27.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4026  -30.2244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3969  -28.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5562  -31.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1059  -28.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8123  -28.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8098  -27.7602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5213  -28.9838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2277  -28.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9367  -28.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6431  -28.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3488  -28.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0547  -28.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0526  -27.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3387  -27.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6356  -27.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2227  -27.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9291  -27.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5137  -27.3478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  0
  1  4  2  0
  3  2  2  0
  2 10  1  0
  3  4  1  0
  3  8  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  9  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  8 18  1  0
  6 19  2  0
  7 20  1  0
  1 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 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
 34 35  1  0
 34 36  2  0
 26 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2322558

   2-[3-(3-Tert-butyl-5,9-dimethyl-7-oxofuro[3,2-g]chromen-6-yl)propanoylamino]-3-phenylpropanoic acid

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: 489.57

Molecular Weight (Monoisotopic): 489.2151

AlogP: 5.20

#Rotatable Bonds: 7

Polar Surface Area: 109.75

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.57

CX Basic pKa: ┄

CX LogP: 5.38

CX LogD: 2.03

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.35

Np Likeness Score: -0.23

References

1. Marzaro G, Guiotto A, Borgatti M, Finotti A, Gambari R, Breveglieri G, Chilin A..  (2013)  Psoralen derivatives as inhibitors of NF-κB/DNA interaction: synthesis, molecular modeling, 3D-QSAR, and biological evaluation.,  56  (5): [PMID:23414143] [10.1021/jm3009647]

Source

Source(1):

• Scientific Literature