US9187397, 1::US9187406, Curcumin::curcumin

ID: ALA3892642

PubChem CID: 58963267

Max Phase: Preclinical

Molecular Formula: C21H20O6

Molecular Weight: 368.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)CC(=O)/C=C/c2ccc(O)c(CO)c2)ccc1O

Standard InChI:  InChI=1S/C21H20O6/c1-27-21-11-15(5-9-20(21)26)3-7-18(24)12-17(23)6-2-14-4-8-19(25)16(10-14)13-22/h2-11,22,25-26H,12-13H2,1H3/b6-2+,7-3+

Standard InChI Key:  UAVJPMNEDOIHEI-YPCIICBESA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    3.6387   -0.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070    5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2688    5.8520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6078    5.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6109    7.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5728    8.1014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118    8.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9149    9.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2157   10.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2210   11.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5226   12.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8190   11.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8603   12.5849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8138   10.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1094    9.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1036    8.5310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5122    9.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 23 15  1  0
  5 24  2  0
 24 25  1  0
 25 26  2  0
 26  3  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3892642

   US9187406, Curcumin

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: 368.39

Molecular Weight (Monoisotopic): 368.1260

AlogP: 2.85

#Rotatable Bonds: 8

Polar Surface Area: 104.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.06

CX Basic pKa: ┄

CX LogP: 3.51

CX LogD: 3.51

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.49

Np Likeness Score: 0.98

References

1.  (2015)  Therapeutic curcumin derivatives, 

2.  (2015)  Curcumin analogues as zinc chelators and their uses, 

Source

Source(1):

• BindingDB Database