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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:05 UTC

HMDB ID

HMDB0015705

Secondary Accession Numbers

HMDB15705

Metabolite Identification

Common Name

Ivacaftor

Description

Ivacaftor is only found in individuals that have used or taken this drug. It is a drug for the treatment of cystic fibrosis, developed by Vertex Pharmaceuticals and the Cystic Fibrosis Foundation.Cystic fibrosis is caused by any one of several defects in a protein, cystic fibrosis transmembrane conductance regulator, which regulates fluid flow within cells and affects the components of sweat, digestive fluids, and mucus. The defect, which is caused by a mutation in the individual's DNA, can be in any of several locations along the protein, each of which interferes with a different function of the protein. One mutation, G551D, lets the CFTR protein reach the epithelial cell surface, but doesn't let it transport chloride through the ion channel. Ivacaftor is a potentiator of the CFTR protein. The CFTR protein is a chloride channel present at the surface of epithelial cells in multiple organs. Ivacaftor facilitates increased chloride transport by potentiating the channel-open probability (or gating) of the G551D-CFTR protein.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

[NO NAME]
  Mrv0541 02271202182D          
Created with ChemWriter - http://chemwriter.com
 29 31  0  0  0  0            999 V2000
    3.7934   -1.9841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3658   -0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    0.4909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3658    1.7284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3658    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0802    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0802    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8178    0.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8178    1.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5652    0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5652    1.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  2 20  2  0  0  0  0
  3 22  2  0  0  0  0
  4 11  1  0  0  0  0
  4 20  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  6  8  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  6 14  1  0  0  0  0
  7  9  1  0  0  0  0
  7 16  1  0  0  0  0
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  7 18  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 15  2  0  0  0  0
 11 19  2  0  0  0  0
 15 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 24  2  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  2  0  0  0  0
 25 27  2  0  0  0  0
 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 29  2  0  0  0  0
M  END

HMDB0015705
     RDKit          3D
Ivacaftor
 57 59  0  0  0  0  0  0  0  0999 V2000
   -4.7314    3.2753    0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4367    2.0043    1.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5108    2.3186    2.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5364    1.0135    0.9167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1000    1.4736    0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8953    0.2434    0.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6417   -0.2468   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5358   -1.5832   -0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7275   -2.5771    0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9567   -2.1827   -0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0737   -1.5608   -2.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5146    0.5272    0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7470    0.0328   -0.1750 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0115    0.6202   -0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1105    1.7404    0.5400 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2528   -0.0313   -0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2821   -0.7538   -1.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3929   -1.3735   -2.0568 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5714   -1.3268   -1.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7006   -1.9570   -1.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8614   -1.8757   -1.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8816   -1.1563    0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7388   -0.5299    0.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5565   -0.5989   -0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4295    0.0399    0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4735    0.6749    1.3390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7237    1.7724    0.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981    2.2518    1.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1357    3.5212    1.6571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8144    3.7744    0.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4123    3.0139   -0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3189    3.9545    1.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2654    3.4073    2.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5693    2.2157    3.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9008    1.6493    3.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5176    1.3593    1.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6006    0.7643   -0.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3016    0.0894    1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8076   -0.3498    0.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4092   -3.3600    0.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0117   -3.1468   -0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2868   -2.1224    1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3495   -2.2937    0.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7897   -3.2285   -1.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5954   -1.6442   -1.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7488   -0.5454   -2.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2854   -2.3262   -2.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9032   -1.8702   -2.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7870   -0.9146   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3975   -0.8491   -2.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4065   -1.9211   -2.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6873   -2.5122   -2.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7910   -2.3606   -1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7821   -1.0723    0.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7100    0.0432    1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104    2.4245    0.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    4.0660    1.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
  7 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 12 27  1  0
 27 28  2  0
 28 29  1  0
 28  5  1  0
 25 16  1  0
 24 19  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  6 39  1  0
  9 40  1  0
  9 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 11 48  1  0
 13 49  1  0
 17 50  1  0
 18 51  1  0
 20 52  1  0
 21 53  1  0
 22 54  1  0
 23 55  1  0
 27 56  1  0
 29 57  1  0
M  END

[NO NAME]
  Mrv0541 02271202182D          
Created with ChemWriter - http://chemwriter.com
 29 31  0  0  0  0            999 V2000
    3.7934   -1.9841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3658   -0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    0.4909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3658    1.7284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3658    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0802    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0802    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8178    0.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8178    1.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5652    0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5652    1.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  2 20  2  0  0  0  0
  3 22  2  0  0  0  0
  4 11  1  0  0  0  0
  4 20  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  6  8  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  6 14  1  0  0  0  0
  7  9  1  0  0  0  0
  7 16  1  0  0  0  0
  7 17  1  0  0  0  0
  7 18  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 15  2  0  0  0  0
 11 19  2  0  0  0  0
 15 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 24  2  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  2  0  0  0  0
 25 27  2  0  0  0  0
 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015705

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(C)C1=CC(=C(O)C=C1NC(=O)C1=CNC2=CC=CC=C2C1=O)C(C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C24H28N2O3/c1-23(2,3)16-11-17(24(4,5)6)20(27)12-19(16)26-22(29)15-13-25-18-10-8-7-9-14(18)21(15)28/h7-13,27H,1-6H3,(H,25,28)(H,26,29)

> <INCHI_KEY>
PURKAOJPTOLRMP-UHFFFAOYSA-N

> <FORMULA>
C24H28N2O3

> <MOLECULAR_WEIGHT>
392.4907

> <EXACT_MASS>
392.209992772

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
43.03749629565284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

> <ALOGPS_LOGP>
5.00

> <JCHEM_LOGP>
5.758022158000001

> <ALOGPS_LOGS>
-5.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.728648438086383

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.5695579706912755

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9527882638549876

> <JCHEM_POLAR_SURFACE_AREA>
78.42999999999999

> <JCHEM_REFRACTIVITY>
118.68299999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ivacaftor

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015705
     RDKit          3D
Ivacaftor
 57 59  0  0  0  0  0  0  0  0999 V2000
   -4.7314    3.2753    0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4367    2.0043    1.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5108    2.3186    2.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5364    1.0135    0.9167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1000    1.4736    0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8953    0.2434    0.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6417   -0.2468   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5358   -1.5832   -0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7275   -2.5771    0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9567   -2.1827   -0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0737   -1.5608   -2.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5146    0.5272    0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7470    0.0328   -0.1750 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0115    0.6202   -0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1105    1.7404    0.5400 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2528   -0.0313   -0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2821   -0.7538   -1.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3929   -1.3735   -2.0568 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5714   -1.3268   -1.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7006   -1.9570   -1.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8614   -1.8757   -1.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8816   -1.1563    0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7388   -0.5299    0.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5565   -0.5989   -0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4295    0.0399    0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4735    0.6749    1.3390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7237    1.7724    0.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981    2.2518    1.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1357    3.5212    1.6571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8144    3.7744    0.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4123    3.0139   -0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3189    3.9545    1.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2654    3.4073    2.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5693    2.2157    3.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9008    1.6493    3.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5176    1.3593    1.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6006    0.7643   -0.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3016    0.0894    1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8076   -0.3498    0.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4092   -3.3600    0.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0117   -3.1468   -0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2868   -2.1224    1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3495   -2.2937    0.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7897   -3.2285   -1.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5954   -1.6442   -1.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7488   -0.5454   -2.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2854   -2.3262   -2.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9032   -1.8702   -2.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7870   -0.9146   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3975   -0.8491   -2.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4065   -1.9211   -2.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6873   -2.5122   -2.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7910   -2.3606   -1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7821   -1.0723    0.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7100    0.0432    1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104    2.4245    0.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    4.0660    1.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
  7 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 12 27  1  0
 27 28  2  0
 28 29  1  0
 28  5  1  0
 25 16  1  0
 24 19  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  6 39  1  0
  9 40  1  0
  9 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 11 48  1  0
 13 49  1  0
 17 50  1  0
 18 51  1  0
 20 52  1  0
 21 53  1  0
 22 54  1  0
 23 55  1  0
 27 56  1  0
 29 57  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: [NO NAME]                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0       7.081  -3.704   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.082  -1.394   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.749  -1.394   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       9.748   0.916   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      13.749   3.226   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.081   2.456   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414  -2.164   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081   0.916   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747  -1.394   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747   0.146   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415   0.146   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081   3.996   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.541   2.456   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.621   2.456   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -2.164   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080  -2.934   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.644  -0.830   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.184  -3.497   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415  -1.394   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.082   0.146   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.416   0.916   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.749   0.146   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.083   0.916   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.416   2.456   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.083   2.456   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.460   0.093   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.460   3.280   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.855   0.884   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.855   2.488   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2   20                                                            
CONECT    3   22                                                            
CONECT    4   11   20                                                       
CONECT    5   24   25                                                       
CONECT    6    8   12   13   14                                             
CONECT    7    9   16   17   18                                             
CONECT    8    6   10   11                                                  
CONECT    9    7   10   15                                                  
CONECT   10    8    9                                                       
CONECT   11    4    8   19                                                  
CONECT   12    6                                                            
CONECT   13    6                                                            
CONECT   14    6                                                            
CONECT   15    1    9   19                                                  
CONECT   16    7                                                            
CONECT   17    7                                                            
CONECT   18    7                                                            
CONECT   19   11   15                                                       
CONECT   20    2    4   21                                                  
CONECT   21   20   22   24                                                  
CONECT   22    3   21   23                                                  
CONECT   23   22   25   26                                                  
CONECT   24    5   21                                                       
CONECT   25    5   23   27                                                  
CONECT   26   23   28                                                       
CONECT   27   25   29                                                       
CONECT   28   26   29                                                       
CONECT   29   27   28                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

COMPND    HMDB0015705
HETATM    1  C1  UNL     1      -4.731   3.275   0.454  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.437   2.004   1.212  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.511   2.319   2.700  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.536   1.013   0.917  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.100   1.474   0.853  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.895   0.243   0.293  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.642  -0.247  -0.045  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.536  -1.583  -0.626  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.728  -2.577   0.152  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.957  -2.183  -0.702  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.074  -1.561  -2.079  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.515   0.527   0.184  1.00  0.00           C  
HETATM   13  N1  UNL     1       0.747   0.033  -0.175  1.00  0.00           N  
HETATM   14  C13 UNL     1       2.011   0.620  -0.002  1.00  0.00           C  
HETATM   15  O1  UNL     1       2.111   1.740   0.540  1.00  0.00           O  
HETATM   16  C14 UNL     1       3.253  -0.031  -0.438  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.282  -0.754  -1.606  1.00  0.00           C  
HETATM   18  N2  UNL     1       4.393  -1.374  -2.057  1.00  0.00           N  
HETATM   19  C16 UNL     1       5.571  -1.327  -1.382  1.00  0.00           C  
HETATM   20  C17 UNL     1       6.701  -1.957  -1.840  1.00  0.00           C  
HETATM   21  C18 UNL     1       7.861  -1.876  -1.117  1.00  0.00           C  
HETATM   22  C19 UNL     1       7.882  -1.156   0.071  1.00  0.00           C  
HETATM   23  C20 UNL     1       6.739  -0.530   0.516  1.00  0.00           C  
HETATM   24  C21 UNL     1       5.556  -0.599  -0.197  1.00  0.00           C  
HETATM   25  C22 UNL     1       4.430   0.040   0.277  1.00  0.00           C  
HETATM   26  O2  UNL     1       4.474   0.675   1.339  1.00  0.00           O  
HETATM   27  C23 UNL     1      -0.724   1.772   0.750  1.00  0.00           C  
HETATM   28  C24 UNL     1      -1.998   2.252   1.086  1.00  0.00           C  
HETATM   29  O3  UNL     1      -2.136   3.521   1.657  1.00  0.00           O  
HETATM   30  H1  UNL     1      -3.814   3.774   0.071  1.00  0.00           H  
HETATM   31  H2  UNL     1      -5.412   3.014  -0.382  1.00  0.00           H  
HETATM   32  H3  UNL     1      -5.319   3.954   1.115  1.00  0.00           H  
HETATM   33  H4  UNL     1      -4.265   3.407   2.872  1.00  0.00           H  
HETATM   34  H5  UNL     1      -5.569   2.216   3.013  1.00  0.00           H  
HETATM   35  H6  UNL     1      -3.901   1.649   3.307  1.00  0.00           H  
HETATM   36  H7  UNL     1      -6.518   1.359   1.293  1.00  0.00           H  
HETATM   37  H8  UNL     1      -5.601   0.764  -0.160  1.00  0.00           H  
HETATM   38  H9  UNL     1      -5.302   0.089   1.521  1.00  0.00           H  
HETATM   39  H10 UNL     1      -3.808  -0.350   0.122  1.00  0.00           H  
HETATM   40  H11 UNL     1      -1.409  -3.360   0.543  1.00  0.00           H  
HETATM   41  H12 UNL     1       0.012  -3.147  -0.458  1.00  0.00           H  
HETATM   42  H13 UNL     1      -0.287  -2.122   1.070  1.00  0.00           H  
HETATM   43  H14 UNL     1      -3.349  -2.294   0.325  1.00  0.00           H  
HETATM   44  H15 UNL     1      -2.790  -3.229  -1.067  1.00  0.00           H  
HETATM   45  H16 UNL     1      -3.595  -1.644  -1.395  1.00  0.00           H  
HETATM   46  H17 UNL     1      -0.749  -0.545  -2.407  1.00  0.00           H  
HETATM   47  H18 UNL     1      -0.285  -2.326  -2.226  1.00  0.00           H  
HETATM   48  H19 UNL     1      -1.903  -1.870  -2.760  1.00  0.00           H  
HETATM   49  H20 UNL     1       0.787  -0.915  -0.653  1.00  0.00           H  
HETATM   50  H21 UNL     1       2.398  -0.849  -2.211  1.00  0.00           H  
HETATM   51  H22 UNL     1       4.407  -1.921  -2.947  1.00  0.00           H  
HETATM   52  H23 UNL     1       6.687  -2.512  -2.757  1.00  0.00           H  
HETATM   53  H24 UNL     1       8.791  -2.361  -1.439  1.00  0.00           H  
HETATM   54  H25 UNL     1       8.782  -1.072   0.667  1.00  0.00           H  
HETATM   55  H26 UNL     1       6.710   0.043   1.441  1.00  0.00           H  
HETATM   56  H27 UNL     1       0.110   2.424   0.953  1.00  0.00           H  
HETATM   57  H28 UNL     1      -1.299   4.066   1.814  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    4    5
CONECT    3   33   34   35
CONECT    4   36   37   38
CONECT    5    6    6   28
CONECT    6    7   39
CONECT    7    8   12   12
CONECT    8    9   10   11
CONECT    9   40   41   42
CONECT   10   43   44   45
CONECT   11   46   47   48
CONECT   12   13   27
CONECT   13   14   49
CONECT   14   15   15   16
CONECT   16   17   17   25
CONECT   17   18   50
CONECT   18   19   51
CONECT   19   20   20   24
CONECT   20   21   52
CONECT   21   22   22   53
CONECT   22   23   54
CONECT   23   24   24   55
CONECT   24   25
CONECT   25   26   26
CONECT   27   28   28   56
CONECT   28   29
CONECT   29   57
END

HMDB0015705
     RDKit          3D
Ivacaftor
 57 59  0  0  0  0  0  0  0  0999 V2000
   -4.7314    3.2753    0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4367    2.0043    1.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5108    2.3186    2.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5364    1.0135    0.9167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1000    1.4736    0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8953    0.2434    0.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6417   -0.2468   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5358   -1.5832   -0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7275   -2.5771    0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9567   -2.1827   -0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0737   -1.5608   -2.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5146    0.5272    0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7470    0.0328   -0.1750 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0115    0.6202   -0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1105    1.7404    0.5400 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2528   -0.0313   -0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2821   -0.7538   -1.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3929   -1.3735   -2.0568 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5714   -1.3268   -1.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7006   -1.9570   -1.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8614   -1.8757   -1.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8816   -1.1563    0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7388   -0.5299    0.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5565   -0.5989   -0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4295    0.0399    0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4735    0.6749    1.3390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7237    1.7724    0.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981    2.2518    1.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1357    3.5212    1.6571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8144    3.7744    0.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4123    3.0139   -0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3189    3.9545    1.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2654    3.4073    2.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5693    2.2157    3.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9008    1.6493    3.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5176    1.3593    1.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6006    0.7643   -0.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3016    0.0894    1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8076   -0.3498    0.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4092   -3.3600    0.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0117   -3.1468   -0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2868   -2.1224    1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3495   -2.2937    0.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7897   -3.2285   -1.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5954   -1.6442   -1.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7488   -0.5454   -2.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2854   -2.3262   -2.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9032   -1.8702   -2.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7870   -0.9146   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3975   -0.8491   -2.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4065   -1.9211   -2.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6873   -2.5122   -2.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7910   -2.3606   -1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7821   -1.0723    0.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7100    0.0432    1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104    2.4245    0.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    4.0660    1.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
  7 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 12 27  1  0
 27 28  2  0
 28 29  1  0
 28  5  1  0
 25 16  1  0
 24 19  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  6 39  1  0
  9 40  1  0
  9 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 11 48  1  0
 13 49  1  0
 17 50  1  0
 18 51  1  0
 20 52  1  0
 21 53  1  0
 22 54  1  0
 23 55  1  0
 27 56  1  0
 29 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ivacaftorum	ChEBI
Kalydeco	ChEBI
VX-770	ChEBI
N-(2,4-Di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide	HMDB
N-(2,4-Bis(1,1-dimethylethyl)-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide	HMDB

Chemical Formula

C₂₄H₂₈N₂O₃

Average Molecular Weight

392.4907

Monoisotopic Molecular Weight

392.209992772

IUPAC Name

N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

Traditional Name

ivacaftor

CAS Registry Number

873054-44-5

SMILES

CC(C)(C)C1=CC(=C(O)C=C1NC(=O)C1=CNC2=CC=CC=C2C1=O)C(C)(C)C

InChI Identifier

InChI=1S/C24H28N2O3/c1-23(2,3)16-11-17(24(4,5)6)20(27)12-19(16)26-22(29)15-13-25-18-10-8-7-9-14(18)21(15)28/h7-13,27H,1-6H3,(H,25,28)(H,26,29)

InChI Key

PURKAOJPTOLRMP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromatic anilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with an aromatic group. They have the general structure RNC(=O)R', where R= benzene, and R = aryl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Aromatic anilides

Alternative Parents

Substituents

Aromatic anilide
Quinoline-3-carboxamide
Dihydroquinolone
Quinoline
Dihydroquinoline
Phenylpropane
Pyridine carboxylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyridine
Heteroaromatic compound
Vinylogous amide
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:66901 )
phenols (CHEBI:66901 )
aromatic amide (CHEBI:66901 )
quinolone (CHEBI:66901 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015705)

Source

Exogenous

Exogenous (HMDB: HMDB0015705)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.002 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.002 g/L	ALOGPS
logP	5	ALOGPS
logP	5.76	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	6.57	ChemAxon
pKa (Strongest Basic)	-0.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.43 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	118.68 m³·mol⁻¹	ChemAxon
Polarizability	43.04 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	194.217	31661259
DarkChem	[M-H]-	186.853	31661259
DeepCCS	[M+H]+	203.143	30932474
DeepCCS	[M-H]-	200.785	30932474
DeepCCS	[M-2H]-	234.876	30932474
DeepCCS	[M+Na]+	209.93	30932474
AllCCS	[M+H]+	194.9	32859911
AllCCS	[M+H-H2O]+	192.4	32859911
AllCCS	[M+NH4]+	197.2	32859911
AllCCS	[M+Na]+	197.9	32859911
AllCCS	[M-H]-	201.0	32859911
AllCCS	[M+Na-2H]-	200.7	32859911
AllCCS	[M+HCOO]-	200.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.93 minutes	32390414
Predicted by Siyang on May 30, 2022	15.6068 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.33 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2990.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	315.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	194.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	156.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	185.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	723.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	951.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	91.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1172.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	618.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1697.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	528.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	473.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	189.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	135.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ivacaftor	CC(C)(C)C1=CC(=C(O)C=C1NC(=O)C1=CNC2=CC=CC=C2C1=O)C(C)(C)C	3868.3	Standard polar	33892256
Ivacaftor	CC(C)(C)C1=CC(=C(O)C=C1NC(=O)C1=CNC2=CC=CC=C2C1=O)C(C)(C)C	3340.0	Standard non polar	33892256
Ivacaftor	CC(C)(C)C1=CC(=C(O)C=C1NC(=O)C1=CNC2=CC=CC=C2C1=O)C(C)(C)C	3597.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ivacaftor,1TMS,isomer #1	CC(C)(C)C1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C=C1NC(=O)C1=C[NH]C2=CC=CC=C2C1=O	3522.5	Semi standard non polar	33892256
Ivacaftor,1TMS,isomer #2	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=C[NH]C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O	3261.1	Semi standard non polar	33892256
Ivacaftor,1TMS,isomer #3	CC(C)(C)C1=CC(C(C)(C)C)=C(NC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C3C2=O)C=C1O	3492.3	Semi standard non polar	33892256
Ivacaftor,2TMS,isomer #1	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=C[NH]C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O[Si](C)(C)C	3230.7	Semi standard non polar	33892256
Ivacaftor,2TMS,isomer #1	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=C[NH]C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O[Si](C)(C)C	3291.2	Standard non polar	33892256
Ivacaftor,2TMS,isomer #1	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=C[NH]C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O[Si](C)(C)C	3481.6	Standard polar	33892256
Ivacaftor,2TMS,isomer #2	CC(C)(C)C1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C=C1NC(=O)C1=CN([Si](C)(C)C)C2=CC=CC=C2C1=O	3549.1	Semi standard non polar	33892256
Ivacaftor,2TMS,isomer #2	CC(C)(C)C1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C=C1NC(=O)C1=CN([Si](C)(C)C)C2=CC=CC=C2C1=O	3316.6	Standard non polar	33892256
Ivacaftor,2TMS,isomer #2	CC(C)(C)C1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C=C1NC(=O)C1=CN([Si](C)(C)C)C2=CC=CC=C2C1=O	3563.5	Standard polar	33892256
Ivacaftor,2TMS,isomer #3	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O	3299.0	Semi standard non polar	33892256
Ivacaftor,2TMS,isomer #3	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O	3336.5	Standard non polar	33892256
Ivacaftor,2TMS,isomer #3	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O	3520.1	Standard polar	33892256
Ivacaftor,3TMS,isomer #1	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O[Si](C)(C)C	3310.7	Semi standard non polar	33892256
Ivacaftor,3TMS,isomer #1	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O[Si](C)(C)C	3334.4	Standard non polar	33892256
Ivacaftor,3TMS,isomer #1	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C)C=C1O[Si](C)(C)C	3394.0	Standard polar	33892256
Ivacaftor,1TBDMS,isomer #1	CC(C)(C)C1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1NC(=O)C1=C[NH]C2=CC=CC=C2C1=O	3718.3	Semi standard non polar	33892256
Ivacaftor,1TBDMS,isomer #2	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=C[NH]C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O	3521.0	Semi standard non polar	33892256
Ivacaftor,1TBDMS,isomer #3	CC(C)(C)C1=CC(C(C)(C)C)=C(NC(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C3C2=O)C=C1O	3710.5	Semi standard non polar	33892256
Ivacaftor,2TBDMS,isomer #1	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=C[NH]C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3681.9	Semi standard non polar	33892256
Ivacaftor,2TBDMS,isomer #1	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=C[NH]C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3635.9	Standard non polar	33892256
Ivacaftor,2TBDMS,isomer #1	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=C[NH]C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3667.8	Standard polar	33892256
Ivacaftor,2TBDMS,isomer #2	CC(C)(C)C1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1NC(=O)C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C2C1=O	3909.9	Semi standard non polar	33892256
Ivacaftor,2TBDMS,isomer #2	CC(C)(C)C1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1NC(=O)C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C2C1=O	3660.3	Standard non polar	33892256
Ivacaftor,2TBDMS,isomer #2	CC(C)(C)C1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1NC(=O)C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C2C1=O	3731.6	Standard polar	33892256
Ivacaftor,2TBDMS,isomer #3	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O	3706.6	Semi standard non polar	33892256
Ivacaftor,2TBDMS,isomer #3	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O	3649.8	Standard non polar	33892256
Ivacaftor,2TBDMS,isomer #3	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O	3689.3	Standard polar	33892256
Ivacaftor,3TBDMS,isomer #1	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3891.2	Semi standard non polar	33892256
Ivacaftor,3TBDMS,isomer #1	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3808.9	Standard non polar	33892256
Ivacaftor,3TBDMS,isomer #1	CC(C)(C)C1=CC(C(C)(C)C)=C(N(C(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C3C2=O)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3634.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ivacaftor GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0739000000-1b41f2c7ddedd90d43c8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ivacaftor GC-MS (1 TMS) - 70eV, Positive	splash10-006y-3351900000-dc90833dbef87cc492c0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ivacaftor GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ivacaftor GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ivacaftor LC-ESI-qTof , Positive-QTOF	splash10-03gj-1891400000-9f74f1c76f8bde03b286	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ivacaftor , positive-QTOF	splash10-0079-1809000000-c0147e018d786aee606b	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ivacaftor 10V, Positive-QTOF	splash10-0006-0009000000-86c4c1172d1bee0ab8cf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ivacaftor 20V, Positive-QTOF	splash10-00dl-0918000000-00798a3656e171f62c81	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ivacaftor 40V, Positive-QTOF	splash10-0006-0911000000-2fefa753407d0181cec3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ivacaftor 10V, Negative-QTOF	splash10-0006-0409000000-9aa079aa9d35e2f8ab13	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ivacaftor 20V, Negative-QTOF	splash10-0006-0900000000-30095278d7b7875589bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ivacaftor 40V, Negative-QTOF	splash10-0006-0900000000-fc85de7523217af66c4c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ivacaftor 10V, Positive-QTOF	splash10-0079-0509000000-16aa918207aec379d615	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ivacaftor 20V, Positive-QTOF	splash10-00di-0900000000-383766b2b3690775474c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ivacaftor 40V, Positive-QTOF	splash10-0ck9-2619000000-2307c51d7b28f4ff118f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ivacaftor 10V, Negative-QTOF	splash10-0006-0009000000-d21896041c7a6bff6e47	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ivacaftor 20V, Negative-QTOF	splash10-0006-0309000000-696199233265215e456f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ivacaftor 40V, Negative-QTOF	splash10-0006-1913000000-a31f02ed83400d9b16dd	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB08820	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB08820	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08820

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17347474

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ivacaftor

METLIN ID

Not Available

PubChem Compound

16220172

PDB ID

Not Available

ChEBI ID

66901

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Accurso FJ, Rowe SM, Clancy JP, Boyle MP, Dunitz JM, Durie PR, Sagel SD, Hornick DB, Konstan MW, Donaldson SH, Moss RB, Pilewski JM, Rubenstein RC, Uluer AZ, Aitken ML, Freedman SD, Rose LM, Mayer-Hamblett N, Dong Q, Zha J, Stone AJ, Olson ER, Ordonez CL, Campbell PW, Ashlock MA, Ramsey BW: Effect of VX-770 in persons with cystic fibrosis and the G551D-CFTR mutation. N Engl J Med. 2010 Nov 18;363(21):1991-2003. doi: 10.1056/NEJMoa0909825. [PubMed:21083385 ]
Ramsey BW, Davies J, McElvaney NG, Tullis E, Bell SC, Drevinek P, Griese M, McKone EF, Wainwright CE, Konstan MW, Moss R, Ratjen F, Sermet-Gaudelus I, Rowe SM, Dong Q, Rodriguez S, Yen K, Ordonez C, Elborn JS: A CFTR potentiator in patients with cystic fibrosis and the G551D mutation. N Engl J Med. 2011 Nov 3;365(18):1663-72. doi: 10.1056/NEJMoa1105185. [PubMed:22047557 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Enzyme Details

2. Cystic fibrosis transmembrane conductance regulator

General function:: Involved in ATP binding
Specific function:: Involved in the transport of chloride ions. May regulate bicarbonate secretion and salvage in epithelial cells by regulating the SLC4A7 transporter. Can inhibit the chloride channel activity of ANO1.
Gene Name:: CFTR
Uniprot ID:: P13569
Molecular weight:: 168139.895

References

Yu H, Burton B, Huang CJ, Worley J, Cao D, Johnson JP Jr, Urrutia A, Joubran J, Seepersaud S, Sussky K, Hoffman BJ, Van Goor F: Ivacaftor potentiation of multiple CFTR channels with gating mutations. J Cyst Fibros. 2012 May;11(3):237-45. doi: 10.1016/j.jcf.2011.12.005. Epub 2012 Jan 30. [PubMed:22293084 ]

Showing metabocard for Ivacaftor (HMDB0015705)

MOL for HMDB0015705 (Ivacaftor)

3D MOL for HMDB0015705 (Ivacaftor)

3D SDF for HMDB0015705 (Ivacaftor)

3D-SDF for HMDB0015705 (Ivacaftor)

PDB for HMDB0015705 (Ivacaftor)

3D PDB for HMDB0015705 (Ivacaftor)

SMILES for HMDB0015705 (Ivacaftor)

INCHI for HMDB0015705 (Ivacaftor)

Structure for HMDB0015705 (Ivacaftor)

3D Structure for HMDB0015705 (Ivacaftor)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References