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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 20:56:15 UTC

Update Date

2021-09-26 22:50:53 UTC

HMDB ID

HMDB0243698

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(R)-Ruxolitinib

Description

3-cyclopentyl-3-(4-{1H-pyrrolo[2,3-d]pyrimidin-4-yl}-1H-pyrazol-1-yl)propanenitrile belongs to the class of organic compounds known as pyrrolo[2,3-d]pyrimidines. These are aromatic heteropolycyclic compounds containing a pyrrolo[2,3-d]pyrimidine ring system, which is an pyrrolopyrimidine isomers having the 3 ring nitrogen atoms at the 1-, 5-, and 7-positions. Based on a literature review very few articles have been published on 3-cyclopentyl-3-(4-{1H-pyrrolo[2,3-d]pyrimidin-4-yl}-1H-pyrazol-1-yl)propanenitrile. This compound has been identified in human blood as reported by (PMID: 31557052 ). (r)-ruxolitinib is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (R)-Ruxolitinib is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0243698
     RDKit          3D
(R)-Ruxolitinib
 41 44  0  0  0  0  0  0  0  0999 V2000
    0.1036   -2.9815   -1.2628 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8057   -2.3499   -0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799   -1.5653   -0.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5780   -0.1109   -0.5211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6921    0.8123   -0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8392    0.6180   -1.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9572   -0.0154   -0.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7282    0.5793    1.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2240    0.5280    1.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3885    0.1353    0.2651 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8494    0.2481   -0.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7581    0.4805    0.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1967    0.6593    0.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8814    1.6342    1.2279 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2096    1.7912    1.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9622    0.9865    0.3168 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3725   -0.0146   -0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7869   -0.9967   -1.1770 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7442   -1.7513   -1.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5810   -1.2838   -0.9622 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9483   -0.1955   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0034    0.5039    1.9237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2565    0.2944    1.5696 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7733   -1.7316   -1.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2770   -1.9387    0.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3536    0.1375   -1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3070    1.8374   -0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5987   -0.0103   -1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1556    1.6286   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9465    0.3283   -0.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8798   -1.1123   -0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2567    0.0312    1.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0754    1.6474    1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9678    1.3706    1.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9452   -0.4368    1.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0732    0.1641   -1.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7492    2.5992    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9972    1.1105    0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7301   -2.6231   -2.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5716   -1.6796   -1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673    0.6714    2.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 12 22  1  0
 22 23  2  0
  9  5  1  0
 23 10  1  0
 21 13  2  0
 21 17  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 11 36  1  0
 15 37  1  0
 16 38  1  0
 19 39  1  0
 20 40  1  0
 22 41  1  0
M  END


  Mrv1652306031609332D          

 23 26  0  0  0  0            999 V2000
    3.0601    7.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3065    6.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6122    6.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3927    6.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3557    5.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6913    4.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9704    3.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3053    3.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1997    5.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5352    5.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0268    3.5163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2253    4.4425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0503    4.4425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 12  3  1  0  0  0  0
 12  4  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14  6  1  0  0  0  0
 15  5  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17 14  1  0  0  0  0
 18  7  3  0  0  0  0
 19  8  1  0  0  0  0
 19 17  2  0  0  0  0
 20 11  2  0  0  0  0
 20 16  1  0  0  0  0
 21 11  1  0  0  0  0
 21 17  1  0  0  0  0
 22  9  2  0  0  0  0
 23 10  1  0  0  0  0
 23 15  1  0  0  0  0
 23 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0243698

> <DATABASE_NAME>
hmdb

> <SMILES>
N#CCC(C1CCCC1)N1C=C(C=N1)C1=C2C=CN=C2NC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C17H18N6/c18-7-5-15(12-3-1-2-4-12)23-10-13(9-22-23)16-14-6-8-19-17(14)21-11-20-16/h6,8-12,15H,1-5H2,(H,19,20,21)

> <INCHI_KEY>
HFNKQEVNSGCOJV-UHFFFAOYSA-N

> <FORMULA>
C17H18N6

> <MOLECULAR_WEIGHT>
306.373

> <EXACT_MASS>
306.159294604

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
33.09794970893789

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-cyclopentyl-3-(4-{1H-pyrrolo[2,3-d]pyrimidin-4-yl}-1H-pyrazol-1-yl)propanenitrile

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
1.9868056313333333

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.686174784138103

> <JCHEM_PKA_STRONGEST_BASIC>
2.5421183738321593

> <JCHEM_POLAR_SURFACE_AREA>
83.18

> <JCHEM_REFRACTIVITY>
97.38130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-cyclopentyl-3-(4-{1H-pyrrolo[2,3-d]pyrimidin-4-yl}pyrazol-1-yl)propanenitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0243698
     RDKit          3D
(R)-Ruxolitinib
 41 44  0  0  0  0  0  0  0  0999 V2000
    0.1036   -2.9815   -1.2628 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8057   -2.3499   -0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799   -1.5653   -0.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5780   -0.1109   -0.5211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6921    0.8123   -0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8392    0.6180   -1.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9572   -0.0154   -0.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7282    0.5793    1.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2240    0.5280    1.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3885    0.1353    0.2651 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8494    0.2481   -0.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7581    0.4805    0.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1967    0.6593    0.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8814    1.6342    1.2279 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2096    1.7912    1.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9622    0.9865    0.3168 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3725   -0.0146   -0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7869   -0.9967   -1.1770 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7442   -1.7513   -1.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5810   -1.2838   -0.9622 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9483   -0.1955   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0034    0.5039    1.9237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2565    0.2944    1.5696 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7733   -1.7316   -1.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2770   -1.9387    0.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3536    0.1375   -1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3070    1.8374   -0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5987   -0.0103   -1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1556    1.6286   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9465    0.3283   -0.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8798   -1.1123   -0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2567    0.0312    1.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0754    1.6474    1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9678    1.3706    1.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9452   -0.4368    1.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0732    0.1641   -1.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7492    2.5992    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9972    1.1105    0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7301   -2.6231   -2.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5716   -1.6796   -1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673    0.6714    2.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 12 22  1  0
 22 23  2  0
  9  5  1  0
 23 10  1  0
 21 13  2  0
 21 17  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 11 36  1  0
 15 37  1  0
 16 38  1  0
 19 39  1  0
 20 40  1  0
 22 41  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       5.712  13.424   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.305  12.797   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.743  12.279   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.466  11.266   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.131   9.378   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.757   7.971   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.678   6.828   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.170   6.828   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.973  10.945   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.599   9.539   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       9.383   6.564   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       6.258   3.613   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       4.924   1.303   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       4.154   8.293   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0       5.694   8.293   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1   12                                                       
CONECT    4    2   12                                                       
CONECT    5    7   15                                                       
CONECT    6    8   14                                                       
CONECT    7    5   18                                                       
CONECT    8    6   19                                                       
CONECT    9   13   22                                                       
CONECT   10   13   23                                                       
CONECT   11   20   21                                                       
CONECT   12    3    4   15                                                  
CONECT   13    9   10   16                                                  
CONECT   14    6   16   17                                                  
CONECT   15    5   12   23                                                  
CONECT   16   13   14   20                                                  
CONECT   17   14   19   21                                                  
CONECT   18    7                                                            
CONECT   19    8   17                                                       
CONECT   20   11   16                                                       
CONECT   21   11   17                                                       
CONECT   22    9   23                                                       
CONECT   23   10   15   22                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0243698
HETATM    1  N1  UNL     1       0.104  -2.981  -1.263  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.806  -2.350  -0.926  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.980  -1.565  -0.502  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.578  -0.111  -0.521  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.692   0.812  -0.105  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.839   0.618  -1.072  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.957  -0.015  -0.275  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.728   0.579   1.100  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.224   0.528   1.265  1.00  0.00           C  
HETATM   10  N2  UNL     1      -0.389   0.135   0.265  1.00  0.00           N  
HETATM   11  C9  UNL     1       0.849   0.248  -0.247  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.758   0.481   0.759  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.197   0.659   0.611  1.00  0.00           C  
HETATM   14  N3  UNL     1       3.881   1.634   1.228  1.00  0.00           N  
HETATM   15  C12 UNL     1       5.210   1.791   1.087  1.00  0.00           C  
HETATM   16  N4  UNL     1       5.962   0.986   0.317  1.00  0.00           N  
HETATM   17  C13 UNL     1       5.372  -0.015  -0.339  1.00  0.00           C  
HETATM   18  N5  UNL     1       5.787  -0.997  -1.177  1.00  0.00           N  
HETATM   19  C14 UNL     1       4.744  -1.751  -1.552  1.00  0.00           C  
HETATM   20  C15 UNL     1       3.581  -1.284  -0.962  1.00  0.00           C  
HETATM   21  C16 UNL     1       3.948  -0.196  -0.197  1.00  0.00           C  
HETATM   22  C17 UNL     1       1.003   0.504   1.924  1.00  0.00           C  
HETATM   23  N6  UNL     1      -0.256   0.294   1.570  1.00  0.00           N  
HETATM   24  H1  UNL     1      -2.773  -1.732  -1.241  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.277  -1.939   0.474  1.00  0.00           H  
HETATM   26  H3  UNL     1      -1.354   0.138  -1.580  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.307   1.837  -0.139  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.599  -0.010  -1.935  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.156   1.629  -1.415  1.00  0.00           H  
HETATM   30  H7  UNL     1      -5.947   0.328  -0.662  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.880  -1.112  -0.280  1.00  0.00           H  
HETATM   32  H9  UNL     1      -5.257   0.031   1.890  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.075   1.647   1.026  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.968   1.371   1.966  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.945  -0.437   1.682  1.00  0.00           H  
HETATM   36  H13 UNL     1       1.073   0.164  -1.320  1.00  0.00           H  
HETATM   37  H14 UNL     1       5.749   2.599   1.603  1.00  0.00           H  
HETATM   38  H15 UNL     1       6.997   1.111   0.208  1.00  0.00           H  
HETATM   39  H16 UNL     1       4.730  -2.623  -2.220  1.00  0.00           H  
HETATM   40  H17 UNL     1       2.572  -1.680  -1.066  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.467   0.671   2.889  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4   24   25
CONECT    4    5   10   26
CONECT    5    6    9   27
CONECT    6    7   28   29
CONECT    7    8   30   31
CONECT    8    9   32   33
CONECT    9   34   35
CONECT   10   11   23
CONECT   11   12   12   36
CONECT   12   13   22
CONECT   13   14   21   21
CONECT   14   15   15
CONECT   15   16   37
CONECT   16   17   38
CONECT   17   18   18   21
CONECT   18   19
CONECT   19   20   20   39
CONECT   20   21   40
CONECT   22   23   23   41
END

HMDB0243698
     RDKit          3D
(R)-Ruxolitinib
 41 44  0  0  0  0  0  0  0  0999 V2000
    0.1036   -2.9815   -1.2628 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8057   -2.3499   -0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799   -1.5653   -0.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5780   -0.1109   -0.5211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6921    0.8123   -0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8392    0.6180   -1.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9572   -0.0154   -0.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7282    0.5793    1.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2240    0.5280    1.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3885    0.1353    0.2651 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8494    0.2481   -0.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7581    0.4805    0.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1967    0.6593    0.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8814    1.6342    1.2279 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2096    1.7912    1.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9622    0.9865    0.3168 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3725   -0.0146   -0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7869   -0.9967   -1.1770 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7442   -1.7513   -1.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5810   -1.2838   -0.9622 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9483   -0.1955   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0034    0.5039    1.9237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2565    0.2944    1.5696 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7733   -1.7316   -1.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2770   -1.9387    0.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3536    0.1375   -1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3070    1.8374   -0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5987   -0.0103   -1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1556    1.6286   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9465    0.3283   -0.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8798   -1.1123   -0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2567    0.0312    1.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0754    1.6474    1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9678    1.3706    1.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9452   -0.4368    1.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0732    0.1641   -1.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7492    2.5992    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9972    1.1105    0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7301   -2.6231   -2.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5716   -1.6796   -1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673    0.6714    2.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 12 22  1  0
 22 23  2  0
  9  5  1  0
 23 10  1  0
 21 13  2  0
 21 17  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 11 36  1  0
 15 37  1  0
 16 38  1  0
 19 39  1  0
 20 40  1  0
 22 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₁₈N₆

Average Molecular Weight

306.373

Monoisotopic Molecular Weight

306.159294604

IUPAC Name

3-cyclopentyl-3-(4-{1H-pyrrolo[2,3-d]pyrimidin-4-yl}-1H-pyrazol-1-yl)propanenitrile

Traditional Name

3-cyclopentyl-3-(4-{1H-pyrrolo[2,3-d]pyrimidin-4-yl}pyrazol-1-yl)propanenitrile

CAS Registry Number

Not Available

SMILES

N#CCC(C1CCCC1)N1C=C(C=N1)C1=C2C=CN=C2NC=N1

InChI Identifier

InChI=1S/C17H18N6/c18-7-5-15(12-3-1-2-4-12)23-10-13(9-22-23)16-14-6-8-19-17(14)21-11-20-16/h6,8-12,15H,1-5H2,(H,19,20,21)

InChI Key

HFNKQEVNSGCOJV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolo[2,3-d]pyrimidines. These are aromatic heteropolycyclic compounds containing a pyrrolo[2,3-d]pyrimidine ring system, which is an pyrrolopyrimidine isomers having the 3 ring nitrogen atoms at the 1-, 5-, and 7-positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolopyrimidines

Sub Class

Pyrrolo[2,3-d]pyrimidines

Direct Parent

Pyrrolo[2,3-d]pyrimidines

Alternative Parents

Substituents

Pyrrolo[2,3-d]pyrimidine
Pyrimidine
Heteroaromatic compound
Pyrrole
Pyrazole
Azole
Azacycle
Nitrile
Carbonitrile
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.1	ALOGPS
logP	1.99	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.69	ChemAxon
pKa (Strongest Basic)	2.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.18 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.38 m³·mol⁻¹	ChemAxon
Polarizability	33.1 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DeepCCS	[M+H]+	166.683	30932474
DeepCCS	[M-H]-	164.325	30932474
DeepCCS	[M-2H]-	197.212	30932474
DeepCCS	[M+Na]+	172.94	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-Ruxolitinib,1TMS,isomer #1	C[Si](C)(C)N1C=NC(C2=CN(C(CC#N)C3CCCC3)N=C2)=C2C=CN=C21	3144.9	Semi standard non polar	33892256
(R)-Ruxolitinib,1TMS,isomer #1	C[Si](C)(C)N1C=NC(C2=CN(C(CC#N)C3CCCC3)N=C2)=C2C=CN=C21	3138.6	Standard non polar	33892256
(R)-Ruxolitinib,1TMS,isomer #1	C[Si](C)(C)N1C=NC(C2=CN(C(CC#N)C3CCCC3)N=C2)=C2C=CN=C21	4092.2	Standard polar	33892256
(R)-Ruxolitinib,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=NC(C2=CN(C(CC#N)C3CCCC3)N=C2)=C2C=CN=C21	3319.3	Semi standard non polar	33892256
(R)-Ruxolitinib,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=NC(C2=CN(C(CC#N)C3CCCC3)N=C2)=C2C=CN=C21	3354.3	Standard non polar	33892256
(R)-Ruxolitinib,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=NC(C2=CN(C(CC#N)C3CCCC3)N=C2)=C2C=CN=C21	4131.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Ruxolitinib GC-MS (Non-derivatized) - 70eV, Positive	splash10-016r-6490000000-f32e582dec057388a9a7	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Ruxolitinib GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Ruxolitinib GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Ruxolitinib 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Ruxolitinib 10V, Positive-QTOF	splash10-0a4i-0049000000-d015643f3c527963b6fe	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Ruxolitinib 20V, Positive-QTOF	splash10-0a4i-0931000000-0163e9c9fd1906e3f508	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Ruxolitinib 40V, Positive-QTOF	splash10-0006-7910000000-5f2edb2a7381ccd203ba	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Ruxolitinib 10V, Negative-QTOF	splash10-0a4i-0119000000-79098e8dad52259f4c4d	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Ruxolitinib 20V, Negative-QTOF	splash10-0a4i-0933000000-7baff41b4f39eb645835	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Ruxolitinib 40V, Negative-QTOF	splash10-001i-1930000000-c02fc35a0ca25af7c4d4	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Ruxolitinib 10V, Positive-QTOF	splash10-0a4i-0009000000-693aebf8643ec3a388c2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Ruxolitinib 20V, Positive-QTOF	splash10-0a4i-0298000000-a2101da4bab9091da0d0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Ruxolitinib 40V, Positive-QTOF	splash10-001i-1920000000-3d702e83269c9262778b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Ruxolitinib 10V, Negative-QTOF	splash10-0a4i-0109000000-6923f182bfd184e659d8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Ruxolitinib 20V, Negative-QTOF	splash10-115i-0498000000-d5fbc17da73f987444ee	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Ruxolitinib 40V, Negative-QTOF	splash10-0ue9-0924000000-4b5c388e58853f017c58	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24808460

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (R)-Ruxolitinib (HMDB0243698)

MOL for HMDB0243698 ((R)-Ruxolitinib)

3D MOL for HMDB0243698 ((R)-Ruxolitinib)

3D SDF for HMDB0243698 ((R)-Ruxolitinib)

3D-SDF for HMDB0243698 ((R)-Ruxolitinib)

PDB for HMDB0243698 ((R)-Ruxolitinib)

3D PDB for HMDB0243698 ((R)-Ruxolitinib)

SMILES for HMDB0243698 ((R)-Ruxolitinib)

INCHI for HMDB0243698 ((R)-Ruxolitinib)

Structure for HMDB0243698 ((R)-Ruxolitinib)

3D Structure for HMDB0243698 ((R)-Ruxolitinib)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra