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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 18:05:44 UTC

Update Date

2021-09-26 23:13:28 UTC

HMDB ID

HMDB0257236

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Riociguat

Description

Riociguat, also known as adempas or bay 63-2521, belongs to the class of organic compounds known as pyrazolopyridines. Pyrazolopyridines are compounds containing a pyrazolopyridine skeleton, which consists of a pyrazole fused to a pyridine. Pyrazole is 5-membered ring consisting of three carbon atoms and two adjacent nitrogen centers. Pyridine is a 6-membered ring with four carbon and one nitrogen atoms. Based on a literature review a significant number of articles have been published on Riociguat. This compound has been identified in human blood as reported by (PMID: 31557052 ). Riociguat is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Riociguat 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


  Mrv0541 11131316082D          

 31 34  0  0  0  0            999 V2000
    7.9200   -9.6525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9200  -10.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6213  -10.8900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3638  -10.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3638   -9.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6213   -9.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6213   -8.4150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0649   -9.2400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0649  -10.8900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7663   -9.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4675   -9.2400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7663  -10.4775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1688   -9.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0649   -8.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2188  -10.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8988  -10.9313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1463  -11.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9713  -11.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5588  -10.3950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750  -12.4163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875  -13.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125  -13.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1975  -10.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4963  -10.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950  -10.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0525  -10.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0525  -11.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7538  -12.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4963  -11.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1975  -12.1688    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  4  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  1  0  0  0  0
  8 14  1  0  0  0  0
  2 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 15  1  0  0  0  0
 15 19  2  0  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 24 16  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 25 30  2  0  0  0  0
 30 31  1  0  0  0  0
M  END

HMDB0257236
     RDKit          3D
Riociguat
 50 53  0  0  0  0  0  0  0  0999 V2000
    4.6942    3.2449   -0.8103 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361    1.9180   -0.8220 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1039    0.8534   -1.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3391    1.0353   -1.1992 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6280   -0.4859   -1.0252 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5168   -1.5970   -1.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2268   -0.6673   -0.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163   -1.1866    0.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7733   -1.5352    1.4121 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5051   -1.3272    0.6497 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363   -1.0151   -0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773   -1.1392    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9387   -0.8717   -0.6644 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0464   -1.0593   -0.0016 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4431   -0.8411   -0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8094    0.5703   -0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5196    1.0293    0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8224    2.3688    0.9490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4051    3.2740   -0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7016    2.8309   -1.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3920    1.4876   -1.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6985    0.9959   -2.3001 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7424   -1.4643    1.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4616   -1.8005    2.3316 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8642   -2.1828    3.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4944   -2.2476    3.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7291   -1.9093    2.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3765   -1.5225    1.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9522   -0.5162   -1.4074 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2461   -0.3483   -1.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150    0.1974   -2.9616 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0437    3.8752   -1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7531    3.2803   -1.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5508    3.6398    0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9588   -1.5562   -2.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2646   -1.6868   -0.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9070   -2.5427   -1.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356   -2.5350    1.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3084   -0.8041    1.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1403   -1.4261    0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5703   -1.1878   -1.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8696    0.3555    1.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3802    2.7561    1.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6464    4.3345    0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3764    3.5275   -1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4389   -2.4668    4.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921   -2.5581    4.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3422   -1.9497    2.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2550   -0.2747   -3.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2282    1.1306   -3.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 14 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 11 29  1  0
 29 30  2  0
 30 31  1  0
 30  7  1  0
 28 12  1  0
 21 16  1  0
 28 23  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  6 36  1  0
  6 37  1  0
  9 38  1  0
  9 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 25 46  1  0
 26 47  1  0
 27 48  1  0
 31 49  1  0
 31 50  1  0
M  END


  Mrv0541 11131316082D          

 31 34  0  0  0  0            999 V2000
    7.9200   -9.6525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9200  -10.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6213  -10.8900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3638  -10.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3638   -9.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6213   -9.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6213   -8.4150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0649   -9.2400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0649  -10.8900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7663   -9.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4675   -9.2400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7663  -10.4775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1688   -9.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0649   -8.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2188  -10.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8988  -10.9313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1463  -11.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9713  -11.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5588  -10.3950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750  -12.4163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875  -13.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125  -13.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1975  -10.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4963  -10.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950  -10.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0525  -10.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0525  -11.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7538  -12.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4963  -11.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1975  -12.1688    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  4  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  1  0  0  0  0
  8 14  1  0  0  0  0
  2 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 15  1  0  0  0  0
 15 19  2  0  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 24 16  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 25 30  2  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257236

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)N(C)C1=C(N)N=C(N=C1N)C1=NN(CC2=C(F)C=CC=C2)C2=C1C=CC=N2

> <INCHI_IDENTIFIER>
InChI=1S/C20H19FN8O2/c1-28(20(30)31-2)15-16(22)25-18(26-17(15)23)14-12-7-5-9-24-19(12)29(27-14)10-11-6-3-4-8-13(11)21/h3-9H,10H2,1-2H3,(H4,22,23,25,26)

> <INCHI_KEY>
WXXSNCNJFUAIDG-UHFFFAOYSA-N

> <FORMULA>
C20H19FN8O2

> <MOLECULAR_WEIGHT>
422.4157

> <EXACT_MASS>
422.161500097

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
41.89539306218183

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl N-(4,6-diamino-2-{1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}pyrimidin-5-yl)-N-methylcarbamate

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
2.6855664843333336

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.89804552154143

> <JCHEM_PKA_STRONGEST_BASIC>
3.5046847281560796

> <JCHEM_POLAR_SURFACE_AREA>
138.07000000000002

> <JCHEM_REFRACTIVITY>
135.24749999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
riociguat

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0257236
     RDKit          3D
Riociguat
 50 53  0  0  0  0  0  0  0  0999 V2000
    4.6942    3.2449   -0.8103 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361    1.9180   -0.8220 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1039    0.8534   -1.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3391    1.0353   -1.1992 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6280   -0.4859   -1.0252 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5168   -1.5970   -1.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2268   -0.6673   -0.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163   -1.1866    0.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7733   -1.5352    1.4121 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5051   -1.3272    0.6497 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363   -1.0151   -0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773   -1.1392    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9387   -0.8717   -0.6644 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0464   -1.0593   -0.0016 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4431   -0.8411   -0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8094    0.5703   -0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5196    1.0293    0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8224    2.3688    0.9490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4051    3.2740   -0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7016    2.8309   -1.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3920    1.4876   -1.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6985    0.9959   -2.3001 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7424   -1.4643    1.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4616   -1.8005    2.3316 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8642   -2.1828    3.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4944   -2.2476    3.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7291   -1.9093    2.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3765   -1.5225    1.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9522   -0.5162   -1.4074 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2461   -0.3483   -1.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150    0.1974   -2.9616 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0437    3.8752   -1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7531    3.2803   -1.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5508    3.6398    0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9588   -1.5562   -2.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2646   -1.6868   -0.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9070   -2.5427   -1.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356   -2.5350    1.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3084   -0.8041    1.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1403   -1.4261    0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5703   -1.1878   -1.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8696    0.3555    1.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3802    2.7561    1.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6464    4.3345    0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3764    3.5275   -1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4389   -2.4668    4.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921   -2.5581    4.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3422   -1.9497    2.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2550   -0.2747   -3.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2282    1.1306   -3.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 14 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 11 29  1  0
 29 30  2  0
 30 31  1  0
 30  7  1  0
 28 12  1  0
 21 16  1  0
 28 23  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  6 36  1  0
  6 37  1  0
  9 38  1  0
  9 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 25 46  1  0
 26 47  1  0
 27 48  1  0
 31 49  1  0
 31 50  1  0
M  END

HEADER    PROTEIN                                 13-NOV-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-13         0                                  
HETATM    1  N   UNK     0      14.784 -18.018   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      14.784 -19.558   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      16.093 -20.328   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      17.479 -19.558   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.479 -18.018   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.093 -17.248   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      16.093 -15.708   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      18.788 -17.248   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      18.788 -20.328   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      20.097 -18.018   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      21.406 -17.248   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      20.097 -19.558   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      22.715 -18.018   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.788 -15.708   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.475 -20.328   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      11.011 -20.405   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      11.473 -21.791   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.013 -21.791   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      12.243 -19.404   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0      10.780 -23.177   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      11.550 -24.486   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.090 -24.486   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.860 -23.100   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.702 -19.635   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.393 -20.405   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.084 -19.635   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.698 -20.405   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.698 -21.945   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.007 -22.715   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.393 -21.945   0.000  0.00  0.00           C+0
HETATM   31  F   UNK     0       9.702 -22.715   0.000  0.00  0.00           F+0
CONECT    1    2    6                                                       
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5   10   14                                                  
CONECT    9    4                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10   13                                                       
CONECT   12   10                                                            
CONECT   13   11                                                            
CONECT   14    8                                                            
CONECT   15    2   18   19                                                  
CONECT   16   17   19   24                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   15   23                                                  
CONECT   19   15   16                                                       
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   16   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

COMPND    HMDB0257236
HETATM    1  C1  UNL     1       4.694   3.245  -0.810  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.236   1.918  -0.822  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.104   0.853  -1.019  1.00  0.00           C  
HETATM    4  O2  UNL     1       6.339   1.035  -1.199  1.00  0.00           O  
HETATM    5  N1  UNL     1       4.628  -0.486  -1.025  1.00  0.00           N  
HETATM    6  C3  UNL     1       5.517  -1.597  -1.225  1.00  0.00           C  
HETATM    7  C4  UNL     1       3.227  -0.667  -0.809  1.00  0.00           C  
HETATM    8  C5  UNL     1       2.816  -1.187   0.430  1.00  0.00           C  
HETATM    9  N2  UNL     1       3.773  -1.535   1.412  1.00  0.00           N  
HETATM   10  N3  UNL     1       1.505  -1.327   0.650  1.00  0.00           N  
HETATM   11  C6  UNL     1       0.536  -1.015  -0.214  1.00  0.00           C  
HETATM   12  C7  UNL     1      -0.877  -1.139   0.111  1.00  0.00           C  
HETATM   13  N4  UNL     1      -1.939  -0.872  -0.664  1.00  0.00           N  
HETATM   14  N5  UNL     1      -3.046  -1.059  -0.002  1.00  0.00           N  
HETATM   15  C8  UNL     1      -4.443  -0.841  -0.429  1.00  0.00           C  
HETATM   16  C9  UNL     1      -4.809   0.570  -0.266  1.00  0.00           C  
HETATM   17  C10 UNL     1      -5.520   1.029   0.814  1.00  0.00           C  
HETATM   18  C11 UNL     1      -5.822   2.369   0.949  1.00  0.00           C  
HETATM   19  C12 UNL     1      -5.405   3.274  -0.021  1.00  0.00           C  
HETATM   20  C13 UNL     1      -4.702   2.831  -1.095  1.00  0.00           C  
HETATM   21  C14 UNL     1      -4.392   1.488  -1.239  1.00  0.00           C  
HETATM   22  F1  UNL     1      -3.698   0.996  -2.300  1.00  0.00           F  
HETATM   23  C15 UNL     1      -2.742  -1.464   1.250  1.00  0.00           C  
HETATM   24  N6  UNL     1      -3.462  -1.800   2.332  1.00  0.00           N  
HETATM   25  C16 UNL     1      -2.864  -2.183   3.474  1.00  0.00           C  
HETATM   26  C17 UNL     1      -1.494  -2.248   3.588  1.00  0.00           C  
HETATM   27  C18 UNL     1      -0.729  -1.909   2.495  1.00  0.00           C  
HETATM   28  C19 UNL     1      -1.377  -1.523   1.343  1.00  0.00           C  
HETATM   29  N7  UNL     1       0.952  -0.516  -1.407  1.00  0.00           N  
HETATM   30  C20 UNL     1       2.246  -0.348  -1.695  1.00  0.00           C  
HETATM   31  N8  UNL     1       2.615   0.197  -2.962  1.00  0.00           N  
HETATM   32  H1  UNL     1       4.044   3.875  -1.455  1.00  0.00           H  
HETATM   33  H2  UNL     1       5.753   3.280  -1.094  1.00  0.00           H  
HETATM   34  H3  UNL     1       4.551   3.640   0.231  1.00  0.00           H  
HETATM   35  H4  UNL     1       5.959  -1.556  -2.240  1.00  0.00           H  
HETATM   36  H5  UNL     1       6.265  -1.687  -0.409  1.00  0.00           H  
HETATM   37  H6  UNL     1       4.907  -2.543  -1.157  1.00  0.00           H  
HETATM   38  H7  UNL     1       3.936  -2.535   1.620  1.00  0.00           H  
HETATM   39  H8  UNL     1       4.308  -0.804   1.920  1.00  0.00           H  
HETATM   40  H9  UNL     1      -5.140  -1.426   0.225  1.00  0.00           H  
HETATM   41  H10 UNL     1      -4.570  -1.188  -1.472  1.00  0.00           H  
HETATM   42  H11 UNL     1      -5.870   0.355   1.610  1.00  0.00           H  
HETATM   43  H12 UNL     1      -6.380   2.756   1.798  1.00  0.00           H  
HETATM   44  H13 UNL     1      -5.646   4.335   0.083  1.00  0.00           H  
HETATM   45  H14 UNL     1      -4.376   3.527  -1.851  1.00  0.00           H  
HETATM   46  H15 UNL     1      -3.439  -2.467   4.374  1.00  0.00           H  
HETATM   47  H16 UNL     1      -0.992  -2.558   4.517  1.00  0.00           H  
HETATM   48  H17 UNL     1       0.342  -1.950   2.545  1.00  0.00           H  
HETATM   49  H18 UNL     1       3.255  -0.275  -3.630  1.00  0.00           H  
HETATM   50  H19 UNL     1       2.228   1.131  -3.257  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    7
CONECT    6   35   36   37
CONECT    7    8    8   30
CONECT    8    9   10
CONECT    9   38   39
CONECT   10   11   11
CONECT   11   12   29
CONECT   12   13   13   28
CONECT   13   14
CONECT   14   15   23
CONECT   15   16   40   41
CONECT   16   17   17   21
CONECT   17   18   42
CONECT   18   19   19   43
CONECT   19   20   44
CONECT   20   21   21   45
CONECT   21   22
CONECT   23   24   24   28
CONECT   24   25
CONECT   25   26   26   46
CONECT   26   27   47
CONECT   27   28   28   48
CONECT   29   30   30
CONECT   30   31
CONECT   31   49   50
END

HMDB0257236
     RDKit          3D
Riociguat
 50 53  0  0  0  0  0  0  0  0999 V2000
    4.6942    3.2449   -0.8103 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361    1.9180   -0.8220 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1039    0.8534   -1.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3391    1.0353   -1.1992 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6280   -0.4859   -1.0252 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5168   -1.5970   -1.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2268   -0.6673   -0.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163   -1.1866    0.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7733   -1.5352    1.4121 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5051   -1.3272    0.6497 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363   -1.0151   -0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773   -1.1392    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9387   -0.8717   -0.6644 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0464   -1.0593   -0.0016 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4431   -0.8411   -0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8094    0.5703   -0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5196    1.0293    0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8224    2.3688    0.9490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4051    3.2740   -0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7016    2.8309   -1.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3920    1.4876   -1.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6985    0.9959   -2.3001 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7424   -1.4643    1.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4616   -1.8005    2.3316 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8642   -2.1828    3.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4944   -2.2476    3.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7291   -1.9093    2.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3765   -1.5225    1.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9522   -0.5162   -1.4074 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2461   -0.3483   -1.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150    0.1974   -2.9616 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0437    3.8752   -1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7531    3.2803   -1.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5508    3.6398    0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9588   -1.5562   -2.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2646   -1.6868   -0.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9070   -2.5427   -1.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356   -2.5350    1.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3084   -0.8041    1.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1403   -1.4261    0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5703   -1.1878   -1.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8696    0.3555    1.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3802    2.7561    1.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6464    4.3345    0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3764    3.5275   -1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4389   -2.4668    4.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921   -2.5581    4.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3422   -1.9497    2.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2550   -0.2747   -3.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2282    1.1306   -3.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 14 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 11 29  1  0
 29 30  2  0
 30 31  1  0
 30  7  1  0
 28 12  1  0
 21 16  1  0
 28 23  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  6 36  1  0
  6 37  1  0
  9 38  1  0
  9 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 25 46  1  0
 26 47  1  0
 27 48  1  0
 31 49  1  0
 31 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Adempas	ChEBI
BAY 63-2521	ChEBI
Methyl N-(4,6-diamino-2-{1-((2-fluorophenyl)methyl)-1H-pyrazolo(3,4-b)pyridin-3-yl}pyrimidin-5-yl)-N-methylcarbamate	ChEBI
Riociguatum	ChEBI
Methyl N-(4,6-diamino-2-{1-((2-fluorophenyl)methyl)-1H-pyrazolo(3,4-b)pyridin-3-yl}pyrimidin-5-yl)-N-methylcarbamic acid	Generator

Chemical Formula

C₂₀H₁₉FN₈O₂

Average Molecular Weight

422.4157

Monoisotopic Molecular Weight

422.161500097

IUPAC Name

methyl N-(4,6-diamino-2-{1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}pyrimidin-5-yl)-N-methylcarbamate

Traditional Name

riociguat

CAS Registry Number

Not Available

SMILES

COC(=O)N(C)C1=C(N)N=C(N=C1N)C1=NN(CC2=C(F)C=CC=C2)C2=C1C=CC=N2

InChI Identifier

InChI=1S/C20H19FN8O2/c1-28(20(30)31-2)15-16(22)25-18(26-17(15)23)14-12-7-5-9-24-19(12)29(27-14)10-11-6-3-4-8-13(11)21/h3-9H,10H2,1-2H3,(H4,22,23,25,26)

InChI Key

WXXSNCNJFUAIDG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrazolopyridines. Pyrazolopyridines are compounds containing a pyrazolopyridine skeleton, which consists of a pyrazole fused to a pyridine. Pyrazole is 5-membered ring consisting of three carbon atoms and two adjacent nitrogen centers. Pyridine is a 6-membered ring with four carbon and one nitrogen atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrazolopyridines

Sub Class

Not Available

Direct Parent

Pyrazolopyridines

Alternative Parents

Substituents

Pyrazolopyridine
Aminopyrimidine
Halobenzene
Fluorobenzene
Aryl fluoride
Aryl halide
Pyridine
Pyrimidine
Benzenoid
Imidolactam
Monocyclic benzene moiety
Carbamic acid ester
Azole
Heteroaromatic compound
Pyrazole
Carbonic acid derivative
Azacycle
Amine
Organofluoride
Organohalogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:76018 )
carbamate ester (CHEBI:76018 )
aminopyrimidine (CHEBI:76018 )
pyrazolopyridine (CHEBI:76018 )

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	2.27	ALOGPS
logP	2.69	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	18.9	ChemAxon
pKa (Strongest Basic)	3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	138.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	135.25 m³·mol⁻¹	ChemAxon
Polarizability	41.9 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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
DeepCCS	[M+H]+	196.477	30932474
DeepCCS	[M-H]-	194.119	30932474
DeepCCS	[M-2H]-	227.36	30932474
DeepCCS	[M+Na]+	202.57	30932474
AllCCS	[M+H]+	198.5	32859911
AllCCS	[M+H-H2O]+	196.1	32859911
AllCCS	[M+NH4]+	200.7	32859911
AllCCS	[M+Na]+	201.4	32859911
AllCCS	[M-H]-	197.4	32859911
AllCCS	[M+Na-2H]-	197.4	32859911
AllCCS	[M+HCOO]-	197.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Riociguat	COC(=O)N(C)C1=C(N)N=C(N=C1N)C1=NN(CC2=C(F)C=CC=C2)C2=C1C=CC=N2	4123.0	Standard polar	33892256
Riociguat	COC(=O)N(C)C1=C(N)N=C(N=C1N)C1=NN(CC2=C(F)C=CC=C2)C2=C1C=CC=N2	3582.2	Standard non polar	33892256
Riociguat	COC(=O)N(C)C1=C(N)N=C(N=C1N)C1=NN(CC2=C(F)C=CC=C2)C2=C1C=CC=N2	3611.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Riociguat,1TMS,isomer #1	COC(=O)N(C)C1=C(N)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N[Si](C)(C)C	3727.7	Semi standard non polar	33892256
Riociguat,1TMS,isomer #1	COC(=O)N(C)C1=C(N)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N[Si](C)(C)C	3343.5	Standard non polar	33892256
Riociguat,1TMS,isomer #1	COC(=O)N(C)C1=C(N)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N[Si](C)(C)C	5499.2	Standard polar	33892256
Riociguat,2TMS,isomer #1	COC(=O)N(C)C1=C(N[Si](C)(C)C)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N[Si](C)(C)C	3733.5	Semi standard non polar	33892256
Riociguat,2TMS,isomer #1	COC(=O)N(C)C1=C(N[Si](C)(C)C)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N[Si](C)(C)C	3391.4	Standard non polar	33892256
Riociguat,2TMS,isomer #1	COC(=O)N(C)C1=C(N[Si](C)(C)C)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N[Si](C)(C)C	4992.6	Standard polar	33892256
Riociguat,2TMS,isomer #2	COC(=O)N(C)C1=C(N)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N([Si](C)(C)C)[Si](C)(C)C	3668.5	Semi standard non polar	33892256
Riociguat,2TMS,isomer #2	COC(=O)N(C)C1=C(N)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N([Si](C)(C)C)[Si](C)(C)C	3395.6	Standard non polar	33892256
Riociguat,2TMS,isomer #2	COC(=O)N(C)C1=C(N)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N([Si](C)(C)C)[Si](C)(C)C	5194.3	Standard polar	33892256
Riociguat,3TMS,isomer #1	COC(=O)N(C)C1=C(N[Si](C)(C)C)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N([Si](C)(C)C)[Si](C)(C)C	3694.8	Semi standard non polar	33892256
Riociguat,3TMS,isomer #1	COC(=O)N(C)C1=C(N[Si](C)(C)C)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N([Si](C)(C)C)[Si](C)(C)C	3456.0	Standard non polar	33892256
Riociguat,3TMS,isomer #1	COC(=O)N(C)C1=C(N[Si](C)(C)C)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N([Si](C)(C)C)[Si](C)(C)C	4689.7	Standard polar	33892256
Riociguat,4TMS,isomer #1	COC(=O)N(C)C1=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N([Si](C)(C)C)[Si](C)(C)C	3704.5	Semi standard non polar	33892256
Riociguat,4TMS,isomer #1	COC(=O)N(C)C1=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N([Si](C)(C)C)[Si](C)(C)C	3534.5	Standard non polar	33892256
Riociguat,4TMS,isomer #1	COC(=O)N(C)C1=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N([Si](C)(C)C)[Si](C)(C)C	4407.6	Standard polar	33892256
Riociguat,1TBDMS,isomer #1	COC(=O)N(C)C1=C(N)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N[Si](C)(C)C(C)(C)C	3892.3	Semi standard non polar	33892256
Riociguat,1TBDMS,isomer #1	COC(=O)N(C)C1=C(N)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N[Si](C)(C)C(C)(C)C	3519.3	Standard non polar	33892256
Riociguat,1TBDMS,isomer #1	COC(=O)N(C)C1=C(N)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N[Si](C)(C)C(C)(C)C	5466.7	Standard polar	33892256
Riociguat,2TBDMS,isomer #1	COC(=O)N(C)C1=C(N[Si](C)(C)C(C)(C)C)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N[Si](C)(C)C(C)(C)C	4008.1	Semi standard non polar	33892256
Riociguat,2TBDMS,isomer #1	COC(=O)N(C)C1=C(N[Si](C)(C)C(C)(C)C)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N[Si](C)(C)C(C)(C)C	3750.7	Standard non polar	33892256
Riociguat,2TBDMS,isomer #1	COC(=O)N(C)C1=C(N[Si](C)(C)C(C)(C)C)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N[Si](C)(C)C(C)(C)C	5022.1	Standard polar	33892256
Riociguat,2TBDMS,isomer #2	COC(=O)N(C)C1=C(N)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3982.0	Semi standard non polar	33892256
Riociguat,2TBDMS,isomer #2	COC(=O)N(C)C1=C(N)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3728.7	Standard non polar	33892256
Riociguat,2TBDMS,isomer #2	COC(=O)N(C)C1=C(N)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	5142.4	Standard polar	33892256
Riociguat,3TBDMS,isomer #1	COC(=O)N(C)C1=C(N[Si](C)(C)C(C)(C)C)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4128.2	Semi standard non polar	33892256
Riociguat,3TBDMS,isomer #1	COC(=O)N(C)C1=C(N[Si](C)(C)C(C)(C)C)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3972.1	Standard non polar	33892256
Riociguat,3TBDMS,isomer #1	COC(=O)N(C)C1=C(N[Si](C)(C)C(C)(C)C)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4789.5	Standard polar	33892256
Riociguat,4TBDMS,isomer #1	COC(=O)N(C)C1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4287.4	Semi standard non polar	33892256
Riociguat,4TBDMS,isomer #1	COC(=O)N(C)C1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4164.5	Standard non polar	33892256
Riociguat,4TBDMS,isomer #1	COC(=O)N(C)C1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(C2=NN(CC3=CC=CC=C3F)C3=NC=CC=C23)N=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4555.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Riociguat GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0925100000-93aad87940f0e448de81	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Riociguat 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 - Riociguat 10V, Positive-QTOF	splash10-00di-0000900000-2eb077288a86c93f780c	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Riociguat 20V, Positive-QTOF	splash10-00di-1005900000-7c6005c775e96305fd7f	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Riociguat 40V, Positive-QTOF	splash10-0w29-2397000000-9052d0ef265742fb1935	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Riociguat 10V, Negative-QTOF	splash10-00di-0000900000-b0d96020374efcd4f077	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Riociguat 20V, Negative-QTOF	splash10-00di-0202900000-a1a41f5d08fbbe814bd3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Riociguat 40V, Negative-QTOF	splash10-003r-3279000000-fa41ebcd2d0087a3d3dd	2017-07-26	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

DB08931

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9479719

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Riociguat

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

76018

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 Riociguat (HMDB0257236)

MOL for HMDB0257236 (Riociguat)

3D MOL for HMDB0257236 (Riociguat)

3D SDF for HMDB0257236 (Riociguat)

3D-SDF for HMDB0257236 (Riociguat)

PDB for HMDB0257236 (Riociguat)

3D PDB for HMDB0257236 (Riociguat)

SMILES for HMDB0257236 (Riociguat)

INCHI for HMDB0257236 (Riociguat)

Structure for HMDB0257236 (Riociguat)

3D Structure for HMDB0257236 (Riociguat)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra