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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:02:53 UTC

Update Date

2021-09-26 22:56:28 UTC

HMDB ID

HMDB0247030

Secondary Accession Numbers

None

Metabolite Identification

Common Name

6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide

Description

6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide, also known as orteronel or TAK-700, belongs to the class of organic compounds known as naphthalenecarboxamides. Naphthalenecarboxamides are compounds containing a naphthalene moiety, which bears a carboxylic acid amide group at one or more positions. Naphthalene is a bicyclic compound that is made up of two fused benzene rings. Based on a literature review very few articles have been published on 6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). 6-(7-hydroxy-6,7-dihydro-5h-pyrrolo[1,2-c]imidazol-7-yl)-n-methyl-2-naphthamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide 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

HMDB0247363
     RDKit          3D
(R)-Orteronel
 40 43  0  0  0  0  0  0  0  0999 V2000
    6.8026    0.1471    1.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4114    0.2491    0.9503 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6770   -0.8837    0.5283 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2640   -1.9914    0.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562   -0.8379    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5784   -1.9795   -0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2470   -1.9271   -0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5676   -0.7301   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7905   -0.6755   -0.8427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4917    0.5032   -0.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8972    0.5378   -1.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0748    1.4367   -2.2334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5236   -0.7572   -1.5430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9168   -1.3378   -0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3214   -0.1510    0.5271 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0821    0.2141    1.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9508    1.5454    1.6754 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447    2.0330    0.7356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7434    0.9386    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8103    1.6366   -0.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5229    1.6406   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2035    0.4375   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439    0.3437    0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4768    0.3437    0.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0514   -0.8580    1.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0867    0.9352    2.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9817    1.1952    1.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579   -2.8944   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187   -2.8181   -0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2443   -1.5875   -1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4052    2.1366   -2.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4899   -0.5457   -2.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9491   -1.4083   -2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7962   -2.0147   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1303   -1.8510    0.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6851   -0.4471    2.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8762    3.0732    0.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3381    2.5757   -0.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0805    2.5049    0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0335    1.2682    0.4781 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  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
 10 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23  5  1  0
 22  8  1  0
 19 11  1  0
 19 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 18 37  1  0
 20 38  1  0
 21 39  1  0
 23 40  1  0
M  END

  Mrv1652309112102032D          

 23 26  0  0  0  0            999 V2000
    3.6823    7.9460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3468    7.1923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5263    7.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0414    7.7735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1907    6.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3703    6.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0347    5.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    4.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3401    4.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6757    5.6850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1841    4.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3636    4.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1213    4.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2142    5.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0280    3.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4569    2.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0280    1.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8126    2.1715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8126    2.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5973    3.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0822    2.5840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5973    1.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6865    3.6640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  7 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 18 22  1  0  0  0  0
 15 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247030

> <DATABASE_NAME>
hmdb

> <SMILES>
CNC(=O)C1=CC2=C(C=C1)C=C(C=C2)C1(O)CCN2C=NC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C18H17N3O2/c1-19-17(22)14-3-2-13-9-15(5-4-12(13)8-14)18(23)6-7-21-11-20-10-16(18)21/h2-5,8-11,23H,6-7H2,1H3,(H,19,22)

> <INCHI_KEY>
OZPFIJIOIVJZMN-UHFFFAOYSA-N

> <FORMULA>
C18H17N3O2

> <MOLECULAR_WEIGHT>
307.353

> <EXACT_MASS>
307.132076799

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
33.210584674265114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-{7-hydroxy-5H,6H,7H-pyrrolo[1,2-c]imidazol-7-yl}-N-methylnaphthalene-2-carboxamide

> <ALOGPS_LOGP>
1.36

> <JCHEM_LOGP>
0.7526204230000002

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.95161748753764

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.853757070301505

> <JCHEM_PKA_STRONGEST_BASIC>
6.204180076772988

> <JCHEM_POLAR_SURFACE_AREA>
67.15

> <JCHEM_REFRACTIVITY>
88.29799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
orteronel

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247363
     RDKit          3D
(R)-Orteronel
 40 43  0  0  0  0  0  0  0  0999 V2000
    6.8026    0.1471    1.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4114    0.2491    0.9503 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6770   -0.8837    0.5283 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2640   -1.9914    0.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562   -0.8379    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5784   -1.9795   -0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2470   -1.9271   -0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5676   -0.7301   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7905   -0.6755   -0.8427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4917    0.5032   -0.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8972    0.5378   -1.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0748    1.4367   -2.2334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5236   -0.7572   -1.5430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9168   -1.3378   -0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3214   -0.1510    0.5271 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0821    0.2141    1.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9508    1.5454    1.6754 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447    2.0330    0.7356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7434    0.9386    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8103    1.6366   -0.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5229    1.6406   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2035    0.4375   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439    0.3437    0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4768    0.3437    0.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0514   -0.8580    1.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0867    0.9352    2.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9817    1.1952    1.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579   -2.8944   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187   -2.8181   -0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2443   -1.5875   -1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4052    2.1366   -2.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4899   -0.5457   -2.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9491   -1.4083   -2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7962   -2.0147   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1303   -1.8510    0.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6851   -0.4471    2.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8762    3.0732    0.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3381    2.5757   -0.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0805    2.5049    0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0335    1.2682    0.4781 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  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
 10 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23  5  1  0
 22  8  1  0
 19 11  1  0
 19 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 18 37  1  0
 20 38  1  0
 21 39  1  0
 23 40  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       6.874  14.833   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       6.247  13.426   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.716  13.265   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.811  14.511   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.089  11.858   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.558  11.697   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.931  10.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.837   9.044   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.368   9.205   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.995  10.612   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.210   7.637   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.679   7.476   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.227   8.722   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.400  10.129   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.052   6.069   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.853   4.824   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.052   3.578   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.517   4.054   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       1.517   5.594   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.982   6.069   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       3.887   4.824   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       2.982   3.578   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.281   6.839   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   19   23                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   15   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   18                                                       
CONECT   23   15                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0247030
HETATM    1  C1  UNL     1      -6.976   0.630  -0.190  1.00  0.00           C  
HETATM    2  N1  UNL     1      -5.566   0.401   0.025  1.00  0.00           N  
HETATM    3  C2  UNL     1      -4.635   0.649  -0.998  1.00  0.00           C  
HETATM    4  O1  UNL     1      -5.041   1.084  -2.133  1.00  0.00           O  
HETATM    5  C3  UNL     1      -3.213   0.435  -0.831  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.346   0.721  -1.893  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.991   0.530  -1.770  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.452   0.047  -0.585  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.920  -0.148  -0.457  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.463  -0.624   0.707  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.894  -0.852   0.908  1.00  0.00           C  
HETATM   12  O2  UNL     1       3.150  -1.470   2.154  1.00  0.00           O  
HETATM   13  C10 UNL     1       3.575  -1.676  -0.130  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.272  -0.734  -1.053  1.00  0.00           C  
HETATM   15  N2  UNL     1       4.415   0.488  -0.263  1.00  0.00           N  
HETATM   16  C12 UNL     1       5.080   1.672  -0.285  1.00  0.00           C  
HETATM   17  N3  UNL     1       4.725   2.359   0.804  1.00  0.00           N  
HETATM   18  C13 UNL     1       3.853   1.636   1.509  1.00  0.00           C  
HETATM   19  C14 UNL     1       3.657   0.444   0.828  1.00  0.00           C  
HETATM   20  C15 UNL     1       0.580  -0.897   1.737  1.00  0.00           C  
HETATM   21  C16 UNL     1      -0.780  -0.714   1.636  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.327  -0.227   0.443  1.00  0.00           C  
HETATM   23  C18 UNL     1      -2.695  -0.043   0.345  1.00  0.00           C  
HETATM   24  H1  UNL     1      -7.481   1.104   0.655  1.00  0.00           H  
HETATM   25  H2  UNL     1      -7.158   1.270  -1.079  1.00  0.00           H  
HETATM   26  H3  UNL     1      -7.515  -0.335  -0.409  1.00  0.00           H  
HETATM   27  H4  UNL     1      -5.254   0.051   0.944  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.729   1.101  -2.837  1.00  0.00           H  
HETATM   29  H6  UNL     1      -0.307   0.753  -2.600  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.534   0.085  -1.292  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.701  -2.368   2.073  1.00  0.00           H  
HETATM   32  H9  UNL     1       4.375  -2.332   0.325  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.899  -2.391  -0.649  1.00  0.00           H  
HETATM   34  H11 UNL     1       5.295  -1.116  -1.343  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.724  -0.579  -1.988  1.00  0.00           H  
HETATM   36  H13 UNL     1       5.782   1.976  -1.080  1.00  0.00           H  
HETATM   37  H14 UNL     1       3.363   1.890   2.445  1.00  0.00           H  
HETATM   38  H15 UNL     1       0.977  -1.276   2.672  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.465  -0.929   2.445  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.303  -0.286   1.207  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27
CONECT    3    4    4    5
CONECT    5    6    6   23
CONECT    6    7   28
CONECT    7    8    8   29
CONECT    8    9   22
CONECT    9   10   10   30
CONECT   10   11   20
CONECT   11   12   13   19
CONECT   12   31
CONECT   13   14   32   33
CONECT   14   15   34   35
CONECT   15   16   19
CONECT   16   17   17   36
CONECT   17   18
CONECT   18   19   19   37
CONECT   20   21   21   38
CONECT   21   22   39
CONECT   22   23   23
CONECT   23   40
END

HMDB0247363
     RDKit          3D
(R)-Orteronel
 40 43  0  0  0  0  0  0  0  0999 V2000
    6.8026    0.1471    1.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4114    0.2491    0.9503 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6770   -0.8837    0.5283 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2640   -1.9914    0.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562   -0.8379    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5784   -1.9795   -0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2470   -1.9271   -0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5676   -0.7301   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7905   -0.6755   -0.8427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4917    0.5032   -0.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8972    0.5378   -1.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0748    1.4367   -2.2334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5236   -0.7572   -1.5430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9168   -1.3378   -0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3214   -0.1510    0.5271 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0821    0.2141    1.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9508    1.5454    1.6754 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447    2.0330    0.7356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7434    0.9386    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8103    1.6366   -0.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5229    1.6406   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2035    0.4375   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439    0.3437    0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4768    0.3437    0.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0514   -0.8580    1.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0867    0.9352    2.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9817    1.1952    1.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579   -2.8944   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187   -2.8181   -0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2443   -1.5875   -1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4052    2.1366   -2.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4899   -0.5457   -2.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9491   -1.4083   -2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7962   -2.0147   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1303   -1.8510    0.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6851   -0.4471    2.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8762    3.0732    0.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3381    2.5757   -0.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0805    2.5049    0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0335    1.2682    0.4781 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  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
 10 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23  5  1  0
 22  8  1  0
 19 11  1  0
 19 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 18 37  1  0
 20 38  1  0
 21 39  1  0
 23 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Orteronel	MeSH
6-((7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo(1,2-c)imidazol-7-yl)-N-methyl-2-naphthamide	MeSH
TAK-700	MeSH

Chemical Formula

C₁₈H₁₇N₃O₂

Average Molecular Weight

307.353

Monoisotopic Molecular Weight

307.132076799

IUPAC Name

6-{7-hydroxy-5H,6H,7H-pyrrolo[1,2-c]imidazol-7-yl}-N-methylnaphthalene-2-carboxamide

Traditional Name

orteronel

CAS Registry Number

Not Available

SMILES

CNC(=O)C1=CC2=C(C=C1)C=C(C=C2)C1(O)CCN2C=NC=C12

InChI Identifier

InChI=1S/C18H17N3O2/c1-19-17(22)14-3-2-13-9-15(5-4-12(13)8-14)18(23)6-7-21-11-20-10-16(18)21/h2-5,8-11,23H,6-7H2,1H3,(H,19,22)

InChI Key

OZPFIJIOIVJZMN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenecarboxamides. Naphthalenecarboxamides are compounds containing a naphthalene moiety, which bears a carboxylic acid amide group at one or more positions. Naphthalene is a bicyclic compound that is made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthalenecarboxylic acids and derivatives

Direct Parent

Naphthalenecarboxamides

Alternative Parents

Substituents

2-naphthalenecarboxamide
N-substituted imidazole
Azole
Imidazole
Tertiary alcohol
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen 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)

Source

Exogenous

Exogenous (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	1.36	ALOGPS
logP	0.75	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12.85	ChemAxon
pKa (Strongest Basic)	6.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.15 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	88.3 m³·mol⁻¹	ChemAxon
Polarizability	33.21 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-2H]-	202.405	30932474
DeepCCS	[M+Na]+	177.632	30932474
AllCCS	[M+H]+	173.5	32859911
AllCCS	[M+H-H2O]+	170.4	32859911
AllCCS	[M+NH4]+	176.3	32859911
AllCCS	[M+Na]+	177.2	32859911
AllCCS	[M-H]-	174.0	32859911
AllCCS	[M+Na-2H]-	173.6	32859911
AllCCS	[M+HCOO]-	173.2	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide,1TMS,isomer #1	CNC(=O)C1=CC=C2C=C(C3(O[Si](C)(C)C)CCN4C=NC=C43)C=CC2=C1	3142.8	Semi standard non polar	33892256
6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide,1TMS,isomer #1	CNC(=O)C1=CC=C2C=C(C3(O[Si](C)(C)C)CCN4C=NC=C43)C=CC2=C1	2848.9	Standard non polar	33892256
6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide,1TMS,isomer #1	CNC(=O)C1=CC=C2C=C(C3(O[Si](C)(C)C)CCN4C=NC=C43)C=CC2=C1	3647.5	Standard polar	33892256
6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide,2TMS,isomer #1	CN(C(=O)C1=CC=C2C=C(C3(O[Si](C)(C)C)CCN4C=NC=C43)C=CC2=C1)[Si](C)(C)C	3074.9	Semi standard non polar	33892256
6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide,2TMS,isomer #1	CN(C(=O)C1=CC=C2C=C(C3(O[Si](C)(C)C)CCN4C=NC=C43)C=CC2=C1)[Si](C)(C)C	2978.1	Standard non polar	33892256
6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide,2TMS,isomer #1	CN(C(=O)C1=CC=C2C=C(C3(O[Si](C)(C)C)CCN4C=NC=C43)C=CC2=C1)[Si](C)(C)C	3433.8	Standard polar	33892256
6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide,1TBDMS,isomer #1	CNC(=O)C1=CC=C2C=C(C3(O[Si](C)(C)C(C)(C)C)CCN4C=NC=C43)C=CC2=C1	3394.2	Semi standard non polar	33892256
6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide,1TBDMS,isomer #1	CNC(=O)C1=CC=C2C=C(C3(O[Si](C)(C)C(C)(C)C)CCN4C=NC=C43)C=CC2=C1	3127.6	Standard non polar	33892256
6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide,1TBDMS,isomer #1	CNC(=O)C1=CC=C2C=C(C3(O[Si](C)(C)C(C)(C)C)CCN4C=NC=C43)C=CC2=C1	3699.1	Standard polar	33892256
6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide,1TBDMS,isomer #2	CN(C(=O)C1=CC=C2C=C(C3(O)CCN4C=NC=C43)C=CC2=C1)[Si](C)(C)C(C)(C)C	3437.3	Semi standard non polar	33892256
6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide,1TBDMS,isomer #2	CN(C(=O)C1=CC=C2C=C(C3(O)CCN4C=NC=C43)C=CC2=C1)[Si](C)(C)C(C)(C)C	3357.9	Standard non polar	33892256
6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide,1TBDMS,isomer #2	CN(C(=O)C1=CC=C2C=C(C3(O)CCN4C=NC=C43)C=CC2=C1)[Si](C)(C)C(C)(C)C	3702.2	Standard polar	33892256
6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide,2TBDMS,isomer #1	CN(C(=O)C1=CC=C2C=C(C3(O[Si](C)(C)C(C)(C)C)CCN4C=NC=C43)C=CC2=C1)[Si](C)(C)C(C)(C)C	3546.3	Semi standard non polar	33892256
6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide,2TBDMS,isomer #1	CN(C(=O)C1=CC=C2C=C(C3(O[Si](C)(C)C(C)(C)C)CCN4C=NC=C43)C=CC2=C1)[Si](C)(C)C(C)(C)C	3500.3	Standard non polar	33892256
6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide,2TBDMS,isomer #1	CN(C(=O)C1=CC=C2C=C(C3(O[Si](C)(C)C(C)(C)C)CCN4C=NC=C43)C=CC2=C1)[Si](C)(C)C(C)(C)C	3586.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1490000000-93016d1df2d5db2b58e8	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - 6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide 10V, Positive-QTOF	splash10-0a4i-0069000000-c34c650a2f9391038c40	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide 20V, Positive-QTOF	splash10-0a4i-0295000000-2a09988f75b26a33e0ed	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide 40V, Positive-QTOF	splash10-0a59-3690000000-e6b972562e6334408f55	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide 10V, Negative-QTOF	splash10-0a4i-0419000000-fa57ac0e28d357972876	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide 20V, Negative-QTOF	splash10-052b-1093000000-d22ea4895a81ac5d1341	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide 40V, Negative-QTOF	splash10-0aor-8901000000-7f736cb7de40155646d7	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

8058704

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9883029

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 6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide (HMDB0247030)

MOL for HMDB0247030 (6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide)

3D MOL for HMDB0247030 (6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide)

3D SDF for HMDB0247030 (6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide)

3D-SDF for HMDB0247030 (6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide)

PDB for HMDB0247030 (6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide)

3D PDB for HMDB0247030 (6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide)

SMILES for HMDB0247030 (6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide)

INCHI for HMDB0247030 (6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide)

Structure for HMDB0247030 (6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide)

3D Structure for HMDB0247030 (6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra