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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:52:27 UTC

Update Date

2022-11-23 22:29:18 UTC

HMDB ID

HMDB0257154

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Repirinast

Description

Repirinast, also known as romet, belongs to the class of organic compounds known as pyranoquinolines. These are polycyclic compounds containing a pyran ring fused to a quinoline moiety. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine. Based on a literature review a significant number of articles have been published on Repirinast. This compound has been identified in human blood as reported by (PMID: 31557052 ). Repirinast is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Repirinast 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

  Mrv1652309112119522D          

 26 28  0  0  0  0            999 V2000
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 C   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
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  4 25  1  0  0  0  0
  3 26  1  0  0  0  0
M  END

HMDB0257154
     RDKit          3D
repirinast
 47 49  0  0  0  0  0  0  0  0999 V2000
   -6.2325   -2.4319   -0.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0095   -1.6561   -0.5613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7456   -2.1124   -0.8682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6234   -1.3818   -0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7824   -0.1953    0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0284    0.2946    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1882    1.4561    1.1968 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1409    2.2027    1.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2388    3.2766    2.2085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8757    1.7464    1.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7497    2.4457    1.6429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8882    3.5327    2.2720 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4729    1.9330    1.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5728    0.7522    0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9138    0.2091    0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0506   -0.8592   -0.3544 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0669    0.8921    0.6152 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3421    0.4350    0.3074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6278    0.2649   -1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0723   -0.2417   -1.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1630   -1.5582   -0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0345    0.7122   -0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5048    0.1038    0.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6791    0.5687    0.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1221   -0.4661    0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4664    0.0341    0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8086   -2.7562   -0.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8907   -3.3669   -1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8713   -1.8775   -1.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6441   -3.0479   -1.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6249   -1.7175   -0.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1391    1.8146    1.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683    2.4829    1.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5229   -0.5261    0.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0929    1.1492    0.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0059   -0.5421   -1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5174    1.2286   -1.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3104   -0.3887   -2.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0318   -2.1621   -0.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2581   -2.1754   -0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3266   -1.4340    0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0531    0.4737   -0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0489    0.4962    0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8329    1.7685   -0.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5291    1.0839    0.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6407    0.0677    1.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2620   -0.5279   -0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 14 23  1  0
 23 24  1  0
  6 25  2  0
 25 26  1  0
 25  2  1  0
 24  5  1  0
 24 10  2  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  7 32  1  0
 13 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 22 44  1  0
 26 45  1  0
 26 46  1  0
 26 47  1  0
M  END

  Mrv1652309112119522D          

 26 28  0  0  0  0            999 V2000
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 C   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
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  4 25  1  0  0  0  0
  3 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257154

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CCOC(=O)C1=CC(=O)C2=C(O1)C1=C(NC2=O)C(C)=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H21NO5/c1-10(2)7-8-25-20(24)15-9-14(22)16-18(26-15)13-6-5-11(3)12(4)17(13)21-19(16)23/h5-6,9-10H,7-8H2,1-4H3,(H,21,23)

> <INCHI_KEY>
NFQIAEMCQGTTIR-UHFFFAOYSA-N

> <FORMULA>
C20H21NO5

> <MOLECULAR_WEIGHT>
355.39

> <EXACT_MASS>
355.14197278

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
38.830029623496216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methylbutyl 7,8-dimethyl-4,5-dioxo-4H,5H,6H-pyrano[3,2-c]quinoline-2-carboxylate

> <ALOGPS_LOGP>
3.25

> <JCHEM_LOGP>
3.581998044666666

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.209828308814789

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6709241144016738

> <JCHEM_POLAR_SURFACE_AREA>
81.70000000000002

> <JCHEM_REFRACTIVITY>
100.49119999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
repirinast

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0257154
     RDKit          3D
repirinast
 47 49  0  0  0  0  0  0  0  0999 V2000
   -6.2325   -2.4319   -0.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0095   -1.6561   -0.5613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7456   -2.1124   -0.8682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6234   -1.3818   -0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7824   -0.1953    0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0284    0.2946    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1882    1.4561    1.1968 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1409    2.2027    1.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2388    3.2766    2.2085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8757    1.7464    1.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7497    2.4457    1.6429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8882    3.5327    2.2720 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4729    1.9330    1.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5728    0.7522    0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9138    0.2091    0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0506   -0.8592   -0.3544 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0669    0.8921    0.6152 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3421    0.4350    0.3074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6278    0.2649   -1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0723   -0.2417   -1.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1630   -1.5582   -0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0345    0.7122   -0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5048    0.1038    0.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6791    0.5687    0.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1221   -0.4661    0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4664    0.0341    0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8086   -2.7562   -0.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8907   -3.3669   -1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8713   -1.8775   -1.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6441   -3.0479   -1.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6249   -1.7175   -0.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1391    1.8146    1.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683    2.4829    1.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5229   -0.5261    0.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0929    1.1492    0.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0059   -0.5421   -1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5174    1.2286   -1.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3104   -0.3887   -2.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0318   -2.1621   -0.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2581   -2.1754   -0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3266   -1.4340    0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0531    0.4737   -0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0489    0.4962    0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8329    1.7685   -0.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5291    1.0839    0.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6407    0.0677    1.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2620   -0.5279   -0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 14 23  1  0
 23 24  1  0
  6 25  2  0
 25 26  1  0
 25  2  1  0
 24  5  1  0
 24 10  2  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  7 32  1  0
 13 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 22 44  1  0
 26 45  1  0
 26 46  1  0
 26 47  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      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.000   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0      -2.667   4.620   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      -5.335   3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   14                                                  
CONECT    9    8   10   23                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13    8                                                       
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    9   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    4                                                       
CONECT   26    3                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0257154
HETATM    1  C1  UNL     1      -6.232  -2.432  -0.963  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.010  -1.656  -0.561  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.746  -2.112  -0.868  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.623  -1.382  -0.489  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.782  -0.195   0.199  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.028   0.295   0.524  1.00  0.00           C  
HETATM    7  N1  UNL     1      -4.188   1.456   1.197  1.00  0.00           N  
HETATM    8  C7  UNL     1      -3.141   2.203   1.588  1.00  0.00           C  
HETATM    9  O1  UNL     1      -3.239   3.277   2.208  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.876   1.746   1.281  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.750   2.446   1.643  1.00  0.00           C  
HETATM   12  O2  UNL     1      -0.888   3.533   2.272  1.00  0.00           O  
HETATM   13  C10 UNL     1       0.473   1.933   1.305  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.573   0.752   0.623  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.914   0.209   0.264  1.00  0.00           C  
HETATM   16  O3  UNL     1       2.051  -0.859  -0.354  1.00  0.00           O  
HETATM   17  O4  UNL     1       3.067   0.892   0.615  1.00  0.00           O  
HETATM   18  C13 UNL     1       4.342   0.435   0.307  1.00  0.00           C  
HETATM   19  C14 UNL     1       4.628   0.265  -1.142  1.00  0.00           C  
HETATM   20  C15 UNL     1       6.072  -0.242  -1.262  1.00  0.00           C  
HETATM   21  C16 UNL     1       6.163  -1.558  -0.524  1.00  0.00           C  
HETATM   22  C17 UNL     1       7.034   0.712  -0.601  1.00  0.00           C  
HETATM   23  O5  UNL     1      -0.505   0.104   0.289  1.00  0.00           O  
HETATM   24  C18 UNL     1      -1.679   0.569   0.598  1.00  0.00           C  
HETATM   25  C19 UNL     1      -5.122  -0.466   0.126  1.00  0.00           C  
HETATM   26  C20 UNL     1      -6.466   0.034   0.461  1.00  0.00           C  
HETATM   27  H1  UNL     1      -6.809  -2.756  -0.067  1.00  0.00           H  
HETATM   28  H2  UNL     1      -5.891  -3.367  -1.454  1.00  0.00           H  
HETATM   29  H3  UNL     1      -6.871  -1.878  -1.649  1.00  0.00           H  
HETATM   30  H4  UNL     1      -3.644  -3.048  -1.409  1.00  0.00           H  
HETATM   31  H5  UNL     1      -1.625  -1.718  -0.717  1.00  0.00           H  
HETATM   32  H6  UNL     1      -5.139   1.815   1.436  1.00  0.00           H  
HETATM   33  H7  UNL     1       1.368   2.483   1.589  1.00  0.00           H  
HETATM   34  H8  UNL     1       4.523  -0.526   0.854  1.00  0.00           H  
HETATM   35  H9  UNL     1       5.093   1.149   0.725  1.00  0.00           H  
HETATM   36  H10 UNL     1       4.006  -0.542  -1.595  1.00  0.00           H  
HETATM   37  H11 UNL     1       4.517   1.229  -1.670  1.00  0.00           H  
HETATM   38  H12 UNL     1       6.310  -0.389  -2.328  1.00  0.00           H  
HETATM   39  H13 UNL     1       7.032  -2.162  -0.890  1.00  0.00           H  
HETATM   40  H14 UNL     1       5.258  -2.175  -0.649  1.00  0.00           H  
HETATM   41  H15 UNL     1       6.327  -1.434   0.563  1.00  0.00           H  
HETATM   42  H16 UNL     1       8.053   0.474  -0.976  1.00  0.00           H  
HETATM   43  H17 UNL     1       7.049   0.496   0.484  1.00  0.00           H  
HETATM   44  H18 UNL     1       6.833   1.769  -0.836  1.00  0.00           H  
HETATM   45  H19 UNL     1      -6.529   1.084   0.096  1.00  0.00           H  
HETATM   46  H20 UNL     1      -6.641   0.068   1.559  1.00  0.00           H  
HETATM   47  H21 UNL     1      -7.262  -0.528  -0.027  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    3   25
CONECT    3    4   30
CONECT    4    5    5   31
CONECT    5    6   24
CONECT    6    7   25   25
CONECT    7    8   32
CONECT    8    9    9   10
CONECT   10   11   24   24
CONECT   11   12   12   13
CONECT   13   14   14   33
CONECT   14   15   23
CONECT   15   16   16   17
CONECT   17   18
CONECT   18   19   34   35
CONECT   19   20   36   37
CONECT   20   21   22   38
CONECT   21   39   40   41
CONECT   22   42   43   44
CONECT   23   24
CONECT   25   26
CONECT   26   45   46   47
END

HMDB0257154
     RDKit          3D
repirinast
 47 49  0  0  0  0  0  0  0  0999 V2000
   -6.2325   -2.4319   -0.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0095   -1.6561   -0.5613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7456   -2.1124   -0.8682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6234   -1.3818   -0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7824   -0.1953    0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0284    0.2946    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1882    1.4561    1.1968 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1409    2.2027    1.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2388    3.2766    2.2085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8757    1.7464    1.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7497    2.4457    1.6429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8882    3.5327    2.2720 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4729    1.9330    1.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5728    0.7522    0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9138    0.2091    0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0506   -0.8592   -0.3544 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0669    0.8921    0.6152 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3421    0.4350    0.3074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6278    0.2649   -1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0723   -0.2417   -1.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1630   -1.5582   -0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0345    0.7122   -0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5048    0.1038    0.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6791    0.5687    0.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1221   -0.4661    0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4664    0.0341    0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8086   -2.7562   -0.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8907   -3.3669   -1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8713   -1.8775   -1.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6441   -3.0479   -1.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6249   -1.7175   -0.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1391    1.8146    1.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683    2.4829    1.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5229   -0.5261    0.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0929    1.1492    0.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0059   -0.5421   -1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5174    1.2286   -1.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3104   -0.3887   -2.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0318   -2.1621   -0.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2581   -2.1754   -0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3266   -1.4340    0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0531    0.4737   -0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0489    0.4962    0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8329    1.7685   -0.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5291    1.0839    0.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6407    0.0677    1.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2620   -0.5279   -0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 14 23  1  0
 23 24  1  0
  6 25  2  0
 25 26  1  0
 25  2  1  0
 24  5  1  0
 24 10  2  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  7 32  1  0
 13 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 22 44  1  0
 26 45  1  0
 26 46  1  0
 26 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Romet	Kegg
3-Methylbutyl 5-hydroxy-7,8-dimethyl-4-oxo-4H-pyrano[3,2-c]quinoline-2-carboxylic acid	HMDB
Isoamyl 5,6-dihydro-7,8-dimethyl-4,5-dioxo-4H-pyrano(3,2-C)quinoline -2-carboxylate	HMDB

Chemical Formula

C₂₀H₂₁NO₅

Average Molecular Weight

355.39

Monoisotopic Molecular Weight

355.14197278

IUPAC Name

3-methylbutyl 7,8-dimethyl-4,5-dioxo-4H,5H,6H-pyrano[3,2-c]quinoline-2-carboxylate

Traditional Name

repirinast

CAS Registry Number

Not Available

SMILES

CC(C)CCOC(=O)C1=CC(=O)C2=C(O1)C1=C(NC2=O)C(C)=C(C)C=C1

InChI Identifier

InChI=1S/C20H21NO5/c1-10(2)7-8-25-20(24)15-9-14(22)16-18(26-15)13-6-5-11(3)12(4)17(13)21-19(16)23/h5-6,9-10H,7-8H2,1-4H3,(H,21,23)

InChI Key

NFQIAEMCQGTTIR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoquinolines. These are polycyclic compounds containing a pyran ring fused to a quinoline moiety. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Pyranoquinolines

Alternative Parents

Substituents

Pyranoquinoline
Dihydroquinolone
Dihydroquinoline
Pyranopyridine
Pyranone
Pyridinone
Benzenoid
Pyridine
Pyran
Heteroaromatic compound
Vinylogous amide
Carboxylic acid ester
Lactam
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen 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	3.25	ALOGPS
logP	3.58	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	81.7 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	100.49 m³·mol⁻¹	ChemAxon
Polarizability	38.83 Å³	ChemAxon
Number of Rings	3	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]+	199.317	30932474
DeepCCS	[M-H]-	196.847	30932474
DeepCCS	[M-2H]-	231.25	30932474
DeepCCS	[M+Na]+	206.478	30932474
AllCCS	[M+H]+	183.1	32859911
AllCCS	[M+H-H2O]+	180.1	32859911
AllCCS	[M+NH4]+	185.9	32859911
AllCCS	[M+Na]+	186.7	32859911
AllCCS	[M-H]-	189.6	32859911
AllCCS	[M+Na-2H]-	189.5	32859911
AllCCS	[M+HCOO]-	189.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
repirinast	CC(C)CCOC(=O)C1=CC(=O)C2=C(O1)C1=C(NC2=O)C(C)=C(C)C=C1	3888.4	Standard polar	33892256
repirinast	CC(C)CCOC(=O)C1=CC(=O)C2=C(O1)C1=C(NC2=O)C(C)=C(C)C=C1	3071.3	Standard non polar	33892256
repirinast	CC(C)CCOC(=O)C1=CC(=O)C2=C(O1)C1=C(NC2=O)C(C)=C(C)C=C1	3253.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
repirinast,1TMS,isomer #1	CC1=CC=C2C3=C(C(=O)C=C(C(=O)OCCC(C)C)O3)C(=O)N([Si](C)(C)C)C2=C1C	3148.2	Semi standard non polar	33892256
repirinast,1TMS,isomer #1	CC1=CC=C2C3=C(C(=O)C=C(C(=O)OCCC(C)C)O3)C(=O)N([Si](C)(C)C)C2=C1C	2964.8	Standard non polar	33892256
repirinast,1TMS,isomer #1	CC1=CC=C2C3=C(C(=O)C=C(C(=O)OCCC(C)C)O3)C(=O)N([Si](C)(C)C)C2=C1C	3553.5	Standard polar	33892256
repirinast,1TBDMS,isomer #1	CC1=CC=C2C3=C(C(=O)C=C(C(=O)OCCC(C)C)O3)C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C	3317.5	Semi standard non polar	33892256
repirinast,1TBDMS,isomer #1	CC1=CC=C2C3=C(C(=O)C=C(C(=O)OCCC(C)C)O3)C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C	3139.4	Standard non polar	33892256
repirinast,1TBDMS,isomer #1	CC1=CC=C2C3=C(C(=O)C=C(C(=O)OCCC(C)C)O3)C(=O)N([Si](C)(C)C(C)(C)C)C2=C1C	3599.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Repirinast GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ox-9381000000-f6c0b684a415b3f5898d	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Repirinast GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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

4874

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Repirinast

METLIN ID

Not Available

PubChem Compound

5050

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 Repirinast (HMDB0257154)

MOL for HMDB0257154 (Repirinast)

3D MOL for HMDB0257154 (Repirinast)

3D SDF for HMDB0257154 (Repirinast)

3D-SDF for HMDB0257154 (Repirinast)

PDB for HMDB0257154 (Repirinast)

3D PDB for HMDB0257154 (Repirinast)

SMILES for HMDB0257154 (Repirinast)

INCHI for HMDB0257154 (Repirinast)

Structure for HMDB0257154 (Repirinast)

3D Structure for HMDB0257154 (Repirinast)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra