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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:10:10 UTC

Update Date

2022-03-07 02:54:24 UTC

HMDB ID

HMDB0035218

Secondary Accession Numbers

HMDB35218

Metabolite Identification

Common Name

Cinereain

Description

Cinereain belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Cinereain is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cinereain has been detected, but not quantified in, cereals and cereal products. This could make cinereain a potential biomarker for the consumption of these foods.

Structure

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

HMDB0035218
     RDKit          3D
Cinereain
 45 47  0  0  0  0  0  0  0  0999 V2000
    3.3415   -1.5212   -2.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8798   -0.8792   -0.8340 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2444   -0.8177   -0.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0973   -1.7998   -0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9471   -1.5874    0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2906   -2.6163    1.3342 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9509   -2.3282    1.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3530   -3.1419    2.8275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854   -1.1208    1.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7912   -1.6432    0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0916   -2.1870   -0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9335   -0.7297    0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9417   -0.0659    1.0470 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2668   -0.3225    0.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9171    0.6812   -0.1061 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4770    1.9445   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7446    2.1757    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4664    1.1665    1.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5742    1.4757    1.5717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4436    3.4500    0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1107    4.5982   -0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0257    4.9007   -0.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0439    4.1060   -1.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3579    2.8091   -0.8282 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1849   -0.9541   -2.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4892   -1.6581   -2.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7316   -2.5453   -1.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6933    0.1541   -0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9244   -0.1426   -0.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9966   -0.4572    0.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6286   -1.8443   -0.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4719   -2.8457    0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659   -3.5422    1.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2786   -0.7849    2.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2744   -2.5620    1.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294   -3.0114   -0.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8322   -2.6457   -1.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5585   -1.4136   -1.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7425   -1.2926   -0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4692   -0.3673    1.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6222    0.0507   -0.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3354    3.4253    1.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8154    5.4081    0.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0110    5.8977   -1.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7578    4.5841   -1.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 17 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 14  5  1  0
 24 16  1  0
 18 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  0
M  END


  Mrv0541 02241215412D          

 24 26  0  0  0  0            999 V2000
   -1.2371    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9796    0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7221    1.1546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2371   -1.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2371   -0.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5771   -0.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5771    0.7421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246   -2.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5771   -1.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471   -1.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0621    2.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3196    2.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421    2.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296    1.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1646    1.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9071    0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5671    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3921    1.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7221    0.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3921   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5671   -0.5771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9071   -0.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1646   -0.4121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9796   -0.0821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  2  0  0  0  0
  2 24  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5 24  1  0  0  0  0
  6  7  1  0  0  0  0
  6 23  2  0  0  0  0
  7 15  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 22  2  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035218

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)\C=C1\NC(=O)C(C(C)C)N2C(=O)C3=C(OC=CC=C3)N=C12

> <INCHI_IDENTIFIER>
InChI=1S/C18H21N3O3/c1-10(2)9-13-15-20-17-12(7-5-6-8-24-17)18(23)21(15)14(11(3)4)16(22)19-13/h5-11,14H,1-4H3,(H,19,22)/b13-9+

> <INCHI_KEY>
CCHUDPANZXHQCS-UKTHLTGXSA-N

> <FORMULA>
C18H21N3O3

> <MOLECULAR_WEIGHT>
327.3776

> <EXACT_MASS>
327.158291553

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.75973311901882

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4E)-4-(2-methylpropylidene)-7-(propan-2-yl)-15-oxa-2,5,8-triazatricyclo[8.5.0.0³,⁸]pentadeca-1(10),2,11,13-tetraene-6,9-dione

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
2.119725653999999

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.22142626308138

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6502706177341495

> <JCHEM_POLAR_SURFACE_AREA>
71

> <JCHEM_REFRACTIVITY>
102.78320000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4E)-7-isopropyl-4-(2-methylpropylidene)-15-oxa-2,5,8-triazatricyclo[8.5.0.0³,⁸]pentadeca-1(10),2,11,13-tetraene-6,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035218
     RDKit          3D
Cinereain
 45 47  0  0  0  0  0  0  0  0999 V2000
    3.3415   -1.5212   -2.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8798   -0.8792   -0.8340 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2444   -0.8177   -0.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0973   -1.7998   -0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9471   -1.5874    0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2906   -2.6163    1.3342 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9509   -2.3282    1.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3530   -3.1419    2.8275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854   -1.1208    1.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7912   -1.6432    0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0916   -2.1870   -0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9335   -0.7297    0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9417   -0.0659    1.0470 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2668   -0.3225    0.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9171    0.6812   -0.1061 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4770    1.9445   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7446    2.1757    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4664    1.1665    1.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5742    1.4757    1.5717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4436    3.4500    0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1107    4.5982   -0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0257    4.9007   -0.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0439    4.1060   -1.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3579    2.8091   -0.8282 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1849   -0.9541   -2.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4892   -1.6581   -2.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7316   -2.5453   -1.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6933    0.1541   -0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9244   -0.1426   -0.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9966   -0.4572    0.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6286   -1.8443   -0.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4719   -2.8457    0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659   -3.5422    1.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2786   -0.7849    2.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2744   -2.5620    1.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294   -3.0114   -0.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8322   -2.6457   -1.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5585   -1.4136   -1.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7425   -1.2926   -0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4692   -0.3673    1.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6222    0.0507   -0.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3354    3.4253    1.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8154    5.4081    0.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0110    5.8977   -1.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7578    4.5841   -1.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 17 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 14  5  1  0
 24 16  1  0
 18 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.309   2.309   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.695   1.385   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.081   2.155   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.309  -2.463   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.309  -0.923   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.077  -0.153   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.077   1.385   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.539  -4.927   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.077  -3.387   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.461  -3.233   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.849   4.465   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.463   3.849   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.385   4.927   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.615   3.695   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.307   2.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.693   1.385   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.925   2.309   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.465   2.001   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.081   0.615   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.465  -0.769   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.925  -1.077   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.693  -0.153   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       0.307  -0.769   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0      -3.695  -0.153   0.000  0.00  0.00           N+0
CONECT    1    2    7   12                                                  
CONECT    2    1    3   24                                                  
CONECT    3    2                                                            
CONECT    4    5    9                                                       
CONECT    5    4    6   24                                                  
CONECT    6    5    7   23                                                  
CONECT    7    1    6   15                                                  
CONECT    8    9                                                            
CONECT    9    4    8   10                                                  
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12    1   11   13                                                  
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15    7   14   16                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   16   21   23                                                  
CONECT   23    6   22                                                       
CONECT   24    2    5                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0035218
HETATM    1  C1  UNL     1       3.342  -1.521  -2.151  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.880  -0.879  -0.834  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.244  -0.818  -0.049  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.097  -1.800  -0.030  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.947  -1.587   0.563  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.291  -2.616   1.334  1.00  0.00           N  
HETATM    7  C6  UNL     1      -0.951  -2.328   1.947  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.353  -3.142   2.827  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.785  -1.121   1.598  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.791  -1.643   0.590  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.092  -2.187  -0.625  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.933  -0.730   0.285  1.00  0.00           C  
HETATM   13  N2  UNL     1      -0.942  -0.066   1.047  1.00  0.00           N  
HETATM   14  C11 UNL     1       0.267  -0.322   0.469  1.00  0.00           C  
HETATM   15  N3  UNL     1       0.917   0.681  -0.106  1.00  0.00           N  
HETATM   16  C12 UNL     1       0.477   1.944  -0.161  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.745   2.176   0.436  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.466   1.167   1.048  1.00  0.00           C  
HETATM   19  O2  UNL     1      -2.574   1.476   1.572  1.00  0.00           O  
HETATM   20  C15 UNL     1      -1.444   3.450   0.518  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.111   4.598  -0.059  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.026   4.901  -0.921  1.00  0.00           C  
HETATM   23  C18 UNL     1       1.044   4.106  -1.212  1.00  0.00           C  
HETATM   24  O3  UNL     1       1.358   2.809  -0.828  1.00  0.00           O  
HETATM   25  H1  UNL     1       4.185  -0.954  -2.597  1.00  0.00           H  
HETATM   26  H2  UNL     1       2.489  -1.658  -2.850  1.00  0.00           H  
HETATM   27  H3  UNL     1       3.732  -2.545  -1.967  1.00  0.00           H  
HETATM   28  H4  UNL     1       2.693   0.154  -0.907  1.00  0.00           H  
HETATM   29  H5  UNL     1       4.924  -0.143  -0.601  1.00  0.00           H  
HETATM   30  H6  UNL     1       3.997  -0.457   0.967  1.00  0.00           H  
HETATM   31  H7  UNL     1       4.629  -1.844  -0.064  1.00  0.00           H  
HETATM   32  H8  UNL     1       2.472  -2.846   0.144  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.766  -3.542   1.408  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.279  -0.785   2.491  1.00  0.00           H  
HETATM   35  H11 UNL     1      -3.274  -2.562   1.065  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.429  -3.011  -0.293  1.00  0.00           H  
HETATM   37  H13 UNL     1      -2.832  -2.646  -1.311  1.00  0.00           H  
HETATM   38  H14 UNL     1      -1.558  -1.414  -1.211  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.742  -1.293  -0.300  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.469  -0.367   1.161  1.00  0.00           H  
HETATM   41  H17 UNL     1      -3.622   0.051  -0.449  1.00  0.00           H  
HETATM   42  H18 UNL     1      -2.335   3.425   1.129  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.815   5.408   0.170  1.00  0.00           H  
HETATM   44  H20 UNL     1       0.011   5.898  -1.361  1.00  0.00           H  
HETATM   45  H21 UNL     1       1.758   4.584  -1.884  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4   28
CONECT    3   29   30   31
CONECT    4    5    5   32
CONECT    5    6   14
CONECT    6    7   33
CONECT    7    8    8    9
CONECT    9   10   13   34
CONECT   10   11   12   35
CONECT   11   36   37   38
CONECT   12   39   40   41
CONECT   13   14   18
CONECT   14   15   15
CONECT   15   16
CONECT   16   17   17   24
CONECT   17   18   20
CONECT   18   19   19
CONECT   20   21   21   42
CONECT   21   22   43
CONECT   22   23   23   44
CONECT   23   24   45
END

HMDB0035218
     RDKit          3D
Cinereain
 45 47  0  0  0  0  0  0  0  0999 V2000
    3.3415   -1.5212   -2.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8798   -0.8792   -0.8340 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2444   -0.8177   -0.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0973   -1.7998   -0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9471   -1.5874    0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2906   -2.6163    1.3342 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9509   -2.3282    1.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3530   -3.1419    2.8275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854   -1.1208    1.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7912   -1.6432    0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0916   -2.1870   -0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9335   -0.7297    0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9417   -0.0659    1.0470 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2668   -0.3225    0.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9171    0.6812   -0.1061 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4770    1.9445   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7446    2.1757    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4664    1.1665    1.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5742    1.4757    1.5717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4436    3.4500    0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1107    4.5982   -0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0257    4.9007   -0.9207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0439    4.1060   -1.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3579    2.8091   -0.8282 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1849   -0.9541   -2.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4892   -1.6581   -2.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7316   -2.5453   -1.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6933    0.1541   -0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9244   -0.1426   -0.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9966   -0.4572    0.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6286   -1.8443   -0.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4719   -2.8457    0.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659   -3.5422    1.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2786   -0.7849    2.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2744   -2.5620    1.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294   -3.0114   -0.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8322   -2.6457   -1.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5585   -1.4136   -1.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7425   -1.2926   -0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4692   -0.3673    1.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6222    0.0507   -0.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3354    3.4253    1.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8154    5.4081    0.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0110    5.8977   -1.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7578    4.5841   -1.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 17 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 14  5  1  0
 24 16  1  0
 18 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  6 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10,11-Dihydro-8-(1-methylethyl)-11-(2-methylpropylidene)-6H-oxepino[2,3-D]pyrazino[1,2-a]pyrimidine-6,9(8H)-dione, 9ci	HMDB

Chemical Formula

C₁₈H₂₁N₃O₃

Average Molecular Weight

327.3776

Monoisotopic Molecular Weight

327.158291553

IUPAC Name

(4E)-4-(2-methylpropylidene)-7-(propan-2-yl)-15-oxa-2,5,8-triazatricyclo[8.5.0.0³,⁸]pentadeca-1(10),2,11,13-tetraene-6,9-dione

Traditional Name

(4E)-7-isopropyl-4-(2-methylpropylidene)-15-oxa-2,5,8-triazatricyclo[8.5.0.0³,⁸]pentadeca-1(10),2,11,13-tetraene-6,9-dione

CAS Registry Number

117013-51-1

SMILES

CC(C)\C=C1\NC(=O)C(C(C)C)N2C(=O)C3=C(OC=CC=C3)N=C12

InChI Identifier

InChI=1S/C18H21N3O3/c1-10(2)9-13-15-20-17-12(7-5-6-8-24-17)18(23)21(15)14(11(3)4)16(22)19-13/h5-11,14H,1-4H3,(H,19,22)/b13-9+

InChI Key

CCHUDPANZXHQCS-UKTHLTGXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Pyrimidones

Alternative Parents

Substituents

Pyrimidone
Vinylogous ester
Heteroaromatic compound
Carboxamide group
Lactam
Secondary carboxylic acid amide
Oxacycle
Azacycle
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0035218)

Cellular substructure

Membrane (HMDB: HMDB0035218)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035218)

Source

Exogenous

Food

Food (HMDB: HMDB0035218)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Endogenous

Plant

Poaceae (HMDB: HMDB0035218)

Not Available

Nutrient (HMDB: HMDB0035218)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	201 - 203 °C	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
Water Solubility	0.15 g/L	ALOGPS
logP	2.53	ALOGPS
logP	2.12	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	12.22	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	102.78 m³·mol⁻¹	ChemAxon
Polarizability	34.76 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-2H]-	220.576	30932474
DeepCCS	[M+Na]+	196.098	30932474
AllCCS	[M+H]+	177.2	32859911
AllCCS	[M+H-H2O]+	174.1	32859911
AllCCS	[M+NH4]+	180.0	32859911
AllCCS	[M+Na]+	180.8	32859911
AllCCS	[M-H]-	180.9	32859911
AllCCS	[M+Na-2H]-	180.8	32859911
AllCCS	[M+HCOO]-	180.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cinereain	CC(C)\C=C1\NC(=O)C(C(C)C)N2C(=O)C3=C(OC=CC=C3)N=C12	3860.4	Standard polar	33892256
Cinereain	CC(C)\C=C1\NC(=O)C(C(C)C)N2C(=O)C3=C(OC=CC=C3)N=C12	2581.2	Standard non polar	33892256
Cinereain	CC(C)\C=C1\NC(=O)C(C(C)C)N2C(=O)C3=C(OC=CC=C3)N=C12	2746.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cinereain,1TMS,isomer #1	CC(C)/C=C1\C2=NC3=C(C=CC=CO3)C(=O)N2C(C(C)C)C(=O)N1[Si](C)(C)C	2759.7	Semi standard non polar	33892256
Cinereain,1TMS,isomer #1	CC(C)/C=C1\C2=NC3=C(C=CC=CO3)C(=O)N2C(C(C)C)C(=O)N1[Si](C)(C)C	2607.6	Standard non polar	33892256
Cinereain,1TBDMS,isomer #1	CC(C)/C=C1\C2=NC3=C(C=CC=CO3)C(=O)N2C(C(C)C)C(=O)N1[Si](C)(C)C(C)(C)C	2958.0	Semi standard non polar	33892256
Cinereain,1TBDMS,isomer #1	CC(C)/C=C1\C2=NC3=C(C=CC=CO3)C(=O)N2C(C(C)C)C(=O)N1[Si](C)(C)C(C)(C)C	2806.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cinereain GC-MS (Non-derivatized) - 70eV, Positive	splash10-075d-2294000000-9e3ecd38bf87ae1652dd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinereain 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 - Cinereain 10V, Positive-QTOF	splash10-004i-0019000000-79c9743afc472c38e8bb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinereain 20V, Positive-QTOF	splash10-004i-3139000000-6174911fe460746b7737	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinereain 40V, Positive-QTOF	splash10-0nmr-9650000000-73fbffdf511d6bec0ab9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinereain 10V, Negative-QTOF	splash10-004i-0029000000-51fb249be555aca7591d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinereain 20V, Negative-QTOF	splash10-0a59-7493000000-0209f631ef4f9bf3111d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinereain 40V, Negative-QTOF	splash10-0a4i-3970000000-498bdea4f7c821680bdd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinereain 10V, Negative-QTOF	splash10-004i-0039000000-133fca5f99ad6bf17d7f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinereain 20V, Negative-QTOF	splash10-002b-0094000000-f467d8886ec75d541bf3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinereain 40V, Negative-QTOF	splash10-0006-3191000000-226d57eaa764ca775599	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinereain 10V, Positive-QTOF	splash10-004i-0009000000-5b65f30965dc13ccd7b4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinereain 20V, Positive-QTOF	splash10-004i-0019000000-5837a0dd8e829df0106b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinereain 40V, Positive-QTOF	splash10-004i-2397000000-e87a4b491313e3d7c1b1	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB013866

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

51340308

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Cinereain (HMDB0035218)

MOL for HMDB0035218 (Cinereain)

3D MOL for HMDB0035218 (Cinereain)

3D SDF for HMDB0035218 (Cinereain)

3D-SDF for HMDB0035218 (Cinereain)

PDB for HMDB0035218 (Cinereain)

3D PDB for HMDB0035218 (Cinereain)

SMILES for HMDB0035218 (Cinereain)

INCHI for HMDB0035218 (Cinereain)

Structure for HMDB0035218 (Cinereain)

3D Structure for HMDB0035218 (Cinereain)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra