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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:26:02 UTC

Update Date

2021-09-26 23:06:59 UTC

HMDB ID

HMDB0253633

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Isofebrifugine

Description

3-({2-hydroxy-octahydrofuro[3,2-b]pyridin-2-yl}methyl)-3,4-dihydroquinazolin-4-one belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring. 3-({2-hydroxy-octahydrofuro[3,2-b]pyridin-2-yl}methyl)-3,4-dihydroquinazolin-4-one is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Isofebrifugine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Isofebrifugine 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

HMDB0253633
     RDKit          3D
Isofebrifugine
 41 44  0  0  0  0  0  0  0  0999 V2000
    1.8714    1.0982   -1.9462 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1074    0.1917   -1.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.4291   -0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7860    1.6126   -0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7475    1.8482    0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0413    0.8867    1.8213 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3523   -0.3076    1.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3822   -0.5212    0.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6920   -1.6739    0.7634 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7483   -1.9034   -0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4324   -0.9822   -1.1210 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4249   -1.2596   -2.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9614   -0.8752   -1.7003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8482   -1.1999   -2.7425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1473    0.5949   -1.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5661    0.5578   -0.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6655    1.5460    0.1912 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6242    1.2990    1.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1598    0.0220    1.9357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2809   -1.0871    0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6614   -0.8563   -0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3777   -1.4364   -0.4954 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5489    2.3560   -0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2811    2.8045    0.8726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7963    1.0752    2.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5502   -1.0906    2.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1928   -2.8353   -0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3934   -2.3325   -2.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6412   -0.7080   -3.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4943   -0.7254   -3.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4855    0.9241   -0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0785    1.2412   -2.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2762    0.8078   -1.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7859    1.9477    0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6274    1.1257    0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6496    2.1530    1.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0870    0.1846    2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7976   -0.1469    2.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8342   -2.0279    1.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3777   -1.3317    0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2816   -1.4050   -1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  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
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 11  2  1  0
 22 13  1  0
  8  3  1  0
 21 16  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
M  END


  Mrv1533004251504202D          

 22 25  0  0  0  0            999 V2000
    2.9439   -0.8314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5570   -1.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9439   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1593   -1.6805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5462   -2.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7616   -1.9776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5901   -1.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946   -0.9157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3661   -0.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2470    0.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0316    0.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2032   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9878   -0.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6009   -0.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0419   -0.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8266   -0.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5410   -0.5584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2555   -0.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2555   -1.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5410   -2.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8266   -1.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0419   -2.0508    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  1  0  0  0  0
  4  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  2  0  0  0  0
  2 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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253633

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1(CN2C=NC3=CC=CC=C3C2=O)CC2NCCCC2O1

> <INCHI_IDENTIFIER>
InChI=1S/C16H19N3O3/c20-15-11-4-1-2-5-12(11)18-10-19(15)9-16(21)8-13-14(22-16)6-3-7-17-13/h1-2,4-5,10,13-14,17,21H,3,6-9H2

> <INCHI_KEY>
YLYLCQRQSRDSQR-UHFFFAOYSA-N

> <FORMULA>
C16H19N3O3

> <MOLECULAR_WEIGHT>
301.346

> <EXACT_MASS>
301.142641484

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.33789943914499

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-({2-hydroxy-octahydrofuro[3,2-b]pyridin-2-yl}methyl)-3,4-dihydroquinazolin-4-one

> <ALOGPS_LOGP>
0.13

> <JCHEM_LOGP>
1.0312317483333333

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.60697263857697

> <JCHEM_PKA_STRONGEST_BASIC>
9.167425894151183

> <JCHEM_POLAR_SURFACE_AREA>
74.16

> <JCHEM_REFRACTIVITY>
82.06569999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-({2-hydroxy-hexahydro-3H-furo[3,2-b]pyridin-2-yl}methyl)quinazolin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253633
     RDKit          3D
Isofebrifugine
 41 44  0  0  0  0  0  0  0  0999 V2000
    1.8714    1.0982   -1.9462 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1074    0.1917   -1.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.4291   -0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7860    1.6126   -0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7475    1.8482    0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0413    0.8867    1.8213 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3523   -0.3076    1.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3822   -0.5212    0.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6920   -1.6739    0.7634 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7483   -1.9034   -0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4324   -0.9822   -1.1210 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4249   -1.2596   -2.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9614   -0.8752   -1.7003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8482   -1.1999   -2.7425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1473    0.5949   -1.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5661    0.5578   -0.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6655    1.5460    0.1912 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6242    1.2990    1.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1598    0.0220    1.9357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2809   -1.0871    0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6614   -0.8563   -0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3777   -1.4364   -0.4954 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5489    2.3560   -0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2811    2.8045    0.8726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7963    1.0752    2.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5502   -1.0906    2.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1928   -2.8353   -0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3934   -2.3325   -2.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6412   -0.7080   -3.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4943   -0.7254   -3.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4855    0.9241   -0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0785    1.2412   -2.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2762    0.8078   -1.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7859    1.9477    0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6274    1.1257    0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6496    2.1530    1.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0870    0.1846    2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7976   -0.1469    2.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8342   -2.0279    1.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3777   -1.3317    0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2816   -1.4050   -1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  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
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 11  2  1  0
 22 13  1  0
  8  3  1  0
 21 16  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
M  END

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  O   UNK     0       5.495  -1.552   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.640  -2.582   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.495  -3.613   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       4.031  -3.137   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.886  -4.167   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.422  -3.692   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.101  -2.185   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.363  -1.709   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.683  -0.203   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.461   0.828   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.926   0.352   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.246  -1.155   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.711  -1.631   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.855  -0.600   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.545  -1.336   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.010  -1.812   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      10.343  -1.042   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      11.677  -1.812   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.677  -3.352   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.343  -4.122   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.010  -3.352   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.545  -3.828   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15   22                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12    4   14                                                  
CONECT   14   13                                                            
CONECT   15    2   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21    2                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0253633
HETATM    1  O1  UNL     1       1.871   1.098  -1.946  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.107   0.192  -1.097  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.079   0.429  -0.135  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.786   1.613  -0.080  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.748   1.848   0.871  1.00  0.00           C  
HETATM    6  C5  UNL     1       5.041   0.887   1.821  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.352  -0.308   1.794  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.382  -0.521   0.819  1.00  0.00           C  
HETATM    9  N1  UNL     1       2.692  -1.674   0.763  1.00  0.00           N  
HETATM   10  C8  UNL     1       1.748  -1.903  -0.171  1.00  0.00           C  
HETATM   11  N2  UNL     1       1.432  -0.982  -1.121  1.00  0.00           N  
HETATM   12  C9  UNL     1       0.425  -1.260  -2.093  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.961  -0.875  -1.700  1.00  0.00           C  
HETATM   14  O2  UNL     1      -1.848  -1.200  -2.742  1.00  0.00           O  
HETATM   15  C11 UNL     1      -1.147   0.595  -1.408  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.566   0.558  -0.816  1.00  0.00           C  
HETATM   17  N3  UNL     1      -2.665   1.546   0.191  1.00  0.00           N  
HETATM   18  C13 UNL     1      -3.624   1.299   1.221  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.160   0.022   1.936  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.281  -1.087   0.952  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.661  -0.856  -0.368  1.00  0.00           C  
HETATM   22  O3  UNL     1      -1.378  -1.436  -0.495  1.00  0.00           O  
HETATM   23  H1  UNL     1       3.549   2.356  -0.826  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.281   2.804   0.873  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.796   1.075   2.566  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.550  -1.091   2.520  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.193  -2.835  -0.213  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.393  -2.332  -2.400  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.641  -0.708  -3.055  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.494  -0.725  -3.544  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.485   0.924  -0.564  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.078   1.241  -2.282  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.276   0.808  -1.638  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.786   1.948   0.538  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.627   1.126   0.786  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.650   2.153   1.900  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.087   0.185   2.223  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.798  -0.147   2.799  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.834  -2.028   1.385  1.00  0.00           H  
HETATM   40  H18 UNL     1      -4.378  -1.332   0.857  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.282  -1.405  -1.138  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4    4    8
CONECT    4    5   23
CONECT    5    6    6   24
CONECT    6    7   25
CONECT    7    8    8   26
CONECT    8    9
CONECT    9   10   10
CONECT   10   11   27
CONECT   11   12
CONECT   12   13   28   29
CONECT   13   14   15   22
CONECT   14   30
CONECT   15   16   31   32
CONECT   16   17   21   33
CONECT   17   18   34
CONECT   18   19   35   36
CONECT   19   20   37   38
CONECT   20   21   39   40
CONECT   21   22   41
END

HMDB0253633
     RDKit          3D
Isofebrifugine
 41 44  0  0  0  0  0  0  0  0999 V2000
    1.8714    1.0982   -1.9462 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1074    0.1917   -1.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.4291   -0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7860    1.6126   -0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7475    1.8482    0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0413    0.8867    1.8213 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3523   -0.3076    1.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3822   -0.5212    0.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6920   -1.6739    0.7634 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7483   -1.9034   -0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4324   -0.9822   -1.1210 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4249   -1.2596   -2.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9614   -0.8752   -1.7003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8482   -1.1999   -2.7425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1473    0.5949   -1.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5661    0.5578   -0.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6655    1.5460    0.1912 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6242    1.2990    1.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1598    0.0220    1.9357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2809   -1.0871    0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6614   -0.8563   -0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3777   -1.4364   -0.4954 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5489    2.3560   -0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2811    2.8045    0.8726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7963    1.0752    2.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5502   -1.0906    2.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1928   -2.8353   -0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3934   -2.3325   -2.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6412   -0.7080   -3.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4943   -0.7254   -3.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4855    0.9241   -0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0785    1.2412   -2.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2762    0.8078   -1.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7859    1.9477    0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6274    1.1257    0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6496    2.1530    1.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0870    0.1846    2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7976   -0.1469    2.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8342   -2.0279    1.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3777   -1.3317    0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2816   -1.4050   -1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  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
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 11  2  1  0
 22 13  1  0
  8  3  1  0
 21 16  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₉N₃O₃

Average Molecular Weight

301.346

Monoisotopic Molecular Weight

301.142641484

IUPAC Name

3-({2-hydroxy-octahydrofuro[3,2-b]pyridin-2-yl}methyl)-3,4-dihydroquinazolin-4-one

Traditional Name

3-({2-hydroxy-hexahydro-3H-furo[3,2-b]pyridin-2-yl}methyl)quinazolin-4-one

CAS Registry Number

Not Available

SMILES

OC1(CN2C=NC3=CC=CC=C3C2=O)CC2NCCCC2O1

InChI Identifier

InChI=1S/C16H19N3O3/c20-15-11-4-1-2-5-12(11)18-10-19(15)9-16(21)8-13-14(22-16)6-3-7-17-13/h1-2,4-5,10,13-14,17,21H,3,6-9H2

InChI Key

YLYLCQRQSRDSQR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinazolines

Alternative Parents

Substituents

Quinazoline
Pyrimidone
Piperidine
Pyrimidine
Benzenoid
Heteroaromatic compound
Tetrahydrofuran
Hemiacetal
Lactam
Secondary aliphatic amine
Oxacycle
Secondary amine
Azacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Amine
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)

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	0.13	ALOGPS
logP	1.03	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	11.61	ChemAxon
pKa (Strongest Basic)	9.17	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.07 m³·mol⁻¹	ChemAxon
Polarizability	31.34 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	166.314	30932474
DeepCCS	[M-H]-	163.919	30932474
DeepCCS	[M-2H]-	196.802	30932474
DeepCCS	[M+Na]+	172.364	30932474
AllCCS	[M+H]+	171.7	32859911
AllCCS	[M+H-H2O]+	168.3	32859911
AllCCS	[M+NH4]+	174.8	32859911
AllCCS	[M+Na]+	175.7	32859911
AllCCS	[M-H]-	174.8	32859911
AllCCS	[M+Na-2H]-	174.4	32859911
AllCCS	[M+HCOO]-	174.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isofebrifugine	OC1(CN2C=NC3=CC=CC=C3C2=O)CC2NCCCC2O1	3412.6	Standard polar	33892256
Isofebrifugine	OC1(CN2C=NC3=CC=CC=C3C2=O)CC2NCCCC2O1	2621.1	Standard non polar	33892256
Isofebrifugine	OC1(CN2C=NC3=CC=CC=C3C2=O)CC2NCCCC2O1	2836.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isofebrifugine,2TMS,isomer #1	C[Si](C)(C)OC1(CN2C=NC3=CC=CC=C3C2=O)CC2C(CCCN2[Si](C)(C)C)O1	2895.4	Semi standard non polar	33892256
Isofebrifugine,2TMS,isomer #1	C[Si](C)(C)OC1(CN2C=NC3=CC=CC=C3C2=O)CC2C(CCCN2[Si](C)(C)C)O1	2920.6	Standard non polar	33892256
Isofebrifugine,2TMS,isomer #1	C[Si](C)(C)OC1(CN2C=NC3=CC=CC=C3C2=O)CC2C(CCCN2[Si](C)(C)C)O1	3617.7	Standard polar	33892256
Isofebrifugine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1(CN2C=NC3=CC=CC=C3C2=O)CC2C(CCCN2[Si](C)(C)C(C)(C)C)O1	3378.0	Semi standard non polar	33892256
Isofebrifugine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1(CN2C=NC3=CC=CC=C3C2=O)CC2C(CCCN2[Si](C)(C)C(C)(C)C)O1	3342.4	Standard non polar	33892256
Isofebrifugine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1(CN2C=NC3=CC=CC=C3C2=O)CC2C(CCCN2[Si](C)(C)C(C)(C)C)O1	3780.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isofebrifugine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-5930000000-1a46a6836e18d71a976a	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isofebrifugine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isofebrifugine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isofebrifugine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isofebrifugine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isofebrifugine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	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 - Isofebrifugine 10V, Positive-QTOF	splash10-0udi-0009000000-bbeb4192008783263a0d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isofebrifugine 20V, Positive-QTOF	splash10-0udi-0229000000-436362586b5d6a4382d4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isofebrifugine 40V, Positive-QTOF	splash10-05o1-9540000000-6e31af7dfc0ec0da3fe2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isofebrifugine 10V, Negative-QTOF	splash10-0udi-0209000000-357ce591c8da0633d3e1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isofebrifugine 20V, Negative-QTOF	splash10-0udi-0629000000-130ada7b728fe5c54e80	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isofebrifugine 40V, Negative-QTOF	splash10-0007-4900000000-e46f1a9c8ef336e26362	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

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

431195

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 Isofebrifugine (HMDB0253633)

MOL for HMDB0253633 (Isofebrifugine)

3D MOL for HMDB0253633 (Isofebrifugine)

3D SDF for HMDB0253633 (Isofebrifugine)

3D-SDF for HMDB0253633 (Isofebrifugine)

PDB for HMDB0253633 (Isofebrifugine)

3D PDB for HMDB0253633 (Isofebrifugine)

SMILES for HMDB0253633 (Isofebrifugine)

INCHI for HMDB0253633 (Isofebrifugine)

Structure for HMDB0253633 (Isofebrifugine)

3D Structure for HMDB0253633 (Isofebrifugine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra