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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-24 08:48:50 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004808

Secondary Accession Numbers

HMDB04808

Metabolite Identification

Common Name

7C-aglycone

Description

7C-aglycone is one of the two major aglycone urinary water-soluble metabolites of Phylloquinone (Vitamin K1) and menaquinones (vitamin K2), usually excreted as glucuronide conjugates; their structure suggests that they are formed by an oxidative degradation of the phytyl side chain involving enzymes of omega- and beta-oxidation. Newborn infants as a group, are known to have precariously low vitamin K stores and are routinely given vitamin K prophylaxis at birth. (PMIDs 7306367, 4833371, 15722567).

Structure

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

HMDB0004808
     RDKit          3D
7C-aglycone
 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.7500   -2.1087   -1.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795   -0.9858   -0.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8921   -0.1192    0.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5217   -0.0697    0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4489   -1.0516    0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5290   -0.8733   -0.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860   -2.0477   -0.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9566    0.4532   -0.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3609    0.7753   -0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4524    0.7788    1.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4826    0.5417    1.7888 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6817    1.0607    1.6422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7541    0.9555    0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1999    1.7963    1.6245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1540    1.0926    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9431    2.0963    1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2829    2.1872    0.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8949    1.2731    0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1276    0.2588   -0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7675    0.1722   -0.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9307   -0.8796   -0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4866   -1.7340   -1.5105 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1668   -1.8629   -1.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4148   -2.5401   -1.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6968   -2.9475   -0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8911    0.9661    0.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4777   -0.0822    1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2609   -2.1106    0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1991   -2.2104   -0.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7518   -2.9599   -0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8123   -1.9056   -1.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1348    0.3580   -2.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3163    1.2970   -0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1033    0.0861   -0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5739    1.8184   -0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1948    1.8549    1.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5083    2.8386    1.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8864    2.9916    1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9669    1.3313   -0.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5661   -0.4950   -1.1574 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  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  3 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21  2  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 12 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
M  END

Untitled Document-1
  Mrv0541 02231219582D          

 22 23  0  0  0  0            999 V2000
   -2.8875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  1  7  2  0  0  0  0
  1  8  1  0  0  0  0
  4  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 10 19  1  0  0  0  0
 14 19  2  0  0  0  0
 13 20  2  0  0  0  0
 10 21  2  0  0  0  0
 12 22  1  0  0  0  0
  6 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004808

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(CCC(O)=O)=C\CC1=C(C)C(=O)C2=C(C=CC=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O4/c1-11(8-10-16(19)20)7-9-13-12(2)17(21)14-5-3-4-6-15(14)18(13)22/h3-7H,8-10H2,1-2H3,(H,19,20)/b11-7-

> <INCHI_KEY>
BCNIZSHMXASUGF-XFFZJAGNSA-N

> <FORMULA>
C18H18O4

> <MOLECULAR_WEIGHT>
298.3331

> <EXACT_MASS>
298.120509064

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.17674745321396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4Z)-4-methyl-6-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)hex-4-enoic acid

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
3.0694601043333334

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.025595699192459

> <JCHEM_PKA_STRONGEST_BASIC>
-7.2243434145753564

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
84.9664

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7c-aglycone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004808
     RDKit          3D
7C-aglycone
 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.7500   -2.1087   -1.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795   -0.9858   -0.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8921   -0.1192    0.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5217   -0.0697    0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4489   -1.0516    0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5290   -0.8733   -0.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860   -2.0477   -0.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9566    0.4532   -0.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3609    0.7753   -0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4524    0.7788    1.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4826    0.5417    1.7888 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6817    1.0607    1.6422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7541    0.9555    0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1999    1.7963    1.6245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1540    1.0926    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9431    2.0963    1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2829    2.1872    0.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8949    1.2731    0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1276    0.2588   -0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7675    0.1722   -0.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9307   -0.8796   -0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4866   -1.7340   -1.5105 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1668   -1.8629   -1.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4148   -2.5401   -1.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6968   -2.9475   -0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8911    0.9661    0.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4777   -0.0822    1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2609   -2.1106    0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1991   -2.2104   -0.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7518   -2.9599   -0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8123   -1.9056   -1.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1348    0.3580   -2.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3163    1.2970   -0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1033    0.0861   -0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5739    1.8184   -0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1948    1.8549    1.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5083    2.8386    1.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8864    2.9916    1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9669    1.3313   -0.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5661   -0.4950   -1.1574 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  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  3 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21  2  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 12 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-1                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -5.390  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.620   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.620  -2.667   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -6.930  -1.334   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.080   2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.160   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.930  -1.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.160  -2.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.620   2.667   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
CONECT    1    2    7    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5   11                                                       
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9    4                                                            
CONECT   10   11   19   21                                                  
CONECT   11   10   12    6                                                  
CONECT   12   11   13   22                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   10   14                                                  
CONECT   20   13                                                            
CONECT   21   10                                                            
CONECT   22   12                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0004808
HETATM    1  C1  UNL     1      -0.750  -2.109  -1.069  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.479  -0.986  -0.452  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.892  -0.119   0.325  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.522  -0.070   0.729  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.449  -1.052   0.265  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.529  -0.873  -0.456  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.386  -2.048  -0.849  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.957   0.453  -0.911  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.361   0.775  -0.384  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.452   0.779   1.062  1.00  0.00           C  
HETATM   11  O1  UNL     1       3.483   0.542   1.789  1.00  0.00           O  
HETATM   12  O2  UNL     1       5.682   1.061   1.642  1.00  0.00           O  
HETATM   13  C11 UNL     1      -1.754   0.955   0.875  1.00  0.00           C  
HETATM   14  O3  UNL     1      -1.200   1.796   1.625  1.00  0.00           O  
HETATM   15  C12 UNL     1      -3.154   1.093   0.611  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.943   2.096   1.129  1.00  0.00           C  
HETATM   17  C14 UNL     1      -5.283   2.187   0.848  1.00  0.00           C  
HETATM   18  C15 UNL     1      -5.895   1.273   0.031  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.128   0.259  -0.501  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.767   0.172  -0.211  1.00  0.00           C  
HETATM   21  C18 UNL     1      -2.931  -0.880  -0.751  1.00  0.00           C  
HETATM   22  O4  UNL     1      -3.487  -1.734  -1.511  1.00  0.00           O  
HETATM   23  H1  UNL     1       0.167  -1.863  -1.593  1.00  0.00           H  
HETATM   24  H2  UNL     1      -1.415  -2.540  -1.894  1.00  0.00           H  
HETATM   25  H3  UNL     1      -0.697  -2.948  -0.345  1.00  0.00           H  
HETATM   26  H4  UNL     1       0.891   0.966   0.537  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.478  -0.082   1.873  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.261  -2.111   0.554  1.00  0.00           H  
HETATM   29  H7  UNL     1       4.199  -2.210  -0.125  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.752  -2.960  -0.907  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.812  -1.906  -1.874  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.135   0.358  -2.030  1.00  0.00           H  
HETATM   33  H11 UNL     1       2.316   1.297  -0.685  1.00  0.00           H  
HETATM   34  H12 UNL     1       5.103   0.086  -0.848  1.00  0.00           H  
HETATM   35  H13 UNL     1       4.574   1.818  -0.751  1.00  0.00           H  
HETATM   36  H14 UNL     1       6.195   1.855   1.234  1.00  0.00           H  
HETATM   37  H15 UNL     1      -3.508   2.839   1.777  1.00  0.00           H  
HETATM   38  H16 UNL     1      -5.886   2.992   1.270  1.00  0.00           H  
HETATM   39  H17 UNL     1      -6.967   1.331  -0.205  1.00  0.00           H  
HETATM   40  H18 UNL     1      -5.566  -0.495  -1.157  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3   21
CONECT    3    4   13
CONECT    4    5   26   27
CONECT    5    6    6   28
CONECT    6    7    8
CONECT    7   29   30   31
CONECT    8    9   32   33
CONECT    9   10   34   35
CONECT   10   11   11   12
CONECT   12   36
CONECT   13   14   14   15
CONECT   15   16   16   20
CONECT   16   17   37
CONECT   17   18   18   38
CONECT   18   19   39
CONECT   19   20   20   40
CONECT   20   21
CONECT   21   22   22
END

HMDB0004808
     RDKit          3D
7C-aglycone
 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.7500   -2.1087   -1.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795   -0.9858   -0.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8921   -0.1192    0.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5217   -0.0697    0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4489   -1.0516    0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5290   -0.8733   -0.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860   -2.0477   -0.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9566    0.4532   -0.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3609    0.7753   -0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4524    0.7788    1.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4826    0.5417    1.7888 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6817    1.0607    1.6422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7541    0.9555    0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1999    1.7963    1.6245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1540    1.0926    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9431    2.0963    1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2829    2.1872    0.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8949    1.2731    0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1276    0.2588   -0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7675    0.1722   -0.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9307   -0.8796   -0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4866   -1.7340   -1.5105 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1668   -1.8629   -1.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4148   -2.5401   -1.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6968   -2.9475   -0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8911    0.9661    0.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4777   -0.0822    1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2609   -2.1106    0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1991   -2.2104   -0.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7518   -2.9599   -0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8123   -1.9056   -1.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1348    0.3580   -2.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3163    1.2970   -0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1033    0.0861   -0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5739    1.8184   -0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1948    1.8549    1.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5083    2.8386    1.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8864    2.9916    1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9669    1.3313   -0.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5661   -0.4950   -1.1574 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  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  3 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21  2  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 12 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(4Z)-4-Methyl-6-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)hex-4-enoate	HMDB
2-Methyl-3-(5'-carboxy-3'-methyl-2'-pentenyl)-1,4-naphthoquinone	HMDB
Vitamin K1 aglycone I	HMDB
Vitamin K1 aglycone I, (e)-isomer	HMDB
Phylloquinone aglycone I	HMDB
Vitamin K1 aglycone I, (Z)-isomer	HMDB
6-(1,4-Dihydro-3-methyl-1,4-dioxo-2-naphthalenyl)-4-methyl- 4-hexenoate	HMDB
6-(1,4-Dihydro-3-methyl-1,4-dioxo-2-naphthalenyl)-4-methyl- 4-hexenoic acid	HMDB

Chemical Formula

C₁₈H₁₈O₄

Average Molecular Weight

298.3331

Monoisotopic Molecular Weight

298.120509064

IUPAC Name

(4Z)-4-methyl-6-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)hex-4-enoic acid

Traditional Name

7c-aglycone

CAS Registry Number

51732-61-7

SMILES

C\C(CCC(O)=O)=C\CC1=C(C)C(=O)C2=C(C=CC=C2)C1=O

InChI Identifier

InChI=1S/C18H18O4/c1-11(8-10-16(19)20)7-9-13-12(2)17(21)14-5-3-4-6-15(14)18(13)22/h3-7H,8-10H2,1-2H3,(H,19,20)/b11-7-

InChI Key

BCNIZSHMXASUGF-XFFZJAGNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Vitamin K compounds

Alternative Parents

Substituents

Naphthoquinone
Aromatic monoterpenoid
Bicyclic monoterpenoid
Naphthalene
Monoterpenoid
Aryl ketone
Medium-chain fatty acid
Quinone
Branched fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Benzenoid
Unsaturated fatty acid
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 17585028)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0004808)

Cellular substructure

Extracellular (HMDB: HMDB0004808)
Membrane (HMDB: HMDB0004808)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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
Water Solubility	0.011 g/L	ALOGPS
logP	2.49	ALOGPS
logP	3.07	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.03	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	84.97 m³·mol⁻¹	ChemAxon
Polarizability	32.18 Å³	ChemAxon
Number of Rings	2	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]+	179.696	30932474
DeepCCS	[M-H]-	177.338	30932474
DeepCCS	[M-2H]-	211.184	30932474
DeepCCS	[M+Na]+	186.896	30932474
AllCCS	[M+H]+	171.6	32859911
AllCCS	[M+H-H2O]+	168.2	32859911
AllCCS	[M+NH4]+	174.8	32859911
AllCCS	[M+Na]+	175.7	32859911
AllCCS	[M-H]-	174.6	32859911
AllCCS	[M+Na-2H]-	174.4	32859911
AllCCS	[M+HCOO]-	174.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7C-aglycone	C\C(CCC(O)=O)=C\CC1=C(C)C(=O)C2=C(C=CC=C2)C1=O	4171.6	Standard polar	33892256
7C-aglycone	C\C(CCC(O)=O)=C\CC1=C(C)C(=O)C2=C(C=CC=C2)C1=O	2224.3	Standard non polar	33892256
7C-aglycone	C\C(CCC(O)=O)=C\CC1=C(C)C(=O)C2=C(C=CC=C2)C1=O	2523.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7C-aglycone,1TMS,isomer #1	CC1=C(C/C=C(/C)CCC(=O)O[Si](C)(C)C)C(=O)C2=CC=CC=C2C1=O	2646.8	Semi standard non polar	33892256
7C-aglycone,1TBDMS,isomer #1	CC1=C(C/C=C(/C)CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)C2=CC=CC=C2C1=O	2898.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 7C-aglycone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ff9-1190000000-463d381d1a48bcf52c00	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7C-aglycone GC-MS (1 TMS) - 70eV, Positive	splash10-05br-8395000000-d4a5d0d6a22b68178803	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7C-aglycone 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 - 7C-aglycone 10V, Positive-QTOF	splash10-000t-0190000000-174afc595775a629706c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7C-aglycone 20V, Positive-QTOF	splash10-06s9-2960000000-99ce28d05e4cb8e84710	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7C-aglycone 40V, Positive-QTOF	splash10-015c-9200000000-5f53c890b686a5e32c85	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7C-aglycone 10V, Negative-QTOF	splash10-0002-0090000000-e007453c2b4ea3024611	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7C-aglycone 20V, Negative-QTOF	splash10-0f6t-1190000000-42c80bc5ca1423abe051	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7C-aglycone 40V, Negative-QTOF	splash10-0a4i-9530000000-3e7c1717a2f562ccab68	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7C-aglycone 10V, Positive-QTOF	splash10-000j-0690000000-ec96a4a11d14eb685c44	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7C-aglycone 20V, Positive-QTOF	splash10-000i-0930000000-3078ced552e17593c971	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7C-aglycone 40V, Positive-QTOF	splash10-0a7i-3900000000-2c439b37d343c55eb99b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7C-aglycone 10V, Negative-QTOF	splash10-0002-0090000000-4ccaf6c53a74e5f4abe9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7C-aglycone 20V, Negative-QTOF	splash10-0udi-0190000000-6229e8531568660c185a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7C-aglycone 40V, Negative-QTOF	splash10-0002-1920000000-3e3918f5e3d58aa4a2f2	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected and Quantified	0.00028 +/- 0.000035 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17585028	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.00024 +/- 0.000041 umol/mmol creatinine	Adult (>18 years old)	Both	After 15 day of phylloquinone depletion	17585028	details

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

FDB023420

KNApSAcK ID

Not Available

Chemspider ID

13628420

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

7073

PubChem Compound

20348793

PDB ID

Not Available

ChEBI ID

89489

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

Harrington DJ, Soper R, Edwards C, Savidge GF, Hodges SJ, Shearer MJ: Determination of the urinary aglycone metabolites of vitamin K by HPLC with redox-mode electrochemical detection. J Lipid Res. 2005 May;46(5):1053-60. Epub 2005 Feb 1. [PubMed:15722567 ]
Watanabe M, Toyoda M, Imada I, Morimoto H: Ubiquinone and related compounds. XXVI. The urinary metabolites of phylloquinone and alpha-tocopherol. Chem Pharm Bull (Tokyo). 1974 Jan;22(1):176-82. [PubMed:4833371 ]
McBurney A, Shearer MJ, Barkhan P: Preparative isolation and characterization of the urinary aglycones of vitamin K1 (phylloquinone in man. Biochem Med. 1980 Dec;24(3):250-67. [PubMed:7306367 ]

Showing metabocard for 7C-aglycone (HMDB0004808)

MOL for HMDB0004808 (7C-aglycone)

3D MOL for HMDB0004808 (7C-aglycone)

3D SDF for HMDB0004808 (7C-aglycone)

3D-SDF for HMDB0004808 (7C-aglycone)

PDB for HMDB0004808 (7C-aglycone)

3D PDB for HMDB0004808 (7C-aglycone)

SMILES for HMDB0004808 (7C-aglycone)

INCHI for HMDB0004808 (7C-aglycone)

Structure for HMDB0004808 (7C-aglycone)

3D Structure for HMDB0004808 (7C-aglycone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra