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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-09-16 14:15:28 UTC

Update Date

2020-09-04 21:01:36 UTC

HMDB ID

HMDB0129335

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Khrinone B

Description

Khrinone B belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone. BioTransformer predicts that khrinone B is a product of pratensein metabolism via a hydroxylation-of-benzene-para-to-edg reaction catalyzed by CYP1A2, CYP2C9, and CYP2D6 enzymes (PMID: 30612223 ).

Structure

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

HMDB0129335
     RDKit          3D
Khrinone B
 35 37  0  0  0  0  0  0  0  0999 V2000
   -6.1980   -0.4794   -0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2668    0.5578   -0.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8986    0.3390   -0.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3909   -0.8529    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0127   -1.0307    0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5726   -2.2504    0.8822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1220   -0.0169    0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3308   -0.1549    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8282   -0.5715    1.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1150   -0.6774    1.8551 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429   -0.4071    0.9603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3797   -0.5403    1.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3302   -0.2540    0.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6708   -0.4167    0.6540 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336    0.1636   -0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5757    0.3102   -1.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2932    0.7296   -2.4995 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6174    0.0186   -0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2605    0.1460   -0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8747    0.5264   -1.6708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6301    1.1838   -0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0010    1.3564   -0.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5087    2.5536   -0.9166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2311   -0.0488   -0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1860   -1.2965   -0.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9517   -0.9550    0.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0845   -1.6529    0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6161   -2.4685    1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1778   -0.8229    2.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6177   -0.8788    2.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2328    0.2920    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7004    0.3863   -1.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4948    0.9166   -2.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    1.9931   -0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8699    3.3145   -1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
  7 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 19  8  1  0
 18 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 21 34  1  0
 23 35  1  0
M  END


  Mrv1652309042020412D          

 23 25  0  0  0  0            999 V2000
 9999.3090 9998.9513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.0213 9998.5419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.878910000.1923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.455310001.4360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.8789 9998.5419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.5946 9998.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.882910001.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.168310001.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.168310000.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8828 9999.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1655 9999.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.451110000.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7365 9999.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7365 9998.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4510 9998.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1655 9998.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.309210001.4326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.594710001.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.594710000.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3092 9999.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.023710000.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.023710001.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8833 9998.9576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  8  4  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
 14  2  1  0  0  0  0
 11  3  1  0  0  0  0
 16  5  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
 21 22  2  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
  1 20  2  0  0  0  0
 21 13  1  0  0  0  0
 18  7  2  0  0  0  0
 10 19  2  0  0  0  0
 10 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0129335

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(O)=C(C=C1O)C1=COC2=CC(O)=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O7/c1-22-13-5-10(18)8(4-11(13)19)9-6-23-14-3-7(17)2-12(20)15(14)16(9)21/h2-6,17-20H,1H3

> <INCHI_KEY>
HSMWTKNHVZRTCO-UHFFFAOYSA-N

> <FORMULA>
C16H12O7

> <MOLECULAR_WEIGHT>
316.265

> <EXACT_MASS>
316.058302726

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
30.457731952313583

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
2.6156358023333333

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.08737198390752

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.540746141393161

> <JCHEM_PKA_STRONGEST_BASIC>
-4.774016923304983

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
80.12700000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
khrinone B

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0129335
     RDKit          3D
Khrinone B
 35 37  0  0  0  0  0  0  0  0999 V2000
   -6.1980   -0.4794   -0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2668    0.5578   -0.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8986    0.3390   -0.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3909   -0.8529    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0127   -1.0307    0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5726   -2.2504    0.8822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1220   -0.0169    0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3308   -0.1549    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8282   -0.5715    1.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1150   -0.6774    1.8551 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429   -0.4071    0.9603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3797   -0.5403    1.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3302   -0.2540    0.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6708   -0.4167    0.6540 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336    0.1636   -0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5757    0.3102   -1.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2932    0.7296   -2.4995 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6174    0.0186   -0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2605    0.1460   -0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8747    0.5264   -1.6708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6301    1.1838   -0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0010    1.3564   -0.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5087    2.5536   -0.9166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2311   -0.0488   -0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1860   -1.2965   -0.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9517   -0.9550    0.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0845   -1.6529    0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6161   -2.4685    1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1778   -0.8229    2.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6177   -0.8788    2.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2328    0.2920    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7004    0.3863   -1.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4948    0.9166   -2.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    1.9931   -0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8699    3.3145   -1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
  7 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 19  8  1  0
 18 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 21 34  1  0
 23 35  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0    8665.3778664.709   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8666.7068663.945   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8672.0418667.026   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8660.0508669.347   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8672.0418663.945   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8673.3778664.717   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8662.7158669.341   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8661.3818668.571   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8661.3818667.031   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.7158666.261   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8670.7098666.256   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8669.3758667.026   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8668.0418666.256   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8668.0418664.716   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8669.3758663.946   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8670.7098664.716   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8665.3778669.341   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8664.0438668.571   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.0438667.031   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8665.3778666.261   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8666.7118667.031   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8666.7118668.571   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8662.7158664.721   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   14                                                            
CONECT    3   11                                                            
CONECT    4    8                                                            
CONECT    5    6   16                                                       
CONECT    6    5                                                            
CONECT    7    8   18                                                       
CONECT    8    7    9    4                                                  
CONECT    9    8   10                                                       
CONECT   10    9   19   23                                                  
CONECT   11   12   16    3                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15    2                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11    5                                                  
CONECT   17   18   22                                                       
CONECT   18   19   17    7                                                  
CONECT   19   18   20   10                                                  
CONECT   20   19   21    1                                                  
CONECT   21   20   22   13                                                  
CONECT   22   21   17                                                       
CONECT   23   10                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0129335
HETATM    1  C1  UNL     1      -6.198  -0.479  -0.169  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.267   0.558  -0.422  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.899   0.339  -0.211  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.391  -0.853   0.240  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.013  -1.031   0.435  1.00  0.00           C  
HETATM    6  O2  UNL     1      -1.573  -2.250   0.882  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.122  -0.017   0.183  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.331  -0.155   0.422  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.828  -0.572   1.640  1.00  0.00           C  
HETATM   10  O3  UNL     1       2.115  -0.677   1.855  1.00  0.00           O  
HETATM   11  C8  UNL     1       3.043  -0.407   0.960  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.380  -0.540   1.241  1.00  0.00           C  
HETATM   13  C10 UNL     1       5.330  -0.254   0.288  1.00  0.00           C  
HETATM   14  O4  UNL     1       6.671  -0.417   0.654  1.00  0.00           O  
HETATM   15  C11 UNL     1       4.934   0.164  -0.939  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.576   0.310  -1.256  1.00  0.00           C  
HETATM   17  O5  UNL     1       3.293   0.730  -2.499  1.00  0.00           O  
HETATM   18  C13 UNL     1       2.617   0.019  -0.287  1.00  0.00           C  
HETATM   19  C14 UNL     1       1.261   0.146  -0.559  1.00  0.00           C  
HETATM   20  O6  UNL     1       0.875   0.526  -1.671  1.00  0.00           O  
HETATM   21  C15 UNL     1      -1.630   1.184  -0.271  1.00  0.00           C  
HETATM   22  C16 UNL     1      -3.001   1.356  -0.465  1.00  0.00           C  
HETATM   23  O7  UNL     1      -3.509   2.554  -0.917  1.00  0.00           O  
HETATM   24  H1  UNL     1      -7.231  -0.049  -0.036  1.00  0.00           H  
HETATM   25  H2  UNL     1      -6.186  -1.296  -0.893  1.00  0.00           H  
HETATM   26  H3  UNL     1      -5.952  -0.955   0.827  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.084  -1.653   0.438  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.616  -2.468   1.025  1.00  0.00           H  
HETATM   29  H6  UNL     1       0.178  -0.823   2.461  1.00  0.00           H  
HETATM   30  H7  UNL     1       4.618  -0.879   2.247  1.00  0.00           H  
HETATM   31  H8  UNL     1       7.233   0.292   1.060  1.00  0.00           H  
HETATM   32  H9  UNL     1       5.700   0.386  -1.685  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.495   0.917  -2.998  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.935   1.993  -0.472  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.870   3.315  -1.110  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   27
CONECT    5    6    7    7
CONECT    6   28
CONECT    7    8   21
CONECT    8    9    9   19
CONECT    9   10   29
CONECT   10   11
CONECT   11   12   12   18
CONECT   12   13   30
CONECT   13   14   15   15
CONECT   14   31
CONECT   15   16   32
CONECT   16   17   18   18
CONECT   17   33
CONECT   18   19
CONECT   19   20   20
CONECT   21   22   22   34
CONECT   22   23
CONECT   23   35
END

HMDB0129335
     RDKit          3D
Khrinone B
 35 37  0  0  0  0  0  0  0  0999 V2000
   -6.1980   -0.4794   -0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2668    0.5578   -0.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8986    0.3390   -0.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3909   -0.8529    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0127   -1.0307    0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5726   -2.2504    0.8822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1220   -0.0169    0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3308   -0.1549    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8282   -0.5715    1.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1150   -0.6774    1.8551 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429   -0.4071    0.9603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3797   -0.5403    1.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3302   -0.2540    0.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6708   -0.4167    0.6540 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336    0.1636   -0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5757    0.3102   -1.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2932    0.7296   -2.4995 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6174    0.0186   -0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2605    0.1460   -0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8747    0.5264   -1.6708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6301    1.1838   -0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0010    1.3564   -0.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5087    2.5536   -0.9166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2311   -0.0488   -0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1860   -1.2965   -0.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9517   -0.9550    0.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0845   -1.6529    0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6161   -2.4685    1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1778   -0.8229    2.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6177   -0.8788    2.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2328    0.2920    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7004    0.3863   -1.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4948    0.9166   -2.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    1.9931   -0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8699    3.3145   -1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
  7 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 19  8  1  0
 18 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  9 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 21 34  1  0
 23 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(2,5-Dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one	HMDB
Khrinone B	HMDB

Chemical Formula

C₁₆H₁₂O₇

Average Molecular Weight

316.265

Monoisotopic Molecular Weight

316.058302726

IUPAC Name

3-(2,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

Traditional Name

khrinone B

CAS Registry Number

1201493-79-9

SMILES

COC1=CC(O)=C(C=C1O)C1=COC2=CC(O)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C16H12O7/c1-22-13-5-10(18)8(4-11(13)19)9-6-23-14-3-7(17)2-12(20)15(14)16(9)21/h2-6,17-20H,1H3

InChI Key

HSMWTKNHVZRTCO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

3'-hydroxy,4'-methoxyisoflavonoids

Alternative Parents

Substituents

4p-o-methylisoflavone
3'-hydroxy,4'-methoxyisoflavonoid
Isoflavone
Hydroxyisoflavonoid
Chromone
Methoxyphenol
Benzopyran
1-benzopyran
Phenoxy compound
Hydroquinone
Anisole
Phenol ether
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0129335)

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	2.65	ALOGPS
logP	2.62	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.54	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.13 m³·mol⁻¹	ChemAxon
Polarizability	30.46 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	172.058	30932474
DeepCCS	[M-H]-	169.7	30932474
DeepCCS	[M-2H]-	203.075	30932474
DeepCCS	[M+Na]+	178.377	30932474
AllCCS	[M+H]+	171.6	32859911
AllCCS	[M+H-H2O]+	168.1	32859911
AllCCS	[M+NH4]+	174.9	32859911
AllCCS	[M+Na]+	175.8	32859911
AllCCS	[M-H]-	171.5	32859911
AllCCS	[M+Na-2H]-	170.8	32859911
AllCCS	[M+HCOO]-	170.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Khrinone B	COC1=CC(O)=C(C=C1O)C1=COC2=CC(O)=CC(O)=C2C1=O	4985.1	Standard polar	33892256
Khrinone B	COC1=CC(O)=C(C=C1O)C1=COC2=CC(O)=CC(O)=C2C1=O	2973.0	Standard non polar	33892256
Khrinone B	COC1=CC(O)=C(C=C1O)C1=COC2=CC(O)=CC(O)=C2C1=O	3197.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Khrinone B,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1O	3221.5	Semi standard non polar	33892256
Khrinone B,1TMS,isomer #2	COC1=CC(O)=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C	3195.4	Semi standard non polar	33892256
Khrinone B,1TMS,isomer #3	COC1=CC(O)=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C=C1O	3241.4	Semi standard non polar	33892256
Khrinone B,1TMS,isomer #4	COC1=CC(O)=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O	3210.0	Semi standard non polar	33892256
Khrinone B,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C=C1O	3091.2	Semi standard non polar	33892256
Khrinone B,2TMS,isomer #2	COC1=CC(O[Si](C)(C)C)=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O	3066.7	Semi standard non polar	33892256
Khrinone B,2TMS,isomer #3	COC1=CC(O[Si](C)(C)C)=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C	3103.0	Semi standard non polar	33892256
Khrinone B,2TMS,isomer #4	COC1=CC(O)=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C	3060.8	Semi standard non polar	33892256
Khrinone B,2TMS,isomer #5	COC1=CC(O)=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C	3042.3	Semi standard non polar	33892256
Khrinone B,2TMS,isomer #6	COC1=CC(O)=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O	3079.7	Semi standard non polar	33892256
Khrinone B,3TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O	3012.5	Semi standard non polar	33892256
Khrinone B,3TMS,isomer #2	COC1=CC(O[Si](C)(C)C)=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C	3036.4	Semi standard non polar	33892256
Khrinone B,3TMS,isomer #3	COC1=CC(O[Si](C)(C)C)=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C	3020.1	Semi standard non polar	33892256
Khrinone B,3TMS,isomer #4	COC1=CC(O)=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C	2997.9	Semi standard non polar	33892256
Khrinone B,4TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C	3000.1	Semi standard non polar	33892256
Khrinone B,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1O	3487.8	Semi standard non polar	33892256
Khrinone B,1TBDMS,isomer #2	COC1=CC(O)=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3495.0	Semi standard non polar	33892256
Khrinone B,1TBDMS,isomer #3	COC1=CC(O)=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C=C1O	3522.8	Semi standard non polar	33892256
Khrinone B,1TBDMS,isomer #4	COC1=CC(O)=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O	3502.8	Semi standard non polar	33892256
Khrinone B,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C=C1O	3623.0	Semi standard non polar	33892256
Khrinone B,2TBDMS,isomer #2	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O	3596.1	Semi standard non polar	33892256
Khrinone B,2TBDMS,isomer #3	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3643.7	Semi standard non polar	33892256
Khrinone B,2TBDMS,isomer #4	COC1=CC(O)=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3652.3	Semi standard non polar	33892256
Khrinone B,2TBDMS,isomer #5	COC1=CC(O)=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3640.6	Semi standard non polar	33892256
Khrinone B,2TBDMS,isomer #6	COC1=CC(O)=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O	3637.9	Semi standard non polar	33892256
Khrinone B,3TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O	3718.3	Semi standard non polar	33892256
Khrinone B,3TBDMS,isomer #2	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3753.8	Semi standard non polar	33892256
Khrinone B,3TBDMS,isomer #3	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3729.6	Semi standard non polar	33892256
Khrinone B,3TBDMS,isomer #4	COC1=CC(O)=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3734.2	Semi standard non polar	33892256
Khrinone B,4TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3865.3	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 - Khrinone B GC-MS (4 TMS) - 70eV, Positive	splash10-001c-0030190000-47d9ab0e40e72d92050a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Khrinone B GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0392000000-6e1ed8b3f12f12a5b1e7	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Khrinone B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Khrinone B 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 - Khrinone B 10V, Positive-QTOF	splash10-014i-0029000000-a64abdf63ba6c4442dde	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone B 20V, Positive-QTOF	splash10-00kr-0595000000-6fc55ccead5fcc902297	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone B 40V, Positive-QTOF	splash10-0iki-1890000000-a6c11480135afa5c291b	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone B 10V, Negative-QTOF	splash10-014i-0009000000-7570a5299770f1ee67bf	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone B 20V, Negative-QTOF	splash10-00or-0966000000-709deeebbd3302fce62e	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone B 40V, Negative-QTOF	splash10-0pi9-2690000000-81abc48cbe7e4ae98b20	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone B 10V, Negative-QTOF	splash10-014i-0009000000-9039cd212321ec38115d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone B 20V, Negative-QTOF	splash10-00kb-0094000000-362937abc502fc63bfd7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone B 40V, Negative-QTOF	splash10-0udi-0290000000-4c544a85aa10f5f3b155	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone B 10V, Positive-QTOF	splash10-014i-0009000000-86072cf41042a798319c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone B 20V, Positive-QTOF	splash10-014i-0049000000-e5cba97ec986afcf063f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Khrinone B 40V, Positive-QTOF	splash10-0udl-0791000000-4f0b5e7f68aca50294f0	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB088186

KNApSAcK ID

Not Available

Chemspider ID

24660421

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44613667

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

Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5. [PubMed:30612223 ]

Showing metabocard for Khrinone B (HMDB0129335)

MOL for HMDB0129335 (Khrinone B)

3D MOL for HMDB0129335 (Khrinone B)

3D SDF for HMDB0129335 (Khrinone B)

3D-SDF for HMDB0129335 (Khrinone B)

PDB for HMDB0129335 (Khrinone B)

3D PDB for HMDB0129335 (Khrinone B)

SMILES for HMDB0129335 (Khrinone B)

INCHI for HMDB0129335 (Khrinone B)

Structure for HMDB0129335 (Khrinone B)

3D Structure for HMDB0129335 (Khrinone B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra