Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 20:47:10 UTC

Update Date

2021-09-26 22:50:38 UTC

HMDB ID

HMDB0243535

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(+)-cis-Khellactone

Description

9,10-dihydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety. Based on a literature review very few articles have been published on 9,10-dihydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). (+)-cis-khellactone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (+)-cis-Khellactone 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

HMDB0243535
     RDKit          3D
(+)-cis-Khellactone
 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.7545   -0.1984    0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3371   -0.2394   -0.4281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4342   -0.8522   -1.8189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5660   -1.1407    0.3585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1723   -1.1015    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6041   -2.2286    0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9807   -2.1705    0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5832   -0.9172    0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9543   -0.7839    0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793    0.4766    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6280    1.5587    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1620    2.7074   -0.0848 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3267    1.4193    0.0604 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8011    0.2127    0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4038    0.1296    0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4624    1.3243    0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005    2.3526   -0.3994 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7617    1.1224   -0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6801    2.0429    0.0335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1042   -1.2460    0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3587    0.3841   -0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109    0.3050    1.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8000   -1.7545   -1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0267   -0.1220   -2.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4676   -1.1525   -2.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1557   -3.2089    0.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186   -3.0431    0.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5752   -1.6851    0.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5287    0.6120   -0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6015    1.6384    1.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5038    2.1827   -1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6715    1.4336   -1.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5965    1.9422    1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  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  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  2  1  0
 15  5  1  0
 14  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END


  Mrv1652308231918572D          

 19 21  0  0  0  0            999 V2000
    4.6465   -2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  2  0  0  0  0
 11 10  1  0  0  0  0
 12  7  2  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  2  0  0  0  0
 16 11  1  0  0  0  0
 17 13  1  0  0  0  0
 18  9  1  0  0  0  0
 18 12  1  0  0  0  0
 19  8  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0243535

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)OC2=C(C(O)C1O)C1=C(C=CC(=O)O1)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O5/c1-14(2)13(17)11(16)10-8(19-14)5-3-7-4-6-9(15)18-12(7)10/h3-6,11,13,16-17H,1-2H3

> <INCHI_KEY>
HKXQUNNSKMWIKJ-UHFFFAOYSA-N

> <FORMULA>
C14H14O5

> <MOLECULAR_WEIGHT>
262.261

> <EXACT_MASS>
262.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.13669861986301

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9,10-dihydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one

> <ALOGPS_LOGP>
1.21

> <JCHEM_LOGP>
0.8133974599999996

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.00124267753813

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.556364734556386

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7357969855433533

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
67.54840000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9,10-dihydroxy-8,8-dimethyl-9H,10H-pyrano[2,3-h]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0243535
     RDKit          3D
(+)-cis-Khellactone
 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.7545   -0.1984    0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3371   -0.2394   -0.4281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4342   -0.8522   -1.8189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5660   -1.1407    0.3585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1723   -1.1015    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6041   -2.2286    0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9807   -2.1705    0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5832   -0.9172    0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9543   -0.7839    0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793    0.4766    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6280    1.5587    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1620    2.7074   -0.0848 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3267    1.4193    0.0604 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8011    0.2127    0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4038    0.1296    0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4624    1.3243    0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005    2.3526   -0.3994 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7617    1.1224   -0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6801    2.0429    0.0335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1042   -1.2460    0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3587    0.3841   -0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109    0.3050    1.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8000   -1.7545   -1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0267   -0.1220   -2.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4676   -1.1525   -2.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1557   -3.2089    0.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186   -3.0431    0.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5752   -1.6851    0.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5287    0.6120   -0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6015    1.6384    1.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5038    2.1827   -1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6715    1.4336   -1.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5965    1.9422    1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  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  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  2  1  0
 15  5  1  0
 14  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END

HEADER    PROTEIN                                 23-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-AUG-19         0                                  
HETATM    1  C   UNK     0       8.673  -4.840   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.673  -2.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.874  -1.183   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414  -1.183   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.206  -6.517   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.414  -6.517   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.494  -6.517   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.104  -5.184   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.724  -2.516   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3    5    7                                                       
CONECT    4    6    7                                                       
CONECT    5    3    8                                                       
CONECT    6    4    9                                                       
CONECT    7    3    4   12                                                  
CONECT    8    5   10   19                                                  
CONECT    9    6   15   18                                                  
CONECT   10    8   11   12                                                  
CONECT   11   10   13   16                                                  
CONECT   12    7   10   18                                                  
CONECT   13   11   14   17                                                  
CONECT   14    1    2   13   19                                             
CONECT   15    9                                                            
CONECT   16   11                                                            
CONECT   17   13                                                            
CONECT   18    9   12                                                       
CONECT   19    8   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0243535
HETATM    1  C1  UNL     1      -3.755  -0.198   0.134  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.337  -0.239  -0.428  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.434  -0.852  -1.819  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.566  -1.141   0.359  1.00  0.00           O  
HETATM    5  C4  UNL     1      -0.172  -1.102   0.303  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.604  -2.229   0.339  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.981  -2.170   0.282  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.583  -0.917   0.186  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.954  -0.784   0.126  1.00  0.00           C  
HETATM   10  C9  UNL     1       4.479   0.477   0.033  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.628   1.559   0.002  1.00  0.00           C  
HETATM   12  O2  UNL     1       4.162   2.707  -0.085  1.00  0.00           O  
HETATM   13  O3  UNL     1       2.327   1.419   0.060  1.00  0.00           O  
HETATM   14  C11 UNL     1       1.801   0.213   0.151  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.404   0.130   0.209  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.462   1.324   0.173  1.00  0.00           C  
HETATM   17  O4  UNL     1       0.301   2.353  -0.399  1.00  0.00           O  
HETATM   18  C14 UNL     1      -1.762   1.122  -0.516  1.00  0.00           C  
HETATM   19  O5  UNL     1      -2.680   2.043   0.034  1.00  0.00           O  
HETATM   20  H1  UNL     1      -4.104  -1.246   0.242  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.359   0.384  -0.586  1.00  0.00           H  
HETATM   22  H3  UNL     1      -3.811   0.305   1.104  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.800  -1.754  -1.923  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.027  -0.122  -2.575  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.468  -1.153  -2.073  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.156  -3.209   0.413  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.619  -3.043   0.309  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.575  -1.685   0.155  1.00  0.00           H  
HETATM   29  H10 UNL     1       5.529   0.612  -0.015  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.601   1.638   1.250  1.00  0.00           H  
HETATM   31  H12 UNL     1       0.504   2.183  -1.355  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.671   1.434  -1.597  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.596   1.942   1.021  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4   18
CONECT    3   23   24   25
CONECT    4    5
CONECT    5    6    6   15
CONECT    6    7   26
CONECT    7    8    8   27
CONECT    8    9   14
CONECT    9   10   10   28
CONECT   10   11   29
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15   15
CONECT   15   16
CONECT   16   17   18   30
CONECT   17   31
CONECT   18   19   32
CONECT   19   33
END

HMDB0243535
     RDKit          3D
(+)-cis-Khellactone
 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.7545   -0.1984    0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3371   -0.2394   -0.4281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4342   -0.8522   -1.8189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5660   -1.1407    0.3585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1723   -1.1015    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6041   -2.2286    0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9807   -2.1705    0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5832   -0.9172    0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9543   -0.7839    0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793    0.4766    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6280    1.5587    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1620    2.7074   -0.0848 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3267    1.4193    0.0604 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8011    0.2127    0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4038    0.1296    0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4624    1.3243    0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005    2.3526   -0.3994 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7617    1.1224   -0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6801    2.0429    0.0335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1042   -1.2460    0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3587    0.3841   -0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109    0.3050    1.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8000   -1.7545   -1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0267   -0.1220   -2.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4676   -1.1525   -2.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1557   -3.2089    0.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186   -3.0431    0.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5752   -1.6851    0.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5287    0.6120   -0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6015    1.6384    1.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5038    2.1827   -1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6715    1.4336   -1.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5965    1.9422    1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  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  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  2  1  0
 15  5  1  0
 14  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Carduben	MeSH, HMDB
Visnadine	MeSH, HMDB
Visnadin	MeSH, HMDB

Chemical Formula

C₁₄H₁₄O₅

Average Molecular Weight

262.261

Monoisotopic Molecular Weight

262.084123551

IUPAC Name

9,10-dihydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one

Traditional Name

9,10-dihydroxy-8,8-dimethyl-9H,10H-pyrano[2,3-h]chromen-2-one

CAS Registry Number

Not Available

SMILES

CC1(C)OC2=C(C(O)C1O)C1=C(C=CC(=O)O1)C=C2

InChI Identifier

InChI=1S/C14H14O5/c1-14(2)13(17)11(16)10-8(19-14)5-3-7-4-6-9(15)18-12(7)10/h3-6,11,13,16-17H,1-2H3

InChI Key

HKXQUNNSKMWIKJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Angular pyranocoumarins

Alternative Parents

Substituents

Angular pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Secondary alcohol
1,2-diol
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0138052)

Plant

Plant (HMDB: HMDB0138052)

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	1.21	ALOGPS
logP	0.81	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.56	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.55 m³·mol⁻¹	ChemAxon
Polarizability	26.14 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]+	163.786	30932474
DeepCCS	[M-H]-	161.428	30932474
DeepCCS	[M-2H]-	194.314	30932474
DeepCCS	[M+Na]+	169.879	30932474
AllCCS	[M+H]+	159.2	32859911
AllCCS	[M+H-H2O]+	155.3	32859911
AllCCS	[M+NH4]+	162.8	32859911
AllCCS	[M+Na]+	163.9	32859911
AllCCS	[M-H]-	162.6	32859911
AllCCS	[M+Na-2H]-	162.2	32859911
AllCCS	[M+HCOO]-	162.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter)). Predicted by Afia on May 17, 2022.	4.72 minutes	32390414
Predicted by Siyang on May 30, 2022	10.8851 minutes	33406817
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1592.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	289.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	139.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	180.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	65.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	404.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	449.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	95.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	758.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	335.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1233.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	285.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	275.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	313.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	289.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	31.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+)-cis-Khellactone	CC1(C)OC2=C(C(O)C1O)C1=C(C=CC(=O)O1)C=C2	3236.8	Standard polar	33892256
(+)-cis-Khellactone	CC1(C)OC2=C(C(O)C1O)C1=C(C=CC(=O)O1)C=C2	2352.4	Standard non polar	33892256
(+)-cis-Khellactone	CC1(C)OC2=C(C(O)C1O)C1=C(C=CC(=O)O1)C=C2	2457.7	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 - 9,10-dihydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one GC-MS (2 TMS) - 70eV, Positive	splash10-022c-4019000000-d4d9e3bc7bde5612bd43	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9,10-dihydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-008c-0590000000-a4e57786cdd9174c7a06	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9,10-dihydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9,10-dihydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9,10-dihydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9,10-dihydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9,10-dihydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9,10-dihydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9,10-dihydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9,10-dihydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	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 - (+)-cis-Khellactone 10V, Positive-QTOF	splash10-03di-1090000000-a3b6eac71173a66ebeaf	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-Khellactone 20V, Positive-QTOF	splash10-03ds-2690000000-9050c19ca9581179bcdc	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-Khellactone 40V, Positive-QTOF	splash10-00di-7900000000-c763a04df931aa95b82b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-Khellactone 10V, Negative-QTOF	splash10-03di-0190000000-3ce11ed2367cfbc8d68a	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-Khellactone 20V, Negative-QTOF	splash10-03dr-3390000000-0631c36d0921b9717c47	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-Khellactone 40V, Negative-QTOF	splash10-02mj-3910000000-f2285edef93acff8db1b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-Khellactone 10V, Negative-QTOF	splash10-03di-0190000000-eef4ac3339cbd253414e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-Khellactone 20V, Negative-QTOF	splash10-03di-0390000000-017f9e9e796f13bb6af1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-Khellactone 40V, Negative-QTOF	splash10-03l0-1950000000-a4cb6a2213199fe825ad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-Khellactone 10V, Positive-QTOF	splash10-03di-0090000000-8c8a06a3e71d5012f616	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-Khellactone 20V, Positive-QTOF	splash10-03di-0970000000-24f68df2b67be493978b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-cis-Khellactone 40V, Positive-QTOF	splash10-01ox-4920000000-bda11b37d7fcf5f262cf	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

FDB093038

KNApSAcK ID

Not Available

Chemspider ID

222495

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

253856

PDB ID

Not Available

ChEBI ID

168011

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 (+)-cis-Khellactone (HMDB0243535)

MOL for HMDB0243535 ((+)-cis-Khellactone)

3D MOL for HMDB0243535 ((+)-cis-Khellactone)

3D SDF for HMDB0243535 ((+)-cis-Khellactone)

3D-SDF for HMDB0243535 ((+)-cis-Khellactone)

PDB for HMDB0243535 ((+)-cis-Khellactone)

3D PDB for HMDB0243535 ((+)-cis-Khellactone)

SMILES for HMDB0243535 ((+)-cis-Khellactone)

INCHI for HMDB0243535 ((+)-cis-Khellactone)

Structure for HMDB0243535 ((+)-cis-Khellactone)

3D Structure for HMDB0243535 ((+)-cis-Khellactone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra