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

2021-09-11 17:29:36 UTC

Update Date

2021-09-26 23:12:51 UTC

HMDB ID

HMDB0256874

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Protosappanin A

Description

5,14,15-trihydroxy-8-oxatricyclo[10.4.0.0²,⁷]hexadeca-1(16),2(7),3,5,12,14-hexaen-10-one belongs to the class of organic compounds known as alkyl aryl ethers. These are organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R' , where R is an alkyl group and R' is an aryl group. Based on a literature review very few articles have been published on 5,14,15-trihydroxy-8-oxatricyclo[10.4.0.0²,⁷]hexadeca-1(16),2(7),3,5,12,14-hexaen-10-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). Protosappanin a is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Protosappanin A 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

HMDB0256874
     RDKit          3D
Protosappanin A
 32 34  0  0  0  0  0  0  0  0999 V2000
   -0.1943    3.1515    1.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7018    2.5770    0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0557    2.9261   -0.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3164    2.2625   -0.9495 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7039    1.0548   -0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0640    1.0621   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7038   -0.0450    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0901   -0.0213    0.3238 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9598   -1.1399    0.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5867   -1.1736    0.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9756   -0.0679    0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4401   -0.4192    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4446   -1.7404   -0.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6560   -2.3948   -0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7514   -3.7379   -0.6696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8377   -1.7016   -0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0457   -2.3930   -0.1353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935   -0.3539    0.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6056    0.3117    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8867    1.7372    0.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5535    2.6931   -1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2701    4.0185   -0.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6790    1.8973   -0.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6926   -0.3474   -0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5066   -1.9731    1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9934   -1.9702    0.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4492   -2.2385   -0.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513   -4.1735   -0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8954   -1.8962    0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7292    0.1657    0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1554    1.8722    1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048    2.0575   -0.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20  2  1  0
 11  5  1  0
 19 12  1  0
  3 21  1  0
  3 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 13 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 20 31  1  0
 20 32  1  0
M  END


  Mrv1533004171502322D          

 20 22  0  0  0  0            999 V2000
    6.2178   -0.3698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4209   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8376    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407   -0.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8271   -1.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4105   -1.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4105   -2.4188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8271   -3.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0021   -3.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6864   -3.7643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4188   -2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4188   -1.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6219   -1.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4084   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6115   -0.3698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7782    0.7969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7886   -0.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0021   -1.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2074   -1.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
  5 19  1  0  0  0  0
 12 19  1  0  0  0  0
  6 20  2  0  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256874

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C2C(OCC(=O)CC3=CC(O)=C(O)C=C23)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O5/c16-9-1-2-11-12-6-14(19)13(18)4-8(12)3-10(17)7-20-15(11)5-9/h1-2,4-6,16,18-19H,3,7H2

> <INCHI_KEY>
MUKYVRVYBBYJSI-UHFFFAOYSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.256

> <EXACT_MASS>
272.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.825760068477678

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,14,15-trihydroxy-8-oxatricyclo[10.4.0.0²,⁷]hexadeca-1(16),2,4,6,12,14-hexaen-10-one

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
2.2208067819999995

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.692007017082862

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.924880978056045

> <JCHEM_PKA_STRONGEST_BASIC>
-4.910015501832821

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
71.89970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
protosappanin A

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256874
     RDKit          3D
Protosappanin A
 32 34  0  0  0  0  0  0  0  0999 V2000
   -0.1943    3.1515    1.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7018    2.5770    0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0557    2.9261   -0.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3164    2.2625   -0.9495 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7039    1.0548   -0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0640    1.0621   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7038   -0.0450    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0901   -0.0213    0.3238 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9598   -1.1399    0.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5867   -1.1736    0.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9756   -0.0679    0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4401   -0.4192    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4446   -1.7404   -0.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6560   -2.3948   -0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7514   -3.7379   -0.6696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8377   -1.7016   -0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0457   -2.3930   -0.1353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935   -0.3539    0.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6056    0.3117    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8867    1.7372    0.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5535    2.6931   -1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2701    4.0185   -0.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6790    1.8973   -0.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6926   -0.3474   -0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5066   -1.9731    1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9934   -1.9702    0.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4492   -2.2385   -0.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513   -4.1735   -0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8954   -1.8962    0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7292    0.1657    0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1554    1.8722    1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048    2.0575   -0.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20  2  1  0
 11  5  1  0
 19 12  1  0
  3 21  1  0
  3 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 13 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 20 31  1  0
 20 32  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0      11.607  -0.690   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.119  -1.089   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.030   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.543  -0.399   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.144  -1.886   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.233  -2.975   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.233  -4.515   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.144  -5.604   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.604  -5.604   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.015  -7.027   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.515  -4.515   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.515  -2.975   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.028  -2.576   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.629  -1.089   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.141  -0.690   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.718  -0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.319   1.488   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.205  -0.399   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.604  -1.886   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.720  -2.576   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18    5   12                                                  
CONECT   20    6    2                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0256874
HETATM    1  O1  UNL     1      -0.194   3.151   1.289  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.702   2.577   0.318  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.056   2.926  -0.898  1.00  0.00           C  
HETATM    4  O2  UNL     1       1.316   2.263  -0.949  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.704   1.055  -0.398  1.00  0.00           C  
HETATM    6  C4  UNL     1       3.064   1.062  -0.300  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.704  -0.045   0.232  1.00  0.00           C  
HETATM    8  O3  UNL     1       5.090  -0.021   0.324  1.00  0.00           O  
HETATM    9  C6  UNL     1       2.960  -1.140   0.655  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.587  -1.174   0.568  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.976  -0.068   0.036  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.440  -0.419   0.048  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.445  -1.740  -0.284  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.656  -2.395  -0.343  1.00  0.00           C  
HETATM   15  O4  UNL     1      -1.751  -3.738  -0.670  1.00  0.00           O  
HETATM   16  C12 UNL     1      -2.838  -1.702  -0.067  1.00  0.00           C  
HETATM   17  O5  UNL     1      -4.046  -2.393  -0.135  1.00  0.00           O  
HETATM   18  C13 UNL     1      -2.793  -0.354   0.265  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.606   0.312   0.329  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.887   1.737   0.680  1.00  0.00           C  
HETATM   21  H1  UNL     1      -0.553   2.693  -1.802  1.00  0.00           H  
HETATM   22  H2  UNL     1       0.270   4.018  -0.863  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.679   1.897  -0.618  1.00  0.00           H  
HETATM   24  H4  UNL     1       5.693  -0.347  -0.407  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.507  -1.973   1.061  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.993  -1.970   0.930  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.449  -2.238  -0.540  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.651  -4.173  -0.701  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.895  -1.896   0.062  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.729   0.166   0.474  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.155   1.872   1.731  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.705   2.058  -0.027  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4   21   22
CONECT    4    5
CONECT    5    6    6   11
CONECT    6    7   23
CONECT    7    8    9    9
CONECT    8   24
CONECT    9   10   25
CONECT   10   11   11   26
CONECT   11   12
CONECT   12   13   13   19
CONECT   13   14   27
CONECT   14   15   16   16
CONECT   15   28
CONECT   16   17   18
CONECT   17   29
CONECT   18   19   19   30
CONECT   19   20
CONECT   20   31   32
END

HMDB0256874
     RDKit          3D
Protosappanin A
 32 34  0  0  0  0  0  0  0  0999 V2000
   -0.1943    3.1515    1.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7018    2.5770    0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0557    2.9261   -0.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3164    2.2625   -0.9495 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7039    1.0548   -0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0640    1.0621   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7038   -0.0450    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0901   -0.0213    0.3238 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9598   -1.1399    0.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5867   -1.1736    0.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9756   -0.0679    0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4401   -0.4192    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4446   -1.7404   -0.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6560   -2.3948   -0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7514   -3.7379   -0.6696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8377   -1.7016   -0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0457   -2.3930   -0.1353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7935   -0.3539    0.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6056    0.3117    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8867    1.7372    0.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5535    2.6931   -1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2701    4.0185   -0.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6790    1.8973   -0.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6926   -0.3474   -0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5066   -1.9731    1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9934   -1.9702    0.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4492   -2.2385   -0.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513   -4.1735   -0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8954   -1.8962    0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7292    0.1657    0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1554    1.8722    1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048    2.0575   -0.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20  2  1  0
 11  5  1  0
 19 12  1  0
  3 21  1  0
  3 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 13 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 20 31  1  0
 20 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Sappanol b	MeSH

Chemical Formula

C₁₅H₁₂O₅

Average Molecular Weight

272.256

Monoisotopic Molecular Weight

272.068473486

IUPAC Name

5,14,15-trihydroxy-8-oxatricyclo[10.4.0.0²,⁷]hexadeca-1(16),2,4,6,12,14-hexaen-10-one

Traditional Name

protosappanin A

CAS Registry Number

Not Available

SMILES

OC1=CC=C2C(OCC(=O)CC3=CC(O)=C(O)C=C23)=C1

InChI Identifier

InChI=1S/C15H12O5/c16-9-1-2-11-12-6-14(19)13(18)4-8(12)3-10(17)7-20-15(11)5-9/h1-2,4-6,16,18-19H,3,7H2

InChI Key

MUKYVRVYBBYJSI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl aryl ethers. These are organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R' , where R is an alkyl group and R' is an aryl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Alkyl aryl ethers

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Cyclic ketone
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

catechols (CHEBI:69202 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.26	ALOGPS
logP	2.22	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	8.92	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.9 m³·mol⁻¹	ChemAxon
Polarizability	26.83 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	197.507	30932474
DeepCCS	[M+Na]+	173.072	30932474
AllCCS	[M+H]+	161.4	32859911
AllCCS	[M+H-H2O]+	157.9	32859911
AllCCS	[M+NH4]+	164.6	32859911
AllCCS	[M+Na]+	165.6	32859911
AllCCS	[M-H]-	161.6	32859911
AllCCS	[M+Na-2H]-	160.9	32859911
AllCCS	[M+HCOO]-	160.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Protosappanin A	OC1=CC=C2C(OCC(=O)CC3=CC(O)=C(O)C=C23)=C1	4410.1	Standard polar	33892256
Protosappanin A	OC1=CC=C2C(OCC(=O)CC3=CC(O)=C(O)C=C23)=C1	2792.3	Standard non polar	33892256
Protosappanin A	OC1=CC=C2C(OCC(=O)CC3=CC(O)=C(O)C=C23)=C1	2952.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Protosappanin A,4TMS,isomer #1	C[Si](C)(C)OC1=CC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2C2=CC=C(O[Si](C)(C)C)C=C2OC1	2843.5	Semi standard non polar	33892256
Protosappanin A,4TMS,isomer #1	C[Si](C)(C)OC1=CC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2C2=CC=C(O[Si](C)(C)C)C=C2OC1	2794.7	Standard non polar	33892256
Protosappanin A,4TMS,isomer #1	C[Si](C)(C)OC1=CC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2C2=CC=C(O[Si](C)(C)C)C=C2OC1	3128.9	Standard polar	33892256
Protosappanin A,4TMS,isomer #2	C[Si](C)(C)OC1=COC2=CC(O[Si](C)(C)C)=CC=C2C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2C1	2851.5	Semi standard non polar	33892256
Protosappanin A,4TMS,isomer #2	C[Si](C)(C)OC1=COC2=CC(O[Si](C)(C)C)=CC=C2C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2C1	2707.6	Standard non polar	33892256
Protosappanin A,4TMS,isomer #2	C[Si](C)(C)OC1=COC2=CC(O[Si](C)(C)C)=CC=C2C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2C1	3205.9	Standard polar	33892256
Protosappanin A,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC1	3764.7	Semi standard non polar	33892256
Protosappanin A,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC1	3612.0	Standard non polar	33892256
Protosappanin A,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC1	3441.1	Standard polar	33892256
Protosappanin A,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=COC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2C2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2C1	3749.0	Semi standard non polar	33892256
Protosappanin A,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=COC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2C2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2C1	3419.6	Standard non polar	33892256
Protosappanin A,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=COC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2C2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2C1	3519.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (Non-derivatized) - 70eV, Positive	splash10-007o-0290000000-d2d08505cb7096c81bf9	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TMS_3_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protosappanin A GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

113511

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Protosappanin A (HMDB0256874)

MOL for HMDB0256874 (Protosappanin A)

3D MOL for HMDB0256874 (Protosappanin A)

3D SDF for HMDB0256874 (Protosappanin A)

3D-SDF for HMDB0256874 (Protosappanin A)

PDB for HMDB0256874 (Protosappanin A)

3D PDB for HMDB0256874 (Protosappanin A)

SMILES for HMDB0256874 (Protosappanin A)

INCHI for HMDB0256874 (Protosappanin A)

Structure for HMDB0256874 (Protosappanin A)

3D Structure for HMDB0256874 (Protosappanin A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra