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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:50:50 UTC

Update Date

2021-09-26 23:12:03 UTC

HMDB ID

HMDB0256412

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Phenolphthalein

Description

Phenolphthalein, also known as modane, belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone. Phenolphthalein is a drug which is used for over a century as a laxative. Phenolphthalein is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Based on a literature review very few articles have been published on Phenolphthalein. This compound has been identified in human blood as reported by (PMID: 31557052 ). Phenolphthalein is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Phenolphthalein 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

HMDB0256412
     RDKit          3D
Phenolphthalein
 38 41  0  0  0  0  0  0  0  0999 V2000
   -0.3525    3.1199   -2.6197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068    2.3471   -1.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1895    0.9877   -1.7156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0195    0.3636   -0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2441   -0.4560   -0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6043   -1.3613   -1.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7262   -2.1520   -1.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5280   -2.0402   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6505   -2.8351    0.0787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -1.1350    0.9543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0498   -0.3545    0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2054   -0.4622   -0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5400   -1.2515    0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6859   -2.0126    0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4847   -2.0088   -0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6267   -2.7962   -0.7117 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1595   -1.2210   -1.7566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0174   -0.4648   -1.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0852    1.5019    0.4808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2656    1.6521    1.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3229    2.9065    2.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2008    4.0453    1.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0220    3.9295    0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0329    2.6904   -0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9906   -1.4777   -2.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9931   -2.8547   -1.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2947   -2.8373    0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7810   -1.0469    1.8255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8193    0.3317    1.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9399   -1.2922    1.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9333   -2.6348    1.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6054   -3.7405   -1.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8001   -1.2385   -2.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7508    0.1536   -2.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3682    0.7964    2.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4623    2.9812    3.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2436    5.0293    2.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0768    4.8378   -0.2625 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  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  4 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24  2  1  0
 11  5  1  0
 18 12  1  0
 24 19  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
 21 36  1  0
 22 37  1  0
 23 38  1  0
M  END

4824
  Mrv0541 02231217562D          

 24 27  0  0  0  0            999 V2000
    4.3411   -1.2316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -2.6797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1421   -0.2284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8453    2.5725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -0.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6802   -0.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6060    0.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -1.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1640   -1.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1591    0.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171    0.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7993    0.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9846   -1.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9055    1.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8377    0.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5457    1.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3215   -0.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0989    1.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1 10  1  0  0  0  0
  2 10  2  0  0  0  0
  3 23  1  0  0  0  0
  4 24  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  2  0  0  0  0
  7 14  1  0  0  0  0
  8 13  2  0  0  0  0
  8 15  1  0  0  0  0
  9 10  1  0  0  0  0
  9 16  2  0  0  0  0
 11 17  1  0  0  0  0
 12 19  1  0  0  0  0
 13 20  1  0  0  0  0
 14 21  2  0  0  0  0
 15 22  2  0  0  0  0
 16 18  1  0  0  0  0
 17 18  2  0  0  0  0
 19 23  2  0  0  0  0
 20 24  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256412

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)C1(OC(=O)C2=CC=CC=C12)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H14O4/c21-15-9-5-13(6-10-15)20(14-7-11-16(22)12-8-14)18-4-2-1-3-17(18)19(23)24-20/h1-12,21-22H

> <INCHI_KEY>
KJFMBFZCATUALV-UHFFFAOYSA-N

> <FORMULA>
C20H14O4

> <MOLECULAR_WEIGHT>
318.3228

> <EXACT_MASS>
318.089208936

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.65116169123185

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,3-bis(4-hydroxyphenyl)-1,3-dihydro-2-benzofuran-1-one

> <ALOGPS_LOGP>
4.41

> <JCHEM_LOGP>
4.353301456333334

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.759493314012811

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.157433300427105

> <JCHEM_PKA_STRONGEST_BASIC>
-5.959855476912179

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
91.03730000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.92e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenolphthalein

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256412
     RDKit          3D
Phenolphthalein
 38 41  0  0  0  0  0  0  0  0999 V2000
   -0.3525    3.1199   -2.6197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068    2.3471   -1.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1895    0.9877   -1.7156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0195    0.3636   -0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2441   -0.4560   -0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6043   -1.3613   -1.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7262   -2.1520   -1.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5280   -2.0402   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6505   -2.8351    0.0787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -1.1350    0.9543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0498   -0.3545    0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2054   -0.4622   -0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5400   -1.2515    0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6859   -2.0126    0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4847   -2.0088   -0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6267   -2.7962   -0.7117 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1595   -1.2210   -1.7566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0174   -0.4648   -1.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0852    1.5019    0.4808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2656    1.6521    1.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3229    2.9065    2.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2008    4.0453    1.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0220    3.9295    0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0329    2.6904   -0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9906   -1.4777   -2.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9931   -2.8547   -1.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2947   -2.8373    0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7810   -1.0469    1.8255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8193    0.3317    1.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9399   -1.2922    1.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9333   -2.6348    1.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6054   -3.7405   -1.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8001   -1.2385   -2.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7508    0.1536   -2.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3682    0.7964    2.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4623    2.9812    3.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2436    5.0293    2.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0768    4.8378   -0.2625 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  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  4 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24  2  1  0
 11  5  1  0
 18 12  1  0
 24 19  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
 21 36  1  0
 22 37  1  0
 23 38  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 4824                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.103  -2.299   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.683  -5.002   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.332  -0.426   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.311   4.802   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.205  -1.060   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747  -1.529   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.736  -0.902   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.731   0.406   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747  -3.069   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.205  -3.538   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -0.759   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.639  -2.149   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.764   1.548   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.365   0.504   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.225   0.728   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414  -3.839   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080  -1.529   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.080  -3.069   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.171  -1.991   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.290   3.014   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.897   0.663   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.752   2.194   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.800  -0.585   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.785   3.336   0.000  0.00  0.00           C+0
CONECT    1    5   10                                                       
CONECT    2   10                                                            
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5    1    6    7    8                                             
CONECT    6    5    9   11                                                  
CONECT    7    5   12   14                                                  
CONECT    8    5   13   15                                                  
CONECT    9    6   10   16                                                  
CONECT   10    1    2    9                                                  
CONECT   11    6   17                                                       
CONECT   12    7   19                                                       
CONECT   13    8   20                                                       
CONECT   14    7   21                                                       
CONECT   15    8   22                                                       
CONECT   16    9   18                                                       
CONECT   17   11   18                                                       
CONECT   18   16   17                                                       
CONECT   19   12   23                                                       
CONECT   20   13   24                                                       
CONECT   21   14   23                                                       
CONECT   22   15   24                                                       
CONECT   23    3   19   21                                                  
CONECT   24    4   20   22                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0256412
HETATM    1  O1  UNL     1      -0.352   3.120  -2.620  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.207   2.347  -1.627  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.190   0.988  -1.716  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.020   0.364  -0.437  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.244  -0.456  -0.257  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.604  -1.361  -1.236  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.726  -2.152  -1.137  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.528  -2.040  -0.015  1.00  0.00           C  
HETATM    9  O3  UNL     1      -4.651  -2.835   0.079  1.00  0.00           O  
HETATM   10  C7  UNL     1      -3.160  -1.135   0.954  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.050  -0.355   0.853  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.205  -0.462  -0.526  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.540  -1.252   0.554  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.686  -2.013   0.452  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.485  -2.009  -0.666  1.00  0.00           C  
HETATM   16  O4  UNL     1       4.627  -2.796  -0.712  1.00  0.00           O  
HETATM   17  C13 UNL     1       3.160  -1.221  -1.757  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.017  -0.465  -1.650  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.085   1.502   0.481  1.00  0.00           C  
HETATM   20  C16 UNL     1       0.266   1.652   1.848  1.00  0.00           C  
HETATM   21  C17 UNL     1       0.323   2.907   2.451  1.00  0.00           C  
HETATM   22  C18 UNL     1       0.201   4.045   1.699  1.00  0.00           C  
HETATM   23  C19 UNL     1       0.022   3.929   0.349  1.00  0.00           C  
HETATM   24  C20 UNL     1      -0.033   2.690  -0.236  1.00  0.00           C  
HETATM   25  H1  UNL     1      -0.991  -1.478  -2.142  1.00  0.00           H  
HETATM   26  H2  UNL     1      -2.993  -2.855  -1.912  1.00  0.00           H  
HETATM   27  H3  UNL     1      -5.295  -2.837   0.837  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.781  -1.047   1.826  1.00  0.00           H  
HETATM   29  H5  UNL     1      -1.819   0.332   1.643  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.940  -1.292   1.466  1.00  0.00           H  
HETATM   31  H7  UNL     1       2.933  -2.635   1.326  1.00  0.00           H  
HETATM   32  H8  UNL     1       4.605  -3.741  -1.058  1.00  0.00           H  
HETATM   33  H9  UNL     1       3.800  -1.239  -2.612  1.00  0.00           H  
HETATM   34  H10 UNL     1       1.751   0.154  -2.490  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.368   0.796   2.484  1.00  0.00           H  
HETATM   36  H12 UNL     1       0.462   2.981   3.502  1.00  0.00           H  
HETATM   37  H13 UNL     1       0.244   5.029   2.158  1.00  0.00           H  
HETATM   38  H14 UNL     1      -0.077   4.838  -0.263  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   24
CONECT    3    4
CONECT    4    5   12   19
CONECT    5    6    6   11
CONECT    6    7   25
CONECT    7    8    8   26
CONECT    8    9   10
CONECT    9   27
CONECT   10   11   11   28
CONECT   11   29
CONECT   12   13   13   18
CONECT   13   14   30
CONECT   14   15   15   31
CONECT   15   16   17
CONECT   16   32
CONECT   17   18   18   33
CONECT   18   34
CONECT   19   20   20   24
CONECT   20   21   35
CONECT   21   22   22   36
CONECT   22   23   37
CONECT   23   24   24   38
END

HMDB0256412
     RDKit          3D
Phenolphthalein
 38 41  0  0  0  0  0  0  0  0999 V2000
   -0.3525    3.1199   -2.6197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068    2.3471   -1.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1895    0.9877   -1.7156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0195    0.3636   -0.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2441   -0.4560   -0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6043   -1.3613   -1.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7262   -2.1520   -1.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5280   -2.0402   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6505   -2.8351    0.0787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -1.1350    0.9543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0498   -0.3545    0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2054   -0.4622   -0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5400   -1.2515    0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6859   -2.0126    0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4847   -2.0088   -0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6267   -2.7962   -0.7117 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1595   -1.2210   -1.7566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0174   -0.4648   -1.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0852    1.5019    0.4808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2656    1.6521    1.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3229    2.9065    2.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2008    4.0453    1.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0220    3.9295    0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0329    2.6904   -0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9906   -1.4777   -2.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9931   -2.8547   -1.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2947   -2.8373    0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7810   -1.0469    1.8255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8193    0.3317    1.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9399   -1.2922    1.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9333   -2.6348    1.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6054   -3.7405   -1.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8001   -1.2385   -2.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7508    0.1536   -2.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3682    0.7964    2.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4623    2.9812    3.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2436    5.0293    2.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0768    4.8378   -0.2625 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  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  4 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24  2  1  0
 11  5  1  0
 18 12  1  0
 24 19  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
 21 36  1  0
 22 37  1  0
 23 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Modane	Kegg
3,3-Bis(4-hydroxyphenyl)phthalide	Kegg
Ap-la-day	MeSH
Mentholatum brand OF phenolphthalein	MeSH
Novartis brand OF phenolphthalein	MeSH
Schering-plough brand OF phenolphthalein	MeSH
Ex-lax	MeSH
manesco Brand OF phenolphthalein	MeSH
Thalinol	MeSH
Laxettes	MeSH
Feen-a-mint	MeSH
Key brand OF phenolphthalein	MeSH
Laxatone	MeSH
Thompson brand OF phenolphthalein	MeSH

Chemical Formula

C₂₀H₁₄O₄

Average Molecular Weight

318.3228

Monoisotopic Molecular Weight

318.089208936

IUPAC Name

3,3-bis(4-hydroxyphenyl)-1,3-dihydro-2-benzofuran-1-one

Traditional Name

phenolphthalein

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C1(OC(=O)C2=CC=CC=C12)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C20H14O4/c21-15-9-5-13(6-10-15)20(14-7-11-16(22)12-8-14)18-4-2-1-3-17(18)19(23)24-20/h1-12,21-22H

InChI Key

KJFMBFZCATUALV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Benzofuranones

Direct Parent

Benzofuranones

Alternative Parents

Substituents

Benzofuranone
Phthalide
Isobenzofuranone
Isocoumaran
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:34914 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0256412)

Source

Exogenous

Exogenous (HMDB: HMDB0256412)

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	4.41	ALOGPS
logP	4.35	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.16	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.04 m³·mol⁻¹	ChemAxon
Polarizability	32.65 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	207.841	30932474
DeepCCS	[M+Na]+	183.147	30932474
AllCCS	[M+H]+	174.8	32859911
AllCCS	[M+H-H2O]+	171.4	32859911
AllCCS	[M+NH4]+	178.0	32859911
AllCCS	[M+Na]+	178.9	32859911
AllCCS	[M-H]-	176.6	32859911
AllCCS	[M+Na-2H]-	175.4	32859911
AllCCS	[M+HCOO]-	174.3	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. Predicted by Afia on May 17, 2022.	7.32 minutes	32390414
Predicted by Siyang on May 30, 2022	14.7228 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.42 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3091.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	379.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	189.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	211.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	491.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	764.4 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	596.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	71.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1386.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	550.5 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	1465.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	451.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	510.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	366.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	198.9 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	52.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenolphthalein	OC1=CC=C(C=C1)C1(OC(=O)C2=CC=CC=C12)C1=CC=C(O)C=C1	4207.5	Standard polar	33892256
Phenolphthalein	OC1=CC=C(C=C1)C1(OC(=O)C2=CC=CC=C12)C1=CC=C(O)C=C1	2836.0	Standard non polar	33892256
Phenolphthalein	OC1=CC=C(C=C1)C1(OC(=O)C2=CC=CC=C12)C1=CC=C(O)C=C1	3240.8	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 - Phenolphthalein GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xr-2592000000-d2bcec49a8083604a09a	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenolphthalein GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenolphthalein GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenolphthalein GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenolphthalein GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenolphthalein GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00fr-2690000000-8c929a0403799e4cd208	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenolphthalein LC-ESI-qTof , Positive-QTOF	splash10-004i-2950000000-2239a8a809fdd9396eaf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenolphthalein , positive-QTOF	splash10-004i-2950000000-2239a8a809fdd9396eaf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenolphthalein 60V, Negative-QTOF	splash10-0006-9000000000-7a5eb6309afb884c913c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenolphthalein 45V, Negative-QTOF	splash10-0006-9020000000-4bd55923e6b1a862ccdb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenolphthalein 90V, Positive-QTOF	splash10-014l-0900000000-b5db4dfe68685f5d0076	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenolphthalein 75V, Positive-QTOF	splash10-00kf-0900000000-972ff44a32df263bacd4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenolphthalein 15V, Negative-QTOF	splash10-0006-9000000000-5eb567dd72ea0ec54c42	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenolphthalein 30V, Negative-QTOF	splash10-0006-9020000000-0df8205f0ce2cb779ee4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenolphthalein 60V, Positive-QTOF	splash10-004m-0930000000-9bb4dffb81d39cc30175	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenolphthalein 45V, Positive-QTOF	splash10-004i-0290000000-582ef3c15cb87c4c8c15	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenolphthalein 15V, Positive-QTOF	splash10-014i-0019000000-333e80eef9eaed246bcc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenolphthalein 30V, Positive-QTOF	splash10-004i-0091000000-3949fe0e9e4846cf5036	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenolphthalein 90V, Negative-QTOF	splash10-0006-9000000000-494b0cf212c721029bcc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenolphthalein 75V, Negative-QTOF	splash10-0006-9000000000-4329eccdfee4b908e0ab	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenolphthalein 10V, Positive-QTOF	splash10-014i-0009000000-ea673bbdb67658cda386	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenolphthalein 20V, Positive-QTOF	splash10-014i-0149000000-edeb6f7d40e6c2a246a3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenolphthalein 40V, Positive-QTOF	splash10-004j-5690000000-b9f1fb8a1e6a00ac4204	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenolphthalein 10V, Negative-QTOF	splash10-014i-0019000000-2f93262e833438931955	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenolphthalein 20V, Negative-QTOF	splash10-00xr-0098000000-be431006a7dc4593473d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenolphthalein 40V, Negative-QTOF	splash10-00di-4090000000-b1557e38634d0b6eabb4	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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

DB04824

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4600

KEGG Compound ID

C14286

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenolphthalein

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

rw1273421

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 Phenolphthalein (HMDB0256412)

MOL for HMDB0256412 (Phenolphthalein)

3D MOL for HMDB0256412 (Phenolphthalein)

3D SDF for HMDB0256412 (Phenolphthalein)

3D-SDF for HMDB0256412 (Phenolphthalein)

PDB for HMDB0256412 (Phenolphthalein)

3D PDB for HMDB0256412 (Phenolphthalein)

SMILES for HMDB0256412 (Phenolphthalein)

INCHI for HMDB0256412 (Phenolphthalein)

Structure for HMDB0256412 (Phenolphthalein)

3D Structure for HMDB0256412 (Phenolphthalein)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra