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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:43:49 UTC

Update Date

2021-09-26 23:11:00 UTC

HMDB ID

HMDB0255844

Secondary Accession Numbers

None

Metabolite Identification

Common Name

o-Cresolphthalein

Description

o-Cresolphthalein belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone. Based on a literature review a significant number of articles have been published on o-Cresolphthalein. This compound has been identified in human blood as reported by (PMID: 31557052 ). O-cresolphthalein is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically o-Cresolphthalein 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

  Mrv1652309112117442D          

 26 29  0  0  0  0            999 V2000
   -1.7192   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047    0.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047    1.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902    1.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243    1.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243    0.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4743    0.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894    1.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3249    2.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1454    2.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6303    1.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2948    0.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4810    2.9842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8400    2.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7192    1.6195    0.0000 O   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  2  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  8 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 21 24  1  0  0  0  0
 20 25  1  0  0  0  0
  3 26  1  0  0  0  0
M  END

HMDB0255844
     RDKit          3D
o-Cresolphthalein
 44 47  0  0  0  0  0  0  0  0999 V2000
    3.8871   -1.4216   -1.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8590   -1.3930   -0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9530   -0.3489   -0.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9874   -0.2862    0.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0068    0.8285    0.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3633    0.2223    0.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3979    0.5785    1.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6311   -0.0373    1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8107   -0.9963    0.3938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0251   -1.6161    0.2297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7800   -1.3682   -0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9269   -2.3816   -1.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5625   -0.7373   -0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2127    1.4639    2.0061 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5464    2.7768    1.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8304    3.6806    2.6385 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372    3.0406    0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7825    4.1683   -0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6913    4.1389   -1.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3485    2.9644   -2.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1023    1.8320   -1.6254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1941    1.8593   -0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9599   -1.3117    1.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8520   -2.3607    1.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8139   -2.4125    0.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7235   -3.4696    0.4980 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5094   -0.8049   -2.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8338   -0.9682   -1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1405   -2.4472   -1.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0186    0.4403   -1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2360    1.3297    2.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4785    0.2111    2.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8060   -1.3808    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5033   -2.0178   -2.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2917   -3.2587   -1.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9443   -2.7420   -1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7582   -1.0315   -0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488    5.0729    0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8809    5.0075   -2.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614    2.8837   -3.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1641    0.9286   -2.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1849   -1.2549    2.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -3.1518    2.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7379   -4.2290    1.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  4 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25  2  1  0
 22  5  1  0
 13  6  1  0
 22 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  7 31  1  0
  8 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 23 42  1  0
 24 43  1  0
 26 44  1  0
M  END

  Mrv1652309112117442D          

 26 29  0  0  0  0            999 V2000
   -1.7192   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047    0.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0047    1.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902    1.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243    1.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243    0.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4743    0.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894    1.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3249    2.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1454    2.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6303    1.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2948    0.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4810    2.9842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8400    2.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7192    1.6195    0.0000 O   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  2  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  8 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 21 24  1  0  0  0  0
 20 25  1  0  0  0  0
  3 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255844

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(O)C=CC(=C1)C1(OC(=O)C2=CC=CC=C12)C1=CC(C)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H18O4/c1-13-11-15(7-9-19(13)23)22(16-8-10-20(24)14(2)12-16)18-6-4-3-5-17(18)21(25)26-22/h3-12,23-24H,1-2H3

> <INCHI_KEY>
CPBJMKMKNCRKQB-UHFFFAOYSA-N

> <FORMULA>
C22H18O4

> <MOLECULAR_WEIGHT>
346.382

> <EXACT_MASS>
346.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
36.63071303884429

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.38

> <JCHEM_LOGP>
5.3801442349999995

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.1208283887503

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.518768375348378

> <JCHEM_PKA_STRONGEST_BASIC>
-5.945677348880012

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
101.1197

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.96e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,3-bis(4-hydroxy-3-methylphenyl)-2-benzofuran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255844
     RDKit          3D
o-Cresolphthalein
 44 47  0  0  0  0  0  0  0  0999 V2000
    3.8871   -1.4216   -1.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8590   -1.3930   -0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9530   -0.3489   -0.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9874   -0.2862    0.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0068    0.8285    0.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3633    0.2223    0.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3979    0.5785    1.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6311   -0.0373    1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8107   -0.9963    0.3938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0251   -1.6161    0.2297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7800   -1.3682   -0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9269   -2.3816   -1.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5625   -0.7373   -0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2127    1.4639    2.0061 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5464    2.7768    1.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8304    3.6806    2.6385 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372    3.0406    0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7825    4.1683   -0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6913    4.1389   -1.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3485    2.9644   -2.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1023    1.8320   -1.6254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1941    1.8593   -0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9599   -1.3117    1.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8520   -2.3607    1.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8139   -2.4125    0.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7235   -3.4696    0.4980 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5094   -0.8049   -2.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8338   -0.9682   -1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1405   -2.4472   -1.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0186    0.4403   -1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2360    1.3297    2.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4785    0.2111    2.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8060   -1.3808    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5033   -2.0178   -2.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2917   -3.2587   -1.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9443   -2.7420   -1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7582   -1.0315   -0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488    5.0729    0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8809    5.0075   -2.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614    2.8837   -3.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1641    0.9286   -2.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1849   -1.2549    2.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -3.1518    2.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7379   -4.2290    1.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  4 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25  2  1  0
 22  5  1  0
 13  6  1  0
 22 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  7 31  1  0
  8 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 23 42  1  0
 24 43  1  0
 26 44  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -3.209  -0.057   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.875   0.713   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.875   2.253   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.542   3.023   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.792   2.253   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.792   0.713   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.542  -0.057   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.220  -1.303   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.752   1.350   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.847   2.596   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.473   4.003   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.005   4.164   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.910   2.918   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.284   1.511   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.631   5.571   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.568   5.249   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.209   3.023   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9   17   18                                             
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    8                                                       
CONECT   18    8   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   21                                                            
CONECT   25   20                                                            
CONECT   26    3                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0255844
HETATM    1  C1  UNL     1       3.887  -1.422  -1.434  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.859  -1.393  -0.361  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.953  -0.349  -0.289  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.987  -0.286   0.689  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.007   0.829   0.789  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.363   0.222   0.690  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.398   0.578   1.523  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.631  -0.037   1.372  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.811  -0.996   0.394  1.00  0.00           C  
HETATM   10  O1  UNL     1      -5.025  -1.616   0.230  1.00  0.00           O  
HETATM   11  C10 UNL     1      -2.780  -1.368  -0.454  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.927  -2.382  -1.506  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.562  -0.737  -0.280  1.00  0.00           C  
HETATM   14  O2  UNL     1       0.213   1.464   2.006  1.00  0.00           O  
HETATM   15  C13 UNL     1       0.546   2.777   1.795  1.00  0.00           C  
HETATM   16  O3  UNL     1       0.830   3.681   2.639  1.00  0.00           O  
HETATM   17  C14 UNL     1       0.537   3.041   0.364  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.782   4.168  -0.413  1.00  0.00           C  
HETATM   19  C16 UNL     1       0.691   4.139  -1.782  1.00  0.00           C  
HETATM   20  C17 UNL     1       0.349   2.964  -2.403  1.00  0.00           C  
HETATM   21  C18 UNL     1       0.102   1.832  -1.625  1.00  0.00           C  
HETATM   22  C19 UNL     1       0.194   1.859  -0.240  1.00  0.00           C  
HETATM   23  C20 UNL     1       0.960  -1.312   1.599  1.00  0.00           C  
HETATM   24  C21 UNL     1       1.852  -2.361   1.546  1.00  0.00           C  
HETATM   25  C22 UNL     1       2.814  -2.412   0.563  1.00  0.00           C  
HETATM   26  O4  UNL     1       3.724  -3.470   0.498  1.00  0.00           O  
HETATM   27  H1  UNL     1       3.509  -0.805  -2.269  1.00  0.00           H  
HETATM   28  H2  UNL     1       4.834  -0.968  -1.057  1.00  0.00           H  
HETATM   29  H3  UNL     1       4.140  -2.447  -1.755  1.00  0.00           H  
HETATM   30  H4  UNL     1       2.019   0.440  -1.034  1.00  0.00           H  
HETATM   31  H5  UNL     1      -2.236   1.330   2.280  1.00  0.00           H  
HETATM   32  H6  UNL     1      -4.478   0.211   2.006  1.00  0.00           H  
HETATM   33  H7  UNL     1      -5.806  -1.381   0.821  1.00  0.00           H  
HETATM   34  H8  UNL     1      -2.503  -2.018  -2.480  1.00  0.00           H  
HETATM   35  H9  UNL     1      -2.292  -3.259  -1.204  1.00  0.00           H  
HETATM   36  H10 UNL     1      -3.944  -2.742  -1.645  1.00  0.00           H  
HETATM   37  H11 UNL     1      -0.758  -1.031  -0.940  1.00  0.00           H  
HETATM   38  H12 UNL     1       1.049   5.073   0.102  1.00  0.00           H  
HETATM   39  H13 UNL     1       0.881   5.008  -2.376  1.00  0.00           H  
HETATM   40  H14 UNL     1       0.261   2.884  -3.486  1.00  0.00           H  
HETATM   41  H15 UNL     1      -0.164   0.929  -2.149  1.00  0.00           H  
HETATM   42  H16 UNL     1       0.185  -1.255   2.378  1.00  0.00           H  
HETATM   43  H17 UNL     1       1.789  -3.152   2.292  1.00  0.00           H  
HETATM   44  H18 UNL     1       3.738  -4.229   1.135  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    3   25
CONECT    3    4   30
CONECT    4    5   23   23
CONECT    5    6   14   22
CONECT    6    7    7   13
CONECT    7    8   31
CONECT    8    9    9   32
CONECT    9   10   11
CONECT   10   33
CONECT   11   12   13   13
CONECT   12   34   35   36
CONECT   13   37
CONECT   14   15
CONECT   15   16   16   17
CONECT   17   18   18   22
CONECT   18   19   38
CONECT   19   20   20   39
CONECT   20   21   40
CONECT   21   22   22   41
CONECT   23   24   42
CONECT   24   25   25   43
CONECT   25   26
CONECT   26   44
END

HMDB0255844
     RDKit          3D
o-Cresolphthalein
 44 47  0  0  0  0  0  0  0  0999 V2000
    3.8871   -1.4216   -1.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8590   -1.3930   -0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9530   -0.3489   -0.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9874   -0.2862    0.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0068    0.8285    0.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3633    0.2223    0.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3979    0.5785    1.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6311   -0.0373    1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8107   -0.9963    0.3938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0251   -1.6161    0.2297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7800   -1.3682   -0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9269   -2.3816   -1.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5625   -0.7373   -0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2127    1.4639    2.0061 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5464    2.7768    1.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8304    3.6806    2.6385 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372    3.0406    0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7825    4.1683   -0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6913    4.1389   -1.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3485    2.9644   -2.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1023    1.8320   -1.6254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1941    1.8593   -0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9599   -1.3117    1.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8520   -2.3607    1.5457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8139   -2.4125    0.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7235   -3.4696    0.4980 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5094   -0.8049   -2.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8338   -0.9682   -1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1405   -2.4472   -1.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0186    0.4403   -1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2360    1.3297    2.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4785    0.2111    2.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8060   -1.3808    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5033   -2.0178   -2.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2917   -3.2587   -1.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9443   -2.7420   -1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7582   -1.0315   -0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488    5.0729    0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8809    5.0075   -2.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614    2.8837   -3.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1641    0.9286   -2.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1849   -1.2549    2.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890   -3.1518    2.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7379   -4.2290    1.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  4 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25  2  1  0
 22  5  1  0
 13  6  1  0
 22 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  7 31  1  0
  8 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 23 42  1  0
 24 43  1  0
 26 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,3'-Dimethylphenolphthalein	HMDB
Cresolphthalein	HMDB

Chemical Formula

C₂₂H₁₈O₄

Average Molecular Weight

346.382

Monoisotopic Molecular Weight

346.12050906

IUPAC Name

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

Traditional Name

3,3-bis(4-hydroxy-3-methylphenyl)-2-benzofuran-1-one

CAS Registry Number

Not Available

SMILES

CC1=C(O)C=CC(=C1)C1(OC(=O)C2=CC=CC=C12)C1=CC(C)=C(O)C=C1

InChI Identifier

InChI=1S/C22H18O4/c1-13-11-15(7-9-19(13)23)22(16-8-10-20(24)14(2)12-16)18-6-4-3-5-17(18)21(25)26-22/h3-12,23-24H,1-2H3

InChI Key

CPBJMKMKNCRKQB-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
O-cresol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Toluene
Monocyclic benzene moiety
Benzenoid
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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	3.38	ALOGPS
logP	5.38	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.52	ChemAxon
pKa (Strongest Basic)	-5.9	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	101.12 m³·mol⁻¹	ChemAxon
Polarizability	36.63 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]-	215.501	30932474
DeepCCS	[M+Na]+	190.71	30932474
AllCCS	[M+H]+	182.0	32859911
AllCCS	[M+H-H2O]+	178.7	32859911
AllCCS	[M+NH4]+	185.0	32859911
AllCCS	[M+Na]+	185.9	32859911
AllCCS	[M-H]-	184.3	32859911
AllCCS	[M+Na-2H]-	183.2	32859911
AllCCS	[M+HCOO]-	182.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
o-Cresolphthalein	CC1=C(O)C=CC(=C1)C1(OC(=O)C2=CC=CC=C12)C1=CC(C)=C(O)C=C1	4355.1	Standard polar	33892256
o-Cresolphthalein	CC1=C(O)C=CC(=C1)C1(OC(=O)C2=CC=CC=C12)C1=CC(C)=C(O)C=C1	2943.0	Standard non polar	33892256
o-Cresolphthalein	CC1=C(O)C=CC(=C1)C1(OC(=O)C2=CC=CC=C12)C1=CC(C)=C(O)C=C1	3346.9	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 - o-Cresolphthalein GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ktr-0659000000-f144cb8581a2a342775b	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - o-Cresolphthalein GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - o-Cresolphthalein GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - o-Cresolphthalein GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - o-Cresolphthalein GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - o-Cresolphthalein GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	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

62217

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

O-Cresolphthalein

METLIN ID

Not Available

PubChem Compound

68995

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 o-Cresolphthalein (HMDB0255844)

MOL for HMDB0255844 (o-Cresolphthalein)

3D MOL for HMDB0255844 (o-Cresolphthalein)

3D SDF for HMDB0255844 (o-Cresolphthalein)

3D-SDF for HMDB0255844 (o-Cresolphthalein)

PDB for HMDB0255844 (o-Cresolphthalein)

3D PDB for HMDB0255844 (o-Cresolphthalein)

SMILES for HMDB0255844 (o-Cresolphthalein)

INCHI for HMDB0255844 (o-Cresolphthalein)

Structure for HMDB0255844 (o-Cresolphthalein)

3D Structure for HMDB0255844 (o-Cresolphthalein)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra