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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:37:09 UTC

Update Date

2021-09-26 22:54:06 UTC

HMDB ID

HMDB0245557

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2',7'-Dichlorofluorescein

Description

2',7'-dichlorofluorescein, also known as fluorescein 27, belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring. Based on a literature review very few articles have been published on 2',7'-dichlorofluorescein. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2',7'-dichlorofluorescein is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2',7'-Dichlorofluorescein 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


  Mrv1652309112100372D          

 27 31  0  0  0  0            999 V2000
    6.2233   -2.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9686   -1.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1616   -1.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6094   -1.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8641   -2.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6711   -2.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1966   -3.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1963   -3.9852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5293   -2.6750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7844   -1.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9639   -1.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6281   -2.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8076   -2.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3229   -2.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6587   -1.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -1.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8150   -0.5553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355   -0.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9712    0.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7917    0.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765   -0.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9407   -1.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1202   -1.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0970   -0.2113    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.1275    1.1238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5024   -2.2345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4719   -3.5697    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 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
 10 23  1  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
 14 26  1  0  0  0  0
 13 27  1  0  0  0  0
M  END

HMDB0245557
     RDKit          3D
2',7'-Dichlorofluorescein
 37 41  0  0  0  0  0  0  0  0999 V2000
   -1.4502   -0.1085   -3.8018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0683    0.0098   -2.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1386   -0.7308   -1.9306 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115   -0.2900   -0.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3955    0.1794   -0.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8974    1.2110   -1.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1658    1.6986   -1.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8126    2.9798   -2.0593 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9530    1.1492   -0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2277    1.6194    0.1388 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4591    0.1396    0.7750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1688   -0.3566    0.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7107   -1.3829    1.4674 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4315   -1.8780    1.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0505   -2.8846    2.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3309   -3.3781    1.9768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550   -4.3834    2.8214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1269   -2.8478    0.9903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7606   -3.5053    0.8232 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6801   -1.8567    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3644   -1.3554    0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9546    0.8450   -0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2940    1.6982    0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2306    2.6855    0.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8732    2.8586   -0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5504    2.0177   -1.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5918    1.0139   -1.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2433    1.6178   -1.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5809    2.3446   -0.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0481   -0.3093    1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546   -3.3178    2.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1506   -4.7512    3.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3333   -1.4678   -0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8109    1.5977    1.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794    3.3454    1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6149    3.6458   -0.9227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0511    2.1476   -2.8113 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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  4 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27  2  1  0
 21  4  1  0
 27 22  1  0
 12  5  1  0
 21 14  1  0
  6 28  1  0
 10 29  1  0
 11 30  1  0
 15 31  1  0
 17 32  1  0
 20 33  1  0
 23 34  1  0
 24 35  1  0
 25 36  1  0
 26 37  1  0
M  END


  Mrv1652309112100372D          

 27 31  0  0  0  0            999 V2000
    6.2233   -2.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9686   -1.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1616   -1.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6094   -1.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8641   -2.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6711   -2.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1966   -3.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1963   -3.9852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5293   -2.6750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7844   -1.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9639   -1.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6281   -2.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8076   -2.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3229   -2.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6587   -1.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -1.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8150   -0.5553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355   -0.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9712    0.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7917    0.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765   -0.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9407   -1.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1202   -1.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0970   -0.2113    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.1275    1.1238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5024   -2.2345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4719   -3.5697    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 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
 10 23  1  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
 14 26  1  0  0  0  0
 13 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245557

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=C(Cl)C=C2C(OC3=CC(O)=C(Cl)C=C3C22OC(=O)C3=CC=CC=C23)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H10Cl2O5/c21-13-5-11-17(7-15(13)23)26-18-8-16(24)14(22)6-12(18)20(11)10-4-2-1-3-9(10)19(25)27-20/h1-8,23-24H

> <INCHI_KEY>
VFNKZQNIXUFLBC-UHFFFAOYSA-N

> <FORMULA>
C20H10Cl2O5

> <MOLECULAR_WEIGHT>
401.2

> <EXACT_MASS>
399.9905288

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
37.64144065083486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2',7'-dichloro-3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one

> <ALOGPS_LOGP>
3.95

> <JCHEM_LOGP>
5.0884321759999995

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.737873673443891

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.135351262241989

> <JCHEM_PKA_STRONGEST_BASIC>
-3.733864709074765

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
100.8297

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.39e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dichlorofluorescein

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0245557
     RDKit          3D
2',7'-Dichlorofluorescein
 37 41  0  0  0  0  0  0  0  0999 V2000
   -1.4502   -0.1085   -3.8018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0683    0.0098   -2.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1386   -0.7308   -1.9306 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115   -0.2900   -0.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3955    0.1794   -0.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8974    1.2110   -1.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1658    1.6986   -1.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8126    2.9798   -2.0593 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9530    1.1492   -0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2277    1.6194    0.1388 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4591    0.1396    0.7750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1688   -0.3566    0.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7107   -1.3829    1.4674 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4315   -1.8780    1.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0505   -2.8846    2.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3309   -3.3781    1.9768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550   -4.3834    2.8214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1269   -2.8478    0.9903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7606   -3.5053    0.8232 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6801   -1.8567    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3644   -1.3554    0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9546    0.8450   -0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2940    1.6982    0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2306    2.6855    0.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8732    2.8586   -0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5504    2.0177   -1.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5918    1.0139   -1.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2433    1.6178   -1.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5809    2.3446   -0.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0481   -0.3093    1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546   -3.3178    2.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1506   -4.7512    3.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3333   -1.4678   -0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8109    1.5977    1.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794    3.3454    1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6149    3.6458   -0.9227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0511    2.1476   -2.8113 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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  4 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27  2  1  0
 21  4  1  0
 27 22  1  0
 12  5  1  0
 21 14  1  0
  6 28  1  0
 10 29  1  0
 11 30  1  0
 15 31  1  0
 17 32  1  0
 20 33  1  0
 23 34  1  0
 24 35  1  0
 25 36  1  0
 26 37  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      11.617  -4.171   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.141  -2.706   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.635  -2.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.604  -3.529   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.080  -4.994   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.586  -5.315   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.834  -5.899   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.833  -7.439   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       6.588  -4.993   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.064  -3.529   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.533  -3.689   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.906  -5.096   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.374  -5.257   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.469  -4.011   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.096  -2.604   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.628  -2.443   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.255  -1.037   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.786  -0.876   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.413   0.531   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.945   0.691   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.849  -0.555   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.223  -1.962   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.691  -2.122   0.000  0.00  0.00           C+0
HETATM   24 Cl   UNK     0      11.381  -0.395   0.000  0.00  0.00          Cl+0
HETATM   25  O   UNK     0       9.571   2.098   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.938  -4.171   0.000  0.00  0.00           O+0
HETATM   27 Cl   UNK     0       2.747  -6.663   0.000  0.00  0.00          Cl+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    4   11   23                                             
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   27                                                  
CONECT   14   13   15   26                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22   10   18                                                  
CONECT   24   21                                                            
CONECT   25   20                                                            
CONECT   26   14                                                            
CONECT   27   13                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

COMPND    HMDB0245557
HETATM    1  O1  UNL     1      -1.450  -0.108  -3.802  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.068   0.010  -2.602  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.139  -0.731  -1.931  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.011  -0.290  -0.597  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.395   0.179  -0.362  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.897   1.211  -1.193  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.166   1.699  -1.039  1.00  0.00           C  
HETATM    8 CL1  UNL     1       3.813   2.980  -2.059  1.00  0.00          CL  
HETATM    9  C6  UNL     1       3.953   1.149  -0.037  1.00  0.00           C  
HETATM   10  O3  UNL     1       5.228   1.619   0.139  1.00  0.00           O  
HETATM   11  C7  UNL     1       3.459   0.140   0.775  1.00  0.00           C  
HETATM   12  C8  UNL     1       2.169  -0.357   0.619  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.711  -1.383   1.467  1.00  0.00           O  
HETATM   14  C9  UNL     1       0.432  -1.878   1.316  1.00  0.00           C  
HETATM   15  C10 UNL     1      -0.050  -2.885   2.131  1.00  0.00           C  
HETATM   16  C11 UNL     1      -1.331  -3.378   1.977  1.00  0.00           C  
HETATM   17  O5  UNL     1      -1.755  -4.383   2.821  1.00  0.00           O  
HETATM   18  C12 UNL     1      -2.127  -2.848   0.990  1.00  0.00           C  
HETATM   19 CL2  UNL     1      -3.761  -3.505   0.823  1.00  0.00          CL  
HETATM   20  C13 UNL     1      -1.680  -1.857   0.173  1.00  0.00           C  
HETATM   21  C14 UNL     1      -0.364  -1.355   0.337  1.00  0.00           C  
HETATM   22  C15 UNL     1      -0.955   0.845  -0.494  1.00  0.00           C  
HETATM   23  C16 UNL     1      -1.294   1.698   0.536  1.00  0.00           C  
HETATM   24  C17 UNL     1      -2.231   2.685   0.388  1.00  0.00           C  
HETATM   25  C18 UNL     1      -2.873   2.859  -0.817  1.00  0.00           C  
HETATM   26  C19 UNL     1      -2.550   2.018  -1.861  1.00  0.00           C  
HETATM   27  C20 UNL     1      -1.592   1.014  -1.695  1.00  0.00           C  
HETATM   28  H1  UNL     1       1.243   1.618  -1.973  1.00  0.00           H  
HETATM   29  H2  UNL     1       5.581   2.345  -0.445  1.00  0.00           H  
HETATM   30  H3  UNL     1       4.048  -0.309   1.565  1.00  0.00           H  
HETATM   31  H4  UNL     1       0.555  -3.318   2.913  1.00  0.00           H  
HETATM   32  H5  UNL     1      -1.151  -4.751   3.533  1.00  0.00           H  
HETATM   33  H6  UNL     1      -2.333  -1.468  -0.588  1.00  0.00           H  
HETATM   34  H7  UNL     1      -0.811   1.598   1.507  1.00  0.00           H  
HETATM   35  H8  UNL     1      -2.479   3.345   1.219  1.00  0.00           H  
HETATM   36  H9  UNL     1      -3.615   3.646  -0.923  1.00  0.00           H  
HETATM   37  H10 UNL     1      -3.051   2.148  -2.811  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   27
CONECT    3    4
CONECT    4    5   21   22
CONECT    5    6    6   12
CONECT    6    7   28
CONECT    7    8    9    9
CONECT    9   10   11
CONECT   10   29
CONECT   11   12   12   30
CONECT   12   13
CONECT   13   14
CONECT   14   15   15   21
CONECT   15   16   31
CONECT   16   17   18   18
CONECT   17   32
CONECT   18   19   20
CONECT   20   21   21   33
CONECT   22   23   23   27
CONECT   23   24   34
CONECT   24   25   25   35
CONECT   25   26   36
CONECT   26   27   27   37
END

HMDB0245557
     RDKit          3D
2',7'-Dichlorofluorescein
 37 41  0  0  0  0  0  0  0  0999 V2000
   -1.4502   -0.1085   -3.8018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0683    0.0098   -2.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1386   -0.7308   -1.9306 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115   -0.2900   -0.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3955    0.1794   -0.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8974    1.2110   -1.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1658    1.6986   -1.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8126    2.9798   -2.0593 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9530    1.1492   -0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2277    1.6194    0.1388 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4591    0.1396    0.7750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1688   -0.3566    0.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7107   -1.3829    1.4674 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4315   -1.8780    1.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0505   -2.8846    2.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3309   -3.3781    1.9768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550   -4.3834    2.8214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1269   -2.8478    0.9903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7606   -3.5053    0.8232 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6801   -1.8567    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3644   -1.3554    0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9546    0.8450   -0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2940    1.6982    0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2306    2.6855    0.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8732    2.8586   -0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5504    2.0177   -1.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5918    1.0139   -1.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2433    1.6178   -1.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5809    2.3446   -0.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0481   -0.3093    1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546   -3.3178    2.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1506   -4.7512    3.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3333   -1.4678   -0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8109    1.5977    1.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794    3.3454    1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6149    3.6458   -0.9227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0511    2.1476   -2.8113 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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  4 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27  2  1  0
 21  4  1  0
 27 22  1  0
 12  5  1  0
 21 14  1  0
  6 28  1  0
 10 29  1  0
 11 30  1  0
 15 31  1  0
 17 32  1  0
 20 33  1  0
 23 34  1  0
 24 35  1  0
 25 36  1  0
 26 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Fluorescein 27	ChEBI
2',7'-Dichlorofluorescein, disodium salt	MeSH
2',7'-Dichlorofluorescin	MeSH
Dichlorofluorescin	MeSH
Monohlorofluorescein	MeSH

Chemical Formula

C₂₀H₁₀Cl₂O₅

Average Molecular Weight

401.2

Monoisotopic Molecular Weight

399.9905288

IUPAC Name

2',7'-dichloro-3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one

Traditional Name

dichlorofluorescein

CAS Registry Number

Not Available

SMILES

OC1=C(Cl)C=C2C(OC3=CC(O)=C(Cl)C=C3C22OC(=O)C3=CC=CC=C23)=C1

InChI Identifier

InChI=1S/C20H10Cl2O5/c21-13-5-11-17(7-15(13)23)26-18-8-16(24)14(22)6-12(18)20(11)10-4-2-1-3-9(10)19(25)27-20/h1-8,23-24H

InChI Key

VFNKZQNIXUFLBC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthenes

Alternative Parents

Substituents

Xanthene
Diaryl ether
Benzofuranone
Phthalide
Isobenzofuranone
Isocoumaran
Isobenzofuran
1-hydroxy-2-unsubstituted benzenoid
Aryl chloride
Benzenoid
Aryl halide
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organochloride
Organic oxide
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

2-benzofurans (CHEBI:51596 )

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	3.95	ALOGPS
logP	5.09	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	7.14	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	100.83 m³·mol⁻¹	ChemAxon
Polarizability	37.64 Å³	ChemAxon
Number of Rings	5	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]-	222.49	30932474
DeepCCS	[M+Na]+	197.719	30932474
AllCCS	[M+H]+	185.5	32859911
AllCCS	[M+H-H2O]+	182.6	32859911
AllCCS	[M+NH4]+	188.1	32859911
AllCCS	[M+Na]+	188.9	32859911
AllCCS	[M-H]-	173.0	32859911
AllCCS	[M+Na-2H]-	171.4	32859911
AllCCS	[M+HCOO]-	169.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2',7'-Dichlorofluorescein	OC1=C(Cl)C=C2C(OC3=CC(O)=C(Cl)C=C3C22OC(=O)C3=CC=CC=C23)=C1	5050.6	Standard polar	33892256
2',7'-Dichlorofluorescein	OC1=C(Cl)C=C2C(OC3=CC(O)=C(Cl)C=C3C22OC(=O)C3=CC=CC=C23)=C1	3232.0	Standard non polar	33892256
2',7'-Dichlorofluorescein	OC1=C(Cl)C=C2C(OC3=CC(O)=C(Cl)C=C3C22OC(=O)C3=CC=CC=C23)=C1	3275.4	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 - 2',7'-Dichlorofluorescein GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-1296100000-0cbaa14df3059de65de0	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',7'-Dichlorofluorescein GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',7'-Dichlorofluorescein GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',7'-Dichlorofluorescein GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',7'-Dichlorofluorescein GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',7'-Dichlorofluorescein GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',7'-Dichlorofluorescein 10V, Positive-QTOF	splash10-0udi-0000900000-2e03f49f2ecb69b2167c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',7'-Dichlorofluorescein 20V, Positive-QTOF	splash10-0udi-0000900000-2e03f49f2ecb69b2167c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',7'-Dichlorofluorescein 40V, Positive-QTOF	splash10-0udi-0009400000-8b42614ed310f9b7b60e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',7'-Dichlorofluorescein 10V, Negative-QTOF	splash10-0002-0009000000-bd24b3febb60610ee0a5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',7'-Dichlorofluorescein 20V, Negative-QTOF	splash10-0002-0009000000-f6e63683435565b71fb0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',7'-Dichlorofluorescein 40V, Negative-QTOF	splash10-0002-0039000000-9f828a4face5c4a5b1dd	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58471

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

51596

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 2',7'-Dichlorofluorescein (HMDB0245557)

MOL for HMDB0245557 (2',7'-Dichlorofluorescein)

3D MOL for HMDB0245557 (2',7'-Dichlorofluorescein)

3D SDF for HMDB0245557 (2',7'-Dichlorofluorescein)

3D-SDF for HMDB0245557 (2',7'-Dichlorofluorescein)

PDB for HMDB0245557 (2',7'-Dichlorofluorescein)

3D PDB for HMDB0245557 (2',7'-Dichlorofluorescein)

SMILES for HMDB0245557 (2',7'-Dichlorofluorescein)

INCHI for HMDB0245557 (2',7'-Dichlorofluorescein)

Structure for HMDB0245557 (2',7'-Dichlorofluorescein)

3D Structure for HMDB0245557 (2',7'-Dichlorofluorescein)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra