NP-MRD: Showing NP-Card for phenolphthalein (NP0296098)

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Record Information

Version

2.0

Created at

2022-09-10 05:28:57 UTC

Updated at

2022-09-10 05:28:58 UTC

NP-MRD ID

NP0296098

Secondary Accession Numbers

None

Natural Product Identification

Common Name

phenolphthalein

Description

Phenolphthalein, also known as modane or laxatone, 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Phenolphthalein is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Phenolphthalein adopts four different states in aqueous solution: Under strongly acidic conditions, it exists in protonated form (HIn+), providing an orange coloration. Phenolphthalein can be synthesized by condensation of phthalic anhydride with two equivalents of phenol under acidic conditions (hence the name). phenolphthalein is found in Caragana conferta. It was discovered in 1871 by Adolf von Baeyer.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 41  0  0  0  0  0  0  0  0999 V2000
    0.0501    2.1894    3.4607 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0131    1.6476    2.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1552    0.3128    1.9946 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0501    0.1770    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3129   -0.4449    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1410    0.1864   -0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3276   -0.3931   -1.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6963   -1.6332   -0.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8940   -2.2393   -1.1420 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8616   -2.2653    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6664   -1.6839    0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1195   -0.7055    0.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9825   -1.0066    1.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0822   -1.8153    1.1277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3173   -2.3377   -0.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4080   -3.1500   -0.3421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4509   -2.0434   -1.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3617   -1.2297   -0.9388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1762    1.5082    0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3601    2.0124   -1.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602    3.3724   -1.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5720    4.2337   -0.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3931    3.7741    0.8575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1950    2.4027    1.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9302    1.1612   -1.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9901    0.0968   -1.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7560   -2.0667   -0.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1530   -3.2499    0.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0270   -2.2086    1.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7950   -0.5904    2.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7622   -2.0419    1.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0255   -3.3522    0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6247   -2.4507   -2.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6590   -0.9789   -1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559    1.3565   -2.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998    3.7160   -2.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228    5.3001   -0.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4009    4.4399    1.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5 11  1  0
 11 10  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 24  1  0
 24 23  2  0
 23 22  1  0
 22 21  2  0
 21 20  1  0
 20 19  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
 10  8  1  0
 19  4  1  0
 18 12  1  0
 19 24  1  0
  9 27  1  0
  7 26  1  0
  6 25  1  0
 11 29  1  0
 10 28  1  0
 23 38  1  0
 22 37  1  0
 21 36  1  0
 20 35  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  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>
NP0296098

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

Synonyms

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

Chemical Formula

C₂₀H₁₄O₄

Average Mass

318.3228 Da

Monoisotopic Mass

318.08921 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, DMSO-d6, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Caragana conferta	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted 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

External Links

HMDB ID

Not Available

DrugBank ID

DB04824

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C14286

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenolphthalein

METLIN ID

Not Available

PubChem Compound

4764

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for phenolphthalein (NP0296098)

MOL for NP0296098 (phenolphthalein)

3D MOL for NP0296098 (phenolphthalein)

3D SDF for NP0296098 (phenolphthalein)

3D-SDF for NP0296098 (phenolphthalein)

PDB for NP0296098 (phenolphthalein)

3D PDB for NP0296098 (phenolphthalein)

SMILES for NP0296098 (phenolphthalein)

INCHI for NP0296098 (phenolphthalein)

Structure for NP0296098 (phenolphthalein)

3D Structure for NP0296098 (phenolphthalein)