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Showing NP-Card for phthalic anhydride (NP0265474)

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Record Information
Version2.0
Created at2022-09-08 09:28:07 UTC
Updated at2022-09-08 09:28:07 UTC
NP-MRD IDNP0265474
Secondary Accession NumbersNone
Natural Product Identification
Common Namephthalic anhydride
DescriptionPhthalic anhydride, also known as 1,3-dioxophthalan or 1,3-phthalandione, belongs to the class of organic compounds known as phthalic anhydrides. Phthalic anhydrides are compounds containing a phthalic anhydride moiety (or a derivative thereof), which consists of a benzene fused to a furan-1,3-dione. phthalic anhydride is found in Ligusticum chuanxiong. phthalic anhydride was first documented in 1992 (PMID: 1447476). Phthalic anhydride is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 12269934) (PMID: 21901887) (PMID: 21902644) (PMID: 22222149).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0265474 (phthalic anhydride)


  Mrv1533004241518112D          

 11 12  0  0  0  0            999 V2000
    0.8838   -2.1500    0.0000 O   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
    0.6538   -0.6979    0.0000 O   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
    0.8838    0.7541    0.0000 O   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  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  0  0  0  0
  6 11  1  0  0  0  0
M  END
Download

3D MOL for NP0265474 (phthalic anhydride)

     RDKit          3D

 15 16  0  0  0  0  0  0  0  0999 V2000
    2.7985    1.6559    0.1075 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1087    0.6217    0.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6047   -0.6542    0.0858 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5728   -1.5829    0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6583   -2.8393    0.0388 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3408   -0.7892    0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0033   -1.1515   -0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9965   -0.1976   -0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6491    1.1219   -0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3341    1.5424   -0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6388    0.5582    0.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2002   -2.2228   -0.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0210   -0.5281   -0.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4513    1.8751   -0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0672    2.5904    0.0146 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  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  2  1  0
 11  6  1  0
  7 12  1  0
  8 13  1  0
  9 14  1  0
 10 15  1  0
M  END
Download

3D SDF for NP0265474 (phthalic anhydride)


  Mrv1533004241518112D          

 11 12  0  0  0  0            999 V2000
    0.8838   -2.1500    0.0000 O   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
    0.6538   -0.6979    0.0000 O   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
    0.8838    0.7541    0.0000 O   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  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  0  0  0  0
  6 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0265474

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1OC(=O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C8H4O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4H

> <INCHI_KEY>
LGRFSURHDFAFJT-UHFFFAOYSA-N

> <FORMULA>
C8H4O3

> <MOLECULAR_WEIGHT>
148.117

> <EXACT_MASS>
148.016043989

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
13.172407247321715

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3-dihydro-2-benzofuran-1,3-dione

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
1.4225836423333331

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.888431773047617

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
37.365

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.98e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phthalic anhydride

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0265474 (phthalic anhydride)

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PDB for NP0265474 (phthalic anhydride)
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.220  -1.303   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.650   1.408   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0265474 (phthalic anhydride)
Download
SMILES for NP0265474 (phthalic anhydride)
O=C1OC(=O)C2=CC=CC=C12
Download
INCHI for NP0265474 (phthalic anhydride)
InChI=1S/C8H4O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4H
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View in JSmol
Synonyms
ValueSource
1,2-Benzenedicarboxylic acid anhydrideChEBI
1,3-DioxophthalanChEBI
1,3-IsobenzofurandioneChEBI
1,3-PhthalandioneChEBI
O-Phthalic acid anhydrideChEBI
Ortho-phthalic acid anhydrideChEBI
PhthalsaeureanhydridChEBI
1,2-Benzenedicarboxylate anhydrideGenerator
O-Phthalate anhydrideGenerator
Ortho-phthalate anhydrideGenerator
1,2-Benzenedicarboxylic anhydrideMeSH
Phthalic acid anhydrideMeSH
Phthalic anhydride, 14C-labeled CPDMeSH
Chemical FormulaC8H4O3
Average Mass148.1170 Da
Monoisotopic Mass148.01604 Da
IUPAC Name1,3-dihydro-2-benzofuran-1,3-dione
Traditional Namephthalic anhydride
CAS Registry NumberNot Available
SMILES
O=C1OC(=O)C2=CC=CC=C12
InChI Identifier
InChI=1S/C8H4O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4H
InChI KeyLGRFSURHDFAFJT-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ligusticum chuanxiongLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phthalic anhydrides. Phthalic anhydrides are compounds containing a phthalic anhydride moiety (or a derivative thereof), which consists of a benzene fused to a furan-1,3-dione.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzofurans  
Sub ClassBenzofuranones  
Direct ParentPhthalic anhydrides  
Alternative Parents
Substituents
  • Phthalic anhydride
    • 

  • Phthalic_anhydride
    • 

  • Isobenzofuranone
    • 

  • Isocoumaran
    • 

  • Benzenoid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Carboxylic acid anhydride
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.89ALOGPS
logP1.42ChemAxon
logS-1.5ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity37.36 m³·mol⁻¹ChemAxon
Polarizability13.17 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhthalic_anhydride  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID36605  
Good Scents IDNot Available
References
General References
  1. Pakarinen M, Koivuluhta M, Kalkkinen N, Keskinen H, Nordman H, Estlander T, Tupasela O, Jolanki R, Lauerma AI, Pfaffli P, Alenius H: Phthalic anhydride allergy: development and characterization of optimized hapten-carrier conjugates for improved diagnosis. Allergy. 2002 Oct;57(10):894-9. doi: 10.1034/j.1398-9995.2002.23579.x. [PubMed:12269934  ] 
  2. Dearman RJ, Basketter DA, Kimber I: Variable effects of chemical allergens on serum IgE concentration in mice. Preliminary evaluation of a novel approach to the identification of respiratory sensitizers. J Appl Toxicol. 1992 Oct;12(5):317-23. doi: 10.1002/jat.2550120505. [PubMed:1447476  ] 
  3. Zaitseva NV, Ulanova TS, Karnazhitskaia TD, Antip'eva MV, Kislitsina AV: [Determination of phthalic anhydride in ambient air by high performance liquid chromatography]. Gig Sanit. 2011 Jul-Aug;(4):77-80. [PubMed:21901887  ] 
  4. Woelk HJ, Mestl G: Catalyst optimization strategy: selective oxidation of o-xylene to phthalic anhydride. Comb Chem High Throughput Screen. 2012 Feb 1;15(2):136-9. doi: 10.2174/138620712798868383. [PubMed:21902644  ] 
  5. Abd El-Rehim HA, El-Sawy NM, Hegazy el-SA, Soliman el-SA, Elbarbary AM: Improvement of antioxidant activity of chitosan by chemical treatment and ionizing radiation. Int J Biol Macromol. 2012 Mar 1;50(2):403-13. doi: 10.1016/j.ijbiomac.2011.12.021. Epub 2011 Dec 27. [PubMed:22222149  ] 
  6. LOTUS database [Link]