Np mrd loader

Showing NP-Card for 3-Isochromanone (NP0002782)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2020-11-23 19:40:18 UTC
Updated at2021-08-12 19:52:08 UTC
NP-MRD IDNP0002782
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Isochromanone
Provided ByBMRBBMRB logo
Description 3-Isochromanone was first documented in 2013 (PMID: 24190283). Based on a literature review very few articles have been published on 3,4-dihydro-1H-2-benzopyran-3-one (PMID: 31428061) (PMID: 27780358) (PMID: 23334232).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002782 (3-Isochromanone)


     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    4.1693   -0.6010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7467   -0.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6235   -1.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009   -0.6439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9223   -1.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3449   -1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6443    0.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5211    1.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0985    0.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0247    1.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4473    1.3445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7977   -2.0530    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9081   -2.4379    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6229   -3.1079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4681   -2.1567    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0669    0.7830    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8204    2.7714    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1494    2.7536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7402    3.1385    0.0000 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
  9  4  1  0
  3 12  1  6
  3 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
 10 18  1  1
 10 19  1  0
M  END
Download

3D MOL for NP0002782 (3-Isochromanone)

NP0002782
     RDKit          3D

 19 20  0  0  0  0  0  0  0  0999 V2000
   -3.1686   -1.0398    1.0861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3775   -0.3675    0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4770   -1.0396   -0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0979   -0.5603   -0.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9590   -1.4512   -0.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2336   -1.0054   -0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4432    0.3113    0.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609    1.1675    0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0739    0.7493    0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638    1.7087    0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2725    1.0173    0.4908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5567   -2.1361   -0.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857   -0.6685   -1.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7893   -2.4919   -0.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0395   -1.7198   -0.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4555    0.6433    0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5314    2.1932    0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8952    2.3959    1.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1916    2.2938   -0.6787 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
  9  4  1  0
  3 12  1  0
  3 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
 10 18  1  0
 10 19  1  0
M  END
Download

3D SDF for NP0002782 (3-Isochromanone)


     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    4.1693   -0.6010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7467   -0.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6235   -1.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009   -0.6439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9223   -1.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3449   -1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6443    0.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5211    1.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0985    0.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0247    1.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4473    1.3445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7977   -2.0530    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9081   -2.4379    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6229   -3.1079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4681   -2.1567    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0669    0.7830    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8204    2.7714    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1494    2.7536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7402    3.1385    0.0000 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
  9  4  1  0
  3 12  1  6
  3 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
 10 18  1  1
 10 19  1  0
M  END
> <DATABASE_ID>
NP0002782

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1CC2=C(CO1)C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O2/c10-9-5-7-3-1-2-4-8(7)6-11-9/h1-4H,5-6H2

> <INCHI_KEY>
ILHLUZUMRJQEAH-UHFFFAOYSA-N

> <FORMULA>
C9H8O2

> <MOLECULAR_WEIGHT>
148.161

> <EXACT_MASS>
148.052429498

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.044162658321435

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4-dihydro-1H-2-benzopyran-3-one

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
1.5081154626666664

> <ALOGPS_LOGS>
-1.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.098297626878297

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
40.689299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.91e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-isochromanone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002782 (3-Isochromanone)

NP0002782
     RDKit          3D

 19 20  0  0  0  0  0  0  0  0999 V2000
   -3.1686   -1.0398    1.0861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3775   -0.3675    0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4770   -1.0396   -0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0979   -0.5603   -0.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9590   -1.4512   -0.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2336   -1.0054   -0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4432    0.3113    0.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609    1.1675    0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0739    0.7493    0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638    1.7087    0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2725    1.0173    0.4908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5567   -2.1361   -0.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857   -0.6685   -1.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7893   -2.4919   -0.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0395   -1.7198   -0.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4555    0.6433    0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5314    2.1932    0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8952    2.3959    1.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1916    2.2938   -0.6787 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
  9  4  1  0
  3 12  1  0
  3 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
 10 18  1  0
 10 19  1  0
M  END
Download

PDB for NP0002782 (3-Isochromanone)

HEADER    PROTEIN                                 21-JUL-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUL-15         0                                  
HETATM    1  C   UNK     0      26.892 -18.129   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.917 -19.664   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.211 -17.332   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.541 -17.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.268 -20.403   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.598 -20.454   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.549 -18.167   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.235 -18.173   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      29.587 -19.600   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      24.184 -19.709   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      30.881 -17.402   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   11    9                                                  
CONECT    8    4   10                                                       
CONECT    9    5    7                                                       
CONECT   10    6    8                                                       
CONECT   11    7                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
Download

3D PDB for NP0002782 (3-Isochromanone)

COMPND    NP0002782
HETATM    1  O1  UNL     1      -3.169  -1.040   1.086  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.377  -0.367   0.402  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.477  -1.040  -0.576  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.098  -0.560  -0.284  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.959  -1.451  -0.413  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.234  -1.005  -0.142  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.443   0.311   0.252  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.361   1.168   0.368  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.074   0.749   0.103  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.064   1.709   0.243  1.00  0.00           C  
HETATM   11  O2  UNL     1      -2.273   1.017   0.491  1.00  0.00           O  
HETATM   12  H1  UNL     1      -1.557  -2.136  -0.550  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.786  -0.669  -1.582  1.00  0.00           H  
HETATM   14  H3  UNL     1       0.789  -2.492  -0.725  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.040  -1.720  -0.251  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.455   0.643   0.461  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.531   2.193   0.676  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.895   2.396   1.120  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.192   2.294  -0.679  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4   12   13
CONECT    4    5    5    9
CONECT    5    6   14
CONECT    6    7    7   15
CONECT    7    8   16
CONECT    8    9    9   17
CONECT    9   10
CONECT   10   11   18   19
END
Download

SMILES for NP0002782 (3-Isochromanone)

O=C1CC2=C(CO1)C=CC=C2
Download

INCHI for NP0002782 (3-Isochromanone)

InChI=1S/C9H8O2/c10-9-5-7-3-1-2-4-8(7)6-11-9/h1-4H,5-6H2
Download
View in JSmol
Synonyms
ValueSource
1,4-Dihydro-3H-2-benzopyran-3-oneKegg
Chemical FormulaC9H8O2
Average Mass148.1610 Da
Monoisotopic Mass148.05243 Da
IUPAC Name3,4-dihydro-1H-2-benzopyran-3-one
Traditional Name3-isochromanone
CAS Registry NumberNot Available
SMILES
O=C1CC2=C(CO1)C=CC=C2
InChI Identifier
InChI=1S/C9H8O2/c10-9-5-7-3-1-2-4-8(7)6-11-9/h1-4H,5-6H2
InChI KeyILHLUZUMRJQEAH-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class2-benzopyrans
Direct Parent2-benzopyrans
Alternative Parents
Substituents
  • 2-benzopyran
  • Benzenoid
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
logP1.29ALOGPS
logP1.51ChemAxon
logS-1.7ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.69 m³·mol⁻¹ChemAxon
Polarizability15.04 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID70470
KEGG Compound IDC07728
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Berzaghi R, Agocs A, Curto MA, Gulyas-Fekete G, Kocsis B, Ribas JC, Lorand T: Novel Cell Wall Antifungals Reveal a Special Synergistic Activity in pbr1 Mutants Resistant to the Glucan Synthesis Antifungals Papulacandins and Echinocandins. Front Microbiol. 2019 Jul 24;10:1692. doi: 10.3389/fmicb.2019.01692. eCollection 2019. [PubMed:31428061 ]
  2. Akula R, Guiry PJ: Enantioselective Synthesis of alpha-Allyl-alpha-aryldihydrocoumarins and 3-Isochromanones via Pd-Catalyzed Decarboxylative Asymmetric Allylic Alkylation. Org Lett. 2016 Nov 4;18(21):5472-5475. doi: 10.1021/acs.orglett.6b02584. Epub 2016 Oct 26. [PubMed:27780358 ]
  3. Li Y, Zhu DX, Xu MH: A new versatile approach to synthesise enantioenriched 3-hydroxyoxindoles, 1,3-dihydroisobenzofuran and 3-isochromanone derivatives by a rhodium-catalyzed asymmetric arylation-cyclization sequence. Chem Commun (Camb). 2013 Dec 25;49(99):11659-61. doi: 10.1039/c3cc47927g. [PubMed:24190283 ]
  4. Park J, Kim M, Sharma S, Park E, Kim A, Lee SH, Kwak JH, Jung YH, Kim IS: Pd(II)-catalyzed decarboxylative acylation of phenylacetamides with alpha-oxocarboxylic acids via C-H bond activation. Chem Commun (Camb). 2013 Feb 25;49(16):1654-6. doi: 10.1039/c3cc38764j. [PubMed:23334232 ]