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Showing NP-Card for (+)-Paeonilactone B (NP0057763)

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Record Information
Version2.0
Created at2022-04-28 03:09:47 UTC
Updated at2022-04-28 03:09:47 UTC
NP-MRD IDNP0057763
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Paeonilactone B
DescriptionPaeonilactone B belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. (+)-Paeonilactone B is found in Paeonia albiflora PALLAS var.trichocarpa BUNGE , Paeonia lactiflora and Paeonia officinalis . Based on a literature review very few articles have been published on Paeonilactone B.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0057763 ((+)-Paeonilactone B)


  Mrv1652304282205092D          

 14 15  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1768    1.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7895    0.4108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  1  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  5 12  1  1  0  0  0
  3 13  1  6  0  0  0
  3 14  1  1  0  0  0
M  END
Download

3D MOL for NP0057763 ((+)-Paeonilactone B)

     RDKit          3D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -2.9269    0.8440    0.8300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2499   -0.0749    0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4523   -1.5226    0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5277   -2.0822    0.6550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2854   -2.1245   -0.1714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3463   -1.1467   -0.6076 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7582   -1.0993    0.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6418    0.1082    0.2801 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0484   -0.2317   -0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7551    0.6519    1.5752 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0698    1.0872   -0.6590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606    1.6529   -1.4647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3754    1.3666   -0.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1272    0.0980   -0.7722 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7163    0.5842    1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6856    1.8890    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0390   -1.4881   -1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3192   -1.2188    1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3822   -2.0274    0.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7957    0.3835    0.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2903   -1.3049   -0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1905    0.0243   -1.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5035    1.6019    1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6898    2.1541   -1.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5979    1.7758    0.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5736    0.0993   -1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  1
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 11  8  1  0
 14  6  1  0
  9 20  1  0
  9 21  1  0
  9 22  1  0
 10 23  1  0
  7 18  1  0
  7 19  1  0
  6 17  1  6
  1 15  1  0
  1 16  1  0
 14 26  1  6
 13 24  1  0
 13 25  1  0
M  END
Download

3D SDF for NP0057763 ((+)-Paeonilactone B)


  Mrv1652304282205092D          

 14 15  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1768    1.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7895    0.4108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  1  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  5 12  1  1  0  0  0
  3 13  1  6  0  0  0
  3 14  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0057763

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]1(O)C[C@H]2OC(=O)C(=C)[C@H]2CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O4/c1-5-6-3-8(11)10(2,13)4-7(6)14-9(5)12/h6-7,13H,1,3-4H2,2H3/t6-,7-,10+/m1/s1

> <INCHI_KEY>
GFSTVWDPRTWASK-XSSZXYGBSA-N

> <FORMULA>
C10H12O4

> <MOLECULAR_WEIGHT>
196.202

> <EXACT_MASS>
196.073558866

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
18.939910051158922

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,6S,7aR)-6-hydroxy-6-methyl-3-methylidene-octahydro-1-benzofuran-2,5-dione

> <ALOGPS_LOGP>
-0.42

> <JCHEM_LOGP>
0.4287935306666664

> <ALOGPS_LOGS>
-0.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.689603430455573

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.181882837661234

> <JCHEM_PKA_STRONGEST_BASIC>
-3.591379651024159

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
47.70250000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.43e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,6S,7aR)-6-hydroxy-6-methyl-3-methylidene-tetrahydro-1-benzofuran-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0057763 ((+)-Paeonilactone B)

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PDB for NP0057763 ((+)-Paeonilactone B)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.320   2.843   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.797   2.019   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.074   0.767   0.000  0.00  0.00           O+0
CONECT    1    2    3    7                                                  
CONECT    2    1                                                            
CONECT    3    1    4   13   14                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    3                                                            
CONECT   14    3                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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3D PDB for NP0057763 ((+)-Paeonilactone B)
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SMILES for NP0057763 ((+)-Paeonilactone B)
C[C@]1(O)C[C@H]2OC(=O)C(=C)[C@H]2CC1=O
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INCHI for NP0057763 ((+)-Paeonilactone B)
InChI=1S/C10H12O4/c1-5-6-3-8(11)10(2,13)4-7(6)14-9(5)12/h6-7,13H,1,3-4H2,2H3/t6-,7-,10+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H12O4
Average Mass196.2020 Da
Monoisotopic Mass196.07356 Da
IUPAC Name(3aR,6S,7aR)-6-hydroxy-6-methyl-3-methylidene-octahydro-1-benzofuran-2,5-dione
Traditional Name(3aR,6S,7aR)-6-hydroxy-6-methyl-3-methylidene-tetrahydro-1-benzofuran-2,5-dione
CAS Registry NumberNot Available
SMILES
C[C@]1(O)C[C@H]2OC(=O)C(=C)[C@H]2CC1=O
InChI Identifier
InChI=1S/C10H12O4/c1-5-6-3-8(11)10(2,13)4-7(6)14-9(5)12/h6-7,13H,1,3-4H2,2H3/t6-,7-,10+/m1/s1
InChI KeyGFSTVWDPRTWASK-XSSZXYGBSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Paeonia albiflora PALLAS var.trichocarpa BUNGEPlant
Paeonia lactifloraLOTUS Database
Paeonia officinalisPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzofurans  
Sub ClassNot Available
Direct ParentBenzofurans  
Alternative Parents
Substituents
  • Benzofuran
    • 

  • Acyloin
    • 

  • Gamma butyrolactone
    • 

  • Cyclic alcohol
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Tetrahydrofuran
    • 

  • Tertiary alcohol
    • 

  • Carboxylic acid ester
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP-0.42ALOGPS
logP0.43ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)13.18ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.7 m³·mol⁻¹ChemAxon
Polarizability18.94 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00010956  
Chemspider ID8550865  
KEGG Compound IDC17455  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10375422  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available