NP-MRD: Showing NP-Card for (-)-Obochalcolactone (NP0079232)

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Record Information

Version

2.0

Created at

2022-04-29 00:16:19 UTC

Updated at

2022-04-29 00:16:20 UTC

NP-MRD ID

NP0079232

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Obochalcolactone

Description

(6R)-6-{[(1S,9S,11S)-3,5-dihydroxy-9-[(E)-2-phenylethenyl]-6-[(2E)-3-phenylprop-2-enoyl]-8,10,12-trioxatricyclo[7.3.1.0²,⁷]Trideca-2,4,6-trien-11-yl]methyl}-5,6-dihydro-2H-pyran-2-one belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. (-)-Obochalcolactone is found in Cryptocarya obovata. Based on a literature review very few articles have been published on (6R)-6-{[(1S,9S,11S)-3,5-dihydroxy-9-[(E)-2-phenylethenyl]-6-[(2E)-3-phenylprop-2-enoyl]-8,10,12-trioxatricyclo[7.3.1.0²,⁷]Trideca-2,4,6-trien-11-yl]methyl}-5,6-dihydro-2H-pyran-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202162D          

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M  END

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  Mrv1652304292202162D          

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   -1.9432    2.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3336    3.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5474    2.8285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0622    3.3844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3707    2.0226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  7  9  1  1  0  0  0
  3  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  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
 18 23  1  0  0  0  0
 12 24  1  0  0  0  0
 10 25  1  0  0  0  0
  3 26  1  1  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
  1 34  1  1  0  0  0
 35 34  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 35 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079232

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C(C(=O)\C=C\C2=CC=CC=C2)C2=C1[C@@H]1C[C@@](O[C@@H](C[C@H]3CC=CC(=O)O3)O1)(O2)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H28O8/c34-24(15-14-21-8-3-1-4-9-21)30-25(35)19-26(36)31-27-20-33(41-32(30)31,17-16-22-10-5-2-6-11-22)40-29(39-27)18-23-12-7-13-28(37)38-23/h1-11,13-17,19,23,27,29,35-36H,12,18,20H2/b15-14+,17-16+/t23-,27+,29+,33+/m1/s1

> <INCHI_KEY>
FQYNVJKZIUMNDS-GXGFRNPKSA-N

> <FORMULA>
C33H28O8

> <MOLECULAR_WEIGHT>
552.579

> <EXACT_MASS>
552.178417862

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
57.958968744604995

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R)-6-{[(1S,9S,11S)-3,5-dihydroxy-9-[(E)-2-phenylethenyl]-6-[(2E)-3-phenylprop-2-enoyl]-8,10,12-trioxatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-11-yl]methyl}-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
4.46

> <JCHEM_LOGP>
7.795618874999999

> <ALOGPS_LOGS>
-5.29

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.410644959161262

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.017717042315472

> <JCHEM_PKA_STRONGEST_BASIC>
-4.109486974156573

> <JCHEM_POLAR_SURFACE_AREA>
111.52000000000002

> <JCHEM_REFRACTIVITY>
152.76600000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.84e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-6-{[(1S,9S,11S)-3,5-dihydroxy-9-[(E)-2-phenylethenyl]-6-[(2E)-3-phenylprop-2-enoyl]-8,10,12-trioxatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-11-yl]methyl}-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -0.033   0.767   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.098  -0.767   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.275  -1.760   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.810  -1.630   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.802  -0.452   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.672   1.082   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.495   2.075   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.960   1.944   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.406   0.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.936   1.963   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.330   1.308   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.460  -0.226   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.197  -1.106   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.327  -2.641   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.064  -3.521   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.721  -3.295   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.985  -2.415   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.379  -3.069   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.643  -2.189   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.037  -2.843   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.167  -4.377   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.904  -5.257   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.510  -4.603   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.854  -0.880   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.805   3.497   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.809  -3.228   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.846  -4.366   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.380  -5.833   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.418  -6.971   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.951  -8.439   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.447  -8.768   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.591  -7.631   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.124  -6.163   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.500   1.234   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.830   2.738   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -3.298   3.204   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.627   4.709   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.489   5.746   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.022   5.280   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       0.116   6.318   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -0.692   3.776   0.000  0.00  0.00           O+0
CONECT    1    2    8   34                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    9   26                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    1                                                       
CONECT    9    7    3                                                       
CONECT   10    6   11   25                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12    5   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   12                                                            
CONECT   25   10                                                            
CONECT   26    3   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34    1   35                                                       
CONECT   35   34   36   41                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   35                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₂₈O₈

Average Mass

552.5790 Da

Monoisotopic Mass

552.17842 Da

IUPAC Name

(6R)-6-{[(1S,9S,11S)-3,5-dihydroxy-9-[(E)-2-phenylethenyl]-6-[(2E)-3-phenylprop-2-enoyl]-8,10,12-trioxatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-11-yl]methyl}-5,6-dihydro-2H-pyran-2-one

Traditional Name

(6R)-6-{[(1S,9S,11S)-3,5-dihydroxy-9-[(E)-2-phenylethenyl]-6-[(2E)-3-phenylprop-2-enoyl]-8,10,12-trioxatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-11-yl]methyl}-5,6-dihydropyran-2-one

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C(C(=O)\C=C\C2=CC=CC=C2)C2=C1[C@@H]1C[C@@](O[C@@H](C[C@H]3CC=CC(=O)O3)O1)(O2)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C33H28O8/c34-24(15-14-21-8-3-1-4-9-21)30-25(35)19-26(36)31-27-20-33(41-32(30)31,17-16-22-10-5-2-6-11-22)40-29(39-27)18-23-12-7-13-28(37)38-23/h1-11,13-17,19,23,27,29,35-36H,12,18,20H2/b15-14+,17-16+/t23-,27+,29+,33+/m1/s1

InChI Key

FQYNVJKZIUMNDS-GXGFRNPKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cryptocarya obovata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
1-benzopyran
Benzopyran
Chromane
Aryl ketone
Styrene
1-hydroxy-2-unsubstituted benzenoid
Ketal
Dihydropyranone
Benzenoid
Pyran
Monocyclic benzene moiety
Meta-dioxane
Vinylogous acid
Alpha,beta-unsaturated ketone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enone
Acryloyl-group
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	4.46	ALOGPS
logP	7.8	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	7.02	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	152.77 m³·mol⁻¹	ChemAxon
Polarizability	57.96 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163104032

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Obochalcolactone (NP0079232)

MOL for NP0079232 ((-)-Obochalcolactone)

3D MOL for NP0079232 ((-)-Obochalcolactone)

3D SDF for NP0079232 ((-)-Obochalcolactone)

3D-SDF for NP0079232 ((-)-Obochalcolactone)

PDB for NP0079232 ((-)-Obochalcolactone)

3D PDB for NP0079232 ((-)-Obochalcolactone)

SMILES for NP0079232 ((-)-Obochalcolactone)

INCHI for NP0079232 ((-)-Obochalcolactone)

Structure for NP0079232 ((-)-Obochalcolactone)

3D Structure for NP0079232 ((-)-Obochalcolactone)