NP-MRD: Showing NP-Card for (3R)-Sophorol (NP0045565)

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Record Information

Version

2.0

Created at

2022-03-17 19:31:57 UTC

Updated at

2022-03-17 19:31:57 UTC

NP-MRD ID

NP0045565

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3R)-Sophorol

Description

Not Available

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 02241212132D          

 23 26  0  0  0  0            999 V2000
   -4.3607   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0752   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0752   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3607   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6462   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6462   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9318   -0.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9318   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2173   -1.2964    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2173   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5028   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5640   -0.7927    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9318   -2.5339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7884   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5028   -2.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7884   -2.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739   -2.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6169   -3.7534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2036   -3.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5392   -3.0860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7884   -0.4714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7897   -0.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  1  0  0  0
  9 12  1  6  0  0  0
  8 13  2  0  0  0  0
 14 11  2  0  0  0  0
 11 15  1  0  0  0  0
 14 18  1  0  0  0  0
 15 16  2  0  0  0  0
 17 18  2  0  0  0  0
 17 21  1  0  0  0  0
 17 16  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 22  1  0  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045565

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(COC2=C(C=CC(O)=C2)C1=O)C1=C(O)C=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c17-8-1-2-9-13(3-8)20-6-11(16(9)19)10-4-14-15(5-12(10)18)22-7-21-14/h1-5,11,17-18H,6-7H2/t11-/m0/s1

> <INCHI_KEY>
FAPWSAQOVOBPCP-NSHDSACASA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.481371390684956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-7-hydroxy-3-(6-hydroxy-2H-1,3-benzodioxol-5-yl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
2.0044569033333333

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.516336749212178

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.775250840908228

> <JCHEM_PKA_STRONGEST_BASIC>
-4.514499537337289

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
75.46250000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-sophorol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -8.140  -0.110   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.474  -0.880   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.474  -2.420   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.140  -3.190   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.806  -2.420   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.806  -0.880   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.473  -0.110   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.473  -3.190   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.139  -2.420   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.139  -0.880   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.805  -3.190   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0      -2.919  -1.480   0.000  0.00  0.00           H+0
HETATM   13  O   UNK     0      -5.473  -4.730   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.472  -2.420   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.805  -4.730   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.472  -5.500   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.138  -4.730   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.138  -3.190   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.152  -7.006   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.380  -7.167   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.007  -5.761   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.472  -0.880   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0     -10.807  -0.110   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   13                                                  
CONECT    9    8   10   11   12                                             
CONECT   10    7    9                                                       
CONECT   11    9   14   15                                                  
CONECT   12    9                                                            
CONECT   13    8                                                            
CONECT   14   11   18   22                                                  
CONECT   15   11   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   18   21   16                                                  
CONECT   18   14   17                                                       
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   17   20                                                       
CONECT   22   14                                                            
CONECT   23    2                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₆

Average Mass

300.2629 Da

Monoisotopic Mass

300.06339 Da

IUPAC Name

(3R)-7-hydroxy-3-(6-hydroxy-2H-1,3-benzodioxol-5-yl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(-)-sophorol

CAS Registry Number

133067-72-8

SMILES

[H][C@]1(COC2=C(C=CC(O)=C2)C1=O)C1=C(O)C=C2OCOC2=C1

InChI Identifier

InChI=1S/C16H12O6/c17-8-1-2-9-13(3-8)20-6-11(16(9)19)10-4-14-15(5-12(10)18)22-7-21-14/h1-5,11,17-18H,6-7H2/t11-/m0/s1

InChI Key

FAPWSAQOVOBPCP-NSHDSACASA-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
Pisum sativum	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanones

Alternative Parents

Substituents

Hydroxyisoflavonoid
Isoflavanol
Isoflavanone
Chromone
Chromane
Benzopyran
1-benzopyran
Benzodioxole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Ketone
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoflavanones (CHEBI:80395 )
isoflavanones (C16228 )
Isoflavonoids (LMPK12050461 )

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	2.32	ALOGPS
logP	2	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.78	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.46 m³·mol⁻¹	ChemAxon
Polarizability	29.48 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

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001446

KNApSAcK ID

C00000650

Chemspider ID

Not Available

KEGG Compound ID

C16228

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23724668

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (3R)-Sophorol (NP0045565)

MOL for NP0045565 ((3R)-Sophorol)

3D MOL for NP0045565 ((3R)-Sophorol)

3D SDF for NP0045565 ((3R)-Sophorol)

3D-SDF for NP0045565 ((3R)-Sophorol)

PDB for NP0045565 ((3R)-Sophorol)

3D PDB for NP0045565 ((3R)-Sophorol)

SMILES for NP0045565 ((3R)-Sophorol)

INCHI for NP0045565 ((3R)-Sophorol)

Structure for NP0045565 ((3R)-Sophorol)

3D Structure for NP0045565 ((3R)-Sophorol)