NP-MRD: Showing NP-Card for (+)-Dihydrowighteone (NP0045696)

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Record Information

Version

2.0

Created at

2022-03-17 19:35:57 UTC

Updated at

2022-03-17 19:35:57 UTC

NP-MRD ID

NP0045696

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Dihydrowighteone

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212132D          

 25 27  0  0  0  0            999 V2000
   -3.7714    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4859    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4859    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7714    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0570    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0570    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3425    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3425    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6280    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6280    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9136    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1991    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9136   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1991   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7714   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3425   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9148   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9149   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6293   -0.2062    0.0000 C   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  0  0  0  0
 12 11  2  0  0  0  0
 11 13  1  0  0  0  0
 12 16  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  2 17  1  0  0  0  0
  4 18  1  0  0  0  0
  8 19  2  0  0  0  0
 15 20  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045696

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C2=C(OCC(C2=O)C2=CC=C(O)C=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O5/c1-11(2)3-8-14-16(22)9-17-18(19(14)23)20(24)15(10-25-17)12-4-6-13(21)7-5-12/h3-7,9,15,21-23H,8,10H2,1-2H3

> <INCHI_KEY>
UYDQKAKPHFFLDY-UHFFFAOYSA-N

> <FORMULA>
C20H20O5

> <MOLECULAR_WEIGHT>
340.3698

> <EXACT_MASS>
340.13107375

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
35.90976298536516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
4.456225113333334

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.454908929322874

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.7135139759240205

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9173470558691994

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
95.91929999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-dihydrowighteone

> <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      -7.040   4.235   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.374   3.465   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.374   1.925   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.040   1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.706   1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.706   3.465   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.373   4.235   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.373   1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.039   1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.039   3.465   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.705   1.155   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.372   1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.705  -0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.372  -1.155   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.962  -0.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.962   1.155   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -9.707   4.235   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -7.040  -0.385   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.373  -0.385   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.296  -1.155   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -9.707   1.155   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.707  -0.385   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -11.041  -1.155   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -11.041  -2.695   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -12.375  -0.385   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   19                                                  
CONECT    9    8   10   11                                                  
CONECT   10    7    9                                                       
CONECT   11    9   12   13                                                  
CONECT   12   11   16                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   12   15                                                       
CONECT   17    2                                                            
CONECT   18    4                                                            
CONECT   19    8                                                            
CONECT   20   15                                                            
CONECT   21    3   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₀O₅

Average Mass

340.3698 Da

Monoisotopic Mass

340.13107 Da

IUPAC Name

5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(+)-dihydrowighteone

CAS Registry Number

108026-27-3

SMILES

CC(C)=CCC1=C(O)C2=C(OCC(C2=O)C2=CC=C(O)C=C2)C=C1O

InChI Identifier

InChI=1S/C20H20O5/c1-11(2)3-8-14-16(22)9-17-18(19(14)23)20(24)15(10-25-17)12-4-6-13(21)7-5-12/h3-7,9,15,21-23H,8,10H2,1-2H3

InChI Key

UYDQKAKPHFFLDY-UHFFFAOYSA-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
Vigna angularis	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

Isoflavanone
Isoflavanol
Hydroxyisoflavonoid
Chromone
1-benzopyran
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050473 )

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	3.16	ALOGPS
logP	4.46	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	7.71	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.92 m³·mol⁻¹	ChemAxon
Polarizability	35.91 Å³	ChemAxon
Number of Rings	3	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

FDB001653

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

44257383

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Dihydrowighteone (NP0045696)

MOL for NP0045696 ((+)-Dihydrowighteone)

3D MOL for NP0045696 ((+)-Dihydrowighteone)

3D SDF for NP0045696 ((+)-Dihydrowighteone)

3D-SDF for NP0045696 ((+)-Dihydrowighteone)

PDB for NP0045696 ((+)-Dihydrowighteone)

3D PDB for NP0045696 ((+)-Dihydrowighteone)

SMILES for NP0045696 ((+)-Dihydrowighteone)

INCHI for NP0045696 ((+)-Dihydrowighteone)

Structure for NP0045696 ((+)-Dihydrowighteone)

3D Structure for NP0045696 ((+)-Dihydrowighteone)