NP-MRD: Showing NP-Card for (S)-5,7-Dihydroxy-6-(2-hydroxybenzyl)-8-(2x2-hydroxybenzyl)flavanone (NP0060504)

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Record Information

Version

2.0

Created at

2022-04-28 05:32:38 UTC

Updated at

2022-04-28 05:32:38 UTC

NP-MRD ID

NP0060504

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(S)-5,7-Dihydroxy-6-(2-hydroxybenzyl)-8-(2x2-hydroxybenzyl)flavanone

Description

Isouvarinol belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. Thus, isouvarinol is considered to be a flavonoid. (S)-5,7-Dihydroxy-6-(2-hydroxybenzyl)-8-(2x2-hydroxybenzyl)flavanone is found in Uvaria lucida and Xylopia africana. (S)-5,7-Dihydroxy-6-(2-hydroxybenzyl)-8-(2x2-hydroxybenzyl)flavanone was first documented in 2021 (PMID: 34207059). Based on a literature review very few articles have been published on Isouvarinol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207322D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282207322D          

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    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  8  1  1  0  0  0
  8  9  2  0  0  0  0
  9 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
  8 13  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  1 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  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
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 27  1  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 36 41  1  0  0  0  0
 41 42  1  0  0  0  0
 30 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060504

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC=C1CC1=CC(CC2=C(O)C(CC3=CC=CC=C3O)=C(O)C3=C2O[C@@H](CC3=O)C2=CC=CC=C2)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C36H30O7/c37-28-12-6-4-10-23(28)16-21-14-15-30(39)25(17-21)19-27-34(41)26(18-24-11-5-7-13-29(24)38)35(42)33-31(40)20-32(43-36(27)33)22-8-2-1-3-9-22/h1-15,17,32,37-39,41-42H,16,18-20H2/t32-/m0/s1

> <INCHI_KEY>
GDXLBYLYYIFYFC-YTTGMZPUSA-N

> <FORMULA>
C36H30O7

> <MOLECULAR_WEIGHT>
574.629

> <EXACT_MASS>
574.199153306

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
59.60275495685534

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-5,7-dihydroxy-8-({2-hydroxy-5-[(2-hydroxyphenyl)methyl]phenyl}methyl)-6-[(2-hydroxyphenyl)methyl]-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
5.33

> <JCHEM_LOGP>
8.503359488000001

> <ALOGPS_LOGS>
-5.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.883209285537402

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.268405102276565

> <JCHEM_PKA_STRONGEST_BASIC>
-4.945356315494894

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
164.4632

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isouvarinol

> <JCHEM_VEBER_RULE>
0

$$$$

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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    2    6   17                                                  
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    2   15   28                                                  
CONECT   15   14   16   27                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16    1   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20   26                                                  
CONECT   26   25                                                            
CONECT   27   15                                                            
CONECT   28   14   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31   43                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33   29                                                       
CONECT   35   33   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   36   42                                                  
CONECT   42   41                                                            
CONECT   43   30                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₃₀O₇

Average Mass

574.6290 Da

Monoisotopic Mass

574.19915 Da

IUPAC Name

(2S)-5,7-dihydroxy-8-({2-hydroxy-5-[(2-hydroxyphenyl)methyl]phenyl}methyl)-6-[(2-hydroxyphenyl)methyl]-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

isouvarinol

CAS Registry Number

Not Available

SMILES

OC1=CC=CC=C1CC1=CC(CC2=C(O)C(CC3=CC=CC=C3O)=C(O)C3=C2O[C@@H](CC3=O)C2=CC=CC=C2)=C(O)C=C1

InChI Identifier

InChI=1S/C36H30O7/c37-28-12-6-4-10-23(28)16-21-14-15-30(39)25(17-21)19-27-34(41)26(18-24-11-5-7-13-29(24)38)35(42)33-31(40)20-32(43-36(27)33)22-8-2-1-3-9-22/h1-15,17,32,37-39,41-42H,16,18-20H2/t32-/m0/s1

InChI Key

GDXLBYLYYIFYFC-YTTGMZPUSA-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
Uvaria lucida	LOTUS Database	35616633
Xylopia africana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Linear diarylheptanoids

Alternative Parents

Substituents

Linear 1,7-diphenylheptane skeleton
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Diphenylmethane
Chromone
1-benzopyran
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140151 )

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	5.33	ALOGPS
logP	8.5	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	6.27	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	164.46 m³·mol⁻¹	ChemAxon
Polarizability	59.6 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

C00014264

Chemspider ID

24846301

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42607863

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Costa EV, Soares LDN, Chaar JDS, Silva VR, Santos LS, Koolen HHF, Silva FMAD, Tavares JF, Zengin G, Soares MBP, Bezerra DP: Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities. Molecules. 2021 Jun 18;26(12). pii: molecules26123714. doi: 10.3390/molecules26123714. [PubMed:34207059 ]

Showing NP-Card for (S)-5,7-Dihydroxy-6-(2-hydroxybenzyl)-8-(2x2-hydroxybenzyl)flavanone (NP0060504)

MOL for NP0060504 ((S)-5,7-Dihydroxy-6-(2-hydroxybenzyl)-8-(2x2-hydroxybenzyl)flavanone)

3D MOL for NP0060504 ((S)-5,7-Dihydroxy-6-(2-hydroxybenzyl)-8-(2x2-hydroxybenzyl)flavanone)

3D SDF for NP0060504 ((S)-5,7-Dihydroxy-6-(2-hydroxybenzyl)-8-(2x2-hydroxybenzyl)flavanone)

3D-SDF for NP0060504 ((S)-5,7-Dihydroxy-6-(2-hydroxybenzyl)-8-(2x2-hydroxybenzyl)flavanone)

PDB for NP0060504 ((S)-5,7-Dihydroxy-6-(2-hydroxybenzyl)-8-(2x2-hydroxybenzyl)flavanone)

3D PDB for NP0060504 ((S)-5,7-Dihydroxy-6-(2-hydroxybenzyl)-8-(2x2-hydroxybenzyl)flavanone)

SMILES for NP0060504 ((S)-5,7-Dihydroxy-6-(2-hydroxybenzyl)-8-(2x2-hydroxybenzyl)flavanone)

INCHI for NP0060504 ((S)-5,7-Dihydroxy-6-(2-hydroxybenzyl)-8-(2x2-hydroxybenzyl)flavanone)

Structure for NP0060504 ((S)-5,7-Dihydroxy-6-(2-hydroxybenzyl)-8-(2x2-hydroxybenzyl)flavanone)

3D Structure for NP0060504 ((S)-5,7-Dihydroxy-6-(2-hydroxybenzyl)-8-(2x2-hydroxybenzyl)flavanone)