NP-MRD: Showing NP-Card for Mesuaferrone B (NP0054310)

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Record Information

Version

2.0

Created at

2022-04-28 00:42:33 UTC

Updated at

2022-04-28 00:42:33 UTC

NP-MRD ID

NP0054310

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Mesuaferrone B

Description

Mesuaferrone B belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Mesuaferrone B is found in Mesua ferrea . Mesuaferrone B was first documented in 2012 (PMID: 22579675). Based on a literature review a small amount of articles have been published on Mesuaferrone B (PMID: 31534074) (PMID: 31135222).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202422D          

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M  END

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M  END


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 32 37  1  0  0  0  0
 35 38  1  0  0  0  0
  3 39  1  0  0  0  0
  1 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054310

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)[C@@H]1CC(=O)C2=C(O1)C(=C(O)C=C2O)C1=C2OC(=CC(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H20O10/c31-15-5-1-13(2-6-15)23-11-21(37)25-17(33)9-19(35)27(29(25)39-23)28-20(36)10-18(34)26-22(38)12-24(40-30(26)28)14-3-7-16(32)8-4-14/h1-11,24,31-36H,12H2/t24-/m0/s1

> <INCHI_KEY>
NGFXXUPZBREFSL-DEOSSOPVSA-N

> <FORMULA>
C30H20O10

> <MOLECULAR_WEIGHT>
540.48

> <EXACT_MASS>
540.105646844

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
52.545653195608054

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-[(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
4.17

> <JCHEM_LOGP>
5.21577673

> <ALOGPS_LOGS>
-4.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.453132061711742

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.113527247759751

> <JCHEM_PKA_STRONGEST_BASIC>
-5.066210399365208

> <JCHEM_POLAR_SURFACE_AREA>
173.98

> <JCHEM_REFRACTIVITY>
143.2819

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.76e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

> <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   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   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   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6   40                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   39                                                  
CONECT    4    3    5   30                                                  
CONECT    5    4    6   27                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   25                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16                                                            
CONECT   18   14   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   21                                                            
CONECT   25   10                                                            
CONECT   26    8                                                            
CONECT   27    5   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29    4   31                                                  
CONECT   31   30                                                            
CONECT   32   28   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
CONECT   38   35                                                            
CONECT   39    3                                                            
CONECT   40    1                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
8-((2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-8-yl)-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one	MeSH

Chemical Formula

C₃₀H₂₀O₁₀

Average Mass

540.4800 Da

Monoisotopic Mass

540.10565 Da

IUPAC Name

8-[(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

8-[(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)[C@@H]1CC(=O)C2=C(O1)C(=C(O)C=C2O)C1=C2OC(=CC(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C30H20O10/c31-15-5-1-13(2-6-15)23-11-21(37)25-17(33)9-19(35)27(29(25)39-23)28-20(36)10-18(34)26-22(38)12-24(40-30(26)28)14-3-7-16(32)8-4-14/h1-11,24,31-36H,12H2/t24-/m0/s1

InChI Key

NGFXXUPZBREFSL-DEOSSOPVSA-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
Mesua ferrea	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

Bi- and polyflavonoid skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Flavone
Hydroxyflavonoid
Flavan
Biphenol
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyran
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	4.17	ALOGPS
logP	5.22	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	6.11	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.98 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	143.28 m³·mol⁻¹	ChemAxon
Polarizability	52.55 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00006466

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

90472563

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang X, Gao R, Liu Y, Cong Y, Zhang D, Zhang Y, Yang X, Lu C, Shen Y: Anti-virulence activities of biflavonoids from Mesua ferrea L. flower. Drug Discov Ther. 2019;13(4):222-227. doi: 10.5582/ddt.2019.01053. [PubMed:31534074 ]
Zar Wynn Myint K, Kido T, Kusakari K, Prasad Devkota H, Kawahara T, Watanabe T: Rhusflavanone and mesuaferrone B: tyrosinase and elastase inhibitory biflavonoids extracted from the stamens of Mesua ferrea L. Nat Prod Res. 2021 Mar;35(6):1024-1028. doi: 10.1080/14786419.2019.1613395. Epub 2019 May 28. [PubMed:31135222 ]
Shrestha S, Park JH, Lee DY, Cho JG, Cho S, Yang HJ, Yong HI, Yoon MS, Han DS, Baek NI: Rhus parviflora and its biflavonoid constituent, rhusflavone, induce sleep through the positive allosteric modulation of GABA(A)-benzodiazepine receptors. J Ethnopharmacol. 2012 Jun 26;142(1):213-20. doi: 10.1016/j.jep.2012.04.047. Epub 2012 May 2. [PubMed:22579675 ]

Showing NP-Card for Mesuaferrone B (NP0054310)

MOL for NP0054310 (Mesuaferrone B)

3D MOL for NP0054310 (Mesuaferrone B)

3D SDF for NP0054310 (Mesuaferrone B)

3D-SDF for NP0054310 (Mesuaferrone B)

PDB for NP0054310 (Mesuaferrone B)

3D PDB for NP0054310 (Mesuaferrone B)

SMILES for NP0054310 (Mesuaferrone B)

INCHI for NP0054310 (Mesuaferrone B)

Structure for NP0054310 (Mesuaferrone B)

3D Structure for NP0054310 (Mesuaferrone B)