NP-MRD: Showing NP-Card for Hypnumbiflavonoid A (NP0054367)

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Record Information

Version

2.0

Created at

2022-04-28 00:44:34 UTC

Updated at

2022-04-28 00:44:34 UTC

NP-MRD ID

NP0054367

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hypnumbiflavonoid A

Description

(4S,5R,12S,17R)-5,8-dihydroxy-4-(4-hydroxyphenyl)-17-[(2R,3S)-3,5,7-trihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-3,11-dioxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁷]Heptadeca-1(10),2(7),8,15-tetraene-6,14-dione belongs to the class of organic compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively. Hypnumbiflavonoid A is found in Hypnum cupressiforme. Based on a literature review very few articles have been published on (4S,5R,12S,17R)-5,8-dihydroxy-4-(4-hydroxyphenyl)-17-[(2R,3S)-3,5,7-trihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-3,11-dioxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁷]Heptadeca-1(10),2(7),8,15-tetraene-6,14-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202442D          

 42 48  0  0  1  0            999 V2000
    3.0592   -2.9340    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6854   -3.6695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1355   -4.3609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9593   -4.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 42  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282202442D          

 42 48  0  0  1  0            999 V2000
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    5.6501   -6.5688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2443   -2.9768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5856   -2.7433    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  6  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  3 12  1  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  0  0  0  0
  1 15  1  6  0  0  0
 15 16  1  6  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
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 15 28  1  0  0  0  0
 19 29  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  2  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
 34 39  1  0  0  0  0
 37 40  1  0  0  0  0
 33 41  1  0  0  0  0
 17 41  1  0  0  0  0
 32 42  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0054367

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](OC2=C3C(O[C@H]4CC(=O)C=C[C@@]34[C@H]3OC4=C(C(O)=CC(O)=C4)C(=O)[C@H]3O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H22O12/c31-12-3-1-11(2-4-12)27-25(38)24(37)21-16(35)10-18-22(28(21)42-27)30(6-5-13(32)9-19(30)40-18)29-26(39)23(36)20-15(34)7-14(33)8-17(20)41-29/h1-8,10,19,25-27,29,31,33-35,38-39H,9H2/t19-,25-,26+,27-,29-,30-/m0/s1

> <INCHI_KEY>
KKFWUGTXANEERY-UVBOVUSOSA-N

> <FORMULA>
C30H22O12

> <MOLECULAR_WEIGHT>
574.494

> <EXACT_MASS>
574.111126148

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
54.15185467638153

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,5R,12S,17R)-5,8-dihydroxy-4-(4-hydroxyphenyl)-17-[(2R,3S)-3,5,7-trihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-3,11-dioxatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-1,7,9,15-tetraene-6,14-dione

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
2.8800069406666666

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.488852792217694

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.684857849766548

> <JCHEM_PKA_STRONGEST_BASIC>
-4.014261151287497

> <JCHEM_POLAR_SURFACE_AREA>
200.27999999999997

> <JCHEM_REFRACTIVITY>
142.1598

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5R,12S,17R)-5,8-dihydroxy-4-(4-hydroxyphenyl)-17-[(2R,3S)-3,5,7-trihydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]-3,11-dioxatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-1,7,9,15-tetraene-6,14-dione

> <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       5.711  -5.477   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.013  -6.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.853  -8.140   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.391  -8.058   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.088  -6.685   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.001  -6.718   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.248  -5.395   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.772  -4.274   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.231  -9.349   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.533 -10.722   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.995 -10.804   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.155  -9.513   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.187 -12.218   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      10.052  -9.180   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.870  -4.186   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.242  -3.486   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.680  -4.036   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.876  -3.066   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.633  -1.545   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.195  -0.994   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.999  -1.965   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.478  -1.726   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.780  -3.098   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.293  -3.499   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.896  -4.986   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.338  -5.381   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.986  -6.074   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.473  -5.674   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.766  -0.357   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.314  -3.616   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.697  -2.694   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.557  -5.137   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.361  -6.107   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.603  -7.628   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.042  -8.178   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.284  -9.699   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.088 -10.669   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.650 -10.119   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.408  -8.598   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      10.547 -12.262   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       7.923  -5.557   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      12.293  -5.121   0.000  0.00  0.00           O+0
CONECT    1    2    7   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    1    8                                                  
CONECT    8    7                                                            
CONECT    9    4   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11    3                                                       
CONECT   13   11                                                            
CONECT   14    9                                                            
CONECT   15    1   16   23   28                                             
CONECT   16   15   17   21                                                  
CONECT   17   16   18   41                                                  
CONECT   18   17   19   30                                                  
CONECT   19   18   20   29                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   15   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   15                                                       
CONECT   29   19                                                            
CONECT   30   18   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   42                                                  
CONECT   33   32   34   41                                                  
CONECT   34   33   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38   34                                                       
CONECT   40   37                                                            
CONECT   41   33   17                                                       
CONECT   42   32                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₂O₁₂

Average Mass

574.4940 Da

Monoisotopic Mass

574.11113 Da

IUPAC Name

(4S,5R,12S,17R)-5,8-dihydroxy-4-(4-hydroxyphenyl)-17-[(2R,3S)-3,5,7-trihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-3,11-dioxatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-1,7,9,15-tetraene-6,14-dione

Traditional Name

(4S,5R,12S,17R)-5,8-dihydroxy-4-(4-hydroxyphenyl)-17-[(2R,3S)-3,5,7-trihydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]-3,11-dioxatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-1,7,9,15-tetraene-6,14-dione

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](OC2=C3C(O[C@H]4CC(=O)C=C[C@@]34[C@H]3OC4=C(C(O)=CC(O)=C4)C(=O)[C@H]3O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C30H22O12/c31-12-3-1-11(2-4-12)27-25(38)24(37)21-16(35)10-18-22(28(21)42-27)30(6-5-13(32)9-19(30)40-18)29-26(39)23(36)20-15(34)7-14(33)8-17(20)41-29/h1-8,10,19,25-27,29,31,33-35,38-39H,9H2/t19-,25-,26+,27-,29-,30-/m0/s1

InChI Key

KKFWUGTXANEERY-UVBOVUSOSA-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
Hypnum cupressiforme	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanonols

Alternative Parents

Substituents

Hydroxyflavonoid
Flavanonol
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
Chromone
1-benzopyran
Benzopyran
Chromane
Coumaran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Cyclic ketone
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.09	ALOGPS
logP	2.88	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.68	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	200.28 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	142.16 m³·mol⁻¹	ChemAxon
Polarizability	54.15 Å³	ChemAxon
Number of Rings	7	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

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

163033244

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Hypnumbiflavonoid A (NP0054367)

MOL for NP0054367 (Hypnumbiflavonoid A)

3D MOL for NP0054367 (Hypnumbiflavonoid A)

3D SDF for NP0054367 (Hypnumbiflavonoid A)

3D-SDF for NP0054367 (Hypnumbiflavonoid A)

PDB for NP0054367 (Hypnumbiflavonoid A)

3D PDB for NP0054367 (Hypnumbiflavonoid A)

SMILES for NP0054367 (Hypnumbiflavonoid A)

INCHI for NP0054367 (Hypnumbiflavonoid A)

Structure for NP0054367 (Hypnumbiflavonoid A)

3D Structure for NP0054367 (Hypnumbiflavonoid A)