NP-MRD: Showing NP-Card for Ephedrannin B (NP0085804)

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Record Information

Version

2.0

Created at

2022-04-29 06:16:00 UTC

Updated at

2022-04-29 06:16:00 UTC

NP-MRD ID

NP0085804

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ephedrannin B

Description

(1S,13S)-6,9,17,19-tetrahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]Henicosa-2(11),3(8),5,9,15,17,19-heptaen-7-one 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''. Ephedrannin B is found in Daphniphyllum angustifolium and Ephedra sinica . Based on a literature review very few articles have been published on (1S,13S)-6,9,17,19-tetrahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]Henicosa-2(11),3(8),5,9,15,17,19-heptaen-7-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208162D          

 40 46  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304292208162D          

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 21 28  1  0  0  0  0
 19 29  1  6  0  0  0
 29 30  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 31 37  1  0  0  0  0
 30 38  1  0  0  0  0
 17 38  1  0  0  0  0
 13 39  1  0  0  0  0
  2 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0085804

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O1)C1=C(O[C@@]3(C[C@H]1C1=C(O3)C=C(O)C=C1O)C1=CC=C(O)C=C1)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C30H20O10/c31-15-5-1-13(2-6-15)28-27(37)26(36)25-20(35)11-22-24(29(25)38-28)18-12-30(40-22,14-3-7-16(32)8-4-14)39-21-10-17(33)9-19(34)23(18)21/h1-11,18,31-35,37H,12H2/t18-,30-/m0/s1

> <INCHI_KEY>
PILGQGCHRRYASY-PBYQXAPXSA-N

> <FORMULA>
C30H20O10

> <MOLECULAR_WEIGHT>
540.48

> <EXACT_MASS>
540.105646844

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
54.098121318980475

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,13S)-6,9,17,19-tetrahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),5,9,15(20),16,18-heptaen-7-one

> <ALOGPS_LOGP>
3.74

> <JCHEM_LOGP>
5.327103599666667

> <ALOGPS_LOGS>
-4.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.33380950825461

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.2438677796208895

> <JCHEM_PKA_STRONGEST_BASIC>
-3.937661652077437

> <JCHEM_POLAR_SURFACE_AREA>
166.14

> <JCHEM_REFRACTIVITY>
141.92289999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.25e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,13S)-6,9,17,19-tetrahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),5,9,15(20),16,18-heptaen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      14.515   2.289   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      13.175   1.530   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.848   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.859   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.532   4.630   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.544   6.170   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.883   6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.895   8.470   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.211   6.150   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.199   4.610   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.508   1.550   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.496   0.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.824  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.812  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.139  -3.090   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.472  -3.070   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.144  -2.289   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.156  -0.749   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.076   0.348   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.536   0.360   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.439  -0.721   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.954  -0.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.567   1.180   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.083   1.590   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.665   2.261   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.149   1.850   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.246   2.931   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.427  -2.261   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.755  -1.701   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.507  -3.358   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.907  -4.776   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.835  -6.005   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.235  -7.423   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.706  -7.612   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.106  -9.031   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.778  -6.383   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.379  -4.965   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       8.047  -3.370   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      13.163  -0.010   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      14.491  -0.791   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    4                                                       
CONECT   11    3   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   39                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   38                                                  
CONECT   18   17   12   19                                                  
CONECT   19   18   20   29                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   20   27                                                  
CONECT   27   26                                                            
CONECT   28   21   30                                                       
CONECT   29   19   30                                                       
CONECT   30   29   28   31   38                                             
CONECT   31   30   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   31                                                       
CONECT   38   30   17                                                       
CONECT   39   13    2   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₀O₁₀

Average Mass

540.4800 Da

Monoisotopic Mass

540.10565 Da

IUPAC Name

(1S,13S)-6,9,17,19-tetrahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),5,9,15(20),16,18-heptaen-7-one

Traditional Name

(1S,13S)-6,9,17,19-tetrahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),5,9,15(20),16,18-heptaen-7-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O1)C1=C(O[C@@]3(C[C@H]1C1=C(O3)C=C(O)C=C1O)C1=CC=C(O)C=C1)C=C2O

InChI Identifier

InChI=1S/C30H20O10/c31-15-5-1-13(2-6-15)28-27(37)26(36)25-20(35)11-22-24(29(25)38-28)18-12-30(40-22,14-3-7-16(32)8-4-14)39-21-10-17(33)9-19(34)23(18)21/h1-11,18,31-35,37H,12H2/t18-,30-/m0/s1

InChI Key

PILGQGCHRRYASY-PBYQXAPXSA-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
Daphniphyllum angustifolium	LOTUS Database	35616633
Ephedra sinica	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
Pyranoflavonoid
3-hydroxyflavone
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
7-hydroxyflavonoid
Hydroxyflavonoid
Flavan
Pyranochromene
Chromone
Benzopyran
Chromane
1-benzopyran
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Ketal
Monocyclic benzene moiety
Pyran
Benzenoid
Vinylogous acid
Heteroaromatic compound
Oxacycle
Acetal
Organoheterocyclic compound
Polyol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen 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	3.74	ALOGPS
logP	5.33	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	7.24	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	141.92 m³·mol⁻¹	ChemAxon
Polarizability	54.1 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

C00055820

Chemspider ID

28285892

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162925458

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ephedrannin B (NP0085804)

MOL for NP0085804 (Ephedrannin B)

3D MOL for NP0085804 (Ephedrannin B)

3D SDF for NP0085804 (Ephedrannin B)

3D-SDF for NP0085804 (Ephedrannin B)

PDB for NP0085804 (Ephedrannin B)

3D PDB for NP0085804 (Ephedrannin B)

SMILES for NP0085804 (Ephedrannin B)

INCHI for NP0085804 (Ephedrannin B)

Structure for NP0085804 (Ephedrannin B)

3D Structure for NP0085804 (Ephedrannin B)