NP-MRD: Showing NP-Card for Ephedradine B (NP0085800)

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Record Information

Version

2.0

Created at

2022-04-29 06:15:49 UTC

Updated at

2022-04-29 06:15:50 UTC

NP-MRD ID

NP0085800

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ephedradine B

Description

Ephedradine B belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Ephedradine B is found in Chaenorhinum minus and Ephedra sinica . Ephedradine B was first documented in 1988 (PMID: 17265306). Based on a literature review very few articles have been published on Ephedradine B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208152D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292208152D          

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    3.6139   -3.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5748   -2.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8416   -2.2827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1810   -2.6545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6947   -0.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1050    0.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  1  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 10  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 19 34  1  6  0  0  0
 19 35  1  0  0  0  0
 35 36  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  2  0  0  0  0
 18 38  2  0  0  0  0
 13 38  1  0  0  0  0
  7 39  1  0  0  0  0
 39 40  2  0  0  0  0
  2 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085800

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12[C@@H](OC3=C1C=C(C=C3)[C@]1([H])CC(=O)NCCC[N@](CCCCNCCCN1)C2=O)C1=CC(OC)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H38N4O5/c1-37-25-17-20(6-8-23(25)34)28-27-21-16-19(7-9-24(21)38-28)22-18-26(35)32-13-5-15-33(29(27)36)14-3-2-10-30-11-4-12-31-22/h6-9,16-17,22,27-28,30-31,34H,2-5,10-15,18H2,1H3,(H,32,35)/t22-,27+,28-/m0/s1

> <INCHI_KEY>
OZQWWKNRYQISEO-ZGOJTZKKSA-N

> <FORMULA>
C29H38N4O5

> <MOLECULAR_WEIGHT>
522.646

> <EXACT_MASS>
522.28422034

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
56.858694889802095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,11S,17R,18R)-17-(4-hydroxy-3-methoxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2^{12,15}.0^{14,18}]heptacosa-12,14,26-triene-19,24-dione

> <ALOGPS_LOGP>
1.54

> <JCHEM_LOGP>
0.5345253203005365

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
14.435216936651653

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.98695113664498

> <JCHEM_PKA_STRONGEST_BASIC>
9.122593144205794

> <JCHEM_POLAR_SURFACE_AREA>
112.16

> <JCHEM_REFRACTIVITY>
144.70749999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,11S,17R,18R)-17-(4-hydroxy-3-methoxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2^{12,15}.0^{14,18}]heptacosa-12,14,26-triene-19,24-dione

> <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      -2.054   2.778   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.288   1.442   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.252   1.437   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.026   2.768   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.566   2.764   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.017   0.101   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.243  -1.230   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.009  -2.566   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.643  -2.702   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.944  -1.878   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.308  -2.592   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0       2.276  -1.207   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       2.707  -4.241   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.458  -5.017   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.343  -3.955   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.415  -6.557   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.727  -7.364   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.135  -6.494   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.499  -7.208   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       6.895  -5.959   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       8.164  -7.098   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.465  -6.274   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.401  -4.735   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       8.132  -3.596   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       8.069  -2.057   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.034  -1.863   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.546  -0.229   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.181   0.485   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       3.881  -0.339   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       5.888  -0.319   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.433  -1.760   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.896  -2.597   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       7.969  -4.135   0.000  0.00  0.00           N+0
HETATM   34  H   UNK     0       5.523  -8.748   0.000  0.00  0.00           H+0
HETATM   35  C   UNK     0       6.746  -6.505   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.673  -4.967   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.304  -4.261   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.071  -4.955   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.297  -1.226   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.063   0.111   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   40                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8   39                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10   12   13                                             
CONECT   10    9   11   29                                                  
CONECT   11   10                                                            
CONECT   12    9                                                            
CONECT   13    9   14   38                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14    8                                                       
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   38                                                  
CONECT   19   18   20   34   35                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   10   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   36                                                       
CONECT   34   19                                                            
CONECT   35   19   36                                                       
CONECT   36   35   33   37                                                  
CONECT   37   36                                                            
CONECT   38   18   13                                                       
CONECT   39    7   40                                                       
CONECT   40   39    2                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₈N₄O₅

Average Mass

522.6460 Da

Monoisotopic Mass

522.28422 Da

IUPAC Name

(1S,11S,17R,18R)-17-(4-hydroxy-3-methoxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2^{12,15}.0^{14,18}]heptacosa-12,14,26-triene-19,24-dione

Traditional Name

(1S,11S,17R,18R)-17-(4-hydroxy-3-methoxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2^{12,15}.0^{14,18}]heptacosa-12,14,26-triene-19,24-dione

CAS Registry Number

Not Available

SMILES

[H][C@]12[C@@H](OC3=C1C=C(C=C3)[C@]1([H])CC(=O)NCCC[N@](CCCCNCCCN1)C2=O)C1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C29H38N4O5/c1-37-25-17-20(6-8-23(25)34)28-27-21-16-19(7-9-24(21)38-28)22-18-26(35)32-13-5-15-33(29(27)36)14-3-2-10-30-11-4-12-31-22/h6-9,16-17,22,27-28,30-31,34H,2-5,10-15,18H2,1H3,(H,32,35)/t22-,27+,28-/m0/s1

InChI Key

OZQWWKNRYQISEO-ZGOJTZKKSA-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
Chaenorhinum minus	LOTUS Database	35616633
Ephedra sinica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Neolignan skeleton
Macrolactam
Beta amino acid or derivatives
Methoxyphenol
Benzofuran
Coumaran
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Aralkylamine
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Lactam
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Carboxylic acid derivative
Secondary aliphatic amine
Ether
Hydrocarbon derivative
Carbonyl group
Amine
Organic oxide
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organopnictogen 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	1.54	ALOGPS
logP	0.53	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.99	ChemAxon
pKa (Strongest Basic)	9.12	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	112.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	144.71 m³·mol⁻¹	ChemAxon
Polarizability	56.86 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

C00055816

Chemspider ID

137444

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156055

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhu J, Hesse M: The spermine alkaloids of Chaenorhinum minus. Planta Med. 1988 Oct;54(5):430-3. doi: 10.1055/s-2006-962490. [PubMed:17265306 ]

Showing NP-Card for Ephedradine B (NP0085800)

MOL for NP0085800 (Ephedradine B)

3D MOL for NP0085800 (Ephedradine B)

3D SDF for NP0085800 (Ephedradine B)

3D-SDF for NP0085800 (Ephedradine B)

PDB for NP0085800 (Ephedradine B)

3D PDB for NP0085800 (Ephedradine B)

SMILES for NP0085800 (Ephedradine B)

INCHI for NP0085800 (Ephedradine B)

Structure for NP0085800 (Ephedradine B)

3D Structure for NP0085800 (Ephedradine B)