NP-MRD: Showing NP-Card for (11r,17r,18r)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2¹²,¹⁵.0¹⁴,¹⁸]heptacosa-12(27),13,15(26),23-tetraen-19-one (NP0191596)

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Record Information

Version

2.0

Created at

2022-09-04 08:37:10 UTC

Updated at

2022-09-04 08:37:11 UTC

NP-MRD ID

NP0191596

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(11r,17r,18r)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2¹²,¹⁵.0¹⁴,¹⁸]heptacosa-12(27),13,15(26),23-tetraen-19-one

Description

(-)-Ephedradine A belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (11r,17r,18r)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2¹²,¹⁵.0¹⁴,¹⁸]heptacosa-12(27),13,15(26),23-tetraen-19-one is found in Chaenorhinum minus and Schweinfurthia papilionacea. (11r,17r,18r)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2¹²,¹⁵.0¹⁴,¹⁸]heptacosa-12(27),13,15(26),23-tetraen-19-one was first documented in 2003 (PMID: 12837075). Based on a literature review very few articles have been published on (-)-Ephedradine A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042210372D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042210372D          

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  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 19  6  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  4  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  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
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 19 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0191596

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)[C@@H]1OC2=CC=C3C=C2[C@H]1C(=O)N1CCCCNCCCN[C@@H]3CC(O)=NCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C28H36N4O4/c33-21-8-5-19(6-9-21)27-26-22-17-20(7-10-24(22)36-27)23-18-25(34)31-14-4-16-32(28(26)35)15-2-1-11-29-12-3-13-30-23/h5-10,17,23,26-27,29-30,33H,1-4,11-16,18H2,(H,31,34)/t23-,26-,27+/m1/s1

> <INCHI_KEY>
ASCIWXOCZAWSON-MVNQZMKCSA-N

> <FORMULA>
C28H36N4O4

> <MOLECULAR_WEIGHT>
492.62

> <EXACT_MASS>
492.273655655

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.05321363629671

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(11R,17R,18R)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2^{12,15}.0^{14,18}]heptacosa-12(27),13,15(26),23-tetraen-19-one

> <JCHEM_LOGP>
-0.6268667891641627

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
9.707577897007162

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.284611934829217

> <JCHEM_PKA_STRONGEST_BASIC>
9.096317837890332

> <JCHEM_POLAR_SURFACE_AREA>
106.42

> <JCHEM_REFRACTIVITY>
138.766

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(11R,17R,18R)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2^{12,15}.0^{14,18}]heptacosa-12(27),13,15(26),23-tetraen-19-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0       2.811  -6.796   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.495  -5.416   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.882  -4.271   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.491  -2.977   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.920  -3.003   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.482  -4.365   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.502  -5.852   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.014  -5.914   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.430  -4.550   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.731  -3.596   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.519  -2.705   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.700  -1.176   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.534  -0.255   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.353   1.274   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.061   1.883   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.242   3.412   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.295   0.961   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.115  -0.568   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.863  -3.542   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.441  -5.034   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.355  -6.955   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.848  -7.273   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0       6.079  -8.415   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       7.667  -8.439   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.972  -6.880   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.861  -5.499   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       5.191  -5.948   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       6.794  -6.508   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.268  -5.563   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.780  -5.056   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.736  -3.824   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       9.851  -2.540   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       8.545  -1.688   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.349  -0.681   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.793  -0.528   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       5.288  -2.005   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10    3   12                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12                                                       
CONECT   19    6   20   36                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    2   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   19                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₆N₄O₄

Average Mass

492.6200 Da

Monoisotopic Mass

492.27366 Da

IUPAC Name

(11R,17R,18R)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2^{12,15}.0^{14,18}]heptacosa-12(27),13,15(26),23-tetraen-19-one

Traditional Name

(11R,17R,18R)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2^{12,15}.0^{14,18}]heptacosa-12(27),13,15(26),23-tetraen-19-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)[C@@H]1OC2=CC=C3C=C2[C@H]1C(=O)N1CCCCNCCCN[C@@H]3CC(O)=NCCC1

InChI Identifier

InChI=1S/C28H36N4O4/c33-21-8-5-19(6-9-21)27-26-22-17-20(7-10-24(22)36-27)23-18-25(34)31-14-4-16-32(28(26)35)15-2-1-11-29-12-3-13-30-23/h5-10,17,23,26-27,29-30,33H,1-4,11-16,18H2,(H,31,34)/t23-,26-,27+/m1/s1

InChI Key

ASCIWXOCZAWSON-MVNQZMKCSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Schweinfurthia papilionacea	LOTUS Database	35616633

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
Benzofuran
Coumaran
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Lactam
Secondary carboxylic acid amide
Azacycle
Oxacycle
Ether
Secondary aliphatic amine
Carboxylic acid derivative
Organoheterocyclic compound
Secondary amine
Organonitrogen compound
Organic nitrogen compound
Amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	-0.63	ChemAxon
pKa (Strongest Acidic)	3.28	ChemAxon
pKa (Strongest Basic)	9.1	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.42 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	138.77 m³·mol⁻¹	ChemAxon
Polarizability	53.05 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

23340046

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12877769

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kurosawa W, Kan T, Fukuyama T: Stereocontrolled total synthesis of (-)-ephedradine A (orantine). J Am Chem Soc. 2003 Jul 9;125(27):8112-3. doi: 10.1021/ja036011k. [PubMed:12837075 ]
LOTUS database [Link]

Showing NP-Card for (11r,17r,18r)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2¹²,¹⁵.0¹⁴,¹⁸]heptacosa-12(27),13,15(26),23-tetraen-19-one (NP0191596)

MOL for NP0191596 ((11r,17r,18r)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2¹²,¹⁵.0¹⁴,¹⁸]heptacosa-12(27),13,15(26),23-tetraen-19-one)

3D MOL for NP0191596 ((11r,17r,18r)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2¹²,¹⁵.0¹⁴,¹⁸]heptacosa-12(27),13,15(26),23-tetraen-19-one)

3D SDF for NP0191596 ((11r,17r,18r)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2¹²,¹⁵.0¹⁴,¹⁸]heptacosa-12(27),13,15(26),23-tetraen-19-one)

3D-SDF for NP0191596 ((11r,17r,18r)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2¹²,¹⁵.0¹⁴,¹⁸]heptacosa-12(27),13,15(26),23-tetraen-19-one)

PDB for NP0191596 ((11r,17r,18r)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2¹²,¹⁵.0¹⁴,¹⁸]heptacosa-12(27),13,15(26),23-tetraen-19-one)

3D PDB for NP0191596 ((11r,17r,18r)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2¹²,¹⁵.0¹⁴,¹⁸]heptacosa-12(27),13,15(26),23-tetraen-19-one)

SMILES for NP0191596 ((11r,17r,18r)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2¹²,¹⁵.0¹⁴,¹⁸]heptacosa-12(27),13,15(26),23-tetraen-19-one)

INCHI for NP0191596 ((11r,17r,18r)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2¹²,¹⁵.0¹⁴,¹⁸]heptacosa-12(27),13,15(26),23-tetraen-19-one)

Structure for NP0191596 ((11r,17r,18r)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2¹²,¹⁵.0¹⁴,¹⁸]heptacosa-12(27),13,15(26),23-tetraen-19-one)

3D Structure for NP0191596 ((11r,17r,18r)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2¹²,¹⁵.0¹⁴,¹⁸]heptacosa-12(27),13,15(26),23-tetraen-19-one)