NP-MRD: Showing NP-Card for Ephedrannin D5 (NP0085809)

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Record Information

Version

2.0

Created at

2022-04-29 06:16:13 UTC

Updated at

2022-04-29 06:16:13 UTC

NP-MRD ID

NP0085809

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ephedrannin D5

Description

Ephedrannin D5 is found in Ephedra sinica . Based on a literature review very few articles have been published on (1R,5S,6R,13S)-5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]Henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208162D          

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M  END

     RDKit          3D

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  Mrv1652304292208162D          

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   -0.5741    2.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8957    3.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7144    3.1366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3985    3.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7201    4.4534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4202    3.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174    4.2507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7418    2.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7383    0.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0654    0.5032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4980    0.6384    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0126    0.8266    0.0000 O   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
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 20 28  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 16 31  1  0  0  0  0
 12 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  1  0  0  0  0
 36 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 34 42  1  0  0  0  0
 33 43  1  0  0  0  0
  9 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 33 46  1  0  0  0  0
  7 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085809

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1(O)[C@]2([H])C3=C(O[C@]1(OC1=C2C2=C(C[C@@H](O)[C@@H](O2)C2=CC(O)=C(O)C(O)=C2)C(O)=C1)C1=CC(O)=C(O)C(O)=C1)C=C(O)C=C3O

> <INCHI_IDENTIFIER>
InChI=1S/C30H24O14/c31-11-5-14(33)22-20(6-11)43-30(10-3-17(36)26(40)18(37)4-10)29(41)24(22)23-21(44-30)8-13(32)12-7-19(38)27(42-28(12)23)9-1-15(34)25(39)16(35)2-9/h1-6,8,19,24,27,29,31-41H,7H2/t19-,24-,27+,29?,30+/m1/s1

> <INCHI_KEY>
SJDDGZBVGOKCKT-OYIUYVEZSA-N

> <FORMULA>
C30H24O14

> <MOLECULAR_WEIGHT>
608.508

> <EXACT_MASS>
608.116605453

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
58.584519244478884

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5S,6R,13S)-5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
2.9834014533333333

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.927848058640523

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.418163375582226

> <JCHEM_PKA_STRONGEST_BASIC>
-5.217530837356386

> <JCHEM_POLAR_SURFACE_AREA>
250.21999999999994

> <JCHEM_REFRACTIVITY>
148.1581

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5S,6R,13S)-5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol

> <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       1.796  -3.649   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.699  -2.568   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.786  -2.978   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.883  -1.898   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.367  -2.308   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.496  -0.407   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.012   0.003   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.086  -1.077   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.626  -1.066   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0       3.226  -2.484   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0       3.706   0.032   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.694   1.572   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.022   2.352   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.362   1.592   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.689   2.373   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.374   0.052   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.046  -0.728   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.058  -2.268   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.397  -3.027   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.409  -4.567   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.749  -5.327   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.761  -6.867   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.100  -7.627   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.433  -7.647   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.445  -9.187   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.094  -6.888   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.766  -7.668   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.082  -5.348   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.725  -2.247   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.065  -3.007   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       7.713  -0.707   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.597   2.652   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.057   2.640   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.457   4.059   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.072   4.248   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.672   5.666   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -3.200   5.855   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -0.744   6.895   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.344   8.313   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       0.784   6.706   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       1.712   7.935   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       1.385   5.287   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.378   0.591   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -0.122   0.939   0.000  0.00  0.00           O+0
HETATM   45  H   UNK     0       2.796   1.192   0.000  0.00  0.00           H+0
HETATM   46  O   UNK     0      -0.023   1.543   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   46                                                  
CONECT    8    7    2    9                                                  
CONECT    9    8   10   11   43                                             
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11   13   32                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   31                                                  
CONECT   17   16   11   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   29                                                  
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   20                                                       
CONECT   29   19   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   16                                                       
CONECT   32   12   33                                                       
CONECT   33   32   34   43   46                                             
CONECT   34   33   35   42                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   34                                                       
CONECT   43   33    9   44   45                                             
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   33    7                                                       
MASTER        0    0    0    0    0    0    0    0   46    0  104    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₄O₁₄

Average Mass

608.5080 Da

Monoisotopic Mass

608.11661 Da

IUPAC Name

(1R,5S,6R,13S)-5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol

Traditional Name

(1R,5S,6R,13S)-5,13-bis(3,4,5-trihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol

CAS Registry Number

Not Available

SMILES

[H]C1(O)[C@]2([H])C3=C(O[C@]1(OC1=C2C2=C(C[C@@H](O)[C@@H](O2)C2=CC(O)=C(O)C(O)=C2)C(O)=C1)C1=CC(O)=C(O)C(O)=C1)C=C(O)C=C3O

InChI Identifier

InChI=1S/C30H24O14/c31-11-5-14(33)22-20(6-11)43-30(10-3-17(36)26(40)18(37)4-10)29(41)24(22)23-21(44-30)8-13(32)12-7-19(38)27(42-28(12)23)9-1-15(34)25(39)16(35)2-9/h1-6,8,19,24,27,29,31-41H,7H2/t19-,24-,27+,29?,30+/m1/s1

InChI Key

SJDDGZBVGOKCKT-OYIUYVEZSA-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
Ephedra sinica	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	2.25	ALOGPS
logP	2.98	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.42	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	250.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	148.16 m³·mol⁻¹	ChemAxon
Polarizability	58.58 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

C00055825

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

163184070

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ephedrannin D5 (NP0085809)

MOL for NP0085809 (Ephedrannin D5)

3D MOL for NP0085809 (Ephedrannin D5)

3D SDF for NP0085809 (Ephedrannin D5)

3D-SDF for NP0085809 (Ephedrannin D5)

PDB for NP0085809 (Ephedrannin D5)

3D PDB for NP0085809 (Ephedrannin D5)

SMILES for NP0085809 (Ephedrannin D5)

INCHI for NP0085809 (Ephedrannin D5)

Structure for NP0085809 (Ephedrannin D5)

3D Structure for NP0085809 (Ephedrannin D5)