NP-MRD: Showing NP-Card for 6-O-ethylzephyranine E (NP0333729)

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Record Information

Version

2.0

Created at

2024-08-12 09:46:52 UTC

Updated at

2024-09-16 10:47:02 UTC

NP-MRD ID

NP0333729

Natural Product DOI

https://doi.org/10.57994/3208

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-O-ethylzephyranine E

Description

It was first documented in 2024 (PMID: 39313750). Based on a literature review a significant number of articles have been published on 6-O-ethylzephyranine E (PMID: 39313741) (PMID: 39313725) (PMID: 39313684) (PMID: 39313682).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 04262312202D          

 26 29  0  0  1  0            999 V2000
    1.9504   -0.7283    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3909   -0.1220    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9347   -0.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8090   -0.2977    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4673   -0.7949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3659   -1.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9104    0.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2520    1.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4923    0.6967    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7214    0.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4244   -0.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8410   -0.9034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6575   -1.0216    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9053   -1.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3476   -2.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5422   -2.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2590   -0.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0044   -0.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6833   -0.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4287   -0.6956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1077   -0.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6169    0.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2959    0.9490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2295    1.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8716    0.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1926    0.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  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
 19 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 17 26  1  0  0  0  0
  9 26  1  0  0  0  0
M  END


  Mrv2104 04262312202D          

 26 29  0  0  1  0            999 V2000
    1.9504   -0.7283    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3909   -0.1220    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9347   -0.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8090   -0.2977    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4673   -0.7949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3659   -1.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9104    0.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2520    1.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4923    0.6967    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7214    0.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4244   -0.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8410   -0.9034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6575   -1.0216    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9053   -1.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3476   -2.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5422   -2.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2590   -0.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0044   -0.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6833   -0.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4287   -0.6956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1077   -0.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6169    0.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2959    0.9490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2295    1.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8716    0.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1926    0.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  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
 19 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 17 26  1  0  0  0  0
  9 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333729

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@H](CC[C@@]11CCN2[C@@H](OCC)C2=CC(OC)=C(OC)C=C12)OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H29NO4/c1-5-25-19-14-11-16(23-3)17(24-4)12-15(14)20-7-6-13(22-2)10-18(20)21(19)9-8-20/h11-13,18-19H,5-10H2,1-4H3/t13-,18-,19-,20-/m0/s1

> <INCHI_KEY>
LRRYCKWQNAHRIL-KJYZGMDISA-N

> <FORMULA>
C20H29NO4

> <MOLECULAR_WEIGHT>
347.455

> <EXACT_MASS>
347.209658418

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
39.50740198866263

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,8S,10S,12S)-8-ethoxy-4,5,12-trimethoxy-9-azatetracyclo[7.5.2.0^{1,10}.0^{2,7}]hexadeca-2,4,6-triene

> <JCHEM_LOGP>
2.647894020666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.409567654333284

> <JCHEM_POLAR_SURFACE_AREA>
40.160000000000004

> <JCHEM_REFRACTIVITY>
96.6232

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,8S,10S,12S)-8-ethoxy-4,5,12-trimethoxy-9-azatetracyclo[7.5.2.0^{1,10}.0^{2,7}]hexadeca-2,4,6-triene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-23         0                                  
HETATM    1  H   UNK     0       3.641  -1.359   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       2.596  -0.228   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.611  -1.198   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.243  -0.556   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.472  -1.484   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.283  -3.012   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.433   0.973   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.204   1.901   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.786   1.301   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.347   1.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.792  -0.357   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.570  -1.686   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.094  -1.907   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.556  -3.376   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.516  -4.511   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.012  -4.177   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.217  -0.853   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.608  -1.513   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.876  -0.638   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.267  -1.298   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.534  -0.424   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.752   0.897   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.019   1.772   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.895   3.307   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.360   1.557   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.093   0.682   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9   12                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    2   10   26                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    2   13                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   13   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25   17    9                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₉NO₄

Average Mass

347.4550 Da

Monoisotopic Mass

347.20966 Da

IUPAC Name

(1S,8S,10S,12S)-8-ethoxy-4,5,12-trimethoxy-9-azatetracyclo[7.5.2.0^{1,10}.0^{2,7}]hexadeca-2,4,6-triene

Traditional Name

(1S,8S,10S,12S)-8-ethoxy-4,5,12-trimethoxy-9-azatetracyclo[7.5.2.0^{1,10}.0^{2,7}]hexadeca-2,4,6-triene

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@H](CC[C@@]11CCN2[C@@H](OCC)C2=CC(OC)=C(OC)C=C12)OC

InChI Identifier

InChI=1S/C20H29NO4/c1-5-25-19-14-11-16(23-3)17(24-4)12-15(14)20-7-6-13(22-2)10-18(20)21(19)9-8-20/h11-13,18-19H,5-10H2,1-4H3/t13-,18-,19-,20-/m0/s1

InChI Key

LRRYCKWQNAHRIL-KJYZGMDISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	marikoj2@faf.cuni.cz	Faculty of Pharmacy, Charles University	Jana Křoustková	2024-08-12	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	marikoj2@faf.cuni.cz	Faculty of Pharmacy, Charles University	Jana Křoustková	2024-08-12	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	marikoj2@faf.cuni.cz	Faculty of Pharmacy, Charles University	Jana Křoustková	2024-08-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCL3, experimental)	marikoj2@faf.cuni.cz	Faculty of Pharmacy, Charles University	Jana Křoustková	2024-08-12	View Spectrum
H2BC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	marikoj2@faf.cuni.cz	Faculty of Pharmacy, Charles University	Jana Křoustková	2024-08-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCL3, experimental)	marikoj2@faf.cuni.cz	Faculty of Pharmacy, Charles University	Jana Křoustková	2024-08-12	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	marikoj2@faf.cuni.cz	Faculty of Pharmacy, Charles University	Jana Křoustková	2024-08-12	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
citrina		Not Available

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	2.65	ChemAxon
pKa (Strongest Basic)	7.41	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.16 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.62 m³·mol⁻¹	ChemAxon
Polarizability	39.51 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen Z, Li X, Xu G, Xiao T, Wang D, Wang C, Zhang K, Li J, Pan Y, Qiao Y, Zhang Y: Synergize Strong and Reactive Metal-Support Interactions to Construct Sub-2 nm Metal Phosphide Cluster for Enhanced Selective Hydrogenation Activities. Angew Chem Int Ed Engl. 2024 Sep 23:e202413788. doi: 10.1002/anie.202413788. [PubMed:39313750 ]
Hirai T, Aoyama T, Tsuji Y, Ino K, Ikejiri M, Tawara I, Iwamoto T: Pharmacokinetic Model of Drug Interaction of Tacrolimus with Combined Administration of CYP3A4 Inhibitors Voriconazole and Clarithromycin After Bone Marrow Transplantation. Eur J Drug Metab Pharmacokinet. 2024 Sep 24. doi: 10.1007/s13318-024-00915-2. [PubMed:39313741 ]
Beghini A, Aimo A, Ambrosy AP, Tomasoni D: Modulating energy metabolism to treat non-obstructive hypertrophic cardiomyopathy? Insights from IMPROVE-HCM. Heart Fail Rev. 2024 Sep 23. doi: 10.1007/s10741-024-10440-8. [PubMed:39313725 ]
Frank S, Lessa Derci Augustynczik A, Havlik P, Boere E, Ermolieva T, Fricko O, Di Fulvio F, Gusti M, Krisztin T, Lauri P, Palazzo A, Wogerer M: Enhanced agricultural carbon sinks provide benefits for farmers and the climate. Nat Food. 2024 Sep;5(9):742-753. doi: 10.1038/s43016-024-01039-1. Epub 2024 Sep 23. [PubMed:39313684 ]
Mills ES, Wang JC, Richardson MK, Chung BC, Mayer LW, Gallo MC, Alluri RK, Hah RJ, Heckmann ND: The change in lumbar lordosis from the standing to the lateral position: implications for lateral interbody fusion. Eur Spine J. 2024 Sep 23. doi: 10.1007/s00586-024-08493-2. [PubMed:39313682 ]

Showing NP-Card for 6-O-ethylzephyranine E (NP0333729)

MOL for NP0333729 (6-O-ethylzephyranine E)

3D MOL for NP0333729 (6-O-ethylzephyranine E)

3D SDF for NP0333729 (6-O-ethylzephyranine E)

3D-SDF for NP0333729 (6-O-ethylzephyranine E)

PDB for NP0333729 (6-O-ethylzephyranine E)

3D PDB for NP0333729 (6-O-ethylzephyranine E)

SMILES for NP0333729 (6-O-ethylzephyranine E)

INCHI for NP0333729 (6-O-ethylzephyranine E)

Structure for NP0333729 (6-O-ethylzephyranine E)

3D Structure for NP0333729 (6-O-ethylzephyranine E)