NP-MRD: Showing NP-Card for 6-O-ethylzephyranine F (NP0333728)

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Record Information

Version

2.0

Created at

2024-08-12 09:46:21 UTC

Updated at

2024-09-16 10:47:02 UTC

NP-MRD ID

NP0333728

Natural Product DOI

https://doi.org/10.57994/3207

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-O-ethylzephyranine F

Description

It was first documented in 2024 (PMID: 39313673). Based on a literature review a significant number of articles have been published on 6-O-ethylzephyranine F (PMID: 39313534) (PMID: 39313496) (PMID: 39313329) (PMID: 39313328).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 04262312192D          

 27 30  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
    2.8052    1.6563    0.0000 O   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  1  0  0  0  0
 25 27  2  0  0  0  0
 17 27  1  0  0  0  0
  9 27  1  0  0  0  0
M  END


  Mrv2104 04262312192D          

 27 30  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
    2.8052    1.6563    0.0000 O   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  1  0  0  0  0
 25 27  2  0  0  0  0
 17 27  1  0  0  0  0
  9 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333728

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H29NO5/c1-5-26-19-13-11-14(24-3)18(25-4)17(22)16(13)20-7-6-12(23-2)10-15(20)21(19)9-8-20/h11-12,15,19,22H,5-10H2,1-4H3/t12-,15-,19-,20+/m0/s1

> <INCHI_KEY>
HRRSARMGLRWMTJ-CCQDZNTNSA-N

> <FORMULA>
C20H29NO5

> <MOLECULAR_WEIGHT>
363.454

> <EXACT_MASS>
363.204573038

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.2667961669688

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <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-trien-3-ol

> <JCHEM_LOGP>
2.3443286989999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.289949619266334

> <JCHEM_PKA_STRONGEST_BASIC>
6.86594478488456

> <JCHEM_POLAR_SURFACE_AREA>
60.39

> <JCHEM_REFRACTIVITY>
98.60409999999999

> <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-trien-3-ol

> <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  O   UNK     0       5.236   3.092   0.000  0.00  0.00           O+0
HETATM   27  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   27                                             
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   27                                                  
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   27                                                  
CONECT   26   25                                                            
CONECT   27   25   17    9                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₉NO₅

Average Mass

363.4540 Da

Monoisotopic Mass

363.20457 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-trien-3-ol

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-trien-3-ol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H29NO5/c1-5-26-19-13-11-14(24-3)18(25-4)17(22)16(13)20-7-6-12(23-2)10-15(20)21(19)9-8-20/h11-12,15,19,22H,5-10H2,1-4H3/t12-,15-,19-,20+/m0/s1

InChI Key

HRRSARMGLRWMTJ-CCQDZNTNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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
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
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
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
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
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
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

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	2.34	ChemAxon
pKa (Strongest Acidic)	10.29	ChemAxon
pKa (Strongest Basic)	6.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.39 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	98.6 m³·mol⁻¹	ChemAxon
Polarizability	40.27 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

Nandi A, Nakano M, Brasic JR, Brinson ZS, Kitzmiller K, Mathur A, Mohamed M, Roberts J, Wong DF, Kuwabara H: Improved Quantification of MicroPET/CT Imaging Using CT-derived Scaling Factors. Mol Imaging Biol. 2024 Sep 23. doi: 10.1007/s11307-024-01947-5. [PubMed:39313673 ]
Langer F, Binter M, Hu X, Hufendiek K, Meister R, Tode J, Framme C, Fuchs H: In vitro comparison of human and murine trabecular meshwork cells: implications for glaucoma research. Sci Rep. 2024 Sep 23;14(1):22002. doi: 10.1038/s41598-024-73057-9. [PubMed:39313534 ]
Hegab MAE: Mineral exploration and environmental impact assessment in the Jabal Hamadat Area, Central Eastern Desert, Egypt, using remote sensing and airborne radiometric data. Sci Rep. 2024 Sep 23;14(1):21986. doi: 10.1038/s41598-024-71387-2. [PubMed:39313496 ]
Whitlock BD, Ma Y, Conseil G, O'Brien AR, Banerjee M, Swanlund DP, Lin ZP, Wang Y, Le XC, Schuetz JD, Cole SPC, Leslie EM: Differential Selectivity of Human and Mouse ABCC4/Abcc4 for Arsenic Metabolites. Drug Metab Dispos. 2024 Sep 23:DMD-AR-2024-001852. doi: 10.1124/dmd.124.001852. [PubMed:39313329 ]
Glaenzel U, Huth F, Eggimann F, Hackling M, Leuthold LA, Meissner A, Bebrevska L: Absorption, Distribution, Metabolism, and Excretion of Icenticaftor (QBW251) in Healthy Male Volunteers at Steady State and In Vitro Phenotyping of Major Metabolites. Drug Metab Dispos. 2024 Sep 23:DMD-AR-2024-001751. doi: 10.1124/dmd.124.001751. [PubMed:39313328 ]

Showing NP-Card for 6-O-ethylzephyranine F (NP0333728)

MOL for NP0333728 (6-O-ethylzephyranine F)

3D MOL for NP0333728 (6-O-ethylzephyranine F)

3D SDF for NP0333728 (6-O-ethylzephyranine F)

3D-SDF for NP0333728 (6-O-ethylzephyranine F)

PDB for NP0333728 (6-O-ethylzephyranine F)

3D PDB for NP0333728 (6-O-ethylzephyranine F)

SMILES for NP0333728 (6-O-ethylzephyranine F)

INCHI for NP0333728 (6-O-ethylzephyranine F)

Structure for NP0333728 (6-O-ethylzephyranine F)

3D Structure for NP0333728 (6-O-ethylzephyranine F)