NP-MRD: Showing NP-Card for (4r,6s,9s,10r,11s,16s)-6-ethyl-4,16-dihydroxy-11-{[(2r,5s)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0²,⁶.0¹²,¹⁶]hexadeca-1(15),7,12-triene-3,5,14-trione (NP0157861)

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Record Information

Version

2.0

Created at

2022-09-02 15:20:59 UTC

Updated at

2022-09-02 15:20:59 UTC

NP-MRD ID

NP0157861

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r,6s,9s,10r,11s,16s)-6-ethyl-4,16-dihydroxy-11-{[(2r,5s)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0²,⁶.0¹²,¹⁶]hexadeca-1(15),7,12-triene-3,5,14-trione

Description

(4R,6S,9S,10R,11S,16S)-6-ethyl-4,16-dihydroxy-11-{[(2R,5S)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0²,⁶.0¹²,¹⁶]Hexadeca-1(15),7,12-triene-3,5,14-trione belongs to the class of organic compounds known as azepines. These are organic compounds containing an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom. Based on a literature review very few articles have been published on (4R,6S,9S,10R,11S,16S)-6-ethyl-4,16-dihydroxy-11-{[(2R,5S)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0²,⁶.0¹²,¹⁶]Hexadeca-1(15),7,12-triene-3,5,14-trione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217212D          

 35 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309022217212D          

 35 39  0  0  1  0            999 V2000
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 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  6  0  0  0
 29 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  2  0  0  0  0
 25 34  1  0  0  0  0
 20 34  1  0  0  0  0
  7 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0157861

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]12C=C(C)[C@@H]3[C@@H](C)[C@H](O[C@H]4CC[C@H](O)C(C)O4)C4=CC(=O)C=C(N1C(=O)[C@](C)(O)C2=O)[C@]34O

> <INCHI_IDENTIFIER>
InChI=1S/C26H33NO8/c1-6-25-11-12(2)20-13(3)21(35-19-8-7-17(29)14(4)34-19)16-9-15(28)10-18(26(16,20)33)27(25)23(31)24(5,32)22(25)30/h9-11,13-14,17,19-21,29,32-33H,6-8H2,1-5H3/t13-,14?,17+,19+,20-,21+,24-,25+,26+/m1/s1

> <INCHI_KEY>
YPOBBZYXYSNZKF-IFGWKXESSA-N

> <FORMULA>
C26H33NO8

> <MOLECULAR_WEIGHT>
487.549

> <EXACT_MASS>
487.220617027

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
50.412259478879776

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,6S,9S,10R,11S,16S)-6-ethyl-4,16-dihydroxy-11-{[(2R,5S)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0^{2,6}.0^{12,16}]hexadeca-1(15),7,12-triene-3,5,14-trione

> <ALOGPS_LOGP>
1.36

> <JCHEM_LOGP>
0.9270845049999994

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.91894663087471

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.20971207272382

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1508471092681747

> <JCHEM_POLAR_SURFACE_AREA>
133.6

> <JCHEM_REFRACTIVITY>
126.83569999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,6S,9S,10R,11S,16S)-6-ethyl-4,16-dihydroxy-11-{[(2R,5S)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0^{2,6}.0^{12,16}]hexadeca-1(15),7,12-triene-3,5,14-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       5.064  -2.865   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.987  -1.633   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.382  -0.217   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.422  -1.421   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.882  -1.421   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.214  -2.808   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.922  -0.217   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.388  -0.355   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.402  -1.677   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.217   1.062   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.719   1.404   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.173   2.876   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.674   3.218   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.128   4.690   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.081   5.819   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.534   7.291   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.579   5.476   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.532   6.605   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.125   4.005   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.942   2.075   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.965   3.615   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.310   4.365   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.334   5.904   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.632   3.575   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.652   1.953   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       5.039   1.285   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       6.361   2.075   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.499   3.609   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.521   1.062   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.408   2.321   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.866   0.312   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.916  -0.355   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.706  -1.677   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.264   1.285   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.468   0.325   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26   32                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   34                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12                                                       
CONECT   20   10   21   34                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   34                                                  
CONECT   26   25    3   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29    3   33                                                  
CONECT   33   32                                                            
CONECT   34   25   20    7   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₃NO₈

Average Mass

487.5490 Da

Monoisotopic Mass

487.22062 Da

IUPAC Name

(4R,6S,9S,10R,11S,16S)-6-ethyl-4,16-dihydroxy-11-{[(2R,5S)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0^{2,6}.0^{12,16}]hexadeca-1(15),7,12-triene-3,5,14-trione

Traditional Name

(4R,6S,9S,10R,11S,16S)-6-ethyl-4,16-dihydroxy-11-{[(2R,5S)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0^{2,6}.0^{12,16}]hexadeca-1(15),7,12-triene-3,5,14-trione

CAS Registry Number

Not Available

SMILES

CC[C@@]12C=C(C)[C@@H]3[C@@H](C)[C@H](O[C@H]4CC[C@H](O)C(C)O4)C4=CC(=O)C=C(N1C(=O)[C@](C)(O)C2=O)[C@]34O

InChI Identifier

InChI=1S/C26H33NO8/c1-6-25-11-12(2)20-13(3)21(35-19-8-7-17(29)14(4)34-19)16-9-15(28)10-18(26(16,20)33)27(25)23(31)24(5,32)22(25)30/h9-11,13-14,17,19-21,29,32-33H,6-8H2,1-5H3/t13-,14?,17+,19+,20-,21+,24-,25+,26+/m1/s1

InChI Key

YPOBBZYXYSNZKF-IFGWKXESSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azepines. These are organic compounds containing an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azepines

Sub Class

Not Available

Direct Parent

Azepines

Alternative Parents

Substituents

Azepine
3-pyrrolidone
2-pyrrolidone
Pyrrolidone
Oxane
Acyloin
Vinylogous amide
Tertiary carboxylic acid amide
Tertiary alcohol
Pyrrolidine
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Lactam
Ketone
Carboxamide group
Oxacycle
Azacycle
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.36	ALOGPS
logP	0.93	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11.21	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	133.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	126.84 m³·mol⁻¹	ChemAxon
Polarizability	50.41 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

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

163190743

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4r,6s,9s,10r,11s,16s)-6-ethyl-4,16-dihydroxy-11-{[(2r,5s)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0²,⁶.0¹²,¹⁶]hexadeca-1(15),7,12-triene-3,5,14-trione (NP0157861)

MOL for NP0157861 ((4r,6s,9s,10r,11s,16s)-6-ethyl-4,16-dihydroxy-11-{[(2r,5s)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0²,⁶.0¹²,¹⁶]hexadeca-1(15),7,12-triene-3,5,14-trione)

3D MOL for NP0157861 ((4r,6s,9s,10r,11s,16s)-6-ethyl-4,16-dihydroxy-11-{[(2r,5s)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0²,⁶.0¹²,¹⁶]hexadeca-1(15),7,12-triene-3,5,14-trione)

3D SDF for NP0157861 ((4r,6s,9s,10r,11s,16s)-6-ethyl-4,16-dihydroxy-11-{[(2r,5s)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0²,⁶.0¹²,¹⁶]hexadeca-1(15),7,12-triene-3,5,14-trione)

3D-SDF for NP0157861 ((4r,6s,9s,10r,11s,16s)-6-ethyl-4,16-dihydroxy-11-{[(2r,5s)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0²,⁶.0¹²,¹⁶]hexadeca-1(15),7,12-triene-3,5,14-trione)

PDB for NP0157861 ((4r,6s,9s,10r,11s,16s)-6-ethyl-4,16-dihydroxy-11-{[(2r,5s)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0²,⁶.0¹²,¹⁶]hexadeca-1(15),7,12-triene-3,5,14-trione)

3D PDB for NP0157861 ((4r,6s,9s,10r,11s,16s)-6-ethyl-4,16-dihydroxy-11-{[(2r,5s)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0²,⁶.0¹²,¹⁶]hexadeca-1(15),7,12-triene-3,5,14-trione)

SMILES for NP0157861 ((4r,6s,9s,10r,11s,16s)-6-ethyl-4,16-dihydroxy-11-{[(2r,5s)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0²,⁶.0¹²,¹⁶]hexadeca-1(15),7,12-triene-3,5,14-trione)

INCHI for NP0157861 ((4r,6s,9s,10r,11s,16s)-6-ethyl-4,16-dihydroxy-11-{[(2r,5s)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0²,⁶.0¹²,¹⁶]hexadeca-1(15),7,12-triene-3,5,14-trione)

Structure for NP0157861 ((4r,6s,9s,10r,11s,16s)-6-ethyl-4,16-dihydroxy-11-{[(2r,5s)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0²,⁶.0¹²,¹⁶]hexadeca-1(15),7,12-triene-3,5,14-trione)

3D Structure for NP0157861 ((4r,6s,9s,10r,11s,16s)-6-ethyl-4,16-dihydroxy-11-{[(2r,5s)-5-hydroxy-6-methyloxan-2-yl]oxy}-4,8,10-trimethyl-2-azatetracyclo[7.6.1.0²,⁶.0¹²,¹⁶]hexadeca-1(15),7,12-triene-3,5,14-trione)