NP-MRD: Showing NP-Card for 9-ethyl-4,25-dihydroxy-12-(1-hydroxyethyl)-3,16-dimethyl-13-oxa-20-azatetracyclo[16.6.1.0⁵,²⁴.0²¹,²⁵]pentacosa-1(24),2,4,10,16,21-hexaene-6,14,15,19,23-pentone (NP0330715)

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Record Information

Version

2.0

Created at

2022-09-12 16:20:00 UTC

Updated at

2022-09-12 16:20:00 UTC

NP-MRD ID

NP0330715

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-ethyl-4,25-dihydroxy-12-(1-hydroxyethyl)-3,16-dimethyl-13-oxa-20-azatetracyclo[16.6.1.0⁵,²⁴.0²¹,²⁵]pentacosa-1(24),2,4,10,16,21-hexaene-6,14,15,19,23-pentone

Description

9-Ethyl-4,25-dihydroxy-12-(1-hydroxyethyl)-3,16-dimethyl-13-oxa-20-azatetracyclo[16.6.1.0⁵,²⁴.0²¹,²⁵]Pentacosa-1(24),2,4,10,16,21-hexaene-6,14,15,19,23-pentone belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. Based on a literature review very few articles have been published on 9-ethyl-4,25-dihydroxy-12-(1-hydroxyethyl)-3,16-dimethyl-13-oxa-20-azatetracyclo[16.6.1.0⁵,²⁴.0²¹,²⁵]Pentacosa-1(24),2,4,10,16,21-hexaene-6,14,15,19,23-pentone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122218202D          

 39 42  0  0  0  0            999 V2000
   11.0292    1.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

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M  END


  Mrv1652309122218202D          

 39 42  0  0  0  0            999 V2000
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    9.1403    2.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4861    1.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1865    0.7046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  4  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
  3 37  1  0  0  0  0
 27 38  1  0  0  0  0
 22 38  1  0  0  0  0
 18 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330715

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1CCC(=O)C2=C(O)C(C)=CC3=C2C(=O)C=C2NC(=O)C(C=C(C)C(=O)C(=O)OC(C=C1)C(C)O)C32O

> <INCHI_IDENTIFIER>
InChI=1S/C29H31NO9/c1-5-16-6-8-19(32)24-23-17(10-13(2)25(24)34)29(38)18(27(36)30-22(29)12-20(23)33)11-14(3)26(35)28(37)39-21(9-7-16)15(4)31/h7,9-12,15-16,18,21,31,34,38H,5-6,8H2,1-4H3,(H,30,36)

> <INCHI_KEY>
WXYOJFGZCRSXDT-UHFFFAOYSA-N

> <FORMULA>
C29H31NO9

> <MOLECULAR_WEIGHT>
537.565

> <EXACT_MASS>
537.199881582

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
53.67845854909565

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-ethyl-4,25-dihydroxy-12-(1-hydroxyethyl)-3,16-dimethyl-13-oxa-20-azatetracyclo[16.6.1.0^{5,24}.0^{21,25}]pentacosa-1(24),2,4,10,16,21-hexaene-6,14,15,19,23-pentone

> <JCHEM_LOGP>
3.040702888666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.231477859693587

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.859063286274493

> <JCHEM_PKA_STRONGEST_BASIC>
-3.049297226443926

> <JCHEM_POLAR_SURFACE_AREA>
167.29999999999998

> <JCHEM_REFRACTIVITY>
143.4291

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
9-ethyl-4,25-dihydroxy-12-(1-hydroxyethyl)-3,16-dimethyl-13-oxa-20-azatetracyclo[16.6.1.0^{5,24}.0^{21,25}]pentacosa-1(24),2,4,10,16,21-hexaene-6,14,15,19,23-pentone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      20.588   2.994   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.343   3.900   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.935   3.275   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.291   1.777   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.082   0.251   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.336  -1.096   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.523  -2.077   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.967  -1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      18.268  -3.596   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      16.154  -2.083   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      14.695  -2.576   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      14.911  -4.101   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.156  -2.509   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.807  -4.008   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.746  -1.890   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.879  -3.163   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.655  -0.804   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.029   0.604   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.513   0.334   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.840  -1.052   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0       7.788   1.692   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       8.855   2.802   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.745   4.338   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.020   5.201   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.910   6.737   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.406   4.529   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.516   2.992   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.901   2.320   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.176   3.183   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.562   2.511   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.066   4.719   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      15.605   4.668   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.681   5.392   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.289   5.759   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      14.292   7.299   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      15.789   5.410   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      17.062   4.543   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.241   2.129   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      11.548   1.315   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   38                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   38                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   33                                                  
CONECT   27   26   28   38                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   26   34                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36    3                                                       
CONECT   38   27   22   18   39                                             
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₁NO₉

Average Mass

537.5650 Da

Monoisotopic Mass

537.19988 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCC1CCC(=O)C2=C(O)C(C)=CC3=C2C(=O)C=C2NC(=O)C(C=C(C)C(=O)C(=O)OC(C=C1)C(C)O)C32O

InChI Identifier

InChI=1S/C29H31NO9/c1-5-16-6-8-19(32)24-23-17(10-13(2)25(24)34)29(38)18(27(36)30-22(29)12-20(23)33)11-14(3)26(35)28(37)39-21(9-7-16)15(4)31/h7,9-12,15-16,18,21,31,34,38H,5-6,8H2,1-4H3,(H,30,36)

InChI Key

WXYOJFGZCRSXDT-UHFFFAOYSA-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 macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolactams

Sub Class

Not Available

Direct Parent

Macrolactams

Alternative Parents

Substituents

Macrolide
Macrolactam
Naphthalene
Indole or derivatives
Aryl alkyl ketone
Aryl ketone
Benzenoid
2-pyrrolidone
Pyrrolidone
Vinylogous amide
Vinylogous acid
Tertiary alcohol
Pyrrolidine
Cyclic ketone
Secondary carboxylic acid amide
Secondary alcohol
Lactone
Lactam
Ketone
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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

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

139584755

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-ethyl-4,25-dihydroxy-12-(1-hydroxyethyl)-3,16-dimethyl-13-oxa-20-azatetracyclo[16.6.1.0⁵,²⁴.0²¹,²⁵]pentacosa-1(24),2,4,10,16,21-hexaene-6,14,15,19,23-pentone (NP0330715)

MOL for NP0330715 (9-ethyl-4,25-dihydroxy-12-(1-hydroxyethyl)-3,16-dimethyl-13-oxa-20-azatetracyclo[16.6.1.0⁵,²⁴.0²¹,²⁵]pentacosa-1(24),2,4,10,16,21-hexaene-6,14,15,19,23-pentone)

3D MOL for NP0330715 (9-ethyl-4,25-dihydroxy-12-(1-hydroxyethyl)-3,16-dimethyl-13-oxa-20-azatetracyclo[16.6.1.0⁵,²⁴.0²¹,²⁵]pentacosa-1(24),2,4,10,16,21-hexaene-6,14,15,19,23-pentone)

3D SDF for NP0330715 (9-ethyl-4,25-dihydroxy-12-(1-hydroxyethyl)-3,16-dimethyl-13-oxa-20-azatetracyclo[16.6.1.0⁵,²⁴.0²¹,²⁵]pentacosa-1(24),2,4,10,16,21-hexaene-6,14,15,19,23-pentone)

3D-SDF for NP0330715 (9-ethyl-4,25-dihydroxy-12-(1-hydroxyethyl)-3,16-dimethyl-13-oxa-20-azatetracyclo[16.6.1.0⁵,²⁴.0²¹,²⁵]pentacosa-1(24),2,4,10,16,21-hexaene-6,14,15,19,23-pentone)

PDB for NP0330715 (9-ethyl-4,25-dihydroxy-12-(1-hydroxyethyl)-3,16-dimethyl-13-oxa-20-azatetracyclo[16.6.1.0⁵,²⁴.0²¹,²⁵]pentacosa-1(24),2,4,10,16,21-hexaene-6,14,15,19,23-pentone)

3D PDB for NP0330715 (9-ethyl-4,25-dihydroxy-12-(1-hydroxyethyl)-3,16-dimethyl-13-oxa-20-azatetracyclo[16.6.1.0⁵,²⁴.0²¹,²⁵]pentacosa-1(24),2,4,10,16,21-hexaene-6,14,15,19,23-pentone)

SMILES for NP0330715 (9-ethyl-4,25-dihydroxy-12-(1-hydroxyethyl)-3,16-dimethyl-13-oxa-20-azatetracyclo[16.6.1.0⁵,²⁴.0²¹,²⁵]pentacosa-1(24),2,4,10,16,21-hexaene-6,14,15,19,23-pentone)

INCHI for NP0330715 (9-ethyl-4,25-dihydroxy-12-(1-hydroxyethyl)-3,16-dimethyl-13-oxa-20-azatetracyclo[16.6.1.0⁵,²⁴.0²¹,²⁵]pentacosa-1(24),2,4,10,16,21-hexaene-6,14,15,19,23-pentone)

Structure for NP0330715 (9-ethyl-4,25-dihydroxy-12-(1-hydroxyethyl)-3,16-dimethyl-13-oxa-20-azatetracyclo[16.6.1.0⁵,²⁴.0²¹,²⁵]pentacosa-1(24),2,4,10,16,21-hexaene-6,14,15,19,23-pentone)

3D Structure for NP0330715 (9-ethyl-4,25-dihydroxy-12-(1-hydroxyethyl)-3,16-dimethyl-13-oxa-20-azatetracyclo[16.6.1.0⁵,²⁴.0²¹,²⁵]pentacosa-1(24),2,4,10,16,21-hexaene-6,14,15,19,23-pentone)