NP-MRD: Showing NP-Card for 3-{[4-(2-hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione (NP0319802)

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Record Information

Version

2.0

Created at

2022-09-11 21:01:51 UTC

Updated at

2022-09-11 21:01:51 UTC

NP-MRD ID

NP0319802

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{[4-(2-hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione

Description

3-{[4-(2-Hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group. 3-{[4-(2-Hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241507452D          

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M  END

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 19 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
  6 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0319802

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC1CCC(C)CCCCC(=O)N(C)C(CC2=CC=C(OCCO)C=C2)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C27H43NO5/c1-4-5-6-10-24-15-12-21(2)9-7-8-11-26(30)28(3)25(27(31)33-24)20-22-13-16-23(17-14-22)32-19-18-29/h13-14,16-17,21,24-25,29H,4-12,15,18-20H2,1-3H3

> <INCHI_KEY>
PCRJJAXIHTZHNU-UHFFFAOYSA-N

> <FORMULA>
C27H43NO5

> <MOLECULAR_WEIGHT>
461.643

> <EXACT_MASS>
461.314123489

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
53.831178688671976

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[4-(2-hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione

> <ALOGPS_LOGP>
5.65

> <JCHEM_LOGP>
5.4279272999999995

> <ALOGPS_LOGS>
-5.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.102173101537666

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2672079828083107

> <JCHEM_POLAR_SURFACE_AREA>
76.07000000000001

> <JCHEM_REFRACTIVITY>
130.17609999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.39e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[4-(2-hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -5.475  -0.849   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.142  -0.079   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.808  -0.849   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.474  -0.079   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.140  -0.849   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.193  -0.079   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.018   0.916   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.601   2.341   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.136   2.227   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.548   0.743   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.512   3.200   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.938   2.617   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.146   1.091   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.571   0.508   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.779  -1.018   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.204  -1.601   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       5.561  -1.961   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       5.769  -3.487   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.136  -1.378   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.344  -2.904   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.126  -3.847   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.334  -5.373   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.116  -6.316   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.691  -5.733   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.527  -6.675   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.319  -8.201   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.536  -9.144   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.329 -10.670   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.483  -4.207   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.701  -3.264   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.918  -2.321   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.190  -3.677   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       1.493  -1.738   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   33                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
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   20   31                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   24   30                                                       
CONECT   30   29   21                                                       
CONECT   31   19   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    6                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₃NO₅

Average Mass

461.6430 Da

Monoisotopic Mass

461.31412 Da

IUPAC Name

3-{[4-(2-hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione

Traditional Name

3-{[4-(2-hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione

CAS Registry Number

Not Available

SMILES

CCCCCC1CCC(C)CCCCC(=O)N(C)C(CC2=CC=C(OCCO)C=C2)C(=O)O1

InChI Identifier

InChI=1S/C27H43NO5/c1-4-5-6-10-24-15-12-21(2)9-7-8-11-26(30)28(3)25(27(31)33-24)20-22-13-16-23(17-14-22)32-19-18-29/h13-14,16-17,21,24-25,29H,4-12,15,18-20H2,1-3H3

InChI Key

PCRJJAXIHTZHNU-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 macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolide lactams

Sub Class

Not Available

Direct Parent

Macrolide lactams

Alternative Parents

Substituents

Macrolide lactam
Alpha-amino acid ester
Macrolactam
Macrolide
Alpha-amino acid or derivatives
Phenoxy compound
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Organooxygen compound
Primary alcohol
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	5.65	ALOGPS
logP	5.43	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	15.1	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.07 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	130.18 m³·mol⁻¹	ChemAxon
Polarizability	53.83 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	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

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

9912156

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{[4-(2-hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione (NP0319802)

MOL for NP0319802 (3-{[4-(2-hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione)

3D MOL for NP0319802 (3-{[4-(2-hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione)

3D SDF for NP0319802 (3-{[4-(2-hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione)

3D-SDF for NP0319802 (3-{[4-(2-hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione)

PDB for NP0319802 (3-{[4-(2-hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione)

3D PDB for NP0319802 (3-{[4-(2-hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione)

SMILES for NP0319802 (3-{[4-(2-hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione)

INCHI for NP0319802 (3-{[4-(2-hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione)

Structure for NP0319802 (3-{[4-(2-hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione)

3D Structure for NP0319802 (3-{[4-(2-hydroxyethoxy)phenyl]methyl}-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione)