NP-MRD: Showing NP-Card for 3-{[4-(2,3-dihydroxy-3-methylbutoxy)phenyl]methyl}-13-(2-hydroxypentyl)-4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione (NP0170427)

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Record Information

Version

2.0

Created at

2022-09-03 06:36:05 UTC

Updated at

2022-09-03 06:36:05 UTC

NP-MRD ID

NP0170427

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

3-{[4-(2,3-Dihydroxy-3-methylbutoxy)phenyl]methyl}-13-(2-hydroxypentyl)-4,10-dimethyl-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-(2,3-dihydroxy-3-methylbutoxy)phenyl]methyl}-13-(2-hydroxypentyl)-4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione is found in Penicillium meleagrinum. Based on a literature review very few articles have been published on 3-{[4-(2,3-dihydroxy-3-methylbutoxy)phenyl]methyl}-13-(2-hydroxypentyl)-4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032208362D          

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M  END

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M  END


  Mrv1652309032208362D          

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    1.6747   -2.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860   -2.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1338   -3.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3702   -3.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2821   -3.5761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1708   -4.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8231   -4.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5867   -4.5864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7117   -5.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004   -6.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5292   -5.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1057   -5.6049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588   -2.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9111   -1.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5634   -1.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1729   -1.9700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7998   -0.9309    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 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
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 25 34  1  0  0  0  0
 34 35  2  0  0  0  0
 22 35  1  0  0  0  0
 20 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
  7 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0170427

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(O)CC1CCC(C)CCCCC(=O)N(C)C(CC2=CC=C(OCC(O)C(C)(C)O)C=C2)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C30H49NO7/c1-6-9-23(32)19-25-15-12-21(2)10-7-8-11-28(34)31(5)26(29(35)38-25)18-22-13-16-24(17-14-22)37-20-27(33)30(3,4)36/h13-14,16-17,21,23,25-27,32-33,36H,6-12,15,18-20H2,1-5H3

> <INCHI_KEY>
NQXOQGLCLMWMTQ-UHFFFAOYSA-N

> <FORMULA>
C30H49NO7

> <MOLECULAR_WEIGHT>
535.722

> <EXACT_MASS>
535.350902922

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
59.889350390083294

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.98

> <JCHEM_LOGP>
4.035231517999998

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.850431577775183

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.192084262697893

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2672084953654426

> <JCHEM_POLAR_SURFACE_AREA>
116.53000000000002

> <JCHEM_REFRACTIVITY>
146.8215

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.83e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         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  O   UNK     0      -1.474   1.461   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.140  -0.849   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.193  -0.079   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.018   0.916   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.601   2.341   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.136   2.227   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.548   0.743   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.512   3.200   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.938   2.617   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.146   1.091   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.571   0.508   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.779  -1.018   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.204  -1.601   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0       5.561  -1.961   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       5.769  -3.487   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.136  -1.378   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.344  -2.904   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.126  -3.847   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.334  -5.373   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.116  -6.316   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.691  -5.733   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.527  -6.675   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.319  -8.201   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.536  -9.144   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.962  -8.561   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.329 -10.670   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.121 -12.196   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.854 -10.878   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.197 -10.462   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.483  -4.207   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.701  -3.264   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.918  -2.321   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.190  -3.677   0.000  0.00  0.00           O+0
HETATM   38  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    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   38                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   36                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   35                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
CONECT   34   25   35                                                       
CONECT   35   34   22                                                       
CONECT   36   20   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36    7                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₉NO₇

Average Mass

535.7220 Da

Monoisotopic Mass

535.35090 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCCC(O)CC1CCC(C)CCCCC(=O)N(C)C(CC2=CC=C(OCC(O)C(C)(C)O)C=C2)C(=O)O1

InChI Identifier

InChI=1S/C30H49NO7/c1-6-9-23(32)19-25-15-12-21(2)10-7-8-11-28(34)31(5)26(29(35)38-25)18-22-13-16-24(17-14-22)37-20-27(33)30(3,4)36/h13-14,16-17,21,23,25-27,32-33,36H,6-12,15,18-20H2,1-5H3

InChI Key

NQXOQGLCLMWMTQ-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

Species Name	Source	Reference
Penicillium meleagrinum	LOTUS Database	35616633

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
Macrolide
Macrolactam
Alpha-amino acid or derivatives
Phenoxy compound
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Tertiary alcohol
Secondary alcohol
Lactone
Lactam
Carboxylic acid ester
Carboxamide group
Carboxylic acid derivative
Oxacycle
Ether
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
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	3.98	ALOGPS
logP	4.04	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.19	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	116.53 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	146.82 m³·mol⁻¹	ChemAxon
Polarizability	59.89 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

162816109

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-(2,3-dihydroxy-3-methylbutoxy)phenyl]methyl}-13-(2-hydroxypentyl)-4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione (NP0170427)

MOL for NP0170427 (3-{[4-(2,3-dihydroxy-3-methylbutoxy)phenyl]methyl}-13-(2-hydroxypentyl)-4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione)

3D MOL for NP0170427 (3-{[4-(2,3-dihydroxy-3-methylbutoxy)phenyl]methyl}-13-(2-hydroxypentyl)-4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione)

3D SDF for NP0170427 (3-{[4-(2,3-dihydroxy-3-methylbutoxy)phenyl]methyl}-13-(2-hydroxypentyl)-4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione)

3D-SDF for NP0170427 (3-{[4-(2,3-dihydroxy-3-methylbutoxy)phenyl]methyl}-13-(2-hydroxypentyl)-4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione)

PDB for NP0170427 (3-{[4-(2,3-dihydroxy-3-methylbutoxy)phenyl]methyl}-13-(2-hydroxypentyl)-4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione)

3D PDB for NP0170427 (3-{[4-(2,3-dihydroxy-3-methylbutoxy)phenyl]methyl}-13-(2-hydroxypentyl)-4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione)

SMILES for NP0170427 (3-{[4-(2,3-dihydroxy-3-methylbutoxy)phenyl]methyl}-13-(2-hydroxypentyl)-4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione)

INCHI for NP0170427 (3-{[4-(2,3-dihydroxy-3-methylbutoxy)phenyl]methyl}-13-(2-hydroxypentyl)-4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione)

Structure for NP0170427 (3-{[4-(2,3-dihydroxy-3-methylbutoxy)phenyl]methyl}-13-(2-hydroxypentyl)-4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione)

3D Structure for NP0170427 (3-{[4-(2,3-dihydroxy-3-methylbutoxy)phenyl]methyl}-13-(2-hydroxypentyl)-4,10-dimethyl-1-oxa-4-azacyclotridecane-2,5-dione)