NP-MRD: Showing NP-Card for 11-benzyl-9-hydroxy-6-methyl-3-propyl-3h,4h,8h,11h,14h,15h,16h,16ah-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione (NP0172593)

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Record Information

Version

2.0

Created at

2022-09-03 09:33:16 UTC

Updated at

2022-09-03 09:33:16 UTC

NP-MRD ID

NP0172593

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-benzyl-9-hydroxy-6-methyl-3-propyl-3h,4h,8h,11h,14h,15h,16h,16ah-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione

Description

11-Benzyl-9-hydroxy-6-methyl-3-propyl-1H,3H,4H,7H,8H,11H,12H,14H,15H,16H,16aH-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. 11-benzyl-9-hydroxy-6-methyl-3-propyl-3h,4h,8h,11h,14h,15h,16h,16ah-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione is found in Sarocladium kiliense. Based on a literature review very few articles have been published on 11-benzyl-9-hydroxy-6-methyl-3-propyl-1H,3H,4H,7H,8H,11H,12H,14H,15H,16H,16aH-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032211332D          

 32 34  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309032211332D          

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M  END
> <DATABASE_ID>
NP0172593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC1CC=C(C)C(=O)CC(O)=NC(CC2=CC=CC=C2)C(=O)N2CCCC2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C25H32N2O5/c1-3-8-19-13-12-17(2)22(28)16-23(29)26-20(15-18-9-5-4-6-10-18)24(30)27-14-7-11-21(27)25(31)32-19/h4-6,9-10,12,19-21H,3,7-8,11,13-16H2,1-2H3,(H,26,29)

> <INCHI_KEY>
YSNFMBLAIYADSY-UHFFFAOYSA-N

> <FORMULA>
C25H32N2O5

> <MOLECULAR_WEIGHT>
440.54

> <EXACT_MASS>
440.231122138

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.33370462616935

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11-benzyl-9-hydroxy-6-methyl-3-propyl-1H,3H,4H,7H,8H,11H,12H,14H,15H,16H,16aH-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
4.268572080666667

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.426883112838086

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.7073835677876605

> <JCHEM_PKA_STRONGEST_BASIC>
1.4748635857559038

> <JCHEM_POLAR_SURFACE_AREA>
96.27

> <JCHEM_REFRACTIVITY>
121.22309999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-benzyl-9-hydroxy-6-methyl-3-propyl-3H,4H,8H,11H,14H,15H,16H,16aH-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione

> <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      13.384   2.548   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.992   1.058   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.506   0.653   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.115  -0.837   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.209  -1.921   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.695  -1.515   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.789  -2.599   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.274  -2.193   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.397  -4.088   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      15.491  -5.172   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.912  -4.494   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.520  -5.983   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.614  -7.067   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      11.035  -6.389   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       9.940  -5.305   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.549  -6.794   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.643  -7.878   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.129  -7.473   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.223  -8.556   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.831 -10.046   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.346 -10.451   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.252  -9.368   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.455  -5.711   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.063  -7.200   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0       7.361  -4.627   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       5.823  -4.715   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.264  -3.280   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.457  -2.305   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.752  -3.138   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.238  -2.732   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.332  -3.816   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       9.629  -1.242   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   15   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   25   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    4                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂N₂O₅

Average Mass

440.5400 Da

Monoisotopic Mass

440.23112 Da

IUPAC Name

11-benzyl-9-hydroxy-6-methyl-3-propyl-1H,3H,4H,7H,8H,11H,12H,14H,15H,16H,16aH-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione

Traditional Name

11-benzyl-9-hydroxy-6-methyl-3-propyl-3H,4H,8H,11H,14H,15H,16H,16aH-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione

CAS Registry Number

Not Available

SMILES

CCCC1CC=C(C)C(=O)CC(O)=NC(CC2=CC=CC=C2)C(=O)N2CCCC2C(=O)O1

InChI Identifier

InChI=1S/C25H32N2O5/c1-3-8-19-13-12-17(2)22(28)16-23(29)26-20(15-18-9-5-4-6-10-18)24(30)27-14-7-11-21(27)25(31)32-19/h4-6,9-10,12,19-21H,3,7-8,11,13-16H2,1-2H3,(H,26,29)

InChI Key

YSNFMBLAIYADSY-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
Sarocladium kiliense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Macrolide lactam
Macrolactam
Alpha-amino acid ester
Alpha-amino acid or derivatives
Benzenoid
1,3-dicarbonyl compound
Monocyclic benzene moiety
Tertiary carboxylic acid amide
Pyrrolidine
Cyclic ketone
Secondary carboxylic acid amide
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
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
logP	3.1	ALOGPS
logP	4.27	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.71	ChemAxon
pKa (Strongest Basic)	1.47	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	96.27 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	121.22 m³·mol⁻¹	ChemAxon
Polarizability	46.33 Å³	ChemAxon
Number of Rings	3	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

163058417

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 11-benzyl-9-hydroxy-6-methyl-3-propyl-3h,4h,8h,11h,14h,15h,16h,16ah-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione (NP0172593)

MOL for NP0172593 (11-benzyl-9-hydroxy-6-methyl-3-propyl-3h,4h,8h,11h,14h,15h,16h,16ah-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione)

3D MOL for NP0172593 (11-benzyl-9-hydroxy-6-methyl-3-propyl-3h,4h,8h,11h,14h,15h,16h,16ah-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione)

3D SDF for NP0172593 (11-benzyl-9-hydroxy-6-methyl-3-propyl-3h,4h,8h,11h,14h,15h,16h,16ah-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione)

3D-SDF for NP0172593 (11-benzyl-9-hydroxy-6-methyl-3-propyl-3h,4h,8h,11h,14h,15h,16h,16ah-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione)

PDB for NP0172593 (11-benzyl-9-hydroxy-6-methyl-3-propyl-3h,4h,8h,11h,14h,15h,16h,16ah-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione)

3D PDB for NP0172593 (11-benzyl-9-hydroxy-6-methyl-3-propyl-3h,4h,8h,11h,14h,15h,16h,16ah-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione)

SMILES for NP0172593 (11-benzyl-9-hydroxy-6-methyl-3-propyl-3h,4h,8h,11h,14h,15h,16h,16ah-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione)

INCHI for NP0172593 (11-benzyl-9-hydroxy-6-methyl-3-propyl-3h,4h,8h,11h,14h,15h,16h,16ah-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione)

Structure for NP0172593 (11-benzyl-9-hydroxy-6-methyl-3-propyl-3h,4h,8h,11h,14h,15h,16h,16ah-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione)

3D Structure for NP0172593 (11-benzyl-9-hydroxy-6-methyl-3-propyl-3h,4h,8h,11h,14h,15h,16h,16ah-pyrrolo[2,1-c]1-oxa-4,7-diazacyclotetradecane-1,7,12-trione)