NP-MRD: Showing NP-Card for 9-benzyl-13-hexyl-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one (NP0220944)

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Record Information

Version

2.0

Created at

2022-09-05 22:23:40 UTC

Updated at

2022-09-05 22:23:40 UTC

NP-MRD ID

NP0220944

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-benzyl-13-hexyl-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one

Description

9-Benzyl-13-hexyl-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one 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. 9-benzyl-13-hexyl-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one is found in Beauveria tenella. 9-Benzyl-13-hexyl-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161518472D          

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M  END

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M  END


  Mrv1533004161518472D          

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  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  7 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220944

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC1CC(=O)NC(CC2=CC=CC=C2)C(=O)NC(C)C(=O)NC(CC(C)C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C27H41N3O5/c1-5-6-7-11-14-21-17-24(31)29-22(16-20-12-9-8-10-13-20)26(33)28-19(4)25(32)30-23(15-18(2)3)27(34)35-21/h8-10,12-13,18-19,21-23H,5-7,11,14-17H2,1-4H3,(H,28,33)(H,29,31)(H,30,32)

> <INCHI_KEY>
YUJXCNCSPRKCFX-UHFFFAOYSA-N

> <FORMULA>
C27H41N3O5

> <MOLECULAR_WEIGHT>
487.641

> <EXACT_MASS>
487.304621432

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
53.78433371549719

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-benzyl-13-hexyl-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotridecane-2,5,8,11-tetrone

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
3.8791417123333334

> <ALOGPS_LOGS>
-4.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.650629163418316

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.879463282294568

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1603902481747825

> <JCHEM_POLAR_SURFACE_AREA>
113.60000000000001

> <JCHEM_REFRACTIVITY>
133.0847

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-benzyl-13-hexyl-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotridecane-2,5,8,11-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -4.765  -6.197   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.431  -5.427   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.098  -6.197   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.764  -5.427   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.570  -6.197   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.903  -5.427   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.237  -6.197   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.511  -4.682   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.037  -4.474   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.766  -3.117   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       5.706  -5.861   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       7.237  -6.566   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.474  -5.650   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.887  -6.263   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.125  -5.347   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.537  -5.961   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.712  -7.491   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.474  -8.407   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.061  -7.794   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.445  -8.092   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.870  -8.675   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0       6.227  -9.035   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       6.435 -10.561   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.860 -11.144   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.217 -11.504   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.425 -13.030   0.000  0.00  0.00           O+0
HETATM   27  N   UNK     0       3.792 -10.921   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       3.584  -9.395   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.366 -10.338   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.574 -11.864   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.000 -12.447   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.357 -12.807   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.159  -8.812   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.941  -9.755   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       1.951  -7.286   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                                                       
CONECT    7    6    8   35                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   12   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    7                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Value	Source
cyclo-((R)-beta-Hydroxynonanoyl-L-phenylalanyl-alanyl-D-leucyl)	MeSH
Beauverolide H	MeSH
Beauverolides	MeSH
Beauveriolide III	MeSH
Beauverolide I	MeSH

Chemical Formula

C₂₇H₄₁N₃O₅

Average Mass

487.6410 Da

Monoisotopic Mass

487.30462 Da

IUPAC Name

9-benzyl-13-hexyl-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotridecane-2,5,8,11-tetrone

Traditional Name

9-benzyl-13-hexyl-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotridecane-2,5,8,11-tetrone

CAS Registry Number

Not Available

SMILES

CCCCCCC1CC(=O)NC(CC2=CC=CC=C2)C(=O)NC(C)C(=O)NC(CC(C)C)C(=O)O1

InChI Identifier

InChI=1S/C27H41N3O5/c1-5-6-7-11-14-21-17-24(31)29-22(16-20-12-9-8-10-13-20)26(33)28-19(4)25(32)30-23(15-18(2)3)27(34)35-21/h8-10,12-13,18-19,21-23H,5-7,11,14-17H2,1-4H3,(H,28,33)(H,29,31)(H,30,32)

InChI Key

YUJXCNCSPRKCFX-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
Beauveria tenella	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
Alpha-amino acid ester
Macrolactam
Macrolide
Alpha-amino acid or derivatives
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Secondary carboxylic acid amide
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	3.29	ALOGPS
logP	3.88	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	10.88	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.6 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	133.08 m³·mol⁻¹	ChemAxon
Polarizability	53.78 Å³	ChemAxon
Number of Rings	2	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

194155

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-benzyl-13-hexyl-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one (NP0220944)

MOL for NP0220944 (9-benzyl-13-hexyl-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)

3D MOL for NP0220944 (9-benzyl-13-hexyl-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)

3D SDF for NP0220944 (9-benzyl-13-hexyl-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)

3D-SDF for NP0220944 (9-benzyl-13-hexyl-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)

PDB for NP0220944 (9-benzyl-13-hexyl-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)

3D PDB for NP0220944 (9-benzyl-13-hexyl-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)

SMILES for NP0220944 (9-benzyl-13-hexyl-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)

INCHI for NP0220944 (9-benzyl-13-hexyl-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)

Structure for NP0220944 (9-benzyl-13-hexyl-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)

3D Structure for NP0220944 (9-benzyl-13-hexyl-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)