NP-MRD: Showing NP-Card for 9-benzyl-1,4,7-trihydroxy-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-3h,9h,12h,13h,14h,14ah-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one (NP0208004)

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Record Information

Version

2.0

Created at

2022-09-05 04:50:30 UTC

Updated at

2022-09-05 04:50:30 UTC

NP-MRD ID

NP0208004

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-benzyl-1,4,7-trihydroxy-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-3h,9h,12h,13h,14h,14ah-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one

Description

9-Benzyl-1,4,7-trihydroxy-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-3H,6H,9H,10H,12H,13H,14H,14aH-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. 9-benzyl-1,4,7-trihydroxy-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-3h,9h,12h,13h,14h,14ah-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one is found in Verticillium coccosporum. 9-Benzyl-1,4,7-trihydroxy-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-3H,6H,9H,10H,12H,13H,14H,14aH-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171520112D          

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M  END

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M  END


  Mrv1533004171520112D          

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   10.2237    7.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0802    8.6033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6677    9.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0802   10.0322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427    9.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9860   10.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0675    9.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    8.6033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    8.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    8.6033    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
  2  4  1  0  0  0  0
  4  5  2  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
 11 12  1  0  0  0  0
 12 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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 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
 24 25  2  0  0  0  0
 25 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
 24 29  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 11 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0208004

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)C(=O)CCCCCC1NC(=O)C2CCCN2C(=O)C(CC2=CC=CC=C2)NC(=O)C(C)(C)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H40N4O6/c1-18(33)23(34)15-9-5-8-13-20-24(35)31-28(2,3)27(38)30-21(17-19-11-6-4-7-12-19)26(37)32-16-10-14-22(32)25(36)29-20/h4,6-7,11-12,18,20-22,33H,5,8-10,13-17H2,1-3H3,(H,29,36)(H,30,38)(H,31,35)

> <INCHI_KEY>
UXOLDMJAFJDQSE-UHFFFAOYSA-N

> <FORMULA>
C28H40N4O6

> <MOLECULAR_WEIGHT>
528.65

> <EXACT_MASS>
528.294785024

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
56.992058963765665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-benzyl-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-tetradecahydropyrrolo[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone

> <ALOGPS_LOGP>
1.44

> <JCHEM_LOGP>
1.2773788510000013

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.30204289260571

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.732220168021877

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2939264311426553

> <JCHEM_POLAR_SURFACE_AREA>
144.91

> <JCHEM_REFRACTIVITY>
140.55160000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-benzyl-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-octahydro-2H-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  13.749   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  12.979   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  11.439   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667  13.749   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667  15.289   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  12.979   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  13.749   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  12.979   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  13.749   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  12.979   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  13.749   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      12.003  12.979   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      12.773  11.646   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.003  10.312   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.313  11.646   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.344  10.501   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.750  11.128   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.589  12.659   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      15.083  12.979   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      16.417  13.749   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      17.750  12.979   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      16.417  15.289   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.750  16.059   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.084  15.289   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.418  16.059   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      21.752  15.289   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      21.752  13.749   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.418  12.979   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      19.084  13.749   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      15.083  16.059   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0      14.313  17.393   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      15.083  18.727   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.773  17.393   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.041  18.910   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.326  17.920   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      12.003  16.059   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0      10.669  15.289   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       9.336  16.059   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   37                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30   22   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33   37                                                       
CONECT   37   36   11   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₀N₄O₆

Average Mass

528.6500 Da

Monoisotopic Mass

528.29479 Da

IUPAC Name

9-benzyl-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-tetradecahydropyrrolo[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone

Traditional Name

9-benzyl-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-octahydro-2H-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone

CAS Registry Number

Not Available

SMILES

CC(O)C(=O)CCCCCC1NC(=O)C2CCCN2C(=O)C(CC2=CC=CC=C2)NC(=O)C(C)(C)NC1=O

InChI Identifier

InChI=1S/C28H40N4O6/c1-18(33)23(34)15-9-5-8-13-20-24(35)31-28(2,3)27(38)30-21(17-19-11-6-4-7-12-19)26(37)32-16-10-14-22(32)25(36)29-20/h4,6-7,11-12,18,20-22,33H,5,8-10,13-17H2,1-3H3,(H,29,36)(H,30,38)(H,31,35)

InChI Key

UXOLDMJAFJDQSE-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
[Verticillium] coccosporum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Cyclic alpha peptide
Macrolactam
Alpha-amino acid or derivatives
Acyloin
Monosaccharide
Benzenoid
Monocyclic benzene moiety
Tertiary carboxylic acid amide
Pyrrolidine
Alpha-hydroxy ketone
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Ketone
Lactam
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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
logP	1.44	ALOGPS
logP	1.28	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	10.73	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	144.91 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	140.55 m³·mol⁻¹	ChemAxon
Polarizability	56.99 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

9914893

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-1,4,7-trihydroxy-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-3h,9h,12h,13h,14h,14ah-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one (NP0208004)

MOL for NP0208004 (9-benzyl-1,4,7-trihydroxy-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-3h,9h,12h,13h,14h,14ah-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one)

3D MOL for NP0208004 (9-benzyl-1,4,7-trihydroxy-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-3h,9h,12h,13h,14h,14ah-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one)

3D SDF for NP0208004 (9-benzyl-1,4,7-trihydroxy-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-3h,9h,12h,13h,14h,14ah-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one)

3D-SDF for NP0208004 (9-benzyl-1,4,7-trihydroxy-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-3h,9h,12h,13h,14h,14ah-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one)

PDB for NP0208004 (9-benzyl-1,4,7-trihydroxy-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-3h,9h,12h,13h,14h,14ah-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one)

3D PDB for NP0208004 (9-benzyl-1,4,7-trihydroxy-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-3h,9h,12h,13h,14h,14ah-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one)

SMILES for NP0208004 (9-benzyl-1,4,7-trihydroxy-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-3h,9h,12h,13h,14h,14ah-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one)

INCHI for NP0208004 (9-benzyl-1,4,7-trihydroxy-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-3h,9h,12h,13h,14h,14ah-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one)

Structure for NP0208004 (9-benzyl-1,4,7-trihydroxy-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-3h,9h,12h,13h,14h,14ah-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one)

3D Structure for NP0208004 (9-benzyl-1,4,7-trihydroxy-3-(7-hydroxy-6-oxooctyl)-6,6-dimethyl-3h,9h,12h,13h,14h,14ah-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-10-one)