NP-MRD: Showing NP-Card for n-[7-(butanoyloxy)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid (NP0160150)

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Record Information

Version

2.0

Created at

2022-09-02 18:02:22 UTC

Updated at

2022-09-02 18:02:22 UTC

NP-MRD ID

NP0160150

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[7-(butanoyloxy)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid

Description

N-[7-(butanoyloxy)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzene-1-carboximidic acid belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated. n-[7-(butanoyloxy)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid is found in Streptomyces argillaceus. N-[7-(butanoyloxy)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzene-1-carboximidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191513512D          

 38 39  0  0  0  0            999 V2000
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 36 37  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004191513512D          

 38 39  0  0  0  0            999 V2000
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    2.3186   -7.1448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4062   -5.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -5.8220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2629   -4.5970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6754   -3.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1451   -3.2506    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
  5  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  2  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
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  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
 22 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  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 28 32  2  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
 20 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0160150

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC1C(OC(=O)CCC)C(C)OC(=O)C(NC(=O)C2=CC=CC(NC=O)=C2O)C(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H38N2O9/c1-5-7-8-9-12-19-24(38-21(31)11-6-2)17(4)37-27(35)22(16(3)36-26(19)34)29-25(33)18-13-10-14-20(23(18)32)28-15-30/h10,13-17,19,22,24,32H,5-9,11-12H2,1-4H3,(H,28,30)(H,29,33)

> <INCHI_KEY>
LYDAGTPXPZARPR-UHFFFAOYSA-N

> <FORMULA>
C27H38N2O9

> <MOLECULAR_WEIGHT>
534.606

> <EXACT_MASS>
534.257730812

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
56.15231960737964

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(3-formamido-2-hydroxybenzamido)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl butanoate

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
4.663081956

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.422264782292086

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.510311860761116

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8657019198190818

> <JCHEM_POLAR_SURFACE_AREA>
157.32999999999996

> <JCHEM_REFRACTIVITY>
137.3286

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.36e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3-formamido-2-hydroxybenzamido)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       3.506  -4.411   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.840  -5.181   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.174  -4.411   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.507  -5.181   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.841  -4.411   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.175  -5.181   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.175  -6.721   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.622  -7.247   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.612  -6.068   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.085  -4.621   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.568  -4.353   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      13.075  -3.441   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.548  -1.994   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.538  -0.814   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.392  -8.581   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.908  -8.314   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.124 -10.098   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.945 -11.088   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.471 -12.535   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.405 -11.088   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       8.878 -12.535   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       7.361 -12.802   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.371 -11.622   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.835 -14.249   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.824 -15.429   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.298 -16.876   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.781 -17.144   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.791 -15.964   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       3.275 -16.231   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       2.285 -15.052   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.768 -15.319   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.318 -14.517   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.328 -13.337   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.225 -10.098   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.891 -10.868   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.957  -8.581   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.727  -7.247   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       7.738  -6.068   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   37                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    8   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   34                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   28   24   33                                                  
CONECT   33   32                                                            
CONECT   34   20   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36    7   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

View in JSmol

Synonyms

Value	Source
N-[7-(Butanoyloxy)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzene-1-carboximidate	Generator

Chemical Formula

C₂₇H₃₈N₂O₉

Average Mass

534.6060 Da

Monoisotopic Mass

534.25773 Da

IUPAC Name

3-(3-formamido-2-hydroxybenzamido)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl butanoate

Traditional Name

3-(3-formamido-2-hydroxybenzamido)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl butanoate

CAS Registry Number

Not Available

SMILES

CCCCCCC1C(OC(=O)CCC)C(C)OC(=O)C(NC(=O)C2=CC=CC(NC=O)=C2O)C(C)OC1=O

InChI Identifier

InChI=1S/C27H38N2O9/c1-5-7-8-9-12-19-24(38-21(31)11-6-2)17(4)37-27(35)22(16(3)36-26(19)34)29-25(33)18-13-10-14-20(23(18)32)28-15-30/h10,13-17,19,22,24,32H,5-9,11-12H2,1-4H3,(H,28,30)(H,29,33)

InChI Key

LYDAGTPXPZARPR-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
Streptomyces argillaceus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Acylaminobenzoic acid and derivatives

Alternative Parents

Substituents

Alpha-amino acid ester
Acylaminobenzoic acid or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Salicylamide
Salicylic acid or derivatives
Benzamide
Anilide
Tricarboxylic acid or derivatives
Benzoyl
N-arylamide
1-hydroxy-4-unsubstituted benzenoid
Fatty acid ester
Phenol
Fatty acyl
Vinylogous acid
Carboxamide group
Carboxylic acid ester
Lactone
Secondary carboxylic acid amide
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
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	3.2	ALOGPS
logP	4.66	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	7.51	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	157.33 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	137.33 m³·mol⁻¹	ChemAxon
Polarizability	56.15 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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

3084471

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[7-(butanoyloxy)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid (NP0160150)

MOL for NP0160150 (n-[7-(butanoyloxy)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)

3D MOL for NP0160150 (n-[7-(butanoyloxy)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)

3D SDF for NP0160150 (n-[7-(butanoyloxy)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)

3D-SDF for NP0160150 (n-[7-(butanoyloxy)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)

PDB for NP0160150 (n-[7-(butanoyloxy)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)

3D PDB for NP0160150 (n-[7-(butanoyloxy)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)

SMILES for NP0160150 (n-[7-(butanoyloxy)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)

INCHI for NP0160150 (n-[7-(butanoyloxy)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)

Structure for NP0160150 (n-[7-(butanoyloxy)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)

3D Structure for NP0160150 (n-[7-(butanoyloxy)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzenecarboximidic acid)