NP-MRD: Showing NP-Card for (1s,14s)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0²,⁷]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-hydroxyphenoxy)-4-methoxybenzoate (NP0326336)

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Record Information

Version

2.0

Created at

2022-09-12 07:47:56 UTC

Updated at

2022-09-12 07:47:56 UTC

NP-MRD ID

NP0326336

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,14s)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0²,⁷]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-hydroxyphenoxy)-4-methoxybenzoate

Description

Aurantioemestrin belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group. (1s,14s)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0²,⁷]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-hydroxyphenoxy)-4-methoxybenzoate is found in Aspergillus foveolatus and Aspergillus striatus. Based on a literature review very few articles have been published on Aurantioemestrin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122209472D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309122209472D          

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 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 31 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0326336

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1OC1=CC(C=O)=CC=C1O)C(=O)O[C@H]1C=COC=C2C=C3N([C@H]12)C(=O)C(=S)N(C)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H20N2O9S/c1-28-24(32)17-10-16-13-36-8-7-20(23(16)29(17)25(33)26(28)39)38-27(34)15-4-6-19(35-2)22(11-15)37-21-9-14(12-30)3-5-18(21)31/h3-13,20,23,31H,1-2H3/t20-,23-/m0/s1

> <INCHI_KEY>
WRIFWCQWEAILFB-REWPJTCUSA-N

> <FORMULA>
C27H20N2O9S

> <MOLECULAR_WEIGHT>
548.52

> <EXACT_MASS>
548.088951406

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
53.65031603716069

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,14S)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0^{2,7}]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-hydroxyphenoxy)-4-methoxybenzoate

> <JCHEM_LOGP>
2.2339805693333337

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.270731588235569

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1454057396301427

> <JCHEM_POLAR_SURFACE_AREA>
131.91

> <JCHEM_REFRACTIVITY>
143.12929999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,14S)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0^{2,7}]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-hydroxyphenoxy)-4-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.450  -2.088   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.683  -3.423   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.143  -3.426   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.370  -2.094   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.170  -2.098   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.937  -3.433   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.477  -3.436   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.245  -4.771   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.250  -2.104   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.483  -0.769   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.947  -0.881   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.098   0.250   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.135   1.773   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.470   2.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.902   1.974   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.164   2.858   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.394   1.932   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.905   2.226   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.406   3.683   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       7.916   1.064   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       9.428   1.359   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.415  -0.392   0.000  0.00  0.00           C+0
HETATM   23  S   UNK     0       8.426  -1.554   0.000  0.00  0.00           S+0
HETATM   24  C   UNK     0       5.904  -0.686   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.403  -2.143   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0       4.893   0.476   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       3.353   0.502   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.165  -4.765   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.375  -4.762   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.148  -6.094   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -3.688  -6.091   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.455  -4.755   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.995  -4.752   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -6.763  -3.417   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -5.990  -2.085   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -6.768  -6.084   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.001  -7.419   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.461  -7.423   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -3.694  -8.758   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   27                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   17   27                                                  
CONECT   27   26   15   10                                                  
CONECT   28    6   29                                                       
CONECT   29   28    3   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   38                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   31   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₀N₂O₉S

Average Mass

548.5200 Da

Monoisotopic Mass

548.08895 Da

IUPAC Name

(1S,14S)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0^{2,7}]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-hydroxyphenoxy)-4-methoxybenzoate

Traditional Name

(1S,14S)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0^{2,7}]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-hydroxyphenoxy)-4-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1OC1=CC(C=O)=CC=C1O)C(=O)O[C@H]1C=COC=C2C=C3N([C@H]12)C(=O)C(=S)N(C)C3=O

InChI Identifier

InChI=1S/C27H20N2O9S/c1-28-24(32)17-10-16-13-36-8-7-20(23(16)29(17)25(33)26(28)39)38-27(34)15-4-6-19(35-2)22(11-15)37-21-9-14(12-30)3-5-18(21)31/h3-13,20,23,31H,1-2H3/t20-,23-/m0/s1

InChI Key

WRIFWCQWEAILFB-REWPJTCUSA-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
Emericella foveolata	LOTUS Database	35616633
Emericella striata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Diphenylethers

Alternative Parents

Substituents

Diphenylether
Diaryl ether
P-methoxybenzoic acid or derivatives
Alpha-amino acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Hydroxybenzaldehyde
Anisole
Benzaldehyde
Phenoxy compound
Benzoyl
Dioxopiperazine
Phenol ether
2,5-dioxopiperazine
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
N-alkylpiperazine
Alkyl aryl ether
Phenol
Aryl-aldehyde
N-methylpiperazine
Piperazine
1,4-diazinane
Tertiary carboxylic acid amide
Pyrroline
Lactam
Carboxamide group
Carboxylic acid ester
Organoheterocyclic compound
Azacycle
Oxacycle
Ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Aldehyde
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Organosulfur compound
Organopnictogen compound
Thiocarbonyl group
Organic oxide
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	2.23	ChemAxon
pKa (Strongest Acidic)	6.27	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	131.91 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	143.13 m³·mol⁻¹	ChemAxon
Polarizability	53.65 Å³	ChemAxon
Number of Rings	5	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

10227301

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21599098

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,14s)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0²,⁷]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-hydroxyphenoxy)-4-methoxybenzoate (NP0326336)

MOL for NP0326336 ((1s,14s)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0²,⁷]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-hydroxyphenoxy)-4-methoxybenzoate)

3D MOL for NP0326336 ((1s,14s)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0²,⁷]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-hydroxyphenoxy)-4-methoxybenzoate)

3D SDF for NP0326336 ((1s,14s)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0²,⁷]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-hydroxyphenoxy)-4-methoxybenzoate)

3D-SDF for NP0326336 ((1s,14s)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0²,⁷]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-hydroxyphenoxy)-4-methoxybenzoate)

PDB for NP0326336 ((1s,14s)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0²,⁷]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-hydroxyphenoxy)-4-methoxybenzoate)

3D PDB for NP0326336 ((1s,14s)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0²,⁷]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-hydroxyphenoxy)-4-methoxybenzoate)

SMILES for NP0326336 ((1s,14s)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0²,⁷]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-hydroxyphenoxy)-4-methoxybenzoate)

INCHI for NP0326336 ((1s,14s)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0²,⁷]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-hydroxyphenoxy)-4-methoxybenzoate)

Structure for NP0326336 ((1s,14s)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0²,⁷]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-hydroxyphenoxy)-4-methoxybenzoate)

3D Structure for NP0326336 ((1s,14s)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0²,⁷]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-hydroxyphenoxy)-4-methoxybenzoate)