NP-MRD: Showing NP-Card for (5e,11e)-19-benzyl-7,21-dihydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-5,11,20-triene-3,8-dione (NP0290427)

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Record Information

Version

2.0

Created at

2022-09-09 21:06:25 UTC

Updated at

2022-09-09 21:06:25 UTC

NP-MRD ID

NP0290427

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5e,11e)-19-benzyl-7,21-dihydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-5,11,20-triene-3,8-dione

Description

Cytochalasin E, Aspergillus clavatus belongs to the class of organic compounds known as cytochalasans. These are fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D, H, and K. (5e,11e)-19-benzyl-7,21-dihydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-5,11,20-triene-3,8-dione is found in Arthrinium sacchari, Dematophora necatrix and Mariannaea elegans. Based on a literature review very few articles have been published on Cytochalasin E, Aspergillus clavatus.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092223062D          

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M  END

     RDKit          3D

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  Mrv1652309092223062D          

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 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  6 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0290427

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3=CC=CC=C3)N=C(O)C22OC(=O)O\C=C\C(C)(O)C(=O)C(C)C\C=C\C2C2OC12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H33NO7/c1-16-9-8-12-19-23-27(4,35-23)17(2)21-20(15-18-10-6-5-7-11-18)29-24(31)28(19,21)36-25(32)34-14-13-26(3,33)22(16)30/h5-8,10-14,16-17,19-21,23,33H,9,15H2,1-4H3,(H,29,31)/b12-8+,14-13+

> <INCHI_KEY>
LAJXCUNOQSHRJO-KRQHZRJMSA-N

> <FORMULA>
C28H33NO7

> <MOLECULAR_WEIGHT>
495.572

> <EXACT_MASS>
495.225702407

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.508170704663996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5E,11E)-19-benzyl-7,21-dihydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0^{1,18}.0^{14,16}]henicosa-5,11,20-triene-3,8-dione

> <JCHEM_LOGP>
3.150801675960399

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.78628852407929

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6941093351564467

> <JCHEM_PKA_STRONGEST_BASIC>
4.590186944913687

> <JCHEM_POLAR_SURFACE_AREA>
117.95000000000002

> <JCHEM_REFRACTIVITY>
131.84860000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5E,11E)-19-benzyl-7,21-dihydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0^{1,18}.0^{14,16}]henicosa-5,11,20-triene-3,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       3.884   0.428   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.069   1.735   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.022   2.944   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.467   2.410   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.406   0.871   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.426  -0.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.944  -0.210   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.462   0.050   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.928  -1.394   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.373  -1.928   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.394  -2.839   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.379  -4.023   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.877  -3.099   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.054  -4.401   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.624  -5.832   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.671  -7.041   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.241  -8.472   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.287  -9.681   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.763  -9.459   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.193  -8.028   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.147  -6.819   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       4.562  -4.022   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       4.817  -2.737   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.160  -1.663   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.892  -1.915   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.374  -2.175   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.841  -3.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.825  -4.804   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.323  -3.880   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.339  -2.696   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.872  -1.251   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.888  -0.067   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.107  -1.242   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.442   0.710   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.422   1.378   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.412   2.541   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    9                                                       
CONECT    9    8    7   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   25                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   14   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    6   13   26                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32    2   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₃NO₇

Average Mass

495.5720 Da

Monoisotopic Mass

495.22570 Da

IUPAC Name

(5E,11E)-19-benzyl-7,21-dihydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0^{1,18}.0^{14,16}]henicosa-5,11,20-triene-3,8-dione

Traditional Name

(5E,11E)-19-benzyl-7,21-dihydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0^{1,18}.0^{14,16}]henicosa-5,11,20-triene-3,8-dione

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3=CC=CC=C3)N=C(O)C22OC(=O)O\C=C\C(C)(O)C(=O)C(C)C\C=C\C2C2OC12C

InChI Identifier

InChI=1S/C28H33NO7/c1-16-9-8-12-19-23-27(4,35-23)17(2)21-20(15-18-10-6-5-7-11-18)29-24(31)28(19,21)36-25(32)34-14-13-26(3,33)22(16)30/h5-8,10-14,16-17,19-21,23,33H,9,15H2,1-4H3,(H,29,31)/b12-8+,14-13+

InChI Key

LAJXCUNOQSHRJO-KRQHZRJMSA-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
Arthrinium sacchari	LOTUS Database	35616633
Dematophora necatrix	LOTUS Database	35616633
Mariannaea elegans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cytochalasans. These are fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D, H, and K.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cytochalasans

Sub Class

Not Available

Direct Parent

Cytochalasans

Alternative Parents

Substituents

Cytoglobosin skeleton
Cytochalasan
Macrolactam
Isoindolone
Isoindoline
Isoindole or derivatives
Oxepane
Monocyclic benzene moiety
Carbonic acid diester
Benzenoid
2-pyrrolidone
Pyrrolidone
Acyloin
Enol ester
Tertiary alcohol
Pyrrolidine
Carboxamide group
Cyclic ketone
Secondary carboxylic acid amide
Ketone
Lactam
Carbonic acid derivative
Organoheterocyclic compound
Ether
Oxirane
Azacycle
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Alcohol
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organonitrogen compound
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	3.15	ChemAxon
pKa (Strongest Acidic)	1.69	ChemAxon
pKa (Strongest Basic)	4.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	117.95 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	131.85 m³·mol⁻¹	ChemAxon
Polarizability	52.51 Å³	ChemAxon
Number of Rings	5	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

4895550

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6364616

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5e,11e)-19-benzyl-7,21-dihydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-5,11,20-triene-3,8-dione (NP0290427)

MOL for NP0290427 ((5e,11e)-19-benzyl-7,21-dihydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-5,11,20-triene-3,8-dione)

3D MOL for NP0290427 ((5e,11e)-19-benzyl-7,21-dihydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-5,11,20-triene-3,8-dione)

3D SDF for NP0290427 ((5e,11e)-19-benzyl-7,21-dihydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-5,11,20-triene-3,8-dione)

3D-SDF for NP0290427 ((5e,11e)-19-benzyl-7,21-dihydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-5,11,20-triene-3,8-dione)

PDB for NP0290427 ((5e,11e)-19-benzyl-7,21-dihydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-5,11,20-triene-3,8-dione)

3D PDB for NP0290427 ((5e,11e)-19-benzyl-7,21-dihydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-5,11,20-triene-3,8-dione)

SMILES for NP0290427 ((5e,11e)-19-benzyl-7,21-dihydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-5,11,20-triene-3,8-dione)

INCHI for NP0290427 ((5e,11e)-19-benzyl-7,21-dihydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-5,11,20-triene-3,8-dione)

Structure for NP0290427 ((5e,11e)-19-benzyl-7,21-dihydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-5,11,20-triene-3,8-dione)

3D Structure for NP0290427 ((5e,11e)-19-benzyl-7,21-dihydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-5,11,20-triene-3,8-dione)