NP-MRD: Showing NP-Card for 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 (NP0254904)

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Record Information

Version

2.0

Created at

2022-09-07 19:13:00 UTC

Updated at

2022-09-07 19:13:00 UTC

NP-MRD ID

NP0254904

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

AC1L1ERT 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. 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 Aspergillus flavipes, Mariannaea elegans and Rosellinia necatrix. AC1L1ERT is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161513552D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161513552D          

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 16 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  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
 30 29  1  4  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>
NP0254904

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3=CC=CC=C3)NC(=O)C22OC(=O)OC=CC(C)(O)C(=O)C(C)CC=CC2C2OC12C

> <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)

> <INCHI_KEY>
LAJXCUNOQSHRJO-UHFFFAOYSA-N

> <FORMULA>
C28H33NO7

> <MOLECULAR_WEIGHT>
495.572

> <EXACT_MASS>
495.225702407

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.71619857288901

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
19-benzyl-7-hydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-5,11-diene-3,8,21-trione

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
3.7027762763333323

> <ALOGPS_LOGS>
-5.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.194680025531802

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.537550531208712

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7670801772790172

> <JCHEM_POLAR_SURFACE_AREA>
114.46000000000001

> <JCHEM_REFRACTIVITY>
131.32690000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.30e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
19-benzyl-7-hydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-5,11-diene-3,8,21-trione

> <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       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

Value	Source
Cytochalasin e	MeSH

Chemical Formula

C₂₈H₃₃NO₇

Average Mass

495.5720 Da

Monoisotopic Mass

495.22570 Da

IUPAC Name

19-benzyl-7-hydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-5,11-diene-3,8,21-trione

Traditional Name

19-benzyl-7-hydroxy-7,9,16,17-tetramethyl-2,4,15-trioxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-5,11-diene-3,8,21-trione

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3=CC=CC=C3)NC(=O)C22OC(=O)OC=CC(C)(O)C(=O)C(C)CC=CC2C2OC12C

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)

InChI Key

LAJXCUNOQSHRJO-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
Aspergillus flavipes	LOTUS Database	35616633
Mariannaea elegans	LOTUS Database	35616633
Rosellinia necatrix	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
Acyloin
2-pyrrolidone
Pyrrolidone
Enol ester
Tertiary alcohol
Pyrrolidine
Carboxamide group
Cyclic ketone
Ketone
Lactam
Secondary carboxylic acid amide
Carbonic acid derivative
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Ether
Oxirane
Oxacycle
Dialkyl ether
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
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	3.4	ALOGPS
logP	3.7	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	12.54	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	114.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	131.33 m³·mol⁻¹	ChemAxon
Polarizability	51.72 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

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

2920

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 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 (NP0254904)

MOL for NP0254904 (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 NP0254904 (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 NP0254904 (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 NP0254904 (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 NP0254904 (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 NP0254904 (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 NP0254904 (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 NP0254904 (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 NP0254904 (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 NP0254904 (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)