NP-MRD: Showing NP-Card for (1r,3r,5s,6r,7r,8s,10e,12r,13s,14s,16r,17r,18s)-18-benzyl-7,13,20-trihydroxy-6,8,14,16-tetramethyl-4,15-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹⁴,¹⁶]icosa-10,19-dien-2-one (NP0189911)

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Record Information

Version

2.0

Created at

2022-09-04 06:29:08 UTC

Updated at

2022-09-04 06:29:08 UTC

NP-MRD ID

NP0189911

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3r,5s,6r,7r,8s,10e,12r,13s,14s,16r,17r,18s)-18-benzyl-7,13,20-trihydroxy-6,8,14,16-tetramethyl-4,15-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹⁴,¹⁶]icosa-10,19-dien-2-one

Description

18-Deoxy-21-oxo-deacetyl-19,20-epoxycytochalasin N belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. (1r,3r,5s,6r,7r,8s,10e,12r,13s,14s,16r,17r,18s)-18-benzyl-7,13,20-trihydroxy-6,8,14,16-tetramethyl-4,15-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹⁴,¹⁶]icosa-10,19-dien-2-one is found in Xylaria curta. Based on a literature review very few articles have been published on 18-deoxy-21-oxo-deacetyl-19,20-epoxycytochalasin N.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042208292D          

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M  END

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M  END


  Mrv1652309042208292D          

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 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 26 24  1  1  0  0  0
  6 26  1  0  0  0  0
 14 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  1  0  0  0
 31 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0189911

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C\C=C\[C@H]2[C@H](O)[C@]3(C)O[C@]3(C)[C@H]3[C@H](CC4=CC=CC=C4)N=C(O)[C@@]23C(=O)[C@@H]2O[C@H]2[C@H](C)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H35NO6/c1-14-9-8-12-17-23(31)27(4)26(3,35-27)22-18(13-16-10-6-5-7-11-16)29-25(33)28(17,22)24(32)21-20(34-21)15(2)19(14)30/h5-8,10-12,14-15,17-23,30-31H,9,13H2,1-4H3,(H,29,33)/b12-8+/t14-,15+,17-,18-,19+,20-,21+,22+,23-,26+,27-,28-/m0/s1

> <INCHI_KEY>
OTCGMUXCJDAGIF-QLYHLFCPSA-N

> <FORMULA>
C28H35NO6

> <MOLECULAR_WEIGHT>
481.589

> <EXACT_MASS>
481.246437851

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.647168160687244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3R,5S,6R,7R,8S,10E,12R,13S,14S,16R,17R,18S)-18-benzyl-7,13,20-trihydroxy-6,8,14,16-tetramethyl-4,15-dioxa-19-azapentacyclo[10.8.0.0^{1,17}.0^{3,5}.0^{14,16}]icosa-10,19-dien-2-one

> <JCHEM_LOGP>
1.8943586388044686

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.574367055461593

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.578630521334727

> <JCHEM_PKA_STRONGEST_BASIC>
5.218490102746092

> <JCHEM_POLAR_SURFACE_AREA>
115.18000000000002

> <JCHEM_REFRACTIVITY>
129.368

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,5S,6R,7R,8S,10E,12R,13S,14S,16R,17R,18S)-18-benzyl-7,13,20-trihydroxy-6,8,14,16-tetramethyl-4,15-dioxa-19-azapentacyclo[10.8.0.0^{1,17}.0^{3,5}.0^{14,16}]icosa-10,19-dien-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      14.008   0.746   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.010   2.150   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.370   0.750   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.840   0.926   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.535   2.436   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.227   3.498   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.814   2.886   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.632   1.283   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.577   3.804   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.520   2.558   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.341   4.722   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.754   5.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.815   6.664   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.167   5.946   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.658   7.406   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.780   8.693   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.406  10.061   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.514  11.316   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.155  12.717   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.689  12.861   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.581  11.606   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.939  10.206   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      10.198   7.390   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      10.254   6.081   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.911   6.081   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.404   5.028   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.817   5.640   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.826   7.226   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.053   4.722   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.290   3.804   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      13.466   5.334   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.703   4.416   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.163   5.125   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.526   2.886   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      16.012   2.119   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   26                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    9   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15   26                                                  
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   15   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    6   14   27                                             
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29   31                                                       
CONECT   31   30   29   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    2   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₅NO₆

Average Mass

481.5890 Da

Monoisotopic Mass

481.24644 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1C\C=C\[C@H]2[C@H](O)[C@]3(C)O[C@]3(C)[C@H]3[C@H](CC4=CC=CC=C4)N=C(O)[C@@]23C(=O)[C@@H]2O[C@H]2[C@H](C)[C@@H]1O

InChI Identifier

InChI=1S/C28H35NO6/c1-14-9-8-12-17-23(31)27(4)26(3,35-27)22-18(13-16-10-6-5-7-11-16)29-25(33)28(17,22)24(32)21-20(34-21)15(2)19(14)30/h5-8,10-12,14-15,17-23,30-31H,9,13H2,1-4H3,(H,29,33)/b12-8+/t14-,15+,17-,18-,19+,20-,21+,22+,23-,26+,27-,28-/m0/s1

InChI Key

OTCGMUXCJDAGIF-QLYHLFCPSA-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
Xylaria curta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Isoindolones

Alternative Parents

Substituents

Isoindolone
Oxepane
Benzenoid
2-pyrrolidone
Pyrrolidone
Monocyclic benzene moiety
Pyrrolidine
Cyclic alcohol
Secondary carboxylic acid amide
Secondary alcohol
Lactam
Ketone
Carboxamide group
Oxacycle
Azacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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

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

146683440

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3r,5s,6r,7r,8s,10e,12r,13s,14s,16r,17r,18s)-18-benzyl-7,13,20-trihydroxy-6,8,14,16-tetramethyl-4,15-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹⁴,¹⁶]icosa-10,19-dien-2-one (NP0189911)

MOL for NP0189911 ((1r,3r,5s,6r,7r,8s,10e,12r,13s,14s,16r,17r,18s)-18-benzyl-7,13,20-trihydroxy-6,8,14,16-tetramethyl-4,15-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹⁴,¹⁶]icosa-10,19-dien-2-one)

3D MOL for NP0189911 ((1r,3r,5s,6r,7r,8s,10e,12r,13s,14s,16r,17r,18s)-18-benzyl-7,13,20-trihydroxy-6,8,14,16-tetramethyl-4,15-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹⁴,¹⁶]icosa-10,19-dien-2-one)

3D SDF for NP0189911 ((1r,3r,5s,6r,7r,8s,10e,12r,13s,14s,16r,17r,18s)-18-benzyl-7,13,20-trihydroxy-6,8,14,16-tetramethyl-4,15-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹⁴,¹⁶]icosa-10,19-dien-2-one)

3D-SDF for NP0189911 ((1r,3r,5s,6r,7r,8s,10e,12r,13s,14s,16r,17r,18s)-18-benzyl-7,13,20-trihydroxy-6,8,14,16-tetramethyl-4,15-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹⁴,¹⁶]icosa-10,19-dien-2-one)

PDB for NP0189911 ((1r,3r,5s,6r,7r,8s,10e,12r,13s,14s,16r,17r,18s)-18-benzyl-7,13,20-trihydroxy-6,8,14,16-tetramethyl-4,15-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹⁴,¹⁶]icosa-10,19-dien-2-one)

3D PDB for NP0189911 ((1r,3r,5s,6r,7r,8s,10e,12r,13s,14s,16r,17r,18s)-18-benzyl-7,13,20-trihydroxy-6,8,14,16-tetramethyl-4,15-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹⁴,¹⁶]icosa-10,19-dien-2-one)

SMILES for NP0189911 ((1r,3r,5s,6r,7r,8s,10e,12r,13s,14s,16r,17r,18s)-18-benzyl-7,13,20-trihydroxy-6,8,14,16-tetramethyl-4,15-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹⁴,¹⁶]icosa-10,19-dien-2-one)

INCHI for NP0189911 ((1r,3r,5s,6r,7r,8s,10e,12r,13s,14s,16r,17r,18s)-18-benzyl-7,13,20-trihydroxy-6,8,14,16-tetramethyl-4,15-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹⁴,¹⁶]icosa-10,19-dien-2-one)

Structure for NP0189911 ((1r,3r,5s,6r,7r,8s,10e,12r,13s,14s,16r,17r,18s)-18-benzyl-7,13,20-trihydroxy-6,8,14,16-tetramethyl-4,15-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹⁴,¹⁶]icosa-10,19-dien-2-one)

3D Structure for NP0189911 ((1r,3r,5s,6r,7r,8s,10e,12r,13s,14s,16r,17r,18s)-18-benzyl-7,13,20-trihydroxy-6,8,14,16-tetramethyl-4,15-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹⁴,¹⁶]icosa-10,19-dien-2-one)