NP-MRD: Showing NP-Card for (1r,2s,3s,5r,6r,8s,10e,12r,13s,16s,17s)-17-benzyl-2,6,13,19-tetrahydroxy-6,8,14,15-tetramethyl-4-oxa-18-azatetracyclo[10.7.0.0¹,¹⁶.0³,⁵]nonadeca-10,14,18-trien-7-one (NP0255241)

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Record Information

Version

2.0

Created at

2022-09-07 19:39:52 UTC

Updated at

2022-09-07 19:39:52 UTC

NP-MRD ID

NP0255241

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3s,5r,6r,8s,10e,12r,13s,16s,17s)-17-benzyl-2,6,13,19-tetrahydroxy-6,8,14,15-tetramethyl-4-oxa-18-azatetracyclo[10.7.0.0¹,¹⁶.0³,⁵]nonadeca-10,14,18-trien-7-one

Description

Deacetyl-19,20-epoxy-cytochalasin C belongs to the class of organic compounds known as isoindoles and derivatives. These are polycyclic compounds containing an isoindole moiety, which is structurally characterized by a cyclohexadiene fused to a pyrrole ring. (1r,2s,3s,5r,6r,8s,10e,12r,13s,16s,17s)-17-benzyl-2,6,13,19-tetrahydroxy-6,8,14,15-tetramethyl-4-oxa-18-azatetracyclo[10.7.0.0¹,¹⁶.0³,⁵]nonadeca-10,14,18-trien-7-one is found in Xylaria obovata. Based on a literature review very few articles have been published on Deacetyl-19,20-epoxy-cytochalasin C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072221392D          

 35 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072221392D          

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 20 21  1  6  0  0  0
 22 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  1  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 33 32  1  1  0  0  0
 17 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0255241

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C\C=C\[C@H]2[C@H](O)C(C)=C(C)[C@@H]3[C@H](CC4=CC=CC=C4)N=C(O)[C@@]23[C@H](O)[C@@H]2O[C@H]2[C@@](C)(O)C1=O

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

> <INCHI_KEY>
PJQNNAWRTWTXKU-MNUVKCIJSA-N

> <FORMULA>
C28H35NO6

> <MOLECULAR_WEIGHT>
481.589

> <EXACT_MASS>
481.246437851

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.725854033905875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3S,5R,6R,8S,10E,12R,13S,16S,17S)-17-benzyl-2,6,13,19-tetrahydroxy-6,8,14,15-tetramethyl-4-oxa-18-azatetracyclo[10.7.0.0^{1,16}.0^{3,5}]nonadeca-10,14,18-trien-7-one

> <JCHEM_LOGP>
1.9840679288477099

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.213872952809897

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.09753746641233

> <JCHEM_PKA_STRONGEST_BASIC>
5.4231605231907345

> <JCHEM_POLAR_SURFACE_AREA>
122.88000000000001

> <JCHEM_REFRACTIVITY>
131.79519999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,5R,6R,8S,10E,12R,13S,16S,17S)-17-benzyl-2,6,13,19-tetrahydroxy-6,8,14,15-tetramethyl-4-oxa-18-azatetracyclo[10.7.0.0^{1,16}.0^{3,5}]nonadeca-10,14,18-trien-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.746  -3.206   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.173  -3.534   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.854  -2.387   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.242  -0.900   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.361  -2.703   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.605  -1.795   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.543  -0.186   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.933   0.519   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.017   2.056   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.390   2.753   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.680   1.911   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.596   0.373   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.222  -0.323   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.853  -2.697   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.262  -3.980   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.388  -5.163   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.841  -4.166   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.504  -4.441   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.394  -6.022   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.835  -3.667   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.299  -3.188   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.982  -4.695   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.359  -6.103   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.046  -5.569   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.760  -7.025   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.814  -7.726   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.227  -8.602   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.787  -8.873   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.221 -10.445   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.280  -8.557   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.800  -7.093   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.293  -6.777   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.813  -5.313   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.306  -4.997   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.842  -6.195   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   17                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    6   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    5   18   33                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20   22                                                       
CONECT   22   21   20   23                                                  
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   17   34                                                  
CONECT   34   33    2   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    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(C)=C(C)[C@@H]3[C@H](CC4=CC=CC=C4)N=C(O)[C@@]23[C@H](O)[C@@H]2O[C@H]2[C@@](C)(O)C1=O

InChI Identifier

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

InChI Key

PJQNNAWRTWTXKU-MNUVKCIJSA-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 obovata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindoles and derivatives. These are polycyclic compounds containing an isoindole moiety, which is structurally characterized by a cyclohexadiene fused to a pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Not Available

Direct Parent

Isoindoles and derivatives

Alternative Parents

Substituents

Isoindole or derivatives
Acyloin
Monocyclic benzene moiety
Benzenoid
Pyrroline
Tertiary alcohol
Cyclic carboximidic acid
Ketone
Secondary alcohol
Cyclic ketone
Dialkyl ether
Oxirane
Ether
Polyol
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
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

78438125

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587376

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3s,5r,6r,8s,10e,12r,13s,16s,17s)-17-benzyl-2,6,13,19-tetrahydroxy-6,8,14,15-tetramethyl-4-oxa-18-azatetracyclo[10.7.0.0¹,¹⁶.0³,⁵]nonadeca-10,14,18-trien-7-one (NP0255241)

MOL for NP0255241 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,16s,17s)-17-benzyl-2,6,13,19-tetrahydroxy-6,8,14,15-tetramethyl-4-oxa-18-azatetracyclo[10.7.0.0¹,¹⁶.0³,⁵]nonadeca-10,14,18-trien-7-one)

3D MOL for NP0255241 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,16s,17s)-17-benzyl-2,6,13,19-tetrahydroxy-6,8,14,15-tetramethyl-4-oxa-18-azatetracyclo[10.7.0.0¹,¹⁶.0³,⁵]nonadeca-10,14,18-trien-7-one)

3D SDF for NP0255241 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,16s,17s)-17-benzyl-2,6,13,19-tetrahydroxy-6,8,14,15-tetramethyl-4-oxa-18-azatetracyclo[10.7.0.0¹,¹⁶.0³,⁵]nonadeca-10,14,18-trien-7-one)

3D-SDF for NP0255241 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,16s,17s)-17-benzyl-2,6,13,19-tetrahydroxy-6,8,14,15-tetramethyl-4-oxa-18-azatetracyclo[10.7.0.0¹,¹⁶.0³,⁵]nonadeca-10,14,18-trien-7-one)

PDB for NP0255241 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,16s,17s)-17-benzyl-2,6,13,19-tetrahydroxy-6,8,14,15-tetramethyl-4-oxa-18-azatetracyclo[10.7.0.0¹,¹⁶.0³,⁵]nonadeca-10,14,18-trien-7-one)

3D PDB for NP0255241 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,16s,17s)-17-benzyl-2,6,13,19-tetrahydroxy-6,8,14,15-tetramethyl-4-oxa-18-azatetracyclo[10.7.0.0¹,¹⁶.0³,⁵]nonadeca-10,14,18-trien-7-one)

SMILES for NP0255241 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,16s,17s)-17-benzyl-2,6,13,19-tetrahydroxy-6,8,14,15-tetramethyl-4-oxa-18-azatetracyclo[10.7.0.0¹,¹⁶.0³,⁵]nonadeca-10,14,18-trien-7-one)

INCHI for NP0255241 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,16s,17s)-17-benzyl-2,6,13,19-tetrahydroxy-6,8,14,15-tetramethyl-4-oxa-18-azatetracyclo[10.7.0.0¹,¹⁶.0³,⁵]nonadeca-10,14,18-trien-7-one)

Structure for NP0255241 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,16s,17s)-17-benzyl-2,6,13,19-tetrahydroxy-6,8,14,15-tetramethyl-4-oxa-18-azatetracyclo[10.7.0.0¹,¹⁶.0³,⁵]nonadeca-10,14,18-trien-7-one)

3D Structure for NP0255241 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,16s,17s)-17-benzyl-2,6,13,19-tetrahydroxy-6,8,14,15-tetramethyl-4-oxa-18-azatetracyclo[10.7.0.0¹,¹⁶.0³,⁵]nonadeca-10,14,18-trien-7-one)