NP-MRD: Showing NP-Card for (9r,12as,13s,15as,16s,18as)-16-benzyl-13,18-dihydroxy-9,14,15-trimethyl-6h,7h,8h,9h,10h,12ah,13h,15ah,16h-oxacyclotetradeca[2,3-d]isoindole-2,5-dione (NP0179759)

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Record Information

Version

2.0

Created at

2022-09-03 17:59:40 UTC

Updated at

2022-09-03 17:59:40 UTC

NP-MRD ID

NP0179759

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9r,12as,13s,15as,16s,18as)-16-benzyl-13,18-dihydroxy-9,14,15-trimethyl-6h,7h,8h,9h,10h,12ah,13h,15ah,16h-oxacyclotetradeca[2,3-d]isoindole-2,5-dione

Description

Cytochalasin B3 belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. Based on a literature review a small amount of articles have been published on Cytochalasin B3.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032219592D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309032219592D          

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 34 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0179759

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CCCC(=O)\C=C\C(=O)O[C@]23[C@H]([C@H](CC4=CC=CC=C4)N=C2O)C(C)=C(C)[C@@H](O)[C@@H]3\C=C\C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H35NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18,23-24,26-27,33H,7,9-10,13,17H2,1-3H3,(H,30,34)/b14-8+,16-15+/t18-,23+,24+,26+,27-,29-/m1/s1

> <INCHI_KEY>
ARZLNCVUULQBQG-HBEZZINHSA-N

> <FORMULA>
C29H35NO5

> <MOLECULAR_WEIGHT>
477.601

> <EXACT_MASS>
477.251523231

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.39237962332244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9R,13S,15aS,16S,18aS,18bS)-16-benzyl-13,18-dihydroxy-9,14,15-trimethyl-2H,5H,6H,7H,8H,9H,10H,13H,15aH,16H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,5-dione

> <JCHEM_LOGP>
3.892680907394712

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.210571544584539

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8424855878774657

> <JCHEM_PKA_STRONGEST_BASIC>
4.6784960436648415

> <JCHEM_POLAR_SURFACE_AREA>
96.19000000000001

> <JCHEM_REFRACTIVITY>
136.84720000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(9R,13S,15aS,16S,18aS,18bS)-16-benzyl-13,18-dihydroxy-9,14,15-trimethyl-6H,7H,8H,9H,10H,13H,15aH,16H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       3.709  -4.704   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.189  -4.277   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.559  -2.782   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.449  -1.714   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.038  -2.355   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.711  -0.970   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.986   0.389   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.799   1.696   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.074   3.055   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.888   4.362   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.427   4.311   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.152   2.953   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.338   1.645   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       9.236  -1.181   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       9.502  -2.480   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.892  -3.370   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.148  -3.423   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.628  -2.996   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.997  -1.501   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.888  -0.433   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      11.477  -1.074   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.587  -2.142   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.066  -1.714   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.436  -0.219   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      15.176  -2.782   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.806  -4.277   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.327  -4.704   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.957  -6.199   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.066  -7.267   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.477  -6.626   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.367  -5.558   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.888  -5.986   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.778  -4.918   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.298  -5.345   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.929  -6.840   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                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   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   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₅NO₅

Average Mass

477.6010 Da

Monoisotopic Mass

477.25152 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1CCCC(=O)\C=C\C(=O)O[C@]23[C@H]([C@H](CC4=CC=CC=C4)N=C2O)C(C)=C(C)[C@@H](O)[C@@H]3\C=C\C1

InChI Identifier

InChI=1S/C29H35NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18,23-24,26-27,33H,7,9-10,13,17H2,1-3H3,(H,30,34)/b14-8+,16-15+/t18-,23+,24+,26+,27-,29-/m1/s1

InChI Key

ARZLNCVUULQBQG-HBEZZINHSA-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

Not Available

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
Isoindole
Monocyclic benzene moiety
Pyrrolidone
2-pyrrolidone
Benzenoid
Pyrrolidine
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxamide group
Cyclic ketone
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid ester
Ketone
Lactam
Lactone
Azacycle
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Alcohol
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

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

35516915

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

118729815

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (9r,12as,13s,15as,16s,18as)-16-benzyl-13,18-dihydroxy-9,14,15-trimethyl-6h,7h,8h,9h,10h,12ah,13h,15ah,16h-oxacyclotetradeca[2,3-d]isoindole-2,5-dione (NP0179759)

MOL for NP0179759 ((9r,12as,13s,15as,16s,18as)-16-benzyl-13,18-dihydroxy-9,14,15-trimethyl-6h,7h,8h,9h,10h,12ah,13h,15ah,16h-oxacyclotetradeca[2,3-d]isoindole-2,5-dione)

3D MOL for NP0179759 ((9r,12as,13s,15as,16s,18as)-16-benzyl-13,18-dihydroxy-9,14,15-trimethyl-6h,7h,8h,9h,10h,12ah,13h,15ah,16h-oxacyclotetradeca[2,3-d]isoindole-2,5-dione)

3D SDF for NP0179759 ((9r,12as,13s,15as,16s,18as)-16-benzyl-13,18-dihydroxy-9,14,15-trimethyl-6h,7h,8h,9h,10h,12ah,13h,15ah,16h-oxacyclotetradeca[2,3-d]isoindole-2,5-dione)

3D-SDF for NP0179759 ((9r,12as,13s,15as,16s,18as)-16-benzyl-13,18-dihydroxy-9,14,15-trimethyl-6h,7h,8h,9h,10h,12ah,13h,15ah,16h-oxacyclotetradeca[2,3-d]isoindole-2,5-dione)

PDB for NP0179759 ((9r,12as,13s,15as,16s,18as)-16-benzyl-13,18-dihydroxy-9,14,15-trimethyl-6h,7h,8h,9h,10h,12ah,13h,15ah,16h-oxacyclotetradeca[2,3-d]isoindole-2,5-dione)

3D PDB for NP0179759 ((9r,12as,13s,15as,16s,18as)-16-benzyl-13,18-dihydroxy-9,14,15-trimethyl-6h,7h,8h,9h,10h,12ah,13h,15ah,16h-oxacyclotetradeca[2,3-d]isoindole-2,5-dione)

SMILES for NP0179759 ((9r,12as,13s,15as,16s,18as)-16-benzyl-13,18-dihydroxy-9,14,15-trimethyl-6h,7h,8h,9h,10h,12ah,13h,15ah,16h-oxacyclotetradeca[2,3-d]isoindole-2,5-dione)

INCHI for NP0179759 ((9r,12as,13s,15as,16s,18as)-16-benzyl-13,18-dihydroxy-9,14,15-trimethyl-6h,7h,8h,9h,10h,12ah,13h,15ah,16h-oxacyclotetradeca[2,3-d]isoindole-2,5-dione)

Structure for NP0179759 ((9r,12as,13s,15as,16s,18as)-16-benzyl-13,18-dihydroxy-9,14,15-trimethyl-6h,7h,8h,9h,10h,12ah,13h,15ah,16h-oxacyclotetradeca[2,3-d]isoindole-2,5-dione)

3D Structure for NP0179759 ((9r,12as,13s,15as,16s,18as)-16-benzyl-13,18-dihydroxy-9,14,15-trimethyl-6h,7h,8h,9h,10h,12ah,13h,15ah,16h-oxacyclotetradeca[2,3-d]isoindole-2,5-dione)