NP-MRD: Showing NP-Card for (1s,3as,4s,5s,7s,7as)-1-benzyl-3,5-dihydroxy-4-[(1e,4s)-6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl]-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate (NP0283514)

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Record Information

Version

2.0

Created at

2022-09-09 10:48:48 UTC

Updated at

2022-09-09 10:48:48 UTC

NP-MRD ID

NP0283514

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3as,4s,5s,7s,7as)-1-benzyl-3,5-dihydroxy-4-[(1e,4s)-6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl]-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate

Description

Cytochalasin Z19 belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. (1s,3as,4s,5s,7s,7as)-1-benzyl-3,5-dihydroxy-4-[(1e,4s)-6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl]-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate is found in Aspergillus flavipes. Based on a literature review very few articles have been published on Cytochalasin Z19.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092212482D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309092212482D          

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    5.6424    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569    5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 23 37  1  0  0  0  0
  2 37  1  0  0  0  0
 37 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0283514

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)O[C@]12[C@H]([C@H](CC3=CC=CC=C3)N=C1O)[C@H](C)C(=C)[C@@H](O)[C@@H]2\C=C\C[C@H](C)C(=O)C(C)(O)CC=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H37NO8/c1-17(25(33)28(4,36)14-15-31)10-9-13-21-24(32)19(3)18(2)23-22(16-20-11-7-6-8-12-20)30-26(34)29(21,23)38-27(35)37-5/h6-9,11-13,15,17-18,21-24,32,36H,3,10,14,16H2,1-2,4-5H3,(H,30,34)/b13-9+/t17-,18+,21-,22-,23-,24+,28?,29+/m0/s1

> <INCHI_KEY>
BRQWOHZQMWWOCO-UKDBMQGKSA-N

> <FORMULA>
C29H37NO8

> <MOLECULAR_WEIGHT>
527.614

> <EXACT_MASS>
527.251917155

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
55.266179390077106

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3aS,4S,5S,7S,7aS)-1-benzyl-3,5-dihydroxy-4-[(1E,4S)-6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl]-7-methyl-6-methylidene-3a,4,5,6,7,7a-hexahydro-1H-isoindol-3a-yl methyl carbonate

> <JCHEM_LOGP>
2.242582040663209

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.705486051795205

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.609007634439915

> <JCHEM_PKA_STRONGEST_BASIC>
4.491562896298537

> <JCHEM_POLAR_SURFACE_AREA>
142.72

> <JCHEM_REFRACTIVITY>
140.5876

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3aS,4S,5S,7S,7aS)-1-benzyl-3,5-dihydroxy-4-[(1E,4S)-6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl]-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1H-isoindol-3a-yl methyl carbonate

> <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       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.530  -0.237   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.744   0.132   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.250  -0.188   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.726  -1.652   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.232  -1.973   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.263  -0.828   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.787   0.636   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.281   0.957   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -1.173   2.843   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.173   5.335   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.036   5.144   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.371   5.771   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.911   5.771   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.532   7.302   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.939   7.929   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.530   5.923   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.864   6.693   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.864   8.233   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.198   9.003   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.198  10.543   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.531   8.233   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.531   6.693   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       7.865   9.003   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.635   7.669   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.095  10.337   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.199   9.773   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.533   9.003   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      11.866   9.773   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   37                                                  
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   23                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   17   24   37                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   23    2   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₇NO₈

Average Mass

527.6140 Da

Monoisotopic Mass

527.25192 Da

IUPAC Name

(1S,3aS,4S,5S,7S,7aS)-1-benzyl-3,5-dihydroxy-4-[(1E,4S)-6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl]-7-methyl-6-methylidene-3a,4,5,6,7,7a-hexahydro-1H-isoindol-3a-yl methyl carbonate

Traditional Name

(1S,3aS,4S,5S,7S,7aS)-1-benzyl-3,5-dihydroxy-4-[(1E,4S)-6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl]-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1H-isoindol-3a-yl methyl carbonate

CAS Registry Number

Not Available

SMILES

COC(=O)O[C@]12[C@H]([C@H](CC3=CC=CC=C3)N=C1O)[C@H](C)C(=C)[C@@H](O)[C@@H]2\C=C\C[C@H](C)C(=O)C(C)(O)CC=O

InChI Identifier

InChI=1S/C29H37NO8/c1-17(25(33)28(4,36)14-15-31)10-9-13-21-24(32)19(3)18(2)23-22(16-20-11-7-6-8-12-20)30-26(34)29(21,23)38-27(35)37-5/h6-9,11-13,15,17-18,21-24,32,36H,3,10,14,16H2,1-2,4-5H3,(H,30,34)/b13-9+/t17-,18+,21-,22-,23-,24+,28?,29+/m0/s1

InChI Key

BRQWOHZQMWWOCO-UKDBMQGKSA-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

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
Acyloin
Monocyclic benzene moiety
Beta-hydroxy aldehyde
Carbonic acid diester
Benzenoid
2-pyrrolidone
Pyrrolidone
Alpha-hydrogen aldehyde
Alpha-hydroxy ketone
Tertiary alcohol
Cyclic alcohol
Pyrrolidine
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Ketone
Lactam
Carbonic acid derivative
Carboxylic acid derivative
Azacycle
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aldehyde
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
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	2.24	ChemAxon
pKa (Strongest Acidic)	1.61	ChemAxon
pKa (Strongest Basic)	4.49	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	142.72 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	140.59 m³·mol⁻¹	ChemAxon
Polarizability	55.27 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

27024304

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101491662

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3as,4s,5s,7s,7as)-1-benzyl-3,5-dihydroxy-4-[(1e,4s)-6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl]-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate (NP0283514)

MOL for NP0283514 ((1s,3as,4s,5s,7s,7as)-1-benzyl-3,5-dihydroxy-4-[(1e,4s)-6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl]-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)

3D MOL for NP0283514 ((1s,3as,4s,5s,7s,7as)-1-benzyl-3,5-dihydroxy-4-[(1e,4s)-6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl]-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)

3D SDF for NP0283514 ((1s,3as,4s,5s,7s,7as)-1-benzyl-3,5-dihydroxy-4-[(1e,4s)-6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl]-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)

3D-SDF for NP0283514 ((1s,3as,4s,5s,7s,7as)-1-benzyl-3,5-dihydroxy-4-[(1e,4s)-6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl]-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)

PDB for NP0283514 ((1s,3as,4s,5s,7s,7as)-1-benzyl-3,5-dihydroxy-4-[(1e,4s)-6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl]-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)

3D PDB for NP0283514 ((1s,3as,4s,5s,7s,7as)-1-benzyl-3,5-dihydroxy-4-[(1e,4s)-6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl]-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)

SMILES for NP0283514 ((1s,3as,4s,5s,7s,7as)-1-benzyl-3,5-dihydroxy-4-[(1e,4s)-6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl]-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)

INCHI for NP0283514 ((1s,3as,4s,5s,7s,7as)-1-benzyl-3,5-dihydroxy-4-[(1e,4s)-6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl]-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)

Structure for NP0283514 ((1s,3as,4s,5s,7s,7as)-1-benzyl-3,5-dihydroxy-4-[(1e,4s)-6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl]-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)

3D Structure for NP0283514 ((1s,3as,4s,5s,7s,7as)-1-benzyl-3,5-dihydroxy-4-[(1e,4s)-6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl]-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)