NP-MRD: Showing NP-Card for (5r,9r,12as,13s,15s,15as,16s,18as)-5,13,18-trihydroxy-16-[(4-hydroxyphenyl)methyl]-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one (NP0197723)

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Record Information

Version

2.0

Created at

2022-09-04 16:02:11 UTC

Updated at

2022-09-04 16:02:11 UTC

NP-MRD ID

NP0197723

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5r,9r,12as,13s,15s,15as,16s,18as)-5,13,18-trihydroxy-16-[(4-hydroxyphenyl)methyl]-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one

Description

Cytochalasin Z5 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. (5r,9r,12as,13s,15s,15as,16s,18as)-5,13,18-trihydroxy-16-[(4-hydroxyphenyl)methyl]-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one is found in Boeremia exigua. Based on a literature review very few articles have been published on Cytochalasin Z5.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042218022D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042218022D          

 36 39  0  0  1  0            999 V2000
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  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
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 16  1  1  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 34 33  1  1  0  0  0
 18 34  1  0  0  0  0
 34 35  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0197723

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@H](CC3=CC=C(O)C=C3)N=C(O)[C@]22OC(=O)\C=C\[C@H](O)CCC[C@@H](C)C\C=C\[C@H]2[C@H](O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C29H37NO6/c1-17-6-4-8-21(31)14-15-25(33)36-29-23(9-5-7-17)27(34)19(3)18(2)26(29)24(30-28(29)35)16-20-10-12-22(32)13-11-20/h5,9-15,17-18,21,23-24,26-27,31-32,34H,3-4,6-8,16H2,1-2H3,(H,30,35)/b9-5+,15-14+/t17-,18-,21-,23+,24+,26+,27-,29-/m1/s1

> <INCHI_KEY>
AJMKPZXRIKVSAQ-LFOGIAMQSA-N

> <FORMULA>
C29H37NO6

> <MOLECULAR_WEIGHT>
495.616

> <EXACT_MASS>
495.262087915

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.57237552771173

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R,9R,13S,15S,15aS,16S,18aS,18bS)-5,13,18-trihydroxy-16-[(4-hydroxyphenyl)methyl]-9,15-dimethyl-14-methylidene-2H,5H,6H,7H,8H,9H,10H,13H,14H,15H,15aH,16H,18bH-oxacyclotetradeca[3,2-e]isoindol-2-one

> <JCHEM_LOGP>
3.2374292947654926

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.504988397679526

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8129987715129863

> <JCHEM_PKA_STRONGEST_BASIC>
4.694210262323623

> <JCHEM_POLAR_SURFACE_AREA>
119.58000000000003

> <JCHEM_REFRACTIVITY>
138.91960000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5R,9R,13S,15S,15aS,16S,18aS,18bS)-5,13,18-trihydroxy-16-[(4-hydroxyphenyl)methyl]-9,15-dimethyl-14-methylidene-5H,6H,7H,8H,9H,10H,13H,15H,15aH,16H,18bH-oxacyclotetradeca[3,2-e]isoindol-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       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  O   UNK     0      10.240   5.618   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.152   2.953   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.338   1.645   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       9.236  -1.181   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       9.502  -2.480   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.892  -3.370   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.148  -3.423   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.628  -2.996   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.997  -1.501   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.888  -0.433   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.477  -1.074   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.587  -2.142   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.066  -1.714   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      14.436  -0.219   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      15.176  -2.782   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.806  -4.277   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.327  -4.704   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.957  -6.199   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.066  -7.267   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.477  -6.626   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.367  -5.558   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.888  -5.986   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.778  -4.918   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.298  -5.345   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.929  -6.840   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   18                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8                                                       
CONECT   15    6   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    5   19   34                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   18   35                                                  
CONECT   35   34    2   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₇NO₆

Average Mass

495.6160 Da

Monoisotopic Mass

495.26209 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@H](CC3=CC=C(O)C=C3)N=C(O)[C@]22OC(=O)\C=C\[C@H](O)CCC[C@@H](C)C\C=C\[C@H]2[C@H](O)C1=C

InChI Identifier

InChI=1S/C29H37NO6/c1-17-6-4-8-21(31)14-15-25(33)36-29-23(9-5-7-17)27(34)19(3)18(2)26(29)24(30-28(29)35)16-20-10-12-22(32)13-11-20/h5,9-15,17-18,21,23-24,26-27,31-32,34H,3-4,6-8,16H2,1-2H3,(H,30,35)/b9-5+,15-14+/t17-,18-,21-,23+,24+,26+,27-,29-/m1/s1

InChI Key

AJMKPZXRIKVSAQ-LFOGIAMQSA-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
Phoma exigua	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

Lactone cytochalasan skeleton
Cytochalasan
Isoindolone
Isoindoline
Isoindole
Isoindole or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Pyrrolidone
2-pyrrolidone
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Pyrrolidine
Enoate ester
Cyclic alcohol
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Lactone
Lactam
Carboxylic acid ester
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Alcohol
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Carbonyl group
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

C00044681

Chemspider ID

10181895

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21574192

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5r,9r,12as,13s,15s,15as,16s,18as)-5,13,18-trihydroxy-16-[(4-hydroxyphenyl)methyl]-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one (NP0197723)

MOL for NP0197723 ((5r,9r,12as,13s,15s,15as,16s,18as)-5,13,18-trihydroxy-16-[(4-hydroxyphenyl)methyl]-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)

3D MOL for NP0197723 ((5r,9r,12as,13s,15s,15as,16s,18as)-5,13,18-trihydroxy-16-[(4-hydroxyphenyl)methyl]-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)

3D SDF for NP0197723 ((5r,9r,12as,13s,15s,15as,16s,18as)-5,13,18-trihydroxy-16-[(4-hydroxyphenyl)methyl]-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)

3D-SDF for NP0197723 ((5r,9r,12as,13s,15s,15as,16s,18as)-5,13,18-trihydroxy-16-[(4-hydroxyphenyl)methyl]-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)

PDB for NP0197723 ((5r,9r,12as,13s,15s,15as,16s,18as)-5,13,18-trihydroxy-16-[(4-hydroxyphenyl)methyl]-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)

3D PDB for NP0197723 ((5r,9r,12as,13s,15s,15as,16s,18as)-5,13,18-trihydroxy-16-[(4-hydroxyphenyl)methyl]-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)

SMILES for NP0197723 ((5r,9r,12as,13s,15s,15as,16s,18as)-5,13,18-trihydroxy-16-[(4-hydroxyphenyl)methyl]-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)

INCHI for NP0197723 ((5r,9r,12as,13s,15s,15as,16s,18as)-5,13,18-trihydroxy-16-[(4-hydroxyphenyl)methyl]-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)

Structure for NP0197723 ((5r,9r,12as,13s,15s,15as,16s,18as)-5,13,18-trihydroxy-16-[(4-hydroxyphenyl)methyl]-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)

3D Structure for NP0197723 ((5r,9r,12as,13s,15s,15as,16s,18as)-5,13,18-trihydroxy-16-[(4-hydroxyphenyl)methyl]-9,15-dimethyl-14-methylidene-5h,6h,7h,8h,9h,10h,12ah,13h,15h,15ah,16h-oxacyclotetradeca[2,3-d]isoindol-2-one)