NP-MRD: Showing NP-Card for n-(2-{[(3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-12,15-dioxo-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindol-14-yl]sulfanyl}ethyl)ethanimidic acid (NP0148529)

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Record Information

Version

2.0

Created at

2022-09-02 04:17:34 UTC

Updated at

2022-09-02 04:17:34 UTC

NP-MRD ID

NP0148529

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-(2-{[(3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-12,15-dioxo-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindol-14-yl]sulfanyl}ethyl)ethanimidic acid

Description

Cyschalasin A belongs to the class of organic compounds known as isoindoles. These are heteropolycyclic compounds with a structure containing isoindole, a benzo-fused pyrrole. n-(2-{[(3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-12,15-dioxo-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindol-14-yl]sulfanyl}ethyl)ethanimidic acid is found in Aspergillus micronesiensis. Based on a literature review very few articles have been published on Cyschalasin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022206172D          

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M  END

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M  END


  Mrv1652309022206172D          

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    0.9585   -5.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4476   -5.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6033   -2.8800    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0491   -2.3750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8126   -2.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  4  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 34 29  1  6  0  0  0
 25 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>
NP0148529

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@@H]1N=C(O)[C@]23[C@H]1[C@H](C)C(C)=C[C@@H]2\C=C(C)\CC[C@@H](O)C(=O)C[C@@H](SCCN=C(C)O)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H42N2O5S/c1-15(2)11-21-25-18(5)17(4)13-20-12-16(3)7-8-22(32)23(33)14-24(36-10-9-29-19(6)31)26(34)28(20,25)27(35)30-21/h12-13,15,18,20-22,24-25,32H,7-11,14H2,1-6H3,(H,29,31)(H,30,35)/b16-12+/t18-,20+,21+,22-,24-,25+,28+/m1/s1

> <INCHI_KEY>
XEUIJZSFKASMIJ-HBBZWIBTSA-N

> <FORMULA>
C28H42N2O5S

> <MOLECULAR_WEIGHT>
518.71

> <EXACT_MASS>
518.281443634

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
57.63564118872527

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(2-{[(3S,4S,6aS,11R,14R,15aR,15bR)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-12,15-dioxo-3H,4H,6aH,9H,10H,11H,12H,13H,14H,15H,15bH-cycloundeca[e]isoindol-14-yl]sulfanyl}ethyl)ethanimidic acid

> <ALOGPS_LOGP>
3.02

> <JCHEM_LOGP>
2.4317617044271342

> <ALOGPS_LOGS>
-4.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.085118836485092

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.609979789467587

> <JCHEM_PKA_STRONGEST_BASIC>
6.228935199014058

> <JCHEM_POLAR_SURFACE_AREA>
119.55

> <JCHEM_REFRACTIVITY>
145.17960000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(2-{[(3S,4S,6aS,11R,14R,15aR,15bR)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-12,15-dioxo-3H,4H,6aH,9H,10H,11H,13H,14H,15bH-cycloundeca[e]isoindol-14-yl]sulfanyl}ethyl)ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.102  -1.965   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.116  -2.907   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.541  -2.324   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.759  -3.267   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.289  -2.561   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.958  -1.174   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.229   0.182   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.484  -1.381   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.758  -2.897   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.045  -3.985   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.483  -3.433   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.838  -5.511   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.055  -6.454   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.412  -6.095   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.195  -5.152   0.000  0.00  0.00           C+0
HETATM   16  S   UNK     0       4.987  -6.678   0.000  0.00  0.00           S+0
HETATM   17  C   UNK     0       6.205  -7.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.630  -7.037   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       8.848  -7.980   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       8.641  -9.506   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.858 -10.448   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.215 -10.089   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.853  -5.534   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.562  -7.261   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.551  -4.793   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.547  -5.968   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.082  -5.853   0.000  0.00  0.00           O+0
HETATM   28  N   UNK     0       2.737  -7.278   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       1.241  -6.912   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.065  -7.907   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.340  -9.422   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.789  -9.942   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.836 -10.418   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.126  -5.376   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.092  -4.433   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.517  -5.017   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   25                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   15   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    4   26   34                                             
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   29   25   35                                                  
CONECT   35   34    2   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₂N₂O₅S

Average Mass

518.7100 Da

Monoisotopic Mass

518.28144 Da

IUPAC Name

N-(2-{[(3S,4S,6aS,11R,14R,15aR,15bR)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-12,15-dioxo-3H,4H,6aH,9H,10H,11H,12H,13H,14H,15H,15bH-cycloundeca[e]isoindol-14-yl]sulfanyl}ethyl)ethanimidic acid

Traditional Name

N-(2-{[(3S,4S,6aS,11R,14R,15aR,15bR)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-12,15-dioxo-3H,4H,6aH,9H,10H,11H,13H,14H,15bH-cycloundeca[e]isoindol-14-yl]sulfanyl}ethyl)ethanimidic acid

CAS Registry Number

Not Available

SMILES

CC(C)C[C@@H]1N=C(O)[C@]23[C@H]1[C@H](C)C(C)=C[C@@H]2\C=C(C)\CC[C@@H](O)C(=O)C[C@@H](SCCN=C(C)O)C3=O

InChI Identifier

InChI=1S/C28H42N2O5S/c1-15(2)11-21-25-18(5)17(4)13-20-12-16(3)7-8-22(32)23(33)14-24(36-10-9-29-19(6)31)26(34)28(20,25)27(35)30-21/h12-13,15,18,20-22,24-25,32H,7-11,14H2,1-6H3,(H,29,31)(H,30,35)/b16-12+/t18-,20+,21+,22-,24-,25+,28+/m1/s1

InChI Key

XEUIJZSFKASMIJ-HBBZWIBTSA-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 micronesiensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindoles. These are heteropolycyclic compounds with a structure containing isoindole, a benzo-fused pyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindoles

Direct Parent

Isoindoles

Alternative Parents

Substituents

Isoindole
Cyclic carboximidic acid
Pyrroline
Cyclic ketone
Secondary alcohol
Ketone
Azacycle
Dialkylthioether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Thioether
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	3.02	ALOGPS
logP	2.43	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	2.61	ChemAxon
pKa (Strongest Basic)	6.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	119.55 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	145.18 m³·mol⁻¹	ChemAxon
Polarizability	57.64 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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

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

145721091

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-(2-{[(3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-12,15-dioxo-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindol-14-yl]sulfanyl}ethyl)ethanimidic acid (NP0148529)

MOL for NP0148529 (n-(2-{[(3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-12,15-dioxo-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindol-14-yl]sulfanyl}ethyl)ethanimidic acid)

3D MOL for NP0148529 (n-(2-{[(3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-12,15-dioxo-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindol-14-yl]sulfanyl}ethyl)ethanimidic acid)

3D SDF for NP0148529 (n-(2-{[(3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-12,15-dioxo-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindol-14-yl]sulfanyl}ethyl)ethanimidic acid)

3D-SDF for NP0148529 (n-(2-{[(3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-12,15-dioxo-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindol-14-yl]sulfanyl}ethyl)ethanimidic acid)

PDB for NP0148529 (n-(2-{[(3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-12,15-dioxo-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindol-14-yl]sulfanyl}ethyl)ethanimidic acid)

3D PDB for NP0148529 (n-(2-{[(3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-12,15-dioxo-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindol-14-yl]sulfanyl}ethyl)ethanimidic acid)

SMILES for NP0148529 (n-(2-{[(3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-12,15-dioxo-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindol-14-yl]sulfanyl}ethyl)ethanimidic acid)

INCHI for NP0148529 (n-(2-{[(3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-12,15-dioxo-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindol-14-yl]sulfanyl}ethyl)ethanimidic acid)

Structure for NP0148529 (n-(2-{[(3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-12,15-dioxo-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindol-14-yl]sulfanyl}ethyl)ethanimidic acid)

3D Structure for NP0148529 (n-(2-{[(3s,3ar,4s,6as,11r,14r,15ar)-1,11-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-12,15-dioxo-3h,3ah,4h,6ah,9h,10h,11h,13h,14h-cycloundeca[d]isoindol-14-yl]sulfanyl}ethyl)ethanimidic acid)