NP-MRD: Showing NP-Card for (1s,7s,9e,11r,12s,14r,15s,16r,17s)-19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione (NP0319423)

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Record Information

Version

2.0

Created at

2022-09-11 20:26:26 UTC

Updated at

2022-09-11 20:26:26 UTC

NP-MRD ID

NP0319423

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,7s,9e,11r,12s,14r,15s,16r,17s)-19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione

Description

Cytochalasin G belongs to the class of organic compounds known as chaetoglobosins. These are cytochalasans with a structure in which the hydrogenated isoindole bears an (indol-3-yl)methyl group. (1s,7s,9e,11r,12s,14r,15s,16r,17s)-19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione is found in Pseudeurotium zonatum. It was first documented in 2002 (PMID: 12350146). Based on a literature review very few articles have been published on Cytochalasin G.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112222262D          

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M  END

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M  END


  Mrv1652309112222262D          

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 19 24  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 28 26  1  1  0  0  0
  6 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 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
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  2 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0319423

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@H](CC3=CNC4=CC=CC=C34)N=C(O)[C@@]22[C@@H](\C=C\C[C@H](C)CC(=O)CCC2=O)[C@@H]2O[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H34N2O4/c1-16-7-6-9-21-26-28(3,35-26)17(2)25-23(14-18-15-30-22-10-5-4-8-20(18)22)31-27(34)29(21,25)24(33)12-11-19(32)13-16/h4-6,8-10,15-17,21,23,25-26,30H,7,11-14H2,1-3H3,(H,31,34)/b9-6+/t16-,17-,21-,23-,25-,26-,28+,29+/m0/s1

> <INCHI_KEY>
YGKUXRWMCOUTAL-LGUVXVKNSA-N

> <FORMULA>
C29H34N2O4

> <MOLECULAR_WEIGHT>
474.601

> <EXACT_MASS>
474.251857583

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.75077279050235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,7S,9E,11R,12S,14R,15S,16R,17S)-19-hydroxy-17-[(1H-indol-3-yl)methyl]-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0^{1,16}.0^{12,14}]nonadeca-9,18-diene-2,5-dione

> <JCHEM_LOGP>
3.600883770824114

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.05427597426843

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.811808155468294

> <JCHEM_PKA_STRONGEST_BASIC>
5.465518075765654

> <JCHEM_POLAR_SURFACE_AREA>
95.04999999999998

> <JCHEM_REFRACTIVITY>
134.35770000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,7S,9E,11R,12S,14R,15S,16R,17S)-19-hydroxy-17-(1H-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0^{1,16}.0^{12,14}]nonadeca-9,18-diene-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       0.819   2.518   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.893   1.257   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.656   2.594   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.164   2.281   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.333   0.750   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.541  -0.425   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.003   0.058   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.465   0.541   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.152  -0.967   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.756  -1.212   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.839  -2.474   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.043  -3.544   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.377  -2.957   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.758  -4.367   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.587  -5.726   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.771  -7.035   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.348  -8.462   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       5.169  -9.453   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.862  -8.637   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.382  -9.062   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.274  -7.993   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.646  -6.498   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.126  -6.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.234  -7.143   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       4.225  -4.214   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       4.287  -2.905   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.548  -2.422   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.228  -1.933   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.765  -2.416   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.723  -3.806   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.616  -1.391   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.154  -1.874   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.004  -0.849   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.531  -1.313   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.317   0.659   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    9                                                       
CONECT    9    8    7   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   28                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   16   19                                                  
CONECT   25   14   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    6   13   29                                             
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    2                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₄N₂O₄

Average Mass

474.6010 Da

Monoisotopic Mass

474.25186 Da

IUPAC Name

(1S,7S,9E,11R,12S,14R,15S,16R,17S)-19-hydroxy-17-[(1H-indol-3-yl)methyl]-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0^{1,16}.0^{12,14}]nonadeca-9,18-diene-2,5-dione

Traditional Name

(1S,7S,9E,11R,12S,14R,15S,16R,17S)-19-hydroxy-17-(1H-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0^{1,16}.0^{12,14}]nonadeca-9,18-diene-2,5-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@H](CC3=CNC4=CC=CC=C34)N=C(O)[C@@]22[C@@H](\C=C\C[C@H](C)CC(=O)CCC2=O)[C@@H]2O[C@]12C

InChI Identifier

InChI=1S/C29H34N2O4/c1-16-7-6-9-21-26-28(3,35-26)17(2)25-23(14-18-15-30-22-10-5-4-8-20(18)22)31-27(34)29(21,25)24(33)12-11-19(32)13-16/h4-6,8-10,15-17,21,23,25-26,30H,7,11-14H2,1-3H3,(H,31,34)/b9-6+/t16-,17-,21-,23-,25-,26-,28+,29+/m0/s1

InChI Key

YGKUXRWMCOUTAL-LGUVXVKNSA-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
Pseudeurotium zonatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chaetoglobosins. These are cytochalasans with a structure in which the hydrogenated isoindole bears an (indol-3-yl)methyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cytochalasans

Sub Class

Chaetoglobosins

Direct Parent

Chaetoglobosins

Alternative Parents

Substituents

Carbocyclic chaetoglobosin skeleton
Isoindolone
3-alkylindole
Indole
Indole or derivatives
Isoindoline
Isoindole or derivatives
Oxepane
Benzenoid
Substituted pyrrole
2-pyrrolidone
Pyrrolidone
Heteroaromatic compound
Pyrrolidine
Pyrrole
Carboxamide group
Ketone
Cyclic ketone
Lactam
Secondary carboxylic acid amide
Azacycle
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Organoheterocyclic compound
Aldehyde
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen 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	3.6	ChemAxon
pKa (Strongest Acidic)	2.81	ChemAxon
pKa (Strongest Basic)	5.47	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.05 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	134.36 m³·mol⁻¹	ChemAxon
Polarizability	51.75 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00011356

Chemspider ID

4944757

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440497

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Feng Y, Blunt JW, Cole AL, Munro MH: Three novel cytochalasins X, Y, and Z from Pseudeurotium zonatum. J Nat Prod. 2002 Sep;65(9):1274-7. doi: 10.1021/np020159k. [PubMed:12350146 ]
LOTUS database [Link]

Showing NP-Card for (1s,7s,9e,11r,12s,14r,15s,16r,17s)-19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione (NP0319423)

MOL for NP0319423 ((1s,7s,9e,11r,12s,14r,15s,16r,17s)-19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)

3D MOL for NP0319423 ((1s,7s,9e,11r,12s,14r,15s,16r,17s)-19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)

3D SDF for NP0319423 ((1s,7s,9e,11r,12s,14r,15s,16r,17s)-19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)

3D-SDF for NP0319423 ((1s,7s,9e,11r,12s,14r,15s,16r,17s)-19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)

PDB for NP0319423 ((1s,7s,9e,11r,12s,14r,15s,16r,17s)-19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)

3D PDB for NP0319423 ((1s,7s,9e,11r,12s,14r,15s,16r,17s)-19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)

SMILES for NP0319423 ((1s,7s,9e,11r,12s,14r,15s,16r,17s)-19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)

INCHI for NP0319423 ((1s,7s,9e,11r,12s,14r,15s,16r,17s)-19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)

Structure for NP0319423 ((1s,7s,9e,11r,12s,14r,15s,16r,17s)-19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)

3D Structure for NP0319423 ((1s,7s,9e,11r,12s,14r,15s,16r,17s)-19-hydroxy-17-(1h-indol-3-ylmethyl)-7,14,15-trimethyl-13-oxa-18-azatetracyclo[9.8.0.0¹,¹⁶.0¹²,¹⁴]nonadeca-9,18-diene-2,5-dione)