NP-MRD: Showing NP-Card for (1s,4r,8r,9s,11e,13r,14s,16s,17r,18s)-6,14,20-trihydroxy-18-(1h-indol-3-ylmethyl)-7,9,16-trimethyl-15-methylidene-19-azatetracyclo[11.7.0.0¹,¹⁷.0⁴,⁸]icosa-6,11,19-triene-2,5-dione (NP0234648)

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Record Information

Version

2.0

Created at

2022-09-06 16:48:38 UTC

Updated at

2022-09-06 16:48:39 UTC

NP-MRD ID

NP0234648

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4r,8r,9s,11e,13r,14s,16s,17r,18s)-6,14,20-trihydroxy-18-(1h-indol-3-ylmethyl)-7,9,16-trimethyl-15-methylidene-19-azatetracyclo[11.7.0.0¹,¹⁷.0⁴,⁸]icosa-6,11,19-triene-2,5-dione

Description

Cytoglobosin A belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. Cytoglobosin A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on cytoglobosin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062218482D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309062218482D          

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    2.1549   -5.9157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3312   -5.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8785   -5.2733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2493   -4.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0730   -4.4891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8188   -1.6491    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1247   -1.2032    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3915   -1.5814    0.0000 C   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  6  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 18 16  1  1  0  0  0
 11 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
  5 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 28 36  1  0  0  0  0
 31 36  1  0  0  0  0
 37 26  1  6  0  0  0
 22 37  1  0  0  0  0
 37 38  1  0  0  0  0
  2 38  1  0  0  0  0
 38 39  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0234648

> <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)[C@@H]3[C@@H](CC2=O)C(=O)C(O)=C3C)[C@H](O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C32H36N2O5/c1-15-8-7-10-22-28(36)17(3)16(2)27-24(12-19-14-33-23-11-6-5-9-20(19)23)34-31(39)32(22,27)25(35)13-21-26(15)18(4)29(37)30(21)38/h5-7,9-11,14-16,21-22,24,26-28,33,36-37H,3,8,12-13H2,1-2,4H3,(H,34,39)/b10-7+/t15-,16+,21+,22-,24-,26-,27-,28+,32+/m0/s1

> <INCHI_KEY>
VROGJHMZKMLYET-NKUOSLKNSA-N

> <FORMULA>
C32H36N2O5

> <MOLECULAR_WEIGHT>
528.649

> <EXACT_MASS>
528.262422267

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
58.62179534477722

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4R,8R,9S,11E,13R,14S,16S,17R,18S)-6,14,20-trihydroxy-18-[(1H-indol-3-yl)methyl]-7,9,16-trimethyl-15-methylidene-19-azatetracyclo[11.7.0.0^{1,17}.0^{4,8}]icosa-6,11,19-triene-2,5-dione

> <JCHEM_LOGP>
3.3394913496631244

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.027611062349752

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.772259255213978

> <JCHEM_PKA_STRONGEST_BASIC>
5.432344098409239

> <JCHEM_POLAR_SURFACE_AREA>
122.98

> <JCHEM_REFRACTIVITY>
150.78080000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,8R,9S,11E,13R,14S,16S,17R,18S)-6,14,20-trihydroxy-18-(1H-indol-3-ylmethyl)-7,9,16-trimethyl-15-methylidene-19-azatetracyclo[11.7.0.0^{1,17}.0^{4,8}]icosa-6,11,19-triene-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       2.743   0.125   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.039  -0.708   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.408  -0.002   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.481   1.537   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.703  -0.834   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.072  -0.128   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.145   1.410   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.514   2.116   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.809   1.284   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.178   1.990   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.736  -0.254   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.831  -1.338   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.351  -1.089   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.138  -2.714   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.844  -4.082   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.829  -2.434   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.533  -3.575   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.368  -0.960   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.295  -2.499   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.305  -2.899   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.853  -4.743   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.630  -2.372   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.725  -3.456   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.245  -3.207   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0       7.032  -4.831   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       5.510  -4.598   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.427  -5.692   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.833  -7.178   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.273  -7.723   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       6.200  -9.261   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       4.715  -9.667   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.022 -11.043   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.485 -11.131   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.640  -9.843   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.332  -8.468   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.870  -8.380   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.262  -3.078   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.966  -2.246   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.597  -2.952   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   18                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   11   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    5   23   37                                             
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   37                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   36                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   28   31                                                  
CONECT   37   26   22   38                                                  
CONECT   38   37    2   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₆N₂O₅

Average Mass

528.6490 Da

Monoisotopic Mass

528.26242 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=CNC4=CC=CC=C34)N=C(O)[C@@]22[C@@H](\C=C\C[C@H](C)[C@@H]3[C@@H](CC2=O)C(=O)C(O)=C3C)[C@H](O)C1=C

InChI Identifier

InChI=1S/C32H36N2O5/c1-15-8-7-10-22-28(36)17(3)16(2)27-24(12-19-14-33-23-11-6-5-9-20(19)23)34-31(39)32(22,27)25(35)13-21-26(15)18(4)29(37)30(21)38/h5-7,9-11,14-16,21-22,24,26-28,33,36-37H,3,8,12-13H2,1-2,4H3,(H,34,39)/b10-7+/t15-,16+,21+,22-,24-,26-,27-,28+,32+/m0/s1

InChI Key

VROGJHMZKMLYET-NKUOSLKNSA-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
3-alkylindole
Indole
Indole or derivatives
Pyrrolidone
2-pyrrolidone
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Cyclic alcohol
Pyrrole
Pyrrolidine
Carboxamide group
Ketone
Lactam
Secondary carboxylic acid amide
Secondary alcohol
Azacycle
Enol
Carboxylic acid derivative
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:68814 )
macrocycle (CHEBI:68814 )
cytochalasan alkaloid (CHEBI:68814 )

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

24676268

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46209792

PDB ID

Not Available

ChEBI ID

68814

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4r,8r,9s,11e,13r,14s,16s,17r,18s)-6,14,20-trihydroxy-18-(1h-indol-3-ylmethyl)-7,9,16-trimethyl-15-methylidene-19-azatetracyclo[11.7.0.0¹,¹⁷.0⁴,⁸]icosa-6,11,19-triene-2,5-dione (NP0234648)

MOL for NP0234648 ((1s,4r,8r,9s,11e,13r,14s,16s,17r,18s)-6,14,20-trihydroxy-18-(1h-indol-3-ylmethyl)-7,9,16-trimethyl-15-methylidene-19-azatetracyclo[11.7.0.0¹,¹⁷.0⁴,⁸]icosa-6,11,19-triene-2,5-dione)

3D MOL for NP0234648 ((1s,4r,8r,9s,11e,13r,14s,16s,17r,18s)-6,14,20-trihydroxy-18-(1h-indol-3-ylmethyl)-7,9,16-trimethyl-15-methylidene-19-azatetracyclo[11.7.0.0¹,¹⁷.0⁴,⁸]icosa-6,11,19-triene-2,5-dione)

3D SDF for NP0234648 ((1s,4r,8r,9s,11e,13r,14s,16s,17r,18s)-6,14,20-trihydroxy-18-(1h-indol-3-ylmethyl)-7,9,16-trimethyl-15-methylidene-19-azatetracyclo[11.7.0.0¹,¹⁷.0⁴,⁸]icosa-6,11,19-triene-2,5-dione)

3D-SDF for NP0234648 ((1s,4r,8r,9s,11e,13r,14s,16s,17r,18s)-6,14,20-trihydroxy-18-(1h-indol-3-ylmethyl)-7,9,16-trimethyl-15-methylidene-19-azatetracyclo[11.7.0.0¹,¹⁷.0⁴,⁸]icosa-6,11,19-triene-2,5-dione)

PDB for NP0234648 ((1s,4r,8r,9s,11e,13r,14s,16s,17r,18s)-6,14,20-trihydroxy-18-(1h-indol-3-ylmethyl)-7,9,16-trimethyl-15-methylidene-19-azatetracyclo[11.7.0.0¹,¹⁷.0⁴,⁸]icosa-6,11,19-triene-2,5-dione)

3D PDB for NP0234648 ((1s,4r,8r,9s,11e,13r,14s,16s,17r,18s)-6,14,20-trihydroxy-18-(1h-indol-3-ylmethyl)-7,9,16-trimethyl-15-methylidene-19-azatetracyclo[11.7.0.0¹,¹⁷.0⁴,⁸]icosa-6,11,19-triene-2,5-dione)

SMILES for NP0234648 ((1s,4r,8r,9s,11e,13r,14s,16s,17r,18s)-6,14,20-trihydroxy-18-(1h-indol-3-ylmethyl)-7,9,16-trimethyl-15-methylidene-19-azatetracyclo[11.7.0.0¹,¹⁷.0⁴,⁸]icosa-6,11,19-triene-2,5-dione)

INCHI for NP0234648 ((1s,4r,8r,9s,11e,13r,14s,16s,17r,18s)-6,14,20-trihydroxy-18-(1h-indol-3-ylmethyl)-7,9,16-trimethyl-15-methylidene-19-azatetracyclo[11.7.0.0¹,¹⁷.0⁴,⁸]icosa-6,11,19-triene-2,5-dione)

Structure for NP0234648 ((1s,4r,8r,9s,11e,13r,14s,16s,17r,18s)-6,14,20-trihydroxy-18-(1h-indol-3-ylmethyl)-7,9,16-trimethyl-15-methylidene-19-azatetracyclo[11.7.0.0¹,¹⁷.0⁴,⁸]icosa-6,11,19-triene-2,5-dione)

3D Structure for NP0234648 ((1s,4r,8r,9s,11e,13r,14s,16s,17r,18s)-6,14,20-trihydroxy-18-(1h-indol-3-ylmethyl)-7,9,16-trimethyl-15-methylidene-19-azatetracyclo[11.7.0.0¹,¹⁷.0⁴,⁸]icosa-6,11,19-triene-2,5-dione)