NP-MRD: Showing NP-Card for 3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,12h,13h,14h-cycloundeca[d]isoindole-11,15-dione (NP0244516)

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Record Information

Version

2.0

Created at

2022-09-07 05:19:59 UTC

Updated at

2022-09-07 05:19:59 UTC

NP-MRD ID

NP0244516

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,12h,13h,14h-cycloundeca[d]isoindole-11,15-dione

Description

3-Benzyl-1-hydroxy-4,5,10,12-tetramethyl-3H,4H,6aH,9H,10H,11H,12H,13H,14H,15H,15bH-cycloundeca[e]isoindole-11,15-dione 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. 3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,12h,13h,14h-cycloundeca[d]isoindole-11,15-dione is found in Daldinia eschscholtzii. Based on a literature review very few articles have been published on 3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-3H,4H,6aH,9H,10H,11H,12H,13H,14H,15H,15bH-cycloundeca[e]isoindole-11,15-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072207202D          

 32 35  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072207202D          

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M  END
> <DATABASE_ID>
NP0244516

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3=CC=CC=C3)N=C(O)C22C(C=C1C)C=CCC(C)C(=O)C(C)CCC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H35NO3/c1-17-9-8-12-22-15-19(3)20(4)25-23(16-21-10-6-5-7-11-21)29-27(32)28(22,25)24(30)14-13-18(2)26(17)31/h5-8,10-12,15,17-18,20,22-23,25H,9,13-14,16H2,1-4H3,(H,29,32)

> <INCHI_KEY>
XXCJVNMYGXUDBR-UHFFFAOYSA-N

> <FORMULA>
C28H35NO3

> <MOLECULAR_WEIGHT>
433.592

> <EXACT_MASS>
433.261693991

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
49.725061625867156

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-3H,4H,6aH,9H,10H,11H,12H,13H,14H,15H,15bH-cycloundeca[e]isoindole-11,15-dione

> <JCHEM_LOGP>
5.024420272547884

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.73396327505293

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.900043939214701

> <JCHEM_PKA_STRONGEST_BASIC>
5.5669973024226

> <JCHEM_POLAR_SURFACE_AREA>
66.73

> <JCHEM_REFRACTIVITY>
129.26510000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-3H,4H,6aH,9H,10H,12H,13H,14H,15bH-cycloundeca[e]isoindole-11,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.119  -1.907   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       6.484  -1.381   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.758  -2.897   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.139  -2.011   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       9.635  -3.746   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  C   UNK     0       9.108  -6.501   0.000  0.00  0.00           C+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  C   UNK     0       3.853  -5.534   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.982  -7.361   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.551  -4.793   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.547  -5.968   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.180  -6.328   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0       2.737  -7.278   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       1.241  -6.912   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.012  -7.912   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.340  -9.422   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.813  -9.870   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.162 -11.370   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.037 -12.422   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.436 -11.974   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.785 -10.474   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.126  -5.376   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.092  -4.433   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.631  -4.855   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    4   19   30                                             
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30   22   18   31                                                  
CONECT   31   30    2   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₅NO₃

Average Mass

433.5920 Da

Monoisotopic Mass

433.26169 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3=CC=CC=C3)N=C(O)C22C(C=C1C)C=CCC(C)C(=O)C(C)CCC2=O

InChI Identifier

InChI=1S/C28H35NO3/c1-17-9-8-12-22-15-19(3)20(4)25-23(16-21-10-6-5-7-11-21)29-27(32)28(22,25)24(30)14-13-18(2)26(17)31/h5-8,10-12,15,17-18,20,22-23,25H,9,13-14,16H2,1-4H3,(H,29,32)

InChI Key

XXCJVNMYGXUDBR-UHFFFAOYSA-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
Daldinia eschscholtzii	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

Carbocyclic cytochalasan skeleton
Cytochalasan
Isoindolone
Isoindoline
Isoindole
Isoindole or derivatives
Monocyclic benzene moiety
Benzenoid
2-pyrrolidone
Pyrrolidone
Pyrrolidine
Carboxamide group
Cyclic ketone
Secondary carboxylic acid amide
Ketone
Lactam
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organooxygen 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	5.02	ChemAxon
pKa (Strongest Acidic)	2.9	ChemAxon
pKa (Strongest Basic)	5.57	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	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

75994997

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,12h,13h,14h-cycloundeca[d]isoindole-11,15-dione (NP0244516)

MOL for NP0244516 (3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,12h,13h,14h-cycloundeca[d]isoindole-11,15-dione)

3D MOL for NP0244516 (3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,12h,13h,14h-cycloundeca[d]isoindole-11,15-dione)

3D SDF for NP0244516 (3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,12h,13h,14h-cycloundeca[d]isoindole-11,15-dione)

3D-SDF for NP0244516 (3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,12h,13h,14h-cycloundeca[d]isoindole-11,15-dione)

PDB for NP0244516 (3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,12h,13h,14h-cycloundeca[d]isoindole-11,15-dione)

3D PDB for NP0244516 (3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,12h,13h,14h-cycloundeca[d]isoindole-11,15-dione)

SMILES for NP0244516 (3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,12h,13h,14h-cycloundeca[d]isoindole-11,15-dione)

INCHI for NP0244516 (3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,12h,13h,14h-cycloundeca[d]isoindole-11,15-dione)

Structure for NP0244516 (3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,12h,13h,14h-cycloundeca[d]isoindole-11,15-dione)

3D Structure for NP0244516 (3-benzyl-1-hydroxy-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,12h,13h,14h-cycloundeca[d]isoindole-11,15-dione)