NP-MRD: Showing NP-Card for 1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,6h,6ah,9h,10h,11h,12h,13h,14h-cycloundeca[d]isoindol-15-one (NP0194470)

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Record Information

Version

2.0

Created at

2022-09-04 12:07:40 UTC

Updated at

2022-09-04 12:07:41 UTC

NP-MRD ID

NP0194470

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,6h,6ah,9h,10h,11h,12h,13h,14h-cycloundeca[d]isoindol-15-one

Description

1,6,11,12-Tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3H,6H,6aH,9H,10H,11H,12H,13H,14H,15H,15bH-cycloundeca[e]isoindol-15-one belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. 1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,6h,6ah,9h,10h,11h,12h,13h,14h-cycloundeca[d]isoindol-15-one is found in Aspergillus flavipes. Based on a literature review very few articles have been published on 1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3H,6H,6aH,9H,10H,11H,12H,13H,14H,15H,15bH-cycloundeca[e]isoindol-15-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042214072D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042214072D          

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M  END
> <DATABASE_ID>
NP0194470

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CC(=O)C23C(C(CC(C)C)N=C2O)C(C)=C(C)C(O)C3C=C(C)CCC(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H39NO6/c1-12(2)9-17-21-14(4)15(5)22(29)16-10-13(3)7-8-18(27)23(30)19(32-6)11-20(28)25(16,21)24(31)26-17/h10,12,16-19,21-23,27,29-30H,7-9,11H2,1-6H3,(H,26,31)

> <INCHI_KEY>
SEJALNVFDONJGO-UHFFFAOYSA-N

> <FORMULA>
C25H39NO6

> <MOLECULAR_WEIGHT>
449.588

> <EXACT_MASS>
449.27773798

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
49.48737132258112

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3H,6H,6aH,9H,10H,11H,12H,13H,14H,15H,15bH-cycloundeca[e]isoindol-15-one

> <JCHEM_LOGP>
0.9926677983176189

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.978536414399148

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.763214499026912

> <JCHEM_PKA_STRONGEST_BASIC>
5.464964742895816

> <JCHEM_POLAR_SURFACE_AREA>
119.58000000000001

> <JCHEM_REFRACTIVITY>
122.9729

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3H,6H,6aH,9H,10H,11H,12H,13H,14H,15bH-cycloundeca[e]isoindol-15-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       7.014  -2.149   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.474  -2.149   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.704  -0.816   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.164  -0.816   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.258   0.606   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.201   1.823   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.794   1.082   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.938   0.051   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.445   0.371   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       1.312  -1.356   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -0.220  -1.195   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.250  -2.339   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.774  -3.804   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.805  -4.948   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.732  -4.124   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.540   0.312   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.874   1.082   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.207   0.312   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.874   2.622   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.207   3.392   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.540   3.392   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.540   4.932   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.794   2.622   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.258   3.098   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.164   4.519   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.423   5.869   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.704   4.519   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.474   3.185   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.704   1.852   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.244   1.852   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.474   0.518   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.014   0.518   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   16   23                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11    7   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    7   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    3   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₉NO₆

Average Mass

449.5880 Da

Monoisotopic Mass

449.27774 Da

IUPAC Name

1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3H,6H,6aH,9H,10H,11H,12H,13H,14H,15H,15bH-cycloundeca[e]isoindol-15-one

Traditional Name

1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3H,6H,6aH,9H,10H,11H,12H,13H,14H,15bH-cycloundeca[e]isoindol-15-one

CAS Registry Number

Not Available

SMILES

COC1CC(=O)C23C(C(CC(C)C)N=C2O)C(C)=C(C)C(O)C3C=C(C)CCC(O)C1O

InChI Identifier

InChI=1S/C25H39NO6/c1-12(2)9-17-21-14(4)15(5)22(29)16-10-13(3)7-8-18(27)23(30)19(32-6)11-20(28)25(16,21)24(31)26-17/h10,12,16-19,21-23,27,29-30H,7-9,11H2,1-6H3,(H,26,31)

InChI Key

SEJALNVFDONJGO-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
Aspergillus flavipes	LOTUS Database	35616633

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
Isoindole
Pyrroline
Cyclic carboximidic acid
Ketone
Secondary alcohol
Dialkyl ether
Ether
Polyol
Azacycle
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organopnictogen compound
Organic oxide
Organic nitrogen compound
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	0.99	ChemAxon
pKa (Strongest Acidic)	2.76	ChemAxon
pKa (Strongest Basic)	5.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	119.58 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	122.97 m³·mol⁻¹	ChemAxon
Polarizability	49.49 Å³	ChemAxon
Number of Rings	3	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

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

72830947

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,6h,6ah,9h,10h,11h,12h,13h,14h-cycloundeca[d]isoindol-15-one (NP0194470)

MOL for NP0194470 (1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,6h,6ah,9h,10h,11h,12h,13h,14h-cycloundeca[d]isoindol-15-one)

3D MOL for NP0194470 (1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,6h,6ah,9h,10h,11h,12h,13h,14h-cycloundeca[d]isoindol-15-one)

3D SDF for NP0194470 (1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,6h,6ah,9h,10h,11h,12h,13h,14h-cycloundeca[d]isoindol-15-one)

3D-SDF for NP0194470 (1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,6h,6ah,9h,10h,11h,12h,13h,14h-cycloundeca[d]isoindol-15-one)

PDB for NP0194470 (1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,6h,6ah,9h,10h,11h,12h,13h,14h-cycloundeca[d]isoindol-15-one)

3D PDB for NP0194470 (1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,6h,6ah,9h,10h,11h,12h,13h,14h-cycloundeca[d]isoindol-15-one)

SMILES for NP0194470 (1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,6h,6ah,9h,10h,11h,12h,13h,14h-cycloundeca[d]isoindol-15-one)

INCHI for NP0194470 (1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,6h,6ah,9h,10h,11h,12h,13h,14h-cycloundeca[d]isoindol-15-one)

Structure for NP0194470 (1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,6h,6ah,9h,10h,11h,12h,13h,14h-cycloundeca[d]isoindol-15-one)

3D Structure for NP0194470 (1,6,11,12-tetrahydroxy-13-methoxy-4,5,8-trimethyl-3-(2-methylpropyl)-3h,3ah,6h,6ah,9h,10h,11h,12h,13h,14h-cycloundeca[d]isoindol-15-one)