NP-MRD: Showing NP-Card for 1-benzyl-3,5-dihydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate (NP0296014)

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Record Information

Version

2.0

Created at

2022-09-10 05:20:59 UTC

Updated at

2022-09-10 05:20:59 UTC

NP-MRD ID

NP0296014

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-benzyl-3,5-dihydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate

Description

1-Benzyl-3,5-dihydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-3a,4,5,6,7,7a-hexahydro-1H-isoindol-3a-yl methyl carbonate belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. 1-benzyl-3,5-dihydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate is found in Aspergillus flavipes. 1-Benzyl-3,5-dihydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-3a,4,5,6,7,7a-hexahydro-1H-isoindol-3a-yl methyl carbonate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161506012D          

 38 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004161506012D          

 38 40  0  0  0  0            999 V2000
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   -1.5371   -2.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5341    0.5965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  7 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
  6 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0296014

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)OC12C(C(CC3=CC=CC=C3)NC1=O)C(C)C(=C)C(O)C2C=CCC(C)C(=O)C(C)(O)CC=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H37NO8/c1-17(25(33)28(4,36)14-15-31)10-9-13-21-24(32)19(3)18(2)23-22(16-20-11-7-6-8-12-20)30-26(34)29(21,23)38-27(35)37-5/h6-9,11-13,15,17-18,21-24,32,36H,3,10,14,16H2,1-2,4-5H3,(H,30,34)

> <INCHI_KEY>
BRQWOHZQMWWOCO-UHFFFAOYSA-N

> <FORMULA>
C29H37NO8

> <MOLECULAR_WEIGHT>
527.614

> <EXACT_MASS>
527.251917155

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
56.00764870108075

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-benzyl-5-hydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-3-oxo-octahydro-1H-isoindol-3a-yl methyl carbonate

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.7799911436666673

> <ALOGPS_LOGS>
-4.53

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.861629114176658

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.444275871502864

> <JCHEM_PKA_STRONGEST_BASIC>
-3.151234706335825

> <JCHEM_POLAR_SURFACE_AREA>
139.23000000000002

> <JCHEM_REFRACTIVITY>
140.06590000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-benzyl-5-hydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-3-oxo-hexahydroisoindol-3a-yl methyl carbonate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       0.296   4.969   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.541   3.918   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.597   2.269   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.155   1.695   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.935   1.147   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.779   1.697   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.779   2.966   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.795   4.606   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.017   5.588   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.453   5.030   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.783   7.110   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.348   7.668   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.984   8.074   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.020   9.275   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.948   6.873   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.185   9.038   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.950  10.560   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.151  11.524   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.909  -0.552   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.587  -3.046   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.371  -4.446   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.770  -4.111   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.869  -4.974   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.393  -3.509   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.887  -3.189   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       1.220  -1.303   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.997   1.113   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   27   37                                             
CONECT    7    6    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21    7   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    6   28                                                  
CONECT   28   27   29   36                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   28   37                                                       
CONECT   37   36    6   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Value	Source
1-Benzyl-3,5-dihydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-3a,4,5,6,7,7a-hexahydro-1H-isoindol-3a-yl methyl carbonic acid	Generator

Chemical Formula

C₂₉H₃₇NO₈

Average Mass

527.6140 Da

Monoisotopic Mass

527.25192 Da

IUPAC Name

1-benzyl-5-hydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-3-oxo-octahydro-1H-isoindol-3a-yl methyl carbonate

Traditional Name

1-benzyl-5-hydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-3-oxo-hexahydroisoindol-3a-yl methyl carbonate

CAS Registry Number

Not Available

SMILES

COC(=O)OC12C(C(CC3=CC=CC=C3)NC1=O)C(C)C(=C)C(O)C2C=CCC(C)C(=O)C(C)(O)CC=O

InChI Identifier

InChI=1S/C29H37NO8/c1-17(25(33)28(4,36)14-15-31)10-9-13-21-24(32)19(3)18(2)23-22(16-20-11-7-6-8-12-20)30-26(34)29(21,23)38-27(35)37-5/h6-9,11-13,15,17-18,21-24,32,36H,3,10,14,16H2,1-2,4-5H3,(H,30,34)

InChI Key

BRQWOHZQMWWOCO-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
Acyloin
Monocyclic benzene moiety
Beta-hydroxy aldehyde
Carbonic acid diester
Benzenoid
2-pyrrolidone
Pyrrolidone
Alpha-hydrogen aldehyde
Alpha-hydroxy ketone
Tertiary alcohol
Cyclic alcohol
Pyrrolidine
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Ketone
Lactam
Carbonic acid derivative
Carboxylic acid derivative
Azacycle
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aldehyde
Organooxygen compound
Organic oxygen compound
Organopnictogen 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	2.5	ALOGPS
logP	2.78	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	12.44	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.23 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	140.07 m³·mol⁻¹	ChemAxon
Polarizability	56.01 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

74976178

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-benzyl-3,5-dihydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate (NP0296014)

MOL for NP0296014 (1-benzyl-3,5-dihydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)

3D MOL for NP0296014 (1-benzyl-3,5-dihydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)

3D SDF for NP0296014 (1-benzyl-3,5-dihydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)

3D-SDF for NP0296014 (1-benzyl-3,5-dihydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)

PDB for NP0296014 (1-benzyl-3,5-dihydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)

3D PDB for NP0296014 (1-benzyl-3,5-dihydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)

SMILES for NP0296014 (1-benzyl-3,5-dihydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)

INCHI for NP0296014 (1-benzyl-3,5-dihydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)

Structure for NP0296014 (1-benzyl-3,5-dihydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)

3D Structure for NP0296014 (1-benzyl-3,5-dihydroxy-4-(6-hydroxy-4,6-dimethyl-5,8-dioxooct-1-en-1-yl)-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl methyl carbonate)