NP-MRD: Showing NP-Card for 2-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one (NP0207736)

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Record Information

Version

2.0

Created at

2022-09-05 04:27:53 UTC

Updated at

2022-09-05 04:27:53 UTC

NP-MRD ID

NP0207736

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one

Description

2-(4,8-Dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-2H,3H,4H,7H,8H,9H-pyrano[2,3-e]isoindol-7-one belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. 2-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one is found in Stachybotrys microspora. 2-(4,8-Dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-2H,3H,4H,7H,8H,9H-pyrano[2,3-e]isoindol-7-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171512572D          

 31 33  0  0  0  0            999 V2000
    5.3700    7.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4878    6.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    5.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9574    4.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3091    4.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4269    3.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7787    3.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8965    2.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6626    1.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5641    1.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8666   -1.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8307   -0.5732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989    1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2538    5.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004171512572D          

 31 33  0  0  0  0            999 V2000
    5.3700    7.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0207736

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC(C)=CCCC1(C)OC2=C(CC1O)C(O)=CC1=C2CN(CCO)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H35NO5/c1-16(2)7-5-8-17(3)9-6-10-25(4)22(29)14-19-21(28)13-18-20(23(19)31-25)15-26(11-12-27)24(18)30/h7,9,13,22,27-29H,5-6,8,10-12,14-15H2,1-4H3

> <INCHI_KEY>
XHODRTXQJFAAJR-UHFFFAOYSA-N

> <FORMULA>
C25H35NO5

> <MOLECULAR_WEIGHT>
429.557

> <EXACT_MASS>
429.251523231

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
49.45599479032751

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-2H,3H,4H,7H,8H,9H-pyrano[2,3-e]isoindol-7-one

> <ALOGPS_LOGP>
3.27

> <JCHEM_LOGP>
3.3752144810000004

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.762612450138164

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.95173579924476

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6174292479889396

> <JCHEM_POLAR_SURFACE_AREA>
90.22999999999999

> <JCHEM_REFRACTIVITY>
124.07809999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3H,4H,9H-pyrano[2,3-e]isoindol-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      10.024  13.129   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.244  11.605   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.034  10.653   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.254   9.128   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.044   8.176   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.264   6.652   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.054   5.699   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.274   4.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.703   3.603   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.923   2.079   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.386   2.560   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.384   2.127   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.573   0.818   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.301  -0.539   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.840  -0.587   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.651   0.722   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.191   0.674   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.490  -1.848   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.218  -3.205   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.950  -1.800   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.222  -0.443   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.727  -0.076   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.551  -1.070   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       2.614   1.460   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       1.305   2.271   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.052   1.543   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.100   0.004   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.039   2.042   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.034   0.866   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.694   6.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.674  11.034   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   16                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   29                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   10   17                                                  
CONECT   17   16                                                            
CONECT   18   14   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   29                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   24   29                                                       
CONECT   29   28   13   21                                                  
CONECT   30    6                                                            
CONECT   31    2                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₅NO₅

Average Mass

429.5570 Da

Monoisotopic Mass

429.25152 Da

IUPAC Name

2-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-2H,3H,4H,7H,8H,9H-pyrano[2,3-e]isoindol-7-one

Traditional Name

2-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3H,4H,9H-pyrano[2,3-e]isoindol-7-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC(C)=CCCC1(C)OC2=C(CC1O)C(O)=CC1=C2CN(CCO)C1=O

InChI Identifier

InChI=1S/C25H35NO5/c1-16(2)7-5-8-17(3)9-6-10-25(4)22(29)14-19-21(28)13-18-20(23(19)31-25)15-26(11-12-27)24(18)30/h7,9,13,22,27-29H,5-6,8,10-12,14-15H2,1-4H3

InChI Key

XHODRTXQJFAAJR-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
Stachybotrys microspora	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

Aromatic monoterpenoid
Chromane
Benzopyran
Isoindolone
1-benzopyran
Monoterpenoid
Isoindole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Secondary alcohol
Alkanolamine
Azacycle
Oxacycle
Ether
Carboxylic acid derivative
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Primary alcohol
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	3.27	ALOGPS
logP	3.38	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.95	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.23 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	124.08 m³·mol⁻¹	ChemAxon
Polarizability	49.46 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

85135297

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one (NP0207736)

MOL for NP0207736 (2-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)

3D MOL for NP0207736 (2-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)

3D SDF for NP0207736 (2-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)

3D-SDF for NP0207736 (2-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)

PDB for NP0207736 (2-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)

3D PDB for NP0207736 (2-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)

SMILES for NP0207736 (2-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)

INCHI for NP0207736 (2-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)

Structure for NP0207736 (2-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)

3D Structure for NP0207736 (2-(4,8-dimethylnona-3,7-dien-1-yl)-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)