NP-MRD: Showing NP-Card for (2r,3r)-2-[(3e,7s)-7,8-dihydroxy-4,8-dimethylnon-3-en-1-yl]-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one (NP0318560)

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Record Information

Version

2.0

Created at

2022-09-11 19:07:49 UTC

Updated at

2022-09-11 19:07:49 UTC

NP-MRD ID

NP0318560

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r)-2-[(3e,7s)-7,8-dihydroxy-4,8-dimethylnon-3-en-1-yl]-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one

Description

(2R,3R)-2-[(3E,7S)-7,8-dihydroxy-4,8-dimethylnon-3-en-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. (2r,3r)-2-[(3e,7s)-7,8-dihydroxy-4,8-dimethylnon-3-en-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. Based on a literature review very few articles have been published on (2R,3R)-2-[(3E,7S)-7,8-dihydroxy-4,8-dimethylnon-3-en-1-yl]-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-2H,3H,4H,7H,8H,9H-pyrano[2,3-e]isoindol-7-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112221072D          

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M  END

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  Mrv1652309112221072D          

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> <DATABASE_ID>
NP0318560

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CC[C@H](O)C(C)(C)O)=C/CC[C@@]1(C)OC2=C(C[C@H]1O)C(O)=CC1=C2CN(CCO)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H37NO7/c1-15(7-8-20(29)24(2,3)32)6-5-9-25(4)21(30)13-17-19(28)12-16-18(22(17)33-25)14-26(10-11-27)23(16)31/h6,12,20-21,27-30,32H,5,7-11,13-14H2,1-4H3/b15-6+/t20-,21+,25+/m0/s1

> <INCHI_KEY>
ARJSGSALIJXTLS-OBNQQGLPSA-N

> <FORMULA>
C25H37NO7

> <MOLECULAR_WEIGHT>
463.571

> <EXACT_MASS>
463.257002535

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.70437167305821

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2-[(3E,7S)-7,8-dihydroxy-4,8-dimethylnon-3-en-1-yl]-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-2H,3H,4H,7H,8H,9H-pyrano[2,3-e]isoindol-7-one

> <JCHEM_LOGP>
1.2347756703333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.499676148645765

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.951730213717738

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6174292479889405

> <JCHEM_POLAR_SURFACE_AREA>
130.69

> <JCHEM_REFRACTIVITY>
126.42569999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-[(3E,7S)-7,8-dihydroxy-4,8-dimethylnon-3-en-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                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      12.334   6.461   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.904   7.033   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.694   6.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.914   4.556   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.703   3.603   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.923   2.079   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.386   2.560   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.384   2.127   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.573   0.818   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.301  -0.539   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.490  -1.848   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.218  -3.205   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.950  -1.800   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.222  -0.443   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.034   0.866   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.039   2.042   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.614   1.460   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       1.305   2.271   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.052   1.543   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.361   2.355   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.727  -0.076   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.551  -1.070   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.840  -0.587   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.651   0.722   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.191   0.674   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.684   8.557   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.254   9.128   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.034  10.653   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.604  11.224   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.244  11.605   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.454  12.558   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.196  10.395   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.291  12.815   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   24                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14    9   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   17   14   22                                                  
CONECT   22   21                                                            
CONECT   23   10   24                                                       
CONECT   24   23    6   25                                                  
CONECT   25   24                                                            
CONECT   26    2   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₇NO₇

Average Mass

463.5710 Da

Monoisotopic Mass

463.25700 Da

IUPAC Name

(2R,3R)-2-[(3E,7S)-7,8-dihydroxy-4,8-dimethylnon-3-en-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

(2R,3R)-2-[(3E,7S)-7,8-dihydroxy-4,8-dimethylnon-3-en-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

C\C(CC[C@H](O)C(C)(C)O)=C/CC[C@@]1(C)OC2=C(C[C@H]1O)C(O)=CC1=C2CN(CCO)C1=O

InChI Identifier

InChI=1S/C25H37NO7/c1-15(7-8-20(29)24(2,3)32)6-5-9-25(4)21(30)13-17-19(28)12-16-18(22(17)33-25)14-26(10-11-27)23(16)31/h6,12,20-21,27-30,32H,5,7-11,13-14H2,1-4H3/b15-6+/t20-,21+,25+/m0/s1

InChI Key

ARJSGSALIJXTLS-OBNQQGLPSA-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

Chromane
Benzopyran
Isoindolone
1-benzopyran
Isoindole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Tertiary carboxylic acid amide
Tertiary alcohol
Carboxamide group
Lactam
Secondary alcohol
Alkanolamine
Carboxylic acid derivative
Ether
Oxacycle
Azacycle
Hydrocarbon derivative
Organic nitrogen compound
Alcohol
Organic oxide
Organopnictogen compound
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	1.23	ChemAxon
pKa (Strongest Acidic)	8.95	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	130.69 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.43 m³·mol⁻¹	ChemAxon
Polarizability	51.7 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

163186258

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r)-2-[(3e,7s)-7,8-dihydroxy-4,8-dimethylnon-3-en-1-yl]-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one (NP0318560)

MOL for NP0318560 ((2r,3r)-2-[(3e,7s)-7,8-dihydroxy-4,8-dimethylnon-3-en-1-yl]-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)

3D MOL for NP0318560 ((2r,3r)-2-[(3e,7s)-7,8-dihydroxy-4,8-dimethylnon-3-en-1-yl]-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)

3D SDF for NP0318560 ((2r,3r)-2-[(3e,7s)-7,8-dihydroxy-4,8-dimethylnon-3-en-1-yl]-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)

3D-SDF for NP0318560 ((2r,3r)-2-[(3e,7s)-7,8-dihydroxy-4,8-dimethylnon-3-en-1-yl]-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)

PDB for NP0318560 ((2r,3r)-2-[(3e,7s)-7,8-dihydroxy-4,8-dimethylnon-3-en-1-yl]-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)

3D PDB for NP0318560 ((2r,3r)-2-[(3e,7s)-7,8-dihydroxy-4,8-dimethylnon-3-en-1-yl]-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)

SMILES for NP0318560 ((2r,3r)-2-[(3e,7s)-7,8-dihydroxy-4,8-dimethylnon-3-en-1-yl]-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)

INCHI for NP0318560 ((2r,3r)-2-[(3e,7s)-7,8-dihydroxy-4,8-dimethylnon-3-en-1-yl]-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)

Structure for NP0318560 ((2r,3r)-2-[(3e,7s)-7,8-dihydroxy-4,8-dimethylnon-3-en-1-yl]-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)

3D Structure for NP0318560 ((2r,3r)-2-[(3e,7s)-7,8-dihydroxy-4,8-dimethylnon-3-en-1-yl]-3,5-dihydroxy-8-(2-hydroxyethyl)-2-methyl-3h,4h,9h-pyrano[2,3-e]isoindol-7-one)