NP-MRD: Showing NP-Card for (1s,12r,13s,18r,19r)-3-hydroxy-13,18-dimethyl-19-[(2r)-1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0¹,⁹.0²,⁷]henicosa-2,4,6-triene-8,10-dione (NP0191263)

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Record Information

Version

2.0

Created at

2022-09-04 08:09:30 UTC

Updated at

2022-09-04 08:09:30 UTC

NP-MRD ID

NP0191263

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,12r,13s,18r,19r)-3-hydroxy-13,18-dimethyl-19-[(2r)-1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0¹,⁹.0²,⁷]henicosa-2,4,6-triene-8,10-dione

Description

(1S,12R,13S,18R,19R)-3-hydroxy-13,18-dimethyl-19-[(2R)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0¹,⁹.0²,⁷]Henicosa-2(7),3,5-triene-8,10-dione belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. (1s,12r,13s,18r,19r)-3-hydroxy-13,18-dimethyl-19-[(2r)-1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0¹,⁹.0²,⁷]henicosa-2,4,6-triene-8,10-dione is found in Pinus sylvestris. Based on a literature review very few articles have been published on (1S,12R,13S,18R,19R)-3-hydroxy-13,18-dimethyl-19-[(2R)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0¹,⁹.0²,⁷]Henicosa-2(7),3,5-triene-8,10-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042210092D          

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M  END

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M  END


  Mrv1652309042210092D          

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 22 21  1  6  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 29 35  1  0  0  0  0
 20 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0191263

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]([C@@H]1O[C@]23O[C@H](CC(=O)N2C(=O)C2=CC=CC(O)=C32)[C@@H](C)CCCC[C@H]1C)C(=O)C1=CC=CN1

> <INCHI_IDENTIFIER>
InChI=1S/C27H32N2O6/c1-15-8-4-5-9-16(2)25(17(3)24(32)19-11-7-13-28-19)35-27-23-18(10-6-12-20(23)30)26(33)29(27)22(31)14-21(15)34-27/h6-7,10-13,15-17,21,25,28,30H,4-5,8-9,14H2,1-3H3/t15-,16+,17-,21+,25+,27-/m0/s1

> <INCHI_KEY>
VOVIXJKPXLCBEJ-WVYCKJFQSA-N

> <FORMULA>
C27H32N2O6

> <MOLECULAR_WEIGHT>
480.561

> <EXACT_MASS>
480.226036758

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
49.852893080265666

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,12R,13S,18R,19R)-3-hydroxy-13,18-dimethyl-19-[(2R)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0^{1,9}.0^{2,7}]henicosa-2,4,6-triene-8,10-dione

> <JCHEM_LOGP>
5.008105349333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.958831463399722

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.889629778894969

> <JCHEM_PKA_STRONGEST_BASIC>
-4.179192812653923

> <JCHEM_POLAR_SURFACE_AREA>
108.93000000000002

> <JCHEM_REFRACTIVITY>
129.1974

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,12R,13S,18R,19R)-3-hydroxy-13,18-dimethyl-19-[(2R)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0^{1,9}.0^{2,7}]henicosa-2,4,6-triene-8,10-dione

> <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      -0.408  -3.322   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.745  -2.218   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.249  -0.760   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.304   0.554   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.284   2.094   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.742   2.589   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.664   1.355   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.737   0.139   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.301   0.955   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.616   2.326   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.434   2.479   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.418   3.967   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.001   4.572   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.649   4.892   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.625   6.432   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.082   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.007   5.698   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       9.121   4.439   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       5.767  -0.068   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.781  -1.661   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.270  -1.360   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.255  -2.518   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.750  -3.977   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.261  -4.277   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.752  -5.837   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0       5.276  -3.119   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       6.816  -3.099   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.839  -4.306   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.272  -1.628   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.671  -0.983   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.811   0.551   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.554   1.439   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.155   0.794   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.247   2.314   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.015  -0.739   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   19                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14                                                       
CONECT   19    9   20                                                       
CONECT   20   19   21   26   35                                             
CONECT   21   20   22                                                       
CONECT   22   21    2   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   20   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   29   20                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂N₂O₆

Average Mass

480.5610 Da

Monoisotopic Mass

480.22604 Da

IUPAC Name

(1S,12R,13S,18R,19R)-3-hydroxy-13,18-dimethyl-19-[(2R)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0^{1,9}.0^{2,7}]henicosa-2,4,6-triene-8,10-dione

Traditional Name

(1S,12R,13S,18R,19R)-3-hydroxy-13,18-dimethyl-19-[(2R)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0^{1,9}.0^{2,7}]henicosa-2,4,6-triene-8,10-dione

CAS Registry Number

Not Available

SMILES

C[C@H]([C@@H]1O[C@]23O[C@H](CC(=O)N2C(=O)C2=CC=CC(O)=C32)[C@@H](C)CCCC[C@H]1C)C(=O)C1=CC=CN1

InChI Identifier

InChI=1S/C27H32N2O6/c1-15-8-4-5-9-16(2)25(17(3)24(32)19-11-7-13-28-19)35-27-23-18(10-6-12-20(23)30)26(33)29(27)22(31)14-21(15)34-27/h6-7,10-13,15-17,21,25,28,30H,4-5,8-9,14H2,1-3H3/t15-,16+,17-,21+,25+,27-/m0/s1

InChI Key

VOVIXJKPXLCBEJ-WVYCKJFQSA-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
Pinus sylvestris	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
Aryl ketone
Aryl alkyl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
1,3-oxazinane
Amide acetal
Carboxylic acid imide, n-substituted
Oxazinane
Substituted pyrrole
Benzenoid
Carboxylic acid imide
Dicarboximide
Pyrrole
Heteroaromatic compound
Orthocarboxylic acid derivative
Ketone
Carboxylic acid derivative
Oxacycle
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen 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	5.01	ChemAxon
pKa (Strongest Acidic)	7.89	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	108.93 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	129.2 m³·mol⁻¹	ChemAxon
Polarizability	49.85 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

163097720

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,12r,13s,18r,19r)-3-hydroxy-13,18-dimethyl-19-[(2r)-1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0¹,⁹.0²,⁷]henicosa-2,4,6-triene-8,10-dione (NP0191263)

MOL for NP0191263 ((1s,12r,13s,18r,19r)-3-hydroxy-13,18-dimethyl-19-[(2r)-1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0¹,⁹.0²,⁷]henicosa-2,4,6-triene-8,10-dione)

3D MOL for NP0191263 ((1s,12r,13s,18r,19r)-3-hydroxy-13,18-dimethyl-19-[(2r)-1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0¹,⁹.0²,⁷]henicosa-2,4,6-triene-8,10-dione)

3D SDF for NP0191263 ((1s,12r,13s,18r,19r)-3-hydroxy-13,18-dimethyl-19-[(2r)-1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0¹,⁹.0²,⁷]henicosa-2,4,6-triene-8,10-dione)

3D-SDF for NP0191263 ((1s,12r,13s,18r,19r)-3-hydroxy-13,18-dimethyl-19-[(2r)-1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0¹,⁹.0²,⁷]henicosa-2,4,6-triene-8,10-dione)

PDB for NP0191263 ((1s,12r,13s,18r,19r)-3-hydroxy-13,18-dimethyl-19-[(2r)-1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0¹,⁹.0²,⁷]henicosa-2,4,6-triene-8,10-dione)

3D PDB for NP0191263 ((1s,12r,13s,18r,19r)-3-hydroxy-13,18-dimethyl-19-[(2r)-1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0¹,⁹.0²,⁷]henicosa-2,4,6-triene-8,10-dione)

SMILES for NP0191263 ((1s,12r,13s,18r,19r)-3-hydroxy-13,18-dimethyl-19-[(2r)-1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0¹,⁹.0²,⁷]henicosa-2,4,6-triene-8,10-dione)

INCHI for NP0191263 ((1s,12r,13s,18r,19r)-3-hydroxy-13,18-dimethyl-19-[(2r)-1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0¹,⁹.0²,⁷]henicosa-2,4,6-triene-8,10-dione)

Structure for NP0191263 ((1s,12r,13s,18r,19r)-3-hydroxy-13,18-dimethyl-19-[(2r)-1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0¹,⁹.0²,⁷]henicosa-2,4,6-triene-8,10-dione)

3D Structure for NP0191263 ((1s,12r,13s,18r,19r)-3-hydroxy-13,18-dimethyl-19-[(2r)-1-oxo-1-(1h-pyrrol-2-yl)propan-2-yl]-20,21-dioxa-9-azatetracyclo[10.8.1.0¹,⁹.0²,⁷]henicosa-2,4,6-triene-8,10-dione)