NP-MRD: Showing NP-Card for 2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl}-3-hydroxybutanoic acid (NP0324841)

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Record Information

Version

2.0

Created at

2022-09-12 05:09:40 UTC

Updated at

2022-09-12 05:09:41 UTC

NP-MRD ID

NP0324841

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl}-3-hydroxybutanoic acid

Description

2-{4,6'-Dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,5',6,6',7,7',8,8',8'a-dodecahydro-2'H-spiro[furo[2,3-e]isoindole-2,1'-naphthalene]-7-yl}-3-hydroxybutanoic acid belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. Based on a literature review very few articles have been published on 2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,5',6,6',7,7',8,8',8'a-dodecahydro-2'H-spiro[furo[2,3-e]isoindole-2,1'-naphthalene]-7-yl}-3-hydroxybutanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122207092D          

 35 39  0  0  0  0            999 V2000
    7.8171   -0.0417    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


  Mrv1652309122207092D          

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 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 24 32  1  0  0  0  0
 18 32  1  0  0  0  0
 32 33  1  0  0  0  0
 11 34  1  0  0  0  0
  8 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0324841

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)C(N1CC2=C(C=C(O)C3=C2OC2(C3)C(C)CCC3C(C)(C)C(O)CCC23C)C1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H37NO7/c1-13-6-7-19-25(3,4)20(31)8-9-26(19,5)27(13)11-16-18(30)10-15-17(22(16)35-27)12-28(23(15)32)21(14(2)29)24(33)34/h10,13-14,19-21,29-31H,6-9,11-12H2,1-5H3,(H,33,34)

> <INCHI_KEY>
JEEJYUDPFTZKDZ-UHFFFAOYSA-N

> <FORMULA>
C27H37NO7

> <MOLECULAR_WEIGHT>
487.593

> <EXACT_MASS>
487.257002535

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
52.914152622726114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,5',6,6',7,7',8,8',8'a-dodecahydro-2'H-spiro[furo[2,3-e]isoindole-2,1'-naphthalene]-7-yl}-3-hydroxybutanoic acid

> <JCHEM_LOGP>
2.917201491666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.9445472712447

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.972212550534692

> <JCHEM_PKA_STRONGEST_BASIC>
-0.800298585521546

> <JCHEM_POLAR_SURFACE_AREA>
127.53

> <JCHEM_REFRACTIVITY>
128.5118

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'H-spiro[furo[2,3-e]isoindole-2,1'-naphthalene]-7-yl}-3-hydroxybutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      14.592  -0.078   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.181   0.540   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.011   2.070   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.941  -0.373   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.111  -1.904   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.871  -2.817   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      13.522  -2.521   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      10.530   0.245   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       9.201  -0.534   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.051   0.490   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.668   1.900   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.755   3.141   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.225   2.970   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.312   4.211   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.607   1.560   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.520   0.319   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.623  -0.932   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.155  -0.465   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.146   1.075   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.326  -1.996   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.736  -2.614   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.085  -2.909   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.675  -2.291   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.504  -0.761   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.093  -0.143   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.270  -1.639   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.443  -0.045   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.077   1.388   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.488   2.005   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.163   2.301   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.574   1.683   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.744   0.152   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.642   1.404   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.201   1.749   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      11.224   2.900   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4    9   34                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   34                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   19                                                  
CONECT   16   15   10   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20   32                                             
CONECT   19   18   15                                                       
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   24   18   33                                             
CONECT   33   32                                                            
CONECT   34   11    8   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,5',6,6',7,7',8,8',8'a-dodecahydro-2'H-spiro[furo[2,3-e]isoindole-2,1'-naphthalene]-7-yl}-3-hydroxybutanoate	Generator

Chemical Formula

C₂₇H₃₇NO₇

Average Mass

487.5930 Da

Monoisotopic Mass

487.25700 Da

IUPAC Name

2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,5',6,6',7,7',8,8',8'a-dodecahydro-2'H-spiro[furo[2,3-e]isoindole-2,1'-naphthalene]-7-yl}-3-hydroxybutanoic acid

Traditional Name

2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'H-spiro[furo[2,3-e]isoindole-2,1'-naphthalene]-7-yl}-3-hydroxybutanoic acid

CAS Registry Number

Not Available

SMILES

CC(O)C(N1CC2=C(C=C(O)C3=C2OC2(C3)C(C)CCC3C(C)(C)C(O)CCC23C)C1=O)C(O)=O

InChI Identifier

InChI=1S/C27H37NO7/c1-13-6-7-19-25(3,4)20(31)8-9-26(19,5)27(13)11-16-18(30)10-15-17(22(16)35-27)12-28(23(15)32)21(14(2)29)24(33)34/h10,13-14,19-21,29-31H,6-9,11-12H2,1-5H3,(H,33,34)

InChI Key

JEEJYUDPFTZKDZ-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

Not Available

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

Alpha-amino acid or derivatives
Isoindolone
Coumaran
Isoindole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Hydroxy acid
Benzenoid
Cyclic alcohol
Tertiary carboxylic acid amide
Carboxamide group
Secondary alcohol
Lactam
Carboxylic acid derivative
Carboxylic acid
Ether
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic nitrogen compound
Alcohol
Organic oxide
Organic oxygen compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	2.92	ChemAxon
pKa (Strongest Acidic)	2.97	ChemAxon
pKa (Strongest Basic)	-0.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	127.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	128.51 m³·mol⁻¹	ChemAxon
Polarizability	52.91 Å³	ChemAxon
Number of Rings	5	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

72782885

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl}-3-hydroxybutanoic acid (NP0324841)

MOL for NP0324841 (2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl}-3-hydroxybutanoic acid)

3D MOL for NP0324841 (2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl}-3-hydroxybutanoic acid)

3D SDF for NP0324841 (2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl}-3-hydroxybutanoic acid)

3D-SDF for NP0324841 (2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl}-3-hydroxybutanoic acid)

PDB for NP0324841 (2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl}-3-hydroxybutanoic acid)

3D PDB for NP0324841 (2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl}-3-hydroxybutanoic acid)

SMILES for NP0324841 (2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl}-3-hydroxybutanoic acid)

INCHI for NP0324841 (2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl}-3-hydroxybutanoic acid)

Structure for NP0324841 (2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl}-3-hydroxybutanoic acid)

3D Structure for NP0324841 (2-{4,6'-dihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl}-3-hydroxybutanoic acid)