NP-MRD: Showing NP-Card for 7,9-dihydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]icosa-3,8,19-trien-11-one (NP0319157)

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Record Information

Version

2.0

Created at

2022-09-11 20:03:09 UTC

Updated at

2022-09-11 20:03:09 UTC

NP-MRD ID

NP0319157

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,9-dihydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]icosa-3,8,19-trien-11-one

Description

7,9-Dihydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]Icosa-3,8,19-trien-11-one belongs to the class of organic compounds known as isoindoles and derivatives. These are polycyclic compounds containing an isoindole moiety, which is structurally characterized by a cyclohexadiene fused to a pyrrole ring. 7,9-Dihydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]Icosa-3,8,19-trien-11-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241512272D          

 37 42  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241512272D          

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   -0.8564    4.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881    4.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6237    2.1759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9947    1.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7747    1.2765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1801    1.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6140    1.9670    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  2 12  1  0  0  0  0
  8 13  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
 22 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 14 35  1  0  0  0  0
 21 35  1  0  0  0  0
 35 36  1  0  0  0  0
  6 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0319157

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2C3C(C(C)=CC2(C)C1)C1(C)C=C(C)C(C)C2C(O)(CC4=CC=C(O)C=C4)NC(=O)C12C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H41NO4/c1-17-7-12-23-24-25(19(3)14-29(23,5)13-17)30(6)15-18(2)20(4)26-31(37,16-21-8-10-22(34)11-9-21)33-28(36)32(26,30)27(24)35/h8-11,14-15,17,20,23-26,34,37H,7,12-13,16H2,1-6H3,(H,33,36)

> <INCHI_KEY>
AEKBQYOSHUYACR-UHFFFAOYSA-N

> <FORMULA>
C32H41NO4

> <MOLECULAR_WEIGHT>
503.683

> <EXACT_MASS>
503.303558804

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
57.50684126246193

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-hydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]icosa-3,19-diene-9,11-dione

> <ALOGPS_LOGP>
5.19

> <JCHEM_LOGP>
5.338831947666665

> <ALOGPS_LOGS>
-5.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.048796393768685

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.482700170624883

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3466286133196035

> <JCHEM_POLAR_SURFACE_AREA>
86.63

> <JCHEM_REFRACTIVITY>
145.7615

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.03e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]icosa-3,19-diene-9,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      11.249   0.652   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.645   0.682   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.953   2.057   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.415   2.146   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.570   0.858   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.033   0.946   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.188  -0.341   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.881  -1.717   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.418  -1.805   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.263  -0.517   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.032  -1.987   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.800  -0.606   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.599  -3.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.702   0.064   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.647  -1.599   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.407  -0.768   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.038  -0.063   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.361  -0.882   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.035   1.476   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.618   1.768   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.260   2.308   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.509   3.828   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.096   4.122   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.485   5.517   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.067   6.072   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.136   5.111   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.570   5.672   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.802   7.194   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.236   7.755   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.599   8.156   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.164   7.595   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       3.031   4.062   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       3.723   2.686   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.179   2.383   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.629   1.603   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.070   2.147   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.879   3.672   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   36                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   11   12                                             
CONECT   11   10                                                            
CONECT   12   10    2                                                       
CONECT   13    8                                                            
CONECT   14    7   15   16   35                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   35                                                  
CONECT   22   21   23   24   32                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   25                                                       
CONECT   32   22   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   14   21   36                                             
CONECT   36   35    6   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₁NO₄

Average Mass

503.6830 Da

Monoisotopic Mass

503.30356 Da

IUPAC Name

7-hydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]icosa-3,19-diene-9,11-dione

Traditional Name

7-hydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]icosa-3,19-diene-9,11-dione

CAS Registry Number

Not Available

SMILES

CC1CCC2C3C(C(C)=CC2(C)C1)C1(C)C=C(C)C(C)C2C(O)(CC4=CC=C(O)C=C4)NC(=O)C12C3=O

InChI Identifier

InChI=1S/C32H41NO4/c1-17-7-12-23-24-25(19(3)14-29(23,5)13-17)30(6)15-18(2)20(4)26-31(37,16-21-8-10-22(34)11-9-21)33-28(36)32(26,30)27(24)35/h8-11,14-15,17,20,23-26,34,37H,7,12-13,16H2,1-6H3,(H,33,36)

InChI Key

AEKBQYOSHUYACR-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 isoindoles and derivatives. These are polycyclic compounds containing an isoindole moiety, which is structurally characterized by a cyclohexadiene fused to a pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Not Available

Direct Parent

Isoindoles and derivatives

Alternative Parents

Substituents

Isoindole or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Pyrroline
Cyclic carboximidic acid
Ketone
Propargyl-type 1,3-dipolar organic compound
Azacycle
Alkanolamine
Organic 1,3-dipolar compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen 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	5.19	ALOGPS
logP	5.34	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	9.48	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	145.76 m³·mol⁻¹	ChemAxon
Polarizability	57.51 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7,9-dihydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]icosa-3,8,19-trien-11-one (NP0319157)

MOL for NP0319157 (7,9-dihydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]icosa-3,8,19-trien-11-one)

3D MOL for NP0319157 (7,9-dihydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]icosa-3,8,19-trien-11-one)

3D SDF for NP0319157 (7,9-dihydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]icosa-3,8,19-trien-11-one)

3D-SDF for NP0319157 (7,9-dihydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]icosa-3,8,19-trien-11-one)

PDB for NP0319157 (7,9-dihydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]icosa-3,8,19-trien-11-one)

3D PDB for NP0319157 (7,9-dihydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]icosa-3,8,19-trien-11-one)

SMILES for NP0319157 (7,9-dihydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]icosa-3,8,19-trien-11-one)

INCHI for NP0319157 (7,9-dihydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]icosa-3,8,19-trien-11-one)

Structure for NP0319157 (7,9-dihydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]icosa-3,8,19-trien-11-one)

3D Structure for NP0319157 (7,9-dihydroxy-7-[(4-hydroxyphenyl)methyl]-2,4,5,16,18,20-hexamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹³,¹⁸]icosa-3,8,19-trien-11-one)