NP-MRD: Showing NP-Card for 9,12'-dihydroxy-4,4,4',4',12',14'-hexamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecane]-10',13'-dione (NP0316447)

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Record Information

Version

2.0

Created at

2022-09-11 15:39:13 UTC

Updated at

2022-09-11 15:39:13 UTC

NP-MRD ID

NP0316447

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9,12'-dihydroxy-4,4,4',4',12',14'-hexamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecane]-10',13'-dione

Description

9,12'-Dihydroxy-4,4,4',4',12',14'-hexamethyl-4H-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]Tetradecane]-10',13'-dione belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom. 9,12'-Dihydroxy-4,4,4',4',12',14'-hexamethyl-4H-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]Tetradecane]-10',13'-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251510472D          

 37 43  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1533004251510472D          

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  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  2  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  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 26 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 11 37  1  0  0  0  0
 25 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0316447

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)C23CC4C(C)(C)C5(CC14CN2C(=O)CC3(C)O)C(=O)NC1=C2OC=CC(C)(C)OC2=CC=C51

> <INCHI_IDENTIFIER>
InChI=1S/C28H33N3O6/c1-23(2)9-10-36-20-16(37-23)8-7-15-19(20)29-21(33)27(15)13-26-14-31-18(32)12-25(5,35)28(31,22(34)30(26)6)11-17(26)24(27,3)4/h7-10,17,35H,11-14H2,1-6H3,(H,29,33)

> <INCHI_KEY>
HHMKOJPJOSZYET-UHFFFAOYSA-N

> <FORMULA>
C28H33N3O6

> <MOLECULAR_WEIGHT>
507.587

> <EXACT_MASS>
507.236935795

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
53.82954842531982

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12'-hydroxy-4,4,4',4',12',14'-hexamethyl-9,10-dihydro-4H-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecane]-9,10',13'-trione

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
0.8819494683333329

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.755803357778507

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.588630111607515

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7809988383923097

> <JCHEM_POLAR_SURFACE_AREA>
108.41000000000003

> <JCHEM_REFRACTIVITY>
134.42569999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12'-hydroxy-4,4,4',4',12',14'-hexamethyl-10H-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecane]-9,10',13'-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       4.335  -0.412   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.860   1.053   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.405   1.692   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.343   0.577   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.587   3.333   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.925   4.312   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.480   4.069   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.419   5.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.175   6.227   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.308   6.577   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.711   4.434   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.227   2.915   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.681   2.455   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.075   2.528   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       1.401   1.883   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       0.311   2.983   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.205   2.709   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.047   4.619   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.140   4.006   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.427   4.852   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.574   3.445   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.146   5.911   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.629   7.362   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       8.685   5.954   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       9.202   4.503   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.626   3.917   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.692   5.028   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      13.226   4.886   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.072   3.600   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.593   2.136   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.126   1.995   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.797   0.609   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.150   1.598   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.830   2.390   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.610   1.450   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.186   2.037   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.982   3.564   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   15   19                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   22   37                                             
CONECT   12   11   13                                                       
CONECT   13   12    2    7   14                                             
CONECT   14   13   15                                                       
CONECT   15   14    5   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18    5   20   21                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   11   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   37                                                  
CONECT   26   25   27   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30   34                                                       
CONECT   34   33   26   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   11   25                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₃N₃O₆

Average Mass

507.5870 Da

Monoisotopic Mass

507.23694 Da

IUPAC Name

12'-hydroxy-4,4,4',4',12',14'-hexamethyl-9,10-dihydro-4H-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecane]-9,10',13'-trione

Traditional Name

12'-hydroxy-4,4,4',4',12',14'-hexamethyl-10H-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecane]-9,10',13'-trione

CAS Registry Number

Not Available

SMILES

CN1C(=O)C23CC4C(C)(C)C5(CC14CN2C(=O)CC3(C)O)C(=O)NC1=C2OC=CC(C)(C)OC2=CC=C51

InChI Identifier

InChI=1S/C28H33N3O6/c1-23(2)9-10-36-20-16(37-23)8-7-15-19(20)29-21(33)27(15)13-26-14-31-18(32)12-25(5,35)28(31,22(34)30(26)6)11-17(26)24(27,3)4/h7-10,17,35H,11-14H2,1-6H3,(H,29,33)

InChI Key

HHMKOJPJOSZYET-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 azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaspirodecane derivatives

Sub Class

Not Available

Direct Parent

Azaspirodecane derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Azaspirodecane
Indole or derivatives
Dihydroindole
Indolizidine
1,4-dioxepine
Alkyl aryl ether
Delta-lactam
Dioxepine
Piperidinone
N-methylpiperazine
N-alkylpiperazine
Benzenoid
N-alkylpyrrolidine
2-pyrrolidone
Pyrrolidone
1,4-diazinane
Piperazine
Piperidine
Tertiary alcohol
Tertiary carboxylic acid amide
Pyrrolidine
Lactam
Secondary carboxylic acid amide
Carboxamide group
Azacycle
Carboxylic acid derivative
Oxacycle
Ether
Alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen 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	2.73	ALOGPS
logP	0.88	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	11.59	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	108.41 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	134.43 m³·mol⁻¹	ChemAxon
Polarizability	53.83 Å³	ChemAxon
Number of Rings	7	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

14337024

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9,12'-dihydroxy-4,4,4',4',12',14'-hexamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecane]-10',13'-dione (NP0316447)

MOL for NP0316447 (9,12'-dihydroxy-4,4,4',4',12',14'-hexamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecane]-10',13'-dione)

3D MOL for NP0316447 (9,12'-dihydroxy-4,4,4',4',12',14'-hexamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecane]-10',13'-dione)

3D SDF for NP0316447 (9,12'-dihydroxy-4,4,4',4',12',14'-hexamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecane]-10',13'-dione)

3D-SDF for NP0316447 (9,12'-dihydroxy-4,4,4',4',12',14'-hexamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecane]-10',13'-dione)

PDB for NP0316447 (9,12'-dihydroxy-4,4,4',4',12',14'-hexamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecane]-10',13'-dione)

3D PDB for NP0316447 (9,12'-dihydroxy-4,4,4',4',12',14'-hexamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecane]-10',13'-dione)

SMILES for NP0316447 (9,12'-dihydroxy-4,4,4',4',12',14'-hexamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecane]-10',13'-dione)

INCHI for NP0316447 (9,12'-dihydroxy-4,4,4',4',12',14'-hexamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecane]-10',13'-dione)

Structure for NP0316447 (9,12'-dihydroxy-4,4,4',4',12',14'-hexamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecane]-10',13'-dione)

3D Structure for NP0316447 (9,12'-dihydroxy-4,4,4',4',12',14'-hexamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecane]-10',13'-dione)