NP-MRD: Showing NP-Card for 9-hydroxy-4,4,4',4',14'-pentamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-one (NP0249216)

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Record Information

Version

2.0

Created at

2022-09-07 11:42:52 UTC

Updated at

2022-09-07 11:42:53 UTC

NP-MRD ID

NP0249216

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-hydroxy-4,4,4',4',14'-pentamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-one

Description

9-Hydroxy-4,4,4',4',14'-pentamethyl-4H-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]Tetradecane]-13'-one 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-hydroxy-4,4,4',4',14'-pentamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-one is found in Penicillium charlesii and Penicillium dierckxii. 9-Hydroxy-4,4,4',4',14'-pentamethyl-4H-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]Tetradecane]-13'-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161520052D          

 34 40  0  0  0  0            999 V2000
    2.9233    0.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3693    1.7812    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


  Mrv1533004161520052D          

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 30 33  1  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  0  0  0  0
  5 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249216

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)C23CCCN2CC11CC2(C(=O)NC4=C5OC=CC(C)(C)OC5=CC=C24)C(C)(C)C1C3

> <INCHI_IDENTIFIER>
InChI=1S/C27H33N3O4/c1-23(2)10-12-33-20-17(34-23)8-7-16-19(20)28-21(31)27(16)14-26-15-30-11-6-9-25(30,22(32)29(26)5)13-18(26)24(27,3)4/h7-8,10,12,18H,6,9,11,13-15H2,1-5H3,(H,28,31)

> <INCHI_KEY>
JPDNNPOSGMWCHG-UHFFFAOYSA-N

> <FORMULA>
C27H33N3O4

> <MOLECULAR_WEIGHT>
463.578

> <EXACT_MASS>
463.247106555

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
50.789088186776965

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,4,4',4',14'-pentamethyl-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]-9,13'-dione

> <ALOGPS_LOGP>
3.67

> <JCHEM_LOGP>
2.4722691119999993

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.591878202548349

> <JCHEM_PKA_STRONGEST_BASIC>
8.371949549850665

> <JCHEM_POLAR_SURFACE_AREA>
71.11000000000001

> <JCHEM_REFRACTIVITY>
128.95450000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       4.382  -0.567   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.638   0.782   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.993   0.701   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.216  -0.629   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.228   2.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.272   2.048   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.588   2.942   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.184   4.456   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.600   3.768   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.191   2.845   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.593   2.140   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.148   2.572   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.675   4.070   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.087   5.554   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.128   6.759   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       8.625   5.621   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       9.165   4.178   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.598   3.614   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.646   4.742   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      13.182   4.625   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.048   3.352   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.592   1.881   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.128   1.764   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.820   0.358   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.158   1.320   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.825   2.091   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.620   1.132   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.187   1.697   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.960   3.220   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.327   4.866   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.212   6.126   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.141   5.847   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.229   3.733   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.561   3.579   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    9   34                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10    2   12   33                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   29   30                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   29                                                  
CONECT   18   17   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26                                                       
CONECT   26   25   18   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   13   17                                                  
CONECT   30   13   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30   11   34                                                  
CONECT   34   33    5                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₃N₃O₄

Average Mass

463.5780 Da

Monoisotopic Mass

463.24711 Da

IUPAC Name

4,4,4',4',14'-pentamethyl-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]-9,13'-dione

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CN1C(=O)C23CCCN2CC11CC2(C(=O)NC4=C5OC=CC(C)(C)OC5=CC=C24)C(C)(C)C1C3

InChI Identifier

InChI=1S/C27H33N3O4/c1-23(2)10-12-33-20-17(34-23)8-7-16-19(20)28-21(31)27(16)14-26-15-30-11-6-9-25(30,22(32)29(26)5)13-18(26)24(27,3)4/h7-8,10,12,18H,6,9,11,13-15H2,1-5H3,(H,28,31)

InChI Key

JPDNNPOSGMWCHG-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

Species Name	Source	Reference
Penicillium charlesii	LOTUS Database	35616633
Penicillium dierckxii	LOTUS Database	35616633

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
3-alkylindole
Indole or derivatives
Indolizidine
1,4-dioxepine
Alkyl aryl ether
Delta-lactam
Dioxepine
Aralkylamine
Piperidinone
N-methylpiperazine
N-alkylpiperazine
1,4-diazinane
Piperazine
Piperidine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Tertiary carboxylic acid amide
Cyclic carboximidic acid
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Lactam
Carboxamide group
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Ether
Azacycle
Oxacycle
Carboxylic acid derivative
Organic oxide
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Amine
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	3.67	ALOGPS
logP	2.47	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	11.59	ChemAxon
pKa (Strongest Basic)	8.37	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.11 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	128.95 m³·mol⁻¹	ChemAxon
Polarizability	50.79 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

14734716

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-hydroxy-4,4,4',4',14'-pentamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-one (NP0249216)

MOL for NP0249216 (9-hydroxy-4,4,4',4',14'-pentamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-one)

3D MOL for NP0249216 (9-hydroxy-4,4,4',4',14'-pentamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-one)

3D SDF for NP0249216 (9-hydroxy-4,4,4',4',14'-pentamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-one)

3D-SDF for NP0249216 (9-hydroxy-4,4,4',4',14'-pentamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-one)

PDB for NP0249216 (9-hydroxy-4,4,4',4',14'-pentamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-one)

3D PDB for NP0249216 (9-hydroxy-4,4,4',4',14'-pentamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-one)

SMILES for NP0249216 (9-hydroxy-4,4,4',4',14'-pentamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-one)

INCHI for NP0249216 (9-hydroxy-4,4,4',4',14'-pentamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-one)

Structure for NP0249216 (9-hydroxy-4,4,4',4',14'-pentamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-one)

3D Structure for NP0249216 (9-hydroxy-4,4,4',4',14'-pentamethyl-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-one)