NP-MRD: Showing NP-Card for (1'r,8s,8'r,10's)-9-hydroxy-4,4,11',11',14'-pentamethyl-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0¹,¹⁰.0³,⁸]pentadecan]-15'-one (NP0325114)

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Record Information

Version

2.0

Created at

2022-09-12 05:37:37 UTC

Updated at

2022-09-12 05:37:37 UTC

NP-MRD ID

NP0325114

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,8s,8'r,10's)-9-hydroxy-4,4,11',11',14'-pentamethyl-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0¹,¹⁰.0³,⁸]pentadecan]-15'-one

Description

(1'R,8S,8'R,10'S)-9-hydroxy-4,4,11',11',14'-pentamethyl-4H-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0¹,¹⁰.0³,⁸]Pentadecane]-15'-one belongs to the class of organic compounds known as piperazinopiperidines. These are organic aromatic compounds containing a piperazine ring fused to a piperidine. (1'r,8s,8'r,10's)-9-hydroxy-4,4,11',11',14'-pentamethyl-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0¹,¹⁰.0³,⁸]pentadecan]-15'-one is found in Penicillium roqueforti. Based on a literature review very few articles have been published on (1'R,8S,8'R,10'S)-9-hydroxy-4,4,11',11',14'-pentamethyl-4H-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0¹,¹⁰.0³,⁸]Pentadecane]-15'-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122207372D          

 35 41  0  0  1  0            999 V2000
    4.9329    0.0374    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


  Mrv1652309122207372D          

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  2 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 23 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
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 22 30  1  0  0  0  0
 14 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 12 34  1  0  0  0  0
 34 35  1  6  0  0  0
  5 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325114

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)[C@]23CCCCN2C[C@]11C[C@]2(C(O)=NC4=C2C=CC2=C4OC=CC(C)(C)O2)C(C)(C)[C@@H]1C3

> <INCHI_IDENTIFIER>
InChI=1S/C28H35N3O4/c1-24(2)11-13-34-21-18(35-24)9-8-17-20(21)29-22(32)28(17)15-27-16-31-12-7-6-10-26(31,23(33)30(27)5)14-19(27)25(28,3)4/h8-9,11,13,19H,6-7,10,12,14-16H2,1-5H3,(H,29,32)/t19-,26+,27-,28-/m0/s1

> <INCHI_KEY>
KYKUTNUWXQVSSU-KATYWHKBSA-N

> <FORMULA>
C28H35N3O4

> <MOLECULAR_WEIGHT>
477.605

> <EXACT_MASS>
477.262756619

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.92879089756417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,8S,8'R,10'S)-9-hydroxy-4,4,11',11',14'-pentamethyl-4H-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0^{1,10}.0^{3,8}]pentadecane]-15'-one

> <JCHEM_LOGP>
1.5357674204757714

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.258701495095449

> <JCHEM_PKA_STRONGEST_BASIC>
6.574329110776188

> <JCHEM_POLAR_SURFACE_AREA>
74.60000000000001

> <JCHEM_REFRACTIVITY>
134.3106

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,8S,8'R,10'S)-9-hydroxy-4,4,11',11',14'-pentamethyl-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0^{1,10}.0^{3,8}]pentadecane]-15'-one

> <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       9.175   0.031   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       7.933   0.940   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       6.487   0.039   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.459  -1.501   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.066   0.996   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.586   0.409   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.322   1.339   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.408   2.906   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.879   3.441   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       5.286   2.687   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       6.754   3.580   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.363   2.622   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.341   4.127   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.993   2.818   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.312   2.915   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.112   4.231   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      11.877   1.710   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      10.739   0.490   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.423   1.290   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.458   2.829   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.809   3.569   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.125   2.769   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.090   1.229   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.272   0.242   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.781   0.551   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.480   1.923   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.843   3.325   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.352   3.634   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.878   4.865   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.350   3.702   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.291   3.684   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.217   4.915   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.161   4.730   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.047   2.589   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.477   1.276   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10   35                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11    2   13   34                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   19   31                                             
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   14   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   18   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   22                                                       
CONECT   31   14   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   12   35                                                  
CONECT   35   34    5                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₅N₃O₄

Average Mass

477.6050 Da

Monoisotopic Mass

477.26276 Da

IUPAC Name

(1'R,8S,8'R,10'S)-9-hydroxy-4,4,11',11',14'-pentamethyl-4H-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0^{1,10}.0^{3,8}]pentadecane]-15'-one

Traditional Name

(1'R,8S,8'R,10'S)-9-hydroxy-4,4,11',11',14'-pentamethyl-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0^{1,10}.0^{3,8}]pentadecane]-15'-one

CAS Registry Number

Not Available

SMILES

CN1C(=O)[C@]23CCCCN2C[C@]11C[C@]2(C(O)=NC4=C2C=CC2=C4OC=CC(C)(C)O2)C(C)(C)[C@@H]1C3

InChI Identifier

InChI=1S/C28H35N3O4/c1-24(2)11-13-34-21-18(35-24)9-8-17-20(21)29-22(32)28(17)15-27-16-31-12-7-6-10-26(31,23(33)30(27)5)14-19(27)25(28,3)4/h8-9,11,13,19H,6-7,10,12,14-16H2,1-5H3,(H,29,32)/t19-,26+,27-,28-/m0/s1

InChI Key

KYKUTNUWXQVSSU-KATYWHKBSA-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 roqueforti	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperazinopiperidines. These are organic aromatic compounds containing a piperazine ring fused to a piperidine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperazinopiperidines

Sub Class

Not Available

Direct Parent

Piperazinopiperidines

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Azaspirodecane
Piperazino-1,2-a-piperidine
Quinolizidine
3-alkylindole
Indole or derivatives
1,4-dioxepine
Alkyl aryl ether
Delta-lactam
Dioxepine
Aralkylamine
Piperidinone
N-methylpiperazine
N-alkylpiperazine
1,4-diazinane
Piperazine
Piperidine
Benzenoid
Cyclic carboximidic acid
Tertiary carboxylic acid amide
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Lactam
Carboxamide group
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Ether
Oxacycle
Carboxylic acid derivative
Amine
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
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	1.54	ChemAxon
pKa (Strongest Acidic)	4.26	ChemAxon
pKa (Strongest Basic)	6.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	134.31 m³·mol⁻¹	ChemAxon
Polarizability	52.93 Å³	ChemAxon
Number of Rings	7	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

163186896

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1'r,8s,8'r,10's)-9-hydroxy-4,4,11',11',14'-pentamethyl-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0¹,¹⁰.0³,⁸]pentadecan]-15'-one (NP0325114)

MOL for NP0325114 ((1'r,8s,8'r,10's)-9-hydroxy-4,4,11',11',14'-pentamethyl-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0¹,¹⁰.0³,⁸]pentadecan]-15'-one)

3D MOL for NP0325114 ((1'r,8s,8'r,10's)-9-hydroxy-4,4,11',11',14'-pentamethyl-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0¹,¹⁰.0³,⁸]pentadecan]-15'-one)

3D SDF for NP0325114 ((1'r,8s,8'r,10's)-9-hydroxy-4,4,11',11',14'-pentamethyl-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0¹,¹⁰.0³,⁸]pentadecan]-15'-one)

3D-SDF for NP0325114 ((1'r,8s,8'r,10's)-9-hydroxy-4,4,11',11',14'-pentamethyl-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0¹,¹⁰.0³,⁸]pentadecan]-15'-one)

PDB for NP0325114 ((1'r,8s,8'r,10's)-9-hydroxy-4,4,11',11',14'-pentamethyl-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0¹,¹⁰.0³,⁸]pentadecan]-15'-one)

3D PDB for NP0325114 ((1'r,8s,8'r,10's)-9-hydroxy-4,4,11',11',14'-pentamethyl-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0¹,¹⁰.0³,⁸]pentadecan]-15'-one)

SMILES for NP0325114 ((1'r,8s,8'r,10's)-9-hydroxy-4,4,11',11',14'-pentamethyl-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0¹,¹⁰.0³,⁸]pentadecan]-15'-one)

INCHI for NP0325114 ((1'r,8s,8'r,10's)-9-hydroxy-4,4,11',11',14'-pentamethyl-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0¹,¹⁰.0³,⁸]pentadecan]-15'-one)

Structure for NP0325114 ((1'r,8s,8'r,10's)-9-hydroxy-4,4,11',11',14'-pentamethyl-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0¹,¹⁰.0³,⁸]pentadecan]-15'-one)

3D Structure for NP0325114 ((1'r,8s,8'r,10's)-9-hydroxy-4,4,11',11',14'-pentamethyl-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0¹,¹⁰.0³,⁸]pentadecan]-15'-one)