NP-MRD: Showing NP-Card for 2-hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]heptacosa-8,10,12-trien-7-one (NP0214286)

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Record Information

Version

2.0

Created at

2022-09-05 13:32:41 UTC

Updated at

2022-09-05 13:32:42 UTC

NP-MRD ID

NP0214286

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]heptacosa-8,10,12-trien-7-one

Description

2-Hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]Heptacosa-8,10,12-trien-7-one belongs to the class of organic compounds known as 9b-azaphenalenes. These are alkaloids with a structure based on the perhydro-9b-azaphenalene skeleton. Perhydro-9b-azaphenalene is a tricyclic compound consisting of quinolizidine that share its only nitrogen atom with a piperidine. In some 9b-azaphenalenes, the resulting tricyclic backbone can be unsaturated. 2-hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]heptacosa-8,10,12-trien-7-one is found in Chilocorus renipustulatus. 2-Hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]Heptacosa-8,10,12-trien-7-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261511182D          

 30 36  0  0  0  0            999 V2000
    2.0803    2.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0018    1.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2490    1.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2572    0.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466    0.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1247   -0.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7411   -1.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5549   -0.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8964   -0.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8805    0.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7891    0.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5069    0.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6721    1.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9185   -0.2998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1487   -0.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2287    0.4506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656    0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6318   -0.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792    0.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0696    0.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2604   -0.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0509   -0.9639    0.0000 O   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


  Mrv1533004261511182D          

 30 36  0  0  0  0            999 V2000
    2.0803    2.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0018    1.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2490    1.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6804   -2.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8702   -1.0582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0214286

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2CCCC34CCCC(C1)(N23)C1(O)CC2CCC(=O)C3=CC=C(C=C1C4)N23

> <INCHI_IDENTIFIER>
InChI=1S/C26H34N2O2/c1-17-12-20-4-2-9-24-10-3-11-25(14-17,28(20)24)26(30)16-21-6-8-23(29)22-7-5-19(27(21)22)13-18(26)15-24/h5,7,13,17,20-21,30H,2-4,6,8-12,14-16H2,1H3

> <INCHI_KEY>
GSQRVMWUUVYOJW-UHFFFAOYSA-N

> <FORMULA>
C26H34N2O2

> <MOLECULAR_WEIGHT>
406.57

> <EXACT_MASS>
406.262028343

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.00130360904951

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]heptacosa-8,10,12-trien-7-one

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
3.329191319333334

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.413708165155413

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.409613802960344

> <JCHEM_PKA_STRONGEST_BASIC>
9.2269802369918

> <JCHEM_POLAR_SURFACE_AREA>
45.47

> <JCHEM_REFRACTIVITY>
118.36139999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]heptacosa-8,10,12-trien-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       3.883   4.397   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.737   2.864   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.331   2.185   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.347   0.454   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.647   0.153   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.233  -1.344   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.383  -2.411   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.903  -1.822   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.673  -0.715   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.644   1.014   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.340   1.317   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.680   0.342   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.988   1.931   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.581  -0.560   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       5.878  -0.692   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.027   0.841   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.216   0.070   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.646  -0.501   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.854   0.581   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.330   0.140   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.686  -1.358   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.162  -1.799   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.567  -2.416   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.603  -3.956   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.151  -4.466   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.216  -3.242   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.679  -3.348   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.639  -2.213   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.147  -2.798   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       9.091  -1.975   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   14   29                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12    2                                                       
CONECT   14   12    4    8                                                  
CONECT   15   12   16   17   28                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   30                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   15   29                                                  
CONECT   29   28    8                                                       
CONECT   30   26   18   23                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄N₂O₂

Average Mass

406.5700 Da

Monoisotopic Mass

406.26203 Da

IUPAC Name

2-hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]heptacosa-8,10,12-trien-7-one

Traditional Name

2-hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]heptacosa-8,10,12-trien-7-one

CAS Registry Number

Not Available

SMILES

CC1CC2CCCC34CCCC(C1)(N23)C1(O)CC2CCC(=O)C3=CC=C(C=C1C4)N23

InChI Identifier

InChI=1S/C26H34N2O2/c1-17-12-20-4-2-9-24-10-3-11-25(14-17,28(20)24)26(30)16-21-6-8-23(29)22-7-5-19(27(21)22)13-18(26)15-24/h5,7,13,17,20-21,30H,2-4,6,8-12,14-16H2,1H3

InChI Key

GSQRVMWUUVYOJW-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
Chilocorus renipustulatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 9b-azaphenalenes. These are alkaloids with a structure based on the perhydro-9b-azaphenalene skeleton. Perhydro-9b-azaphenalene is a tricyclic compound consisting of quinolizidine that share its only nitrogen atom with a piperidine. In some 9b-azaphenalenes, the resulting tricyclic backbone can be unsaturated.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

9b-azaphenalenes

Sub Class

Not Available

Direct Parent

9b-azaphenalenes

Alternative Parents

Substituents

9b-azaphenalene skeleton
Pyrroloazepine
Quinolizidine
Aryl alkyl ketone
Aryl ketone
Azepine
Piperidine
Pyrrole
Heteroaromatic compound
Tertiary alcohol
Ketone
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
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	3.57	ALOGPS
logP	3.33	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.41	ChemAxon
pKa (Strongest Basic)	9.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.47 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	118.36 m³·mol⁻¹	ChemAxon
Polarizability	47 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

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 2-hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]heptacosa-8,10,12-trien-7-one (NP0214286)

MOL for NP0214286 (2-hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]heptacosa-8,10,12-trien-7-one)

3D MOL for NP0214286 (2-hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]heptacosa-8,10,12-trien-7-one)

3D SDF for NP0214286 (2-hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]heptacosa-8,10,12-trien-7-one)

3D-SDF for NP0214286 (2-hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]heptacosa-8,10,12-trien-7-one)

PDB for NP0214286 (2-hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]heptacosa-8,10,12-trien-7-one)

3D PDB for NP0214286 (2-hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]heptacosa-8,10,12-trien-7-one)

SMILES for NP0214286 (2-hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]heptacosa-8,10,12-trien-7-one)

INCHI for NP0214286 (2-hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]heptacosa-8,10,12-trien-7-one)

Structure for NP0214286 (2-hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]heptacosa-8,10,12-trien-7-one)

3D Structure for NP0214286 (2-hydroxy-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁸.0²,¹³.0¹¹,²⁷.0¹⁹,²⁶]heptacosa-8,10,12-trien-7-one)