NP-MRD: Showing NP-Card for 7-[(2e)-5-[(1r,2s,4ar,8as)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2h-naphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium (NP0190580)

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Record Information

Version

2.0

Created at

2022-09-04 07:16:50 UTC

Updated at

2022-09-04 07:16:50 UTC

NP-MRD ID

NP0190580

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-[(2e)-5-[(1r,2s,4ar,8as)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2h-naphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium

Description

CHEMBL3586406 belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. 7-[(2e)-5-[(1r,2s,4ar,8as)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2h-naphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium is found in Agelas nakamurai. Based on a literature review very few articles have been published on CHEMBL3586406.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042209162D          

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M  CHG  1  24   1
M  END

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M  END


  Mrv1652309042209162D          

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M  END
> <DATABASE_ID>
NP0190580

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@]2(C)[C@@H](CC(=O)C=C2C)[C@]1(C)CC\C(C)=C\CN1C=[N+](C)C2=NC=NC(N)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C26H38N5O/c1-17(9-12-31-16-30(6)24-22(31)23(27)28-15-29-24)7-10-25(4)18(2)8-11-26(5)19(3)13-20(32)14-21(25)26/h9,13,15-16,18,21H,7-8,10-12,14H2,1-6H3,(H2,27,28,29)/q+1/b17-9+/t18-,21-,25+,26-/m0/s1

> <INCHI_KEY>
RZRLKYGESQIOSC-WYOSMABTSA-N

> <FORMULA>
C26H38N5O

> <MOLECULAR_WEIGHT>
436.623

> <EXACT_MASS>
436.307087284

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
50.843239719738435

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-[(2E)-5-[(1R,2S,4aR,8aS)-1,2,4a,5-tetramethyl-7-oxo-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methyl-7H-purin-9-ium

> <JCHEM_LOGP>
0.5883670795282556

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.516258012616234

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9625119819050565

> <JCHEM_POLAR_SURFACE_AREA>
77.67999999999999

> <JCHEM_REFRACTIVITY>
132.1718

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
7-[(2E)-5-[(1R,2S,4aR,8aS)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2H-naphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.767 -12.933   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.588 -11.943   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.141 -12.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.039 -11.480   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.486 -12.007   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.772  -9.963   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.675  -9.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.855 -10.427   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.035 -11.417   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.302  -9.900   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.570  -8.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.390  -7.393   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.657  -5.877   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.943  -7.920   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.366  -6.492   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.564  -7.600   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.594  -8.744   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.100  -8.424   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.576  -6.960   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.131  -9.569   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.637  -9.249   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       6.113  -7.784   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       5.208  -6.538   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       6.113  -5.292   0.000  0.00  0.00           N+1
HETATM   25  C   UNK     0       5.637  -3.827   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.578  -5.768   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       8.911  -4.998   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      10.245  -5.768   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      10.245  -7.308   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       8.911  -8.078   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       8.911  -9.618   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       7.578  -7.308   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    2    9   10                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   32                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   26   22                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₈N₅O

Average Mass

436.6230 Da

Monoisotopic Mass

436.30709 Da

IUPAC Name

7-[(2E)-5-[(1R,2S,4aR,8aS)-1,2,4a,5-tetramethyl-7-oxo-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methyl-7H-purin-9-ium

Traditional Name

7-[(2E)-5-[(1R,2S,4aR,8aS)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2H-naphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@]2(C)[C@@H](CC(=O)C=C2C)[C@]1(C)CC\C(C)=C\CN1C=[N+](C)C2=NC=NC(N)=C12

InChI Identifier

InChI=1S/C26H38N5O/c1-17(9-12-31-16-30(6)24-22(31)23(27)28-15-29-24)7-10-25(4)18(2)8-11-26(5)19(3)13-20(32)14-21(25)26/h9,13,15-16,18,21H,7-8,10-12,14H2,1-6H3,(H2,27,28,29)/q+1/b17-9+/t18-,21-,25+,26-/m0/s1

InChI Key

RZRLKYGESQIOSC-WYOSMABTSA-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
Agelas nakamurai	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
6-aminopurine
Imidazopyrimidine
Purine
Aminopyrimidine
Cyclohexenone
N-substituted imidazole
Pyrimidine
Imidolactam
Heteroaromatic compound
Azole
Imidazole
Cyclic ketone
Ketone
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Primary amine
Organopnictogen compound
Organic oxide
Carbonyl group
Amine
Organic cation
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	0.59	ChemAxon
pKa (Strongest Acidic)	18.52	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	132.17 m³·mol⁻¹	ChemAxon
Polarizability	50.84 Å³	ChemAxon
Number of Rings	4	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

35517091

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122180314

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-[(2e)-5-[(1r,2s,4ar,8as)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2h-naphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium (NP0190580)

MOL for NP0190580 (7-[(2e)-5-[(1r,2s,4ar,8as)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2h-naphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)

3D MOL for NP0190580 (7-[(2e)-5-[(1r,2s,4ar,8as)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2h-naphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)

3D SDF for NP0190580 (7-[(2e)-5-[(1r,2s,4ar,8as)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2h-naphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)

3D-SDF for NP0190580 (7-[(2e)-5-[(1r,2s,4ar,8as)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2h-naphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)

PDB for NP0190580 (7-[(2e)-5-[(1r,2s,4ar,8as)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2h-naphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)

3D PDB for NP0190580 (7-[(2e)-5-[(1r,2s,4ar,8as)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2h-naphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)

SMILES for NP0190580 (7-[(2e)-5-[(1r,2s,4ar,8as)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2h-naphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)

INCHI for NP0190580 (7-[(2e)-5-[(1r,2s,4ar,8as)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2h-naphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)

Structure for NP0190580 (7-[(2e)-5-[(1r,2s,4ar,8as)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2h-naphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)

3D Structure for NP0190580 (7-[(2e)-5-[(1r,2s,4ar,8as)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2h-naphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)