NP-MRD: Showing NP-Card for 7-[(2e)-5-[(1r,2s,4ar,8as)-5-(hydroxymethyl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium (NP0183757)

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Record Information

Version

2.0

Created at

2022-09-03 22:43:06 UTC

Updated at

2022-09-03 22:43:06 UTC

NP-MRD ID

NP0183757

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-[(2e)-5-[(1r,2s,4ar,8as)-5-(hydroxymethyl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium

Description

Agelasine H 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)-5-(hydroxymethyl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium is found in Agelas mauritiana. Based on a literature review very few articles have been published on agelasine H.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042200432D          

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 32 31  1  1  0  0  0
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 18 32  1  0  0  0  0
M  CHG  1   7   1
M  END

     RDKit          3D

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M  CHG  1   7   1
M  END


  Mrv1652309042200432D          

 32 35  0  0  1  0            999 V2000
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 18 32  1  0  0  0  0
M  CHG  1   7   1
M  END
> <DATABASE_ID>
NP0183757

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@]2(C)[C@@H](CCC=C2CO)[C@]1(C)CC\C(C)=C\CN1C=[N+](C)C2=NC=NC(N)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C26H40N5O/c1-18(11-14-31-17-30(5)24-22(31)23(27)28-16-29-24)9-12-25(3)19(2)10-13-26(4)20(15-32)7-6-8-21(25)26/h7,11,16-17,19,21,32H,6,8-10,12-15H2,1-5H3,(H2,27,28,29)/q+1/b18-11+/t19-,21-,25+,26-/m0/s1

> <INCHI_KEY>
BKQXLKBEZUKCRP-NCDPUURDSA-N

> <FORMULA>
C26H40N5O

> <MOLECULAR_WEIGHT>
438.639

> <EXACT_MASS>
438.322737348

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
50.93473770505177

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-[(2E)-5-[(1R,2S,4aR,8aS)-5-(hydroxymethyl)-1,2,4a-trimethyl-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>
0.1270685018615875

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.52596909135183

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.50011304289489

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5143515822589944

> <JCHEM_POLAR_SURFACE_AREA>
80.84

> <JCHEM_REFRACTIVITY>
133.3284

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
7-[(2E)-5-[(1R,2S,4aR,8aS)-5-(hydroxymethyl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-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       1.741  -8.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.214  -6.887   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.302  -6.619   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.292  -7.799   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -2.809  -7.531   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -3.917  -8.601   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -5.276  -7.878   0.000  0.00  0.00           N+1
HETATM    8  C   UNK     0      -6.660  -8.553   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.009  -6.362   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -5.957  -5.148   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -5.380  -3.720   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -3.855  -3.506   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -2.907  -4.719   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -1.382  -4.505   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -3.484  -6.147   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.204  -5.707   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.677  -4.260   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.657  -4.260   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    9    5                                                  
CONECT   16    2   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   32                                             
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26   32                                             
CONECT   25   24                                                            
CONECT   26   24   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   24   18                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₄₀N₅O

Average Mass

438.6390 Da

Monoisotopic Mass

438.32274 Da

IUPAC Name

7-[(2E)-5-[(1R,2S,4aR,8aS)-5-(hydroxymethyl)-1,2,4a-trimethyl-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)-5-(hydroxymethyl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-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](CCC=C2CO)[C@]1(C)CC\C(C)=C\CN1C=[N+](C)C2=NC=NC(N)=C12

InChI Identifier

InChI=1S/C26H40N5O/c1-18(11-14-31-17-30(5)24-22(31)23(27)28-16-29-24)9-12-25(3)19(2)10-13-26(4)20(15-32)7-6-8-21(25)26/h7,11,16-17,19,21,32H,6,8-10,12-15H2,1-5H3,(H2,27,28,29)/q+1/b18-11+/t19-,21-,25+,26-/m0/s1

InChI Key

BKQXLKBEZUKCRP-NCDPUURDSA-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 mauritiana	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
Imidolactam
N-substituted imidazole
Pyrimidine
Azole
Heteroaromatic compound
Imidazole
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Amine
Primary alcohol
Primary 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	0.13	ChemAxon
pKa (Strongest Acidic)	17.5	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.84 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	133.33 m³·mol⁻¹	ChemAxon
Polarizability	50.93 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00049974

Chemspider ID

8203413

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10027842

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)-5-(hydroxymethyl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium (NP0183757)

MOL for NP0183757 (7-[(2e)-5-[(1r,2s,4ar,8as)-5-(hydroxymethyl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)

3D MOL for NP0183757 (7-[(2e)-5-[(1r,2s,4ar,8as)-5-(hydroxymethyl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)

3D SDF for NP0183757 (7-[(2e)-5-[(1r,2s,4ar,8as)-5-(hydroxymethyl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)

3D-SDF for NP0183757 (7-[(2e)-5-[(1r,2s,4ar,8as)-5-(hydroxymethyl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)

PDB for NP0183757 (7-[(2e)-5-[(1r,2s,4ar,8as)-5-(hydroxymethyl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)

3D PDB for NP0183757 (7-[(2e)-5-[(1r,2s,4ar,8as)-5-(hydroxymethyl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)

SMILES for NP0183757 (7-[(2e)-5-[(1r,2s,4ar,8as)-5-(hydroxymethyl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)

INCHI for NP0183757 (7-[(2e)-5-[(1r,2s,4ar,8as)-5-(hydroxymethyl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)

Structure for NP0183757 (7-[(2e)-5-[(1r,2s,4ar,8as)-5-(hydroxymethyl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)

3D Structure for NP0183757 (7-[(2e)-5-[(1r,2s,4ar,8as)-5-(hydroxymethyl)-1,2,4a-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]-6-amino-9-methylpurin-9-ium)