NP-MRD: Showing NP-Card for (+)-Asmarine G (NP0078930)

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Record Information

Version

2.0

Created at

2022-04-29 00:01:00 UTC

Updated at

2022-04-29 00:01:00 UTC

NP-MRD ID

NP0078930

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Asmarine G

Description

(10S)-10-{2-[(1S,2R,4aS,8aR)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]ethyl}-9-methoxy-10-methyl-1,3,5,7,9-pentaazatricyclo[6.4.1.0⁴,¹³]Trideca-2,4(13),5,7-tetraene 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. (+)-Asmarine G is found in Raspailia sp. Based on a literature review very few articles have been published on (10S)-10-{2-[(1S,2R,4aS,8aR)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]ethyl}-9-methoxy-10-methyl-1,3,5,7,9-pentaazatricyclo[6.4.1.0⁴,¹³]Trideca-2,4(13),5,7-tetraene.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202012D          

 32 36  0  0  1  0            999 V2000
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    5.6797    1.4872    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1 32  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292202012D          

 32 36  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0078930

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CON1C2=C3N(CC[C@]1(C)CC[C@@]1(C)[C@H](C)CC[C@@]4(C)[C@@H]1CCCC4=C)C=NC3=NC=N2

> <INCHI_IDENTIFIER>
InChI=1S/C26H39N5O/c1-18-8-7-9-20-25(18,4)11-10-19(2)26(20,5)13-12-24(3)14-15-30-17-29-22-21(30)23(28-16-27-22)31(24)32-6/h16-17,19-20H,1,7-15H2,2-6H3/t19-,20+,24+,25-,26+/m1/s1

> <INCHI_KEY>
DKZOPFDEEROAIQ-GQKVCYJFSA-N

> <FORMULA>
C26H39N5O

> <MOLECULAR_WEIGHT>
437.632

> <EXACT_MASS>
437.315460896

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
49.82156985364338

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10S)-10-{2-[(1S,2R,4aS,8aR)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]ethyl}-9-methoxy-10-methyl-1,3,5,7,9-pentaazatricyclo[6.4.1.0^{4,13}]trideca-2,4,6,8(13)-tetraene

> <ALOGPS_LOGP>
5.36

> <JCHEM_LOGP>
5.569126888000001

> <ALOGPS_LOGS>
-4.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
1.9160002331259842

> <JCHEM_POLAR_SURFACE_AREA>
56.07000000000001

> <JCHEM_REFRACTIVITY>
140.24130000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(10S)-10-{2-[(1S,2R,4aS,8aR)-1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]ethyl}-9-methoxy-10-methyl-1,3,5,7,9-pentaazatricyclo[6.4.1.0^{4,13}]trideca-2,4,6,8(13)-tetraene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      10.956   1.277   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.431   0.835   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.552   1.891   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.198   3.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.723   3.832   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.602   2.776   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.507   3.859   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.092   2.474   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.598   1.016   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.088   0.714   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       5.596   1.098   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       4.367   0.171   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.325  -1.369   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.502  -2.361   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       7.012  -2.060   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.718  -0.691   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.922  -3.788   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.386  -3.677   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.017  -2.182   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       1.659  -1.456   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       1.609   0.083   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       2.916   0.896   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0       5.295   2.608   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.836   3.102   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.130   2.254   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.369   5.331   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.490   6.387   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.965   5.944   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.319   4.446   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.794   4.003   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.673   2.947   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.835   0.221   0.000  0.00  0.00           C+0
CONECT    1    2    6   32                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   29   31                                             
CONECT    5    4    6   26                                                  
CONECT    6    5    1    7    8                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16   25                                             
CONECT   11   10   12   23                                                  
CONECT   12   11   13   22                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   10                                                       
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   13   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   12                                                       
CONECT   23   11   24                                                       
CONECT   24   23                                                            
CONECT   25   10                                                            
CONECT   26    5   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    4   30                                                  
CONECT   30   29                                                            
CONECT   31    4                                                            
CONECT   32    1                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₉N₅O

Average Mass

437.6320 Da

Monoisotopic Mass

437.31546 Da

IUPAC Name

(10S)-10-{2-[(1S,2R,4aS,8aR)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]ethyl}-9-methoxy-10-methyl-1,3,5,7,9-pentaazatricyclo[6.4.1.0^{4,13}]trideca-2,4,6,8(13)-tetraene

Traditional Name

(10S)-10-{2-[(1S,2R,4aS,8aR)-1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]ethyl}-9-methoxy-10-methyl-1,3,5,7,9-pentaazatricyclo[6.4.1.0^{4,13}]trideca-2,4,6,8(13)-tetraene

CAS Registry Number

Not Available

SMILES

CON1C2=C3N(CC[C@]1(C)CC[C@@]1(C)[C@H](C)CC[C@@]4(C)[C@@H]1CCCC4=C)C=NC3=NC=N2

InChI Identifier

InChI=1S/C26H39N5O/c1-18-8-7-9-20-25(18,4)11-10-19(2)26(20,5)13-12-24(3)14-15-30-17-29-22-21(30)23(28-16-27-22)31(24)32-6/h16-17,19-20H,1,7-15H2,2-6H3/t19-,20+,24+,25-,26+/m1/s1

InChI Key

DKZOPFDEEROAIQ-GQKVCYJFSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Raspailia sp.	-	KNApSAcK

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-alkylaminopurine
Pyrimidodiazepine
Purine
Imidazopyrimidine
Para-diazepine
Imidolactam
Pyrimidine
N-substituted imidazole
Heteroaromatic compound
Imidazole
Azole
Azacycle
N-organohydroxylamine
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	5.36	ALOGPS
logP	5.57	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	1.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	56.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	140.24 m³·mol⁻¹	ChemAxon
Polarizability	49.82 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

163000511

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Asmarine G (NP0078930)

MOL for NP0078930 ((+)-Asmarine G)

3D MOL for NP0078930 ((+)-Asmarine G)

3D SDF for NP0078930 ((+)-Asmarine G)

3D-SDF for NP0078930 ((+)-Asmarine G)

PDB for NP0078930 ((+)-Asmarine G)

3D PDB for NP0078930 ((+)-Asmarine G)

SMILES for NP0078930 ((+)-Asmarine G)

INCHI for NP0078930 ((+)-Asmarine G)

Structure for NP0078930 ((+)-Asmarine G)

3D Structure for NP0078930 ((+)-Asmarine G)