NP-MRD: Showing NP-Card for dimethyl[(1s)-1-[(6r,7s,10s,11r,14r,15s,20s)-6,10,15,19-tetramethyl-17-oxa-19-azapentacyclo[12.8.0.0³,¹¹.0⁶,¹⁰.0¹⁵,²⁰]docosa-1,3-dien-7-yl]ethyl]amine (NP0330372)

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Record Information

Version

1.0

Created at

2022-09-12 15:38:51 UTC

Updated at

2022-09-12 15:38:51 UTC

NP-MRD ID

NP0330372

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dimethyl[(1s)-1-[(6r,7s,10s,11r,14r,15s,20s)-6,10,15,19-tetramethyl-17-oxa-19-azapentacyclo[12.8.0.0³,¹¹.0⁶,¹⁰.0¹⁵,²⁰]docosa-1,3-dien-7-yl]ethyl]amine

Description

Moenjodaramine belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. dimethyl[(1s)-1-[(6r,7s,10s,11r,14r,15s,20s)-6,10,15,19-tetramethyl-17-oxa-19-azapentacyclo[12.8.0.0³,¹¹.0⁶,¹⁰.0¹⁵,²⁰]docosa-1,3-dien-7-yl]ethyl]amine is found in Buxus hildebrandtii, Buxus papillosa and Buxus sempervirens. It was first documented in 2010 (PMID: 20655557). Based on a literature review very few articles have been published on Moenjodaramine (PMID: 25528196).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122217382D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309122217382D          

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 26 27  1  0  0  0  0
 21 27  1  0  0  0  0
 11 27  1  0  0  0  0
 27 28  1  1  0  0  0
  2 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330372

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]([C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4C(CC[C@@H]5N(C)COC[C@@]45C)=CC3=CC[C@]12C)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H46N2O/c1-19(29(5)6)22-13-15-28(4)24-10-9-23-20(16-21(24)12-14-27(22,28)3)8-11-25-26(23,2)17-31-18-30(25)7/h12,16,19,22-25H,8-11,13-15,17-18H2,1-7H3/t19-,22+,23+,24+,25-,26-,27+,28-/m0/s1

> <INCHI_KEY>
QILSEMOPVAZWLY-DSJRXEMUSA-N

> <FORMULA>
C28H46N2O

> <MOLECULAR_WEIGHT>
426.689

> <EXACT_MASS>
426.361014109

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
53.61642257998165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
dimethyl[(1S)-1-[(6R,7S,10S,11R,14R,15S,20S)-6,10,15,19-tetramethyl-17-oxa-19-azapentacyclo[12.8.0.0^{3,11}.0^{6,10}.0^{15,20}]docosa-1,3-dien-7-yl]ethyl]amine

> <JCHEM_LOGP>
4.874244925666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
10.299904925934774

> <JCHEM_POLAR_SURFACE_AREA>
15.71

> <JCHEM_REFRACTIVITY>
131.9255

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
dimethyl[(1S)-1-[(6R,7S,10S,11R,14R,15S,20S)-6,10,15,19-tetramethyl-17-oxa-19-azapentacyclo[12.8.0.0^{3,11}.0^{6,10}.0^{15,20}]docosa-1,3-dien-7-yl]ethyl]amine

> <JCHEM_VEBER_RULE>
1

$$$$

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      12.242   8.115   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.070   6.584   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.659   5.968   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.329   4.464   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.796   4.313   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.179   5.725   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.141   4.587   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.718   6.211   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.732   5.028   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.192   5.062   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.259   6.286   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.634   7.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.036   8.418   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.408   7.719   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.560   8.742   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.021   8.256   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.331   6.747   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.583   7.644   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.528   8.852   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.047   8.430   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.672   6.937   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -0.810   6.515   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      -1.915   7.587   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.185   5.022   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.079   3.950   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.402   4.371   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.777   5.865   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.883   4.793   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      13.310   5.671   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      14.721   6.287   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.138   4.140   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   17                                             
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   27                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    3    6   18                                             
CONECT   18   17                                                            
CONECT   19   12   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   21   11   28                                             
CONECT   28   27                                                            
CONECT   29    2   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₆N₂O

Average Mass

426.6890 Da

Monoisotopic Mass

426.36101 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]([C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4C(CC[C@@H]5N(C)COC[C@@]45C)=CC3=CC[C@]12C)N(C)C

InChI Identifier

InChI=1S/C28H46N2O/c1-19(29(5)6)22-13-15-28(4)24-10-9-23-20(16-21(24)12-14-27(22,28)3)8-11-25-26(23,2)17-31-18-30(25)7/h12,16,19,22-25H,8-11,13-15,17-18H2,1-7H3/t19-,22+,23+,24+,25-,26-,27+,28-/m0/s1

InChI Key

QILSEMOPVAZWLY-DSJRXEMUSA-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
Buxus hildebrandtii	LOTUS Database	35616633
Buxus papillosa	LOTUS Database	35616633
Buxus sempervirens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Pinguisane sesquiterpenoid
1,3-oxazinane
Oxazinane
Hemiaminal
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00025521

Chemspider ID

4590611

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5491626

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ata A, Iverson CD, Kalhari KS, Akhter S, Betteridge J, Meshkatalsadat MH, Orhan I, Sener B: Triterpenoidal alkaloids from Buxus hyrcana and their enzyme inhibitory, anti-fungal and anti-leishmanial activities. Phytochemistry. 2010 Oct;71(14-15):1780-6. doi: 10.1016/j.phytochem.2010.06.017. Epub 2010 Jul 23. [PubMed:20655557 ]
Lam CW, Wakeman A, James A, Ata A, Gengan RM, Ross SA: Bioactive steroidal alkaloids from Buxus macowanii Oliv. Steroids. 2015 Mar;95:73-9. doi: 10.1016/j.steroids.2014.12.002. Epub 2014 Dec 18. [PubMed:25528196 ]
LOTUS database [Link]

Showing NP-Card for dimethyl[(1s)-1-[(6r,7s,10s,11r,14r,15s,20s)-6,10,15,19-tetramethyl-17-oxa-19-azapentacyclo[12.8.0.0³,¹¹.0⁶,¹⁰.0¹⁵,²⁰]docosa-1,3-dien-7-yl]ethyl]amine (NP0330372)

MOL for NP0330372 (dimethyl[(1s)-1-[(6r,7s,10s,11r,14r,15s,20s)-6,10,15,19-tetramethyl-17-oxa-19-azapentacyclo[12.8.0.0³,¹¹.0⁶,¹⁰.0¹⁵,²⁰]docosa-1,3-dien-7-yl]ethyl]amine)

3D MOL for NP0330372 (dimethyl[(1s)-1-[(6r,7s,10s,11r,14r,15s,20s)-6,10,15,19-tetramethyl-17-oxa-19-azapentacyclo[12.8.0.0³,¹¹.0⁶,¹⁰.0¹⁵,²⁰]docosa-1,3-dien-7-yl]ethyl]amine)

3D SDF for NP0330372 (dimethyl[(1s)-1-[(6r,7s,10s,11r,14r,15s,20s)-6,10,15,19-tetramethyl-17-oxa-19-azapentacyclo[12.8.0.0³,¹¹.0⁶,¹⁰.0¹⁵,²⁰]docosa-1,3-dien-7-yl]ethyl]amine)

3D-SDF for NP0330372 (dimethyl[(1s)-1-[(6r,7s,10s,11r,14r,15s,20s)-6,10,15,19-tetramethyl-17-oxa-19-azapentacyclo[12.8.0.0³,¹¹.0⁶,¹⁰.0¹⁵,²⁰]docosa-1,3-dien-7-yl]ethyl]amine)

PDB for NP0330372 (dimethyl[(1s)-1-[(6r,7s,10s,11r,14r,15s,20s)-6,10,15,19-tetramethyl-17-oxa-19-azapentacyclo[12.8.0.0³,¹¹.0⁶,¹⁰.0¹⁵,²⁰]docosa-1,3-dien-7-yl]ethyl]amine)

3D PDB for NP0330372 (dimethyl[(1s)-1-[(6r,7s,10s,11r,14r,15s,20s)-6,10,15,19-tetramethyl-17-oxa-19-azapentacyclo[12.8.0.0³,¹¹.0⁶,¹⁰.0¹⁵,²⁰]docosa-1,3-dien-7-yl]ethyl]amine)

SMILES for NP0330372 (dimethyl[(1s)-1-[(6r,7s,10s,11r,14r,15s,20s)-6,10,15,19-tetramethyl-17-oxa-19-azapentacyclo[12.8.0.0³,¹¹.0⁶,¹⁰.0¹⁵,²⁰]docosa-1,3-dien-7-yl]ethyl]amine)

INCHI for NP0330372 (dimethyl[(1s)-1-[(6r,7s,10s,11r,14r,15s,20s)-6,10,15,19-tetramethyl-17-oxa-19-azapentacyclo[12.8.0.0³,¹¹.0⁶,¹⁰.0¹⁵,²⁰]docosa-1,3-dien-7-yl]ethyl]amine)

Structure for NP0330372 (dimethyl[(1s)-1-[(6r,7s,10s,11r,14r,15s,20s)-6,10,15,19-tetramethyl-17-oxa-19-azapentacyclo[12.8.0.0³,¹¹.0⁶,¹⁰.0¹⁵,²⁰]docosa-1,3-dien-7-yl]ethyl]amine)

3D Structure for NP0330372 (dimethyl[(1s)-1-[(6r,7s,10s,11r,14r,15s,20s)-6,10,15,19-tetramethyl-17-oxa-19-azapentacyclo[12.8.0.0³,¹¹.0⁶,¹⁰.0¹⁵,²⁰]docosa-1,3-dien-7-yl]ethyl]amine)