NP-MRD: Showing NP-Card for 1-[(20r)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl]-4-methylpentan-2-one (NP0202557)

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Record Information

Version

2.0

Created at

2022-09-04 21:47:26 UTC

Updated at

2022-09-04 21:47:26 UTC

NP-MRD ID

NP0202557

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[(20r)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl]-4-methylpentan-2-one

Description

1-[(20R)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]Henicosa-1(13),2,4(8),9,11,14(19),15,17-octaen-20-yl]-4-methylpentan-2-one belongs to the class of organic compounds known as dihydrobenzophenanthridine alkaloids. These are alkaloids containing a dihydrobenzophenanthridine skeleton, which is a tetracyclic compound containing a benzene fused to a dihydrophenanthridine moiety. Based on a literature review very few articles have been published on 1-[(20R)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]Henicosa-1(13),2,4(8),9,11,14(19),15,17-octaen-20-yl]-4-methylpentan-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042223472D          

 33 37  0  0  1  0            999 V2000
    7.2621    1.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

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M  END


  Mrv1652309042223472D          

 33 37  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0202557

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C3=CC=C4C=C5OCOC5=CC4=C3N(C)[C@H](CC(=O)CC(C)C)C2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C27H29NO5/c1-15(2)10-17(29)12-21-25-18(8-9-22(30-4)27(25)31-5)19-7-6-16-11-23-24(33-14-32-23)13-20(16)26(19)28(21)3/h6-9,11,13,15,21H,10,12,14H2,1-5H3/t21-/m1/s1

> <INCHI_KEY>
JCJWAHDPCXAARH-OAQYLSRUSA-N

> <FORMULA>
C27H29NO5

> <MOLECULAR_WEIGHT>
447.531

> <EXACT_MASS>
447.204573038

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
49.6620912261698

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(20R)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1,3,8,10,12,14,16,18-octaen-20-yl]-4-methylpentan-2-one

> <JCHEM_LOGP>
5.313622276666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.540968455627073

> <JCHEM_PKA_STRONGEST_BASIC>
1.896113209355827

> <JCHEM_POLAR_SURFACE_AREA>
57.230000000000004

> <JCHEM_REFRACTIVITY>
127.10269999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
1-[(20R)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1,3,8,10,12,14,16,18-octaen-20-yl]-4-methylpentan-2-one

> <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      13.556   2.601   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.454   3.676   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.971   3.260   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.591   1.767   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.108   1.351   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.006   2.426   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.386   3.918   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.869   4.335   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.249   5.827   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      11.732   6.244   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.284   4.994   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.665   6.486   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.563   7.562   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.080   7.145   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.943   9.054   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.841  10.130   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.358   9.713   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.221  11.622   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       5.802   4.577   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       4.700   5.653   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.421   3.085   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.524   2.009   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.143   0.517   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.661   0.100   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.558   1.176   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.076   0.759   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.974   1.835   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.354   3.327   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.837   3.744   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.939   2.668   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.052   4.150   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.132   3.166   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.563   1.736   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   11   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   30                                                  
CONECT   22   21    6   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29   21   25                                                  
CONECT   31   28   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   27                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₉NO₅

Average Mass

447.5310 Da

Monoisotopic Mass

447.20457 Da

IUPAC Name

1-[(20R)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1,3,8,10,12,14,16,18-octaen-20-yl]-4-methylpentan-2-one

Traditional Name

1-[(20R)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1,3,8,10,12,14,16,18-octaen-20-yl]-4-methylpentan-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C3=CC=C4C=C5OCOC5=CC4=C3N(C)[C@H](CC(=O)CC(C)C)C2=C1OC

InChI Identifier

InChI=1S/C27H29NO5/c1-15(2)10-17(29)12-21-25-18(8-9-22(30-4)27(25)31-5)19-7-6-16-11-23-24(33-14-32-23)13-20(16)26(19)28(21)3/h6-9,11,13,15,21H,10,12,14H2,1-5H3/t21-/m1/s1

InChI Key

JCJWAHDPCXAARH-OAQYLSRUSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydrobenzophenanthridine alkaloids. These are alkaloids containing a dihydrobenzophenanthridine skeleton, which is a tetracyclic compound containing a benzene fused to a dihydrophenanthridine moiety.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Benzophenanthridine alkaloids

Sub Class

Dihydrobenzophenanthridine alkaloids

Direct Parent

Dihydrobenzophenanthridine alkaloids

Alternative Parents

Substituents

Dihydrobenzophenanthridine alkaloid skeleton
Benzoquinoline
Phenanthridine
Naphthalene
Quinoline
Benzodioxole
Anisole
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Alkyl aryl ether
Aralkylamine
Benzenoid
Beta-aminoketone
Tertiary amine
Ketone
Organoheterocyclic compound
Oxacycle
Azacycle
Acetal
Ether
Hydrocarbon derivative
Organopnictogen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
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	5.31	ChemAxon
pKa (Strongest Acidic)	18.54	ChemAxon
pKa (Strongest Basic)	1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.23 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	127.1 m³·mol⁻¹	ChemAxon
Polarizability	49.66 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

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

163044721

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-[(20r)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl]-4-methylpentan-2-one (NP0202557)

MOL for NP0202557 (1-[(20r)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl]-4-methylpentan-2-one)

3D MOL for NP0202557 (1-[(20r)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl]-4-methylpentan-2-one)

3D SDF for NP0202557 (1-[(20r)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl]-4-methylpentan-2-one)

3D-SDF for NP0202557 (1-[(20r)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl]-4-methylpentan-2-one)

PDB for NP0202557 (1-[(20r)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl]-4-methylpentan-2-one)

3D PDB for NP0202557 (1-[(20r)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl]-4-methylpentan-2-one)

SMILES for NP0202557 (1-[(20r)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl]-4-methylpentan-2-one)

INCHI for NP0202557 (1-[(20r)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl]-4-methylpentan-2-one)

Structure for NP0202557 (1-[(20r)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl]-4-methylpentan-2-one)

3D Structure for NP0202557 (1-[(20r)-17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaen-20-yl]-4-methylpentan-2-one)