NP-MRD: Showing NP-Card for (11r,15s,16s)-14,15-dimethoxy-20-methyl-19-oxo-5,7,21-trioxa-20-azahexacyclo[11.4.3.1¹¹,¹⁴.0¹,¹³.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9-trien-16-yl benzoate (NP0179322)

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Record Information

Version

2.0

Created at

2022-09-03 17:29:26 UTC

Updated at

2022-09-03 17:29:26 UTC

NP-MRD ID

NP0179322

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(11r,15s,16s)-14,15-dimethoxy-20-methyl-19-oxo-5,7,21-trioxa-20-azahexacyclo[11.4.3.1¹¹,¹⁴.0¹,¹³.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9-trien-16-yl benzoate

Description

Oxostephabenine belongs to the class of organic compounds known as hasubanan alkaloids. These are alkaloids with a structure based on the hasubanan skeleton, a tetracyclic propellane. (11r,15s,16s)-14,15-dimethoxy-20-methyl-19-oxo-5,7,21-trioxa-20-azahexacyclo[11.4.3.1¹¹,¹⁴.0¹,¹³.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9-trien-16-yl benzoate is found in Stephania japonica. Based on a literature review very few articles have been published on Oxostephabenine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032219292D          

 36 42  0  0  1  0            999 V2000
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   -0.4043   -3.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8407   -3.7290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4202   -3.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566   -2.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6812   -2.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309032219292D          

 36 42  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0179322

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1[C@H](CC23CC(=O)N(C)C22C[C@@H](OC12OC)C1=CC2=C(OCO2)C=C31)OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H27NO8/c1-28-22(29)13-25-11-21(35-24(30)15-7-5-4-6-8-15)23(31-2)27(32-3)26(25,28)12-20(36-27)16-9-18-19(10-17(16)25)34-14-33-18/h4-10,20-21,23H,11-14H2,1-3H3/t20-,21+,23+,25?,26?,27?/m1/s1

> <INCHI_KEY>
RENGMXWYDJJRAP-AVUAEGJXSA-N

> <FORMULA>
C27H27NO8

> <MOLECULAR_WEIGHT>
493.512

> <EXACT_MASS>
493.173666833

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
49.363101419692285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(11R,15S,16S)-14,15-dimethoxy-20-methyl-19-oxo-5,7,21-trioxa-20-azahexacyclo[11.4.3.1^{11,14}.0^{1,13}.0^{2,10}.0^{4,8}]henicosa-2,4(8),9-trien-16-yl benzoate

> <JCHEM_LOGP>
2.6975004436666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4870019178425248

> <JCHEM_POLAR_SURFACE_AREA>
92.76000000000002

> <JCHEM_REFRACTIVITY>
124.26599999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(11R,15S,16S)-14,15-dimethoxy-20-methyl-19-oxo-5,7,21-trioxa-20-azahexacyclo[11.4.3.1^{11,14}.0^{1,13}.0^{2,10}.0^{4,8}]henicosa-2,4(8),9-trien-16-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.840   0.078   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.106  -1.276   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.566  -1.317   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.664  -2.988   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.479  -4.295   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.755  -5.654   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.569  -6.961   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.784  -5.706   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.599  -4.399   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.138  -4.451   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.863  -5.810   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.048  -7.117   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.509  -7.065   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.038  -3.054   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.558  -1.545   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.338  -2.479   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.109  -2.160   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.416  -2.974   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0      -0.752  -0.708   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      -1.889   0.330   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.732  -0.198   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.228   1.514   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.231   1.360   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.236   1.767   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.603   0.262   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.933   1.038   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.926   2.578   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.487   0.246   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.976   0.640   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.062  -0.453   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.658  -1.939   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.169  -2.333   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.084  -1.240   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.947  -2.782   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.147  -1.817   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.600  -0.377   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    4   15                                                       
CONECT   15   14   16   21   33                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   15   22   25                                             
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24    3   21   26                                             
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   23   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   36                                                  
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32   28   15                                                  
CONECT   34   31   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   30                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₇NO₈

Average Mass

493.5120 Da

Monoisotopic Mass

493.17367 Da

IUPAC Name

(11R,15S,16S)-14,15-dimethoxy-20-methyl-19-oxo-5,7,21-trioxa-20-azahexacyclo[11.4.3.1^{11,14}.0^{1,13}.0^{2,10}.0^{4,8}]henicosa-2,4(8),9-trien-16-yl benzoate

Traditional Name

(11R,15S,16S)-14,15-dimethoxy-20-methyl-19-oxo-5,7,21-trioxa-20-azahexacyclo[11.4.3.1^{11,14}.0^{1,13}.0^{2,10}.0^{4,8}]henicosa-2,4(8),9-trien-16-yl benzoate

CAS Registry Number

Not Available

SMILES

CO[C@H]1[C@H](CC23CC(=O)N(C)C22C[C@@H](OC12OC)C1=CC2=C(OCO2)C=C31)OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C27H27NO8/c1-28-22(29)13-25-11-21(35-24(30)15-7-5-4-6-8-15)23(31-2)27(32-3)26(25,28)12-20(36-27)16-9-18-19(10-17(16)25)34-14-33-18/h4-10,20-21,23H,11-14H2,1-3H3/t20-,21+,23+,25?,26?,27?/m1/s1

InChI Key

RENGMXWYDJJRAP-AVUAEGJXSA-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
Stephania japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hasubanan alkaloids. These are alkaloids with a structure based on the hasubanan skeleton, a tetracyclic propellane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Hasubanan alkaloids

Sub Class

Not Available

Direct Parent

Hasubanan alkaloids

Alternative Parents

Substituents

Hasubanan skeleton
Phenanthrene
Tetralin
Benzoate ester
Indole or derivatives
Benzoic acid or derivatives
Benzodioxole
Benzoyl
Ketal
Benzenoid
N-alkylpyrrolidine
2-pyrrolidone
Pyrrolidone
Monocyclic benzene moiety
Tetrahydrofuran
Tertiary carboxylic acid amide
Pyrrolidine
Lactam
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	2.7	ChemAxon
pKa (Strongest Basic)	-0.49	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	92.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	124.27 m³·mol⁻¹	ChemAxon
Polarizability	49.36 Å³	ChemAxon
Number of Rings	7	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

C00025117

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

181354

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (11r,15s,16s)-14,15-dimethoxy-20-methyl-19-oxo-5,7,21-trioxa-20-azahexacyclo[11.4.3.1¹¹,¹⁴.0¹,¹³.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9-trien-16-yl benzoate (NP0179322)

MOL for NP0179322 ((11r,15s,16s)-14,15-dimethoxy-20-methyl-19-oxo-5,7,21-trioxa-20-azahexacyclo[11.4.3.1¹¹,¹⁴.0¹,¹³.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9-trien-16-yl benzoate)

3D MOL for NP0179322 ((11r,15s,16s)-14,15-dimethoxy-20-methyl-19-oxo-5,7,21-trioxa-20-azahexacyclo[11.4.3.1¹¹,¹⁴.0¹,¹³.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9-trien-16-yl benzoate)

3D SDF for NP0179322 ((11r,15s,16s)-14,15-dimethoxy-20-methyl-19-oxo-5,7,21-trioxa-20-azahexacyclo[11.4.3.1¹¹,¹⁴.0¹,¹³.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9-trien-16-yl benzoate)

3D-SDF for NP0179322 ((11r,15s,16s)-14,15-dimethoxy-20-methyl-19-oxo-5,7,21-trioxa-20-azahexacyclo[11.4.3.1¹¹,¹⁴.0¹,¹³.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9-trien-16-yl benzoate)

PDB for NP0179322 ((11r,15s,16s)-14,15-dimethoxy-20-methyl-19-oxo-5,7,21-trioxa-20-azahexacyclo[11.4.3.1¹¹,¹⁴.0¹,¹³.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9-trien-16-yl benzoate)

3D PDB for NP0179322 ((11r,15s,16s)-14,15-dimethoxy-20-methyl-19-oxo-5,7,21-trioxa-20-azahexacyclo[11.4.3.1¹¹,¹⁴.0¹,¹³.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9-trien-16-yl benzoate)

SMILES for NP0179322 ((11r,15s,16s)-14,15-dimethoxy-20-methyl-19-oxo-5,7,21-trioxa-20-azahexacyclo[11.4.3.1¹¹,¹⁴.0¹,¹³.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9-trien-16-yl benzoate)

INCHI for NP0179322 ((11r,15s,16s)-14,15-dimethoxy-20-methyl-19-oxo-5,7,21-trioxa-20-azahexacyclo[11.4.3.1¹¹,¹⁴.0¹,¹³.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9-trien-16-yl benzoate)

Structure for NP0179322 ((11r,15s,16s)-14,15-dimethoxy-20-methyl-19-oxo-5,7,21-trioxa-20-azahexacyclo[11.4.3.1¹¹,¹⁴.0¹,¹³.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9-trien-16-yl benzoate)

3D Structure for NP0179322 ((11r,15s,16s)-14,15-dimethoxy-20-methyl-19-oxo-5,7,21-trioxa-20-azahexacyclo[11.4.3.1¹¹,¹⁴.0¹,¹³.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9-trien-16-yl benzoate)