NP-MRD: Showing NP-Card for (11r,15s,16s)-15-hydroxy-14-methoxy-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 3,4-dimethoxybenzoate (NP0260095)

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Record Information

Version

2.0

Created at

2022-09-08 02:09:41 UTC

Updated at

2022-09-08 02:09:42 UTC

NP-MRD ID

NP0260095

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(11r,15s,16s)-15-hydroxy-14-methoxy-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 3,4-dimethoxybenzoate

Description

152013-83-7 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)-15-hydroxy-14-methoxy-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 3,4-dimethoxybenzoate is found in Stephania abyssinica. Based on a literature review very few articles have been published on 152013-83-7.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082204092D          

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M  END

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  Mrv1652309082204092D          

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 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  6  0  0  0
 18 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 12 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 27 33  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  2  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260095

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1OC)C(=O)O[C@H]1CC23CCNC22C[C@@H](OC2(OC)[C@H]1O)C1=CC2=C(OCO2)C=C31

> <INCHI_IDENTIFIER>
InChI=1S/C27H29NO9/c1-31-17-5-4-14(8-18(17)32-2)24(30)36-22-11-25-6-7-28-26(25)12-21(37-27(26,33-3)23(22)29)15-9-19-20(10-16(15)25)35-13-34-19/h4-5,8-10,21-23,28-29H,6-7,11-13H2,1-3H3/t21-,22+,23+,25?,26?,27?/m1/s1

> <INCHI_KEY>
FQTGWQFUPQBOJP-UHPCZMERSA-N

> <FORMULA>
C27H29NO9

> <MOLECULAR_WEIGHT>
511.527

> <EXACT_MASS>
511.184231518

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
52.38564388171452

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(11R,15S,16S)-15-hydroxy-14-methoxy-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 3,4-dimethoxybenzoate

> <JCHEM_LOGP>
2.3078836363333326

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.238815007682298

> <JCHEM_PKA_STRONGEST_BASIC>
9.09237771611387

> <JCHEM_POLAR_SURFACE_AREA>
113.94000000000003

> <JCHEM_REFRACTIVITY>
127.52099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(11R,15S,16S)-15-hydroxy-14-methoxy-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 3,4-dimethoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.552 -10.829   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.277  -9.470   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.462  -8.164   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.187  -6.805   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.372  -5.498   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.833  -5.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.018  -4.243   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.743  -2.884   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.479  -4.295   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.664  -2.988   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.038  -3.054   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.558  -1.545   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.338  -2.479   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.109  -2.160   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -0.752  -0.708   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       0.732  -0.198   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.228   1.514   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.231   1.360   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.236   1.767   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.603   0.262   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.933   1.038   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.270   0.274   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.566  -1.317   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.106  -1.276   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.487   0.246   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.976   0.640   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.062  -0.453   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.658  -1.939   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.169  -2.333   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.084  -1.240   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.947  -2.782   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.147  -1.817   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.600  -0.377   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -3.108  -6.909   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.923  -8.216   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -3.199  -9.575   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.013 -10.881   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   16   30                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12   17   20                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   16   21   23                                             
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   10   24                                                  
CONECT   24   23                                                            
CONECT   25   18   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29   25   12                                                  
CONECT   31   28   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   27                                                       
CONECT   34    6   35                                                       
CONECT   35   34    3   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Value	Source
4'-O-Methyl-stephavanine	MeSH
4'-O-Methylstephavanine	MeSH

Chemical Formula

C₂₇H₂₉NO₉

Average Mass

511.5270 Da

Monoisotopic Mass

511.18423 Da

IUPAC Name

(11R,15S,16S)-15-hydroxy-14-methoxy-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 3,4-dimethoxybenzoate

Traditional Name

(11R,15S,16S)-15-hydroxy-14-methoxy-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 3,4-dimethoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1OC)C(=O)O[C@H]1CC23CCNC22C[C@@H](OC2(OC)[C@H]1O)C1=CC2=C(OCO2)C=C31

InChI Identifier

InChI=1S/C27H29NO9/c1-31-17-5-4-14(8-18(17)32-2)24(30)36-22-11-25-6-7-28-26(25)12-21(37-27(26,33-3)23(22)29)15-9-19-20(10-16(15)25)35-13-34-19/h4-5,8-10,21-23,28-29H,6-7,11-13H2,1-3H3/t21-,22+,23+,25?,26?,27?/m1/s1

InChI Key

FQTGWQFUPQBOJP-UHPCZMERSA-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 abyssinica	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
P-methoxybenzoic acid or derivatives
M-methoxybenzoic acid or derivatives
O-dimethoxybenzene
Dimethoxybenzene
Tetralin
Benzoate ester
Dihydroindole
Indole or derivatives
Benzoic acid or derivatives
Benzodioxole
Phenoxy compound
Methoxybenzene
Phenol ether
Benzoyl
Anisole
Ketal
Aralkylamine
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Tetrahydrofuran
Pyrrolidine
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Monocarboxylic acid or derivatives
Ether
Secondary aliphatic amine
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
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	2.31	ChemAxon
pKa (Strongest Acidic)	12.24	ChemAxon
pKa (Strongest Basic)	9.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	113.94 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	127.52 m³·mol⁻¹	ChemAxon
Polarizability	52.39 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00025751

Chemspider ID

171072

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

197623

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)-15-hydroxy-14-methoxy-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 3,4-dimethoxybenzoate (NP0260095)

MOL for NP0260095 ((11r,15s,16s)-15-hydroxy-14-methoxy-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 3,4-dimethoxybenzoate)

3D MOL for NP0260095 ((11r,15s,16s)-15-hydroxy-14-methoxy-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 3,4-dimethoxybenzoate)

3D SDF for NP0260095 ((11r,15s,16s)-15-hydroxy-14-methoxy-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 3,4-dimethoxybenzoate)

3D-SDF for NP0260095 ((11r,15s,16s)-15-hydroxy-14-methoxy-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 3,4-dimethoxybenzoate)

PDB for NP0260095 ((11r,15s,16s)-15-hydroxy-14-methoxy-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 3,4-dimethoxybenzoate)

3D PDB for NP0260095 ((11r,15s,16s)-15-hydroxy-14-methoxy-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 3,4-dimethoxybenzoate)

SMILES for NP0260095 ((11r,15s,16s)-15-hydroxy-14-methoxy-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 3,4-dimethoxybenzoate)

INCHI for NP0260095 ((11r,15s,16s)-15-hydroxy-14-methoxy-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 3,4-dimethoxybenzoate)

Structure for NP0260095 ((11r,15s,16s)-15-hydroxy-14-methoxy-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 3,4-dimethoxybenzoate)

3D Structure for NP0260095 ((11r,15s,16s)-15-hydroxy-14-methoxy-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 3,4-dimethoxybenzoate)