NP-MRD: Showing NP-Card for (+)-Stephalonine E (NP0078765)

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Record Information

Version

2.0

Created at

2022-04-28 23:49:58 UTC

Updated at

2022-04-28 23:49:58 UTC

NP-MRD ID

NP0078765

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Stephalonine E

Description

(1R,8S,10S,11R,12S,13S)-3-hydroxy-4,11,12-trimethoxy-17-methyl-16-oxo-18-oxa-17-azapentacyclo[8.4.3.1⁸,¹¹.0¹,¹⁰.0²,⁷]Octadeca-2(7),3,5-trien-13-yl (2E)-3-phenylprop-2-enoate 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. (+)-Stephalonine E is found in Stephania longa . Based on a literature review very few articles have been published on (1R,8S,10S,11R,12S,13S)-3-hydroxy-4,11,12-trimethoxy-17-methyl-16-oxo-18-oxa-17-azapentacyclo[8.4.3.1⁸,¹¹.0¹,¹⁰.0²,⁷]Octadeca-2(7),3,5-trien-13-yl (2E)-3-phenylprop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201492D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292201492D          

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 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  1  0  0  0
 16 25  1  1  0  0  0
 23 26  1  0  0  0  0
 19 27  1  0  0  0  0
  1 27  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 17 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 34  1  0  0  0  0
 14 35  1  1  0  0  0
 35 36  1  0  0  0  0
 13 37  1  6  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078765

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1[C@H](C[C@]23CC(=O)N(C)[C@@]22C[C@H](O[C@@]12OC)C1=C3C(O)=C(OC)C=C1)OC(=O)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H31NO8/c1-30-22(31)16-27-14-21(37-23(32)13-10-17-8-6-5-7-9-17)26(35-3)29(36-4)28(27,30)15-20(38-29)18-11-12-19(34-2)25(33)24(18)27/h5-13,20-21,26,33H,14-16H2,1-4H3/b13-10+/t20-,21-,26-,27+,28-,29-/m0/s1

> <INCHI_KEY>
KOKWRSAOHLOSAI-RDVMOJGNSA-N

> <FORMULA>
C29H31NO8

> <MOLECULAR_WEIGHT>
521.566

> <EXACT_MASS>
521.204966962

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.16203295035241

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,8S,10S,11R,12S,13S)-3-hydroxy-4,11,12-trimethoxy-17-methyl-16-oxo-18-oxa-17-azapentacyclo[8.4.3.1^{8,11}.0^{1,10}.0^{2,7}]octadeca-2(7),3,5-trien-13-yl (2E)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
3.1516212580000005

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.559374835424192

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4877796940803599

> <JCHEM_POLAR_SURFACE_AREA>
103.76000000000002

> <JCHEM_REFRACTIVITY>
136.6889

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8S,10S,11R,12S,13S)-3-hydroxy-4,11,12-trimethoxy-17-methyl-16-oxo-18-oxa-17-azapentacyclo[8.4.3.1^{8,11}.0^{1,10}.0^{2,7}]octadeca-2(7),3,5-trien-13-yl (2E)-3-phenylprop-2-enoate

> <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       1.463   1.304   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.376   0.213   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.776  -1.274   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.311  -2.364   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.265  -1.670   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.665  -3.157   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.154  -3.553   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.241  -2.463   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.729  -2.859   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.130  -4.346   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.042  -5.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.554  -5.040   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.980   3.119   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.177   4.562   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.518   6.087   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.771   5.093   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.897   3.836   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.365   2.391   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.841   2.230   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.459   1.542   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.050   2.181   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.397   1.655   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0       1.739   3.619   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       3.238   3.690   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.109   5.289   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.888   4.903   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.108   0.872   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.350   1.208   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.867   1.469   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.400   2.914   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.415   4.097   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.852   0.285   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.370   0.546   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.817  -0.237   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       1.005   5.562   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.286   7.076   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.524   3.450   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -0.990   4.917   0.000  0.00  0.00           C+0
CONECT    1    2   13   27                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    1   14   37                                                  
CONECT   14   13   15   24   35                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18   31                                                  
CONECT   18   17   19   28                                                  
CONECT   19   18   20   24   27                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   26                                                  
CONECT   24   23   14   19   25                                             
CONECT   25   24   16                                                       
CONECT   26   23                                                            
CONECT   27   19    1                                                       
CONECT   28   18   29   34                                                  
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30   17                                                       
CONECT   32   29   33                                                       
CONECT   33   32                                                            
CONECT   34   28                                                            
CONECT   35   14   36                                                       
CONECT   36   35                                                            
CONECT   37   13   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Value	Source
(1R,8S,10S,11R,12S,13S)-3-Hydroxy-4,11,12-trimethoxy-17-methyl-16-oxo-18-oxa-17-azapentacyclo[8.4.3.1,.0,.0,]octadeca-2(7),3,5-trien-13-yl (2E)-3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₂₉H₃₁NO₈

Average Mass

521.5660 Da

Monoisotopic Mass

521.20497 Da

IUPAC Name

(1R,8S,10S,11R,12S,13S)-3-hydroxy-4,11,12-trimethoxy-17-methyl-16-oxo-18-oxa-17-azapentacyclo[8.4.3.1^{8,11}.0^{1,10}.0^{2,7}]octadeca-2(7),3,5-trien-13-yl (2E)-3-phenylprop-2-enoate

Traditional Name

(1R,8S,10S,11R,12S,13S)-3-hydroxy-4,11,12-trimethoxy-17-methyl-16-oxo-18-oxa-17-azapentacyclo[8.4.3.1^{8,11}.0^{1,10}.0^{2,7}]octadeca-2(7),3,5-trien-13-yl (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

CO[C@H]1[C@H](C[C@]23CC(=O)N(C)[C@@]22C[C@H](O[C@@]12OC)C1=C3C(O)=C(OC)C=C1)OC(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C29H31NO8/c1-30-22(31)16-27-14-21(37-23(32)13-10-17-8-6-5-7-9-17)26(35-3)29(36-4)28(27,30)15-20(38-29)18-11-12-19(34-2)25(33)24(18)27/h5-13,20-21,26,33H,14-16H2,1-4H3/b13-10+/t20-,21-,26-,27+,28-,29-/m0/s1

InChI Key

KOKWRSAOHLOSAI-RDVMOJGNSA-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
Stephania longa	Plant	KNApSAcK

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
Cinnamic acid ester
Cinnamic acid or derivatives
Tetralin
Indole or derivatives
Styrene
Anisole
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Ketal
Fatty acid ester
Pyrrolidone
2-pyrrolidone
Benzenoid
N-alkylpyrrolidine
Fatty acyl
Monocyclic benzene moiety
Oxolane
Pyrrolidine
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Lactam
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Organic oxygen 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	2.78	ALOGPS
logP	3.15	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.56	ChemAxon
pKa (Strongest Basic)	-0.49	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.76 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	136.69 m³·mol⁻¹	ChemAxon
Polarizability	53.16 Å³	ChemAxon
Number of Rings	6	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

Not Available

Chemspider ID

9895287

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11720570

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Stephalonine E (NP0078765)

MOL for NP0078765 ((+)-Stephalonine E)

3D MOL for NP0078765 ((+)-Stephalonine E)

3D SDF for NP0078765 ((+)-Stephalonine E)

3D-SDF for NP0078765 ((+)-Stephalonine E)

PDB for NP0078765 ((+)-Stephalonine E)

3D PDB for NP0078765 ((+)-Stephalonine E)

SMILES for NP0078765 ((+)-Stephalonine E)

INCHI for NP0078765 ((+)-Stephalonine E)

Structure for NP0078765 ((+)-Stephalonine E)

3D Structure for NP0078765 ((+)-Stephalonine E)