NP-MRD: Showing NP-Card for (+)-Pervilleine F (NP0078051)

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Record Information

Version

2.0

Created at

2022-04-28 23:11:17 UTC

Updated at

2022-04-28 23:11:17 UTC

NP-MRD ID

NP0078051

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Pervilleine F

Description

(1S,3S,5R,6R)-8-methyl-3-[(2-phenylacetyl)oxy]-8-azabicyclo[3.2.1]Octan-6-yl (2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. (+)-Pervilleine F is found in Erythroxylum pervillei. Based on a literature review very few articles have been published on (1S,3S,5R,6R)-8-methyl-3-[(2-phenylacetyl)oxy]-8-azabicyclo[3.2.1]Octan-6-yl (2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201112D          

 36 39  0  0  1  0            999 V2000
    0.1593    0.4941    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1593   -0.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6087   -0.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8044    1.0085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0361    0.0816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8207    0.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7916    0.0816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 27 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292201112D          

 36 39  0  0  1  0            999 V2000
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 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 27 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078051

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C/C(=O)O[C@@H]2C[C@@H]3C[C@@H](C[C@H]2N3C)OC(=O)CC2=CC=CC=C2)=CC(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C28H33NO7/c1-29-20-15-21(35-27(31)14-18-8-6-5-7-9-18)17-22(29)23(16-20)36-26(30)11-10-19-12-24(32-2)28(34-4)25(13-19)33-3/h5-13,20-23H,14-17H2,1-4H3/b11-10-/t20-,21-,22+,23+/m0/s1

> <INCHI_KEY>
FKUUUFHXKIFGSF-ZOCBXLDCSA-N

> <FORMULA>
C28H33NO7

> <MOLECULAR_WEIGHT>
495.572

> <EXACT_MASS>
495.225702407

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.90018900777645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,5R,6R)-8-methyl-3-[(2-phenylacetyl)oxy]-8-azabicyclo[3.2.1]octan-6-yl (2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
3.77

> <JCHEM_LOGP>
3.7222052029999997

> <ALOGPS_LOGS>
-5.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.236105246826497

> <JCHEM_POLAR_SURFACE_AREA>
83.53

> <JCHEM_REFRACTIVITY>
134.74239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.04e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,5R,6R)-8-methyl-3-[(2-phenylacetyl)oxy]-8-azabicyclo[3.2.1]octan-6-yl (2Z)-3-(3,4,5-trimethoxyphenyl)prop-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       0.297   0.922   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.297  -0.618   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.501  -1.578   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.003  -1.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.671   0.152   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.003   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.501   1.883   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.934   0.152   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.399   0.628   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.211   0.152   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.981  -1.181   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.211  -2.515   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.521  -1.181   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.291  -2.515   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.831  -2.515   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.601  -3.849   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.831  -5.182   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.291  -5.182   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.521  -3.849   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.090   1.591   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.362   0.723   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.750   1.391   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.247  -0.813   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.520  -1.680   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.907  -1.012   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.180  -1.880   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.567  -1.211   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -7.682   0.324   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -6.410   1.192   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.022   0.524   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.525   2.728   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -5.253   3.595   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -9.070   0.993   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0     -10.342   0.125   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -8.840  -2.079   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0     -10.227  -1.411   0.000  0.00  0.00           C+0
CONECT    1    2    7   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    1   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   35                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   25                                                       
CONECT   31   29   32                                                       
CONECT   32   31                                                            
CONECT   33   28   34                                                       
CONECT   34   33                                                            
CONECT   35   27   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
(1S,3S,5R,6R)-8-Methyl-3-[(2-phenylacetyl)oxy]-8-azabicyclo[3.2.1]octan-6-yl (2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₈H₃₃NO₇

Average Mass

495.5720 Da

Monoisotopic Mass

495.22570 Da

IUPAC Name

(1S,3S,5R,6R)-8-methyl-3-[(2-phenylacetyl)oxy]-8-azabicyclo[3.2.1]octan-6-yl (2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate

Traditional Name

(1S,3S,5R,6R)-8-methyl-3-[(2-phenylacetyl)oxy]-8-azabicyclo[3.2.1]octan-6-yl (2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C/C(=O)O[C@@H]2C[C@@H]3C[C@@H](C[C@H]2N3C)OC(=O)CC2=CC=CC=C2)=CC(OC)=C1OC

InChI Identifier

InChI=1S/C28H33NO7/c1-29-20-15-21(35-27(31)14-18-8-6-5-7-9-18)17-22(29)23(16-20)36-26(30)11-10-19-12-24(32-2)28(34-4)25(13-19)33-3/h5-13,20-23H,14-17H2,1-4H3/b11-10-/t20-,21-,22+,23+/m0/s1

InChI Key

FKUUUFHXKIFGSF-ZOCBXLDCSA-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
Erythroxylum pervillei	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Cinnamic acid ester
Coumaric acid or derivatives
Tropane alkaloid
Phenoxy compound
Methoxybenzene
Styrene
Phenol ether
Anisole
Fatty acid ester
Alkyl aryl ether
Fatty acyl
Benzenoid
N-alkylpyrrolidine
Piperidine
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	3.77	ALOGPS
logP	3.72	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	8.24	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	83.53 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	134.74 m³·mol⁻¹	ChemAxon
Polarizability	51.9 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

163003436

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Pervilleine F (NP0078051)

MOL for NP0078051 ((+)-Pervilleine F)

3D MOL for NP0078051 ((+)-Pervilleine F)

3D SDF for NP0078051 ((+)-Pervilleine F)

3D-SDF for NP0078051 ((+)-Pervilleine F)

PDB for NP0078051 ((+)-Pervilleine F)

3D PDB for NP0078051 ((+)-Pervilleine F)

SMILES for NP0078051 ((+)-Pervilleine F)

INCHI for NP0078051 ((+)-Pervilleine F)

Structure for NP0078051 ((+)-Pervilleine F)

3D Structure for NP0078051 ((+)-Pervilleine F)