NP-MRD: Showing NP-Card for (1s,3s,5r,6r,7s)-7-hydroxy-8-methyl-3-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-6-yl benzoate (NP0268835)

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Record Information

Version

2.0

Created at

2022-09-08 14:05:03 UTC

Updated at

2022-09-08 14:05:03 UTC

NP-MRD ID

NP0268835

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,5r,6r,7s)-7-hydroxy-8-methyl-3-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-6-yl benzoate

Description

(1S,3S,5R,6R,7S)-8-Methyl-8-azabicyclo[3.2.1]Octane-3,6,7-triol 3-(3,4,5-trimethoxy-trans-cinnamate)6-benzoate 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. (1s,3s,5r,6r,7s)-7-hydroxy-8-methyl-3-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-6-yl benzoate is found in Erythroxylum rotundifolium. Based on a literature review very few articles have been published on (1S,3S,5R,6R,7S)-8-Methyl-8-azabicyclo[3.2.1]Octane-3,6,7-triol 3-(3,4,5-trimethoxy-trans-cinnamate)6-benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082216052D          

 36 39  0  0  1  0            999 V2000
    3.6130    6.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    5.6376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    4.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    4.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    3.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    2.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    2.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    1.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8505    1.3508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    0.6363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309082216052D          

 36 39  0  0  1  0            999 V2000
    3.6130    6.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    5.6376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 13 28  1  1  0  0  0
 28 29  1  0  0  0  0
  5 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 31 34  2  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0268835

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)O[C@H]2C[C@H]3[C@H](O)[C@H](OC(=O)C4=CC=CC=C4)[C@@H](C2)N3C)=CC(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C27H31NO8/c1-28-19-14-18(15-20(28)25(24(19)30)36-27(31)17-8-6-5-7-9-17)35-23(29)11-10-16-12-21(32-2)26(34-4)22(13-16)33-3/h5-13,18-20,24-25,30H,14-15H2,1-4H3/b11-10+/t18-,19-,20+,24-,25+/m0/s1

> <INCHI_KEY>
WAJCMVOJBHUQJX-FSWJOOFCSA-N

> <FORMULA>
C27H31NO8

> <MOLECULAR_WEIGHT>
497.544

> <EXACT_MASS>
497.204966962

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
51.72570200204245

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,5R,6R,7S)-7-hydroxy-8-methyl-3-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-6-yl benzoate

> <JCHEM_LOGP>
3.2517451406666664

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.525462274986392

> <JCHEM_PKA_STRONGEST_BASIC>
7.5587176254387

> <JCHEM_POLAR_SURFACE_AREA>
103.76

> <JCHEM_REFRACTIVITY>
131.78810000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,5R,6R,7S)-7-hydroxy-8-methyl-3-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-6-yl benzoate

> <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       6.744  11.857   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.514  10.524   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.744   9.190   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.514   7.856   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.744   6.523   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.514   5.189   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.744   3.855   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.514   2.522   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.054   2.522   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       6.744   1.188   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.204   1.188   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.536   2.575   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.035   2.918   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.831   1.958   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.443   2.626   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.831   0.418   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.443  -0.250   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.328  -1.786   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.059  -2.454   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.600  -2.654   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.988  -1.985   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.260  -2.853   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.145  -4.389   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.758  -5.057   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.485  -4.189   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.035  -0.542   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.536  -0.200   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       2.602   1.188   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       1.062   1.188   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.204   6.523   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.434   7.856   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.894   7.856   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.124   9.190   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.204   9.190   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.434  10.524   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.894  10.524   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   27                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   28                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26   16   27   28                                                  
CONECT   27   26   11                                                       
CONECT   28   26   13   29                                                  
CONECT   29   28                                                            
CONECT   30    5   31                                                       
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31    3   35                                                  
CONECT   35   34   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,7S)-8-Methyl-8-azabicyclo[3.2.1]octane-3,6,7-triol 3-(3,4,5-trimethoxy-trans-cinnamic acid)6-benzoic acid	Generator

Chemical Formula

C₂₇H₃₁NO₈

Average Mass

497.5440 Da

Monoisotopic Mass

497.20497 Da

IUPAC Name

(1S,3S,5R,6R,7S)-7-hydroxy-8-methyl-3-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-6-yl benzoate

Traditional Name

(1S,3S,5R,6R,7S)-7-hydroxy-8-methyl-3-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-6-yl benzoate

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)O[C@H]2C[C@H]3[C@H](O)[C@H](OC(=O)C4=CC=CC=C4)[C@@H](C2)N3C)=CC(OC)=C1OC

InChI Identifier

InChI=1S/C27H31NO8/c1-28-19-14-18(15-20(28)25(24(19)30)36-27(31)17-8-6-5-7-9-17)35-23(29)11-10-16-12-21(32-2)26(34-4)22(13-16)33-3/h5-13,18-20,24-25,30H,14-15H2,1-4H3/b11-10+/t18-,19-,20+,24-,25+/m0/s1

InChI Key

WAJCMVOJBHUQJX-FSWJOOFCSA-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
Erythroxylum rotundifolium	LOTUS Database	35616633

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

Coumaric acid or derivatives
Cinnamic acid ester
Benzoate ester
Benzoic acid or derivatives
Tropane alkaloid
Phenoxy compound
Anisole
Benzoyl
Methoxybenzene
Phenol ether
Styrene
Alkyl aryl ether
Fatty acid ester
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Piperidine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic alcohol
Secondary alcohol
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
1,2-aminoalcohol
Organoheterocyclic compound
Ether
Azacycle
Carboxylic acid derivative
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Alcohol
Organic nitrogen compound
Organonitrogen compound
Organooxygen 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	3.25	ChemAxon
pKa (Strongest Acidic)	13.53	ChemAxon
pKa (Strongest Basic)	7.56	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.76 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	131.79 m³·mol⁻¹	ChemAxon
Polarizability	51.73 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

12047362

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3s,5r,6r,7s)-7-hydroxy-8-methyl-3-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-6-yl benzoate (NP0268835)

MOL for NP0268835 ((1s,3s,5r,6r,7s)-7-hydroxy-8-methyl-3-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-6-yl benzoate)

3D MOL for NP0268835 ((1s,3s,5r,6r,7s)-7-hydroxy-8-methyl-3-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-6-yl benzoate)

3D SDF for NP0268835 ((1s,3s,5r,6r,7s)-7-hydroxy-8-methyl-3-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-6-yl benzoate)

3D-SDF for NP0268835 ((1s,3s,5r,6r,7s)-7-hydroxy-8-methyl-3-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-6-yl benzoate)

PDB for NP0268835 ((1s,3s,5r,6r,7s)-7-hydroxy-8-methyl-3-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-6-yl benzoate)

3D PDB for NP0268835 ((1s,3s,5r,6r,7s)-7-hydroxy-8-methyl-3-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-6-yl benzoate)

SMILES for NP0268835 ((1s,3s,5r,6r,7s)-7-hydroxy-8-methyl-3-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-6-yl benzoate)

INCHI for NP0268835 ((1s,3s,5r,6r,7s)-7-hydroxy-8-methyl-3-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-6-yl benzoate)

Structure for NP0268835 ((1s,3s,5r,6r,7s)-7-hydroxy-8-methyl-3-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-6-yl benzoate)

3D Structure for NP0268835 ((1s,3s,5r,6r,7s)-7-hydroxy-8-methyl-3-{[(2e)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-8-azabicyclo[3.2.1]octan-6-yl benzoate)