NP-MRD: Showing NP-Card for 3-Phenylacetoxynortropane (NP0067746)

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Record Information

Version

2.0

Created at

2022-04-28 12:35:52 UTC

Updated at

2022-04-28 12:35:52 UTC

NP-MRD ID

NP0067746

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Phenylacetoxynortropane

Description

Phenylacetic acid (1S,5R)-3alpha-hydroxy-8-azabicyclo[3.2.1]Octane-7beta-yl ester belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane. 3-Phenylacetoxynortropane is found in Erythroxylum hypericifolium Lam. . Based on a literature review very few articles have been published on Phenylacetic acid (1S,5R)-3alpha-hydroxy-8-azabicyclo[3.2.1]Octane-7beta-yl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    1.5903    0.3422   -1.0423 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2573   -0.1061    0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3099   -0.4881    1.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633   -0.2769    0.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3060   -1.2928   -0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5861   -1.0949   -0.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2178    0.1184   -0.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5958    1.1590    0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3214    0.9065    0.7250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0903   -0.2116    0.3412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1152    0.1324   -0.5438 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0530    1.0793    0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8524    0.1369    1.0542 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3380    0.1892    0.6753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5206   -0.6303   -0.5595 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5030    0.0103   -1.3416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2942   -0.7463   -1.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0502   -1.0798   -0.6597 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4103   -1.2047    0.7587 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1116   -1.5468    1.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1926    0.0852    2.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042   -2.2418   -0.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0436   -1.9219   -1.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2210    0.2786   -0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0925    2.1167    0.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8190    1.7106    1.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8010    0.5132   -1.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3837    1.7399    0.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6537    1.6719   -0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7202    0.3457    2.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8604   -0.3621    1.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7188    1.2079    0.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8929   -1.6657   -0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0949    0.5301   -0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4836   -1.5958   -2.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779    0.1911   -2.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5039   -1.9507   -1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6140   -1.5174    1.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
 11 18  1  0
 18 17  1  0
 18 19  1  0
 17 15  1  0
 19 13  1  0
  9  4  1  0
 16 34  1  0
 15 33  1  1
 14 31  1  0
 14 32  1  0
 13 30  1  1
 12 28  1  0
 12 29  1  0
 11 27  1  6
  3 20  1  0
  3 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 18 37  1  6
 17 35  1  0
 17 36  1  0
 19 38  1  0
M  END


  Mrv1652304282214352D          

 19 21  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
    0.8044   -0.8453    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6087   -0.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9666    0.0816    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6087    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044    1.0085    0.0000 C   0  0  2  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
    2.7916    0.0816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5840    0.8521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6456    1.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0360    2.1395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3889    2.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4506    2.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1939    3.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2555    4.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5739    4.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8306    4.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7689    3.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  3  8  1  1  0  0  0
  5  9  1  6  0  0  0
  1 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067746

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1C[C@@H]2C[C@@H](OC(=O)CC3=CC=CC=C3)[C@H](C1)N2

> <INCHI_IDENTIFIER>
InChI=1S/C15H19NO3/c17-12-7-11-8-14(13(9-12)16-11)19-15(18)6-10-4-2-1-3-5-10/h1-5,11-14,16-17H,6-9H2/t11-,12-,13+,14-/m1/s1

> <INCHI_KEY>
LZGZKTSKMTXSGV-YIYPIFLZSA-N

> <FORMULA>
C15H19NO3

> <MOLECULAR_WEIGHT>
261.321

> <EXACT_MASS>
261.136493476

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.882296574955355

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3R,5S,6R)-3-hydroxy-8-azabicyclo[3.2.1]octan-6-yl 2-phenylacetate

> <ALOGPS_LOGP>
1.06

> <JCHEM_LOGP>
0.7782803446666661

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.156652291716508

> <JCHEM_PKA_STRONGEST_BASIC>
9.551558908753304

> <JCHEM_POLAR_SURFACE_AREA>
58.559999999999995

> <JCHEM_REFRACTIVITY>
70.49040000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,5S,6R)-3-hydroxy-8-azabicyclo[3.2.1]octan-6-yl phenylacetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-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  O   UNK     0       5.211   0.152   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.090   1.591   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.205   3.126   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.067   3.994   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.593   3.794   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.708   5.330   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.095   5.998   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.210   7.534   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.938   8.401   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.550   7.733   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.435   6.198   0.000  0.00  0.00           C+0
CONECT    1    2    7   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7    3                                                       
CONECT    9    5                                                            
CONECT   10    1   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                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
Phenylacetate (1S,5R)-3a-hydroxy-8-azabicyclo[3.2.1]octane-7b-yl ester	Generator
Phenylacetate (1S,5R)-3alpha-hydroxy-8-azabicyclo[3.2.1]octane-7beta-yl ester	Generator
Phenylacetate (1S,5R)-3α-hydroxy-8-azabicyclo[3.2.1]octane-7β-yl ester	Generator
Phenylacetic acid (1S,5R)-3a-hydroxy-8-azabicyclo[3.2.1]octane-7b-yl ester	Generator
Phenylacetic acid (1S,5R)-3α-hydroxy-8-azabicyclo[3.2.1]octane-7β-yl ester	Generator

Chemical Formula

C₁₅H₁₉NO₃

Average Mass

261.3210 Da

Monoisotopic Mass

261.13649 Da

IUPAC Name

(1R,3R,5S,6R)-3-hydroxy-8-azabicyclo[3.2.1]octan-6-yl 2-phenylacetate

Traditional Name

(1R,3R,5S,6R)-3-hydroxy-8-azabicyclo[3.2.1]octan-6-yl phenylacetate

CAS Registry Number

Not Available

SMILES

O[C@@H]1C[C@@H]2C[C@@H](OC(=O)CC3=CC=CC=C3)[C@H](C1)N2

InChI Identifier

InChI=1S/C15H19NO3/c17-12-7-11-8-14(13(9-12)16-11)19-15(18)6-10-4-2-1-3-5-10/h1-5,11-14,16-17H,6-9H2/t11-,12-,13+,14-/m1/s1

InChI Key

LZGZKTSKMTXSGV-YIYPIFLZSA-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 hypericifolium Lam.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Tropane alkaloids

Sub Class

Not Available

Direct Parent

Tropane alkaloids

Alternative Parents

Substituents

Tropane alkaloid
Monocyclic benzene moiety
Piperidine
Benzenoid
Cyclic alcohol
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Secondary amine
Organic nitrogen compound
Amine
Organic oxide
Organopnictogen compound
Alcohol
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen 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	1.06	ALOGPS
logP	0.78	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	15.16	ChemAxon
pKa (Strongest Basic)	9.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.49 m³·mol⁻¹	ChemAxon
Polarizability	26.88 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

Chemspider ID

9304206

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11129086

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3-Phenylacetoxynortropane (NP0067746)

MOL for NP0067746 (3-Phenylacetoxynortropane)

3D MOL for NP0067746 (3-Phenylacetoxynortropane)

3D SDF for NP0067746 (3-Phenylacetoxynortropane)

3D-SDF for NP0067746 (3-Phenylacetoxynortropane)

PDB for NP0067746 (3-Phenylacetoxynortropane)

3D PDB for NP0067746 (3-Phenylacetoxynortropane)

SMILES for NP0067746 (3-Phenylacetoxynortropane)

INCHI for NP0067746 (3-Phenylacetoxynortropane)

Structure for NP0067746 (3-Phenylacetoxynortropane)

3D Structure for NP0067746 (3-Phenylacetoxynortropane)