NP-MRD: Showing NP-Card for hydroxytropacocaine (NP0149669)

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Record Information

Version

2.0

Created at

2022-09-02 05:35:36 UTC

Updated at

2022-09-02 05:35:36 UTC

NP-MRD ID

NP0149669

Secondary Accession Numbers

None

Natural Product Identification

Common Name

hydroxytropacocaine

Description

1-Hydroxy-8-methyl-8-azabicyclo[3.2.1]Octan-3-yl benzoate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. hydroxytropacocaine is found in Erythroxylum coca. 1-Hydroxy-8-methyl-8-azabicyclo[3.2.1]Octan-3-yl benzoate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.5382    1.7573   -0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2598    1.0322   -0.0210 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3460    0.1157   -1.1627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3922   -0.8968   -0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5620   -0.7236    0.7002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3195    0.0951    1.0731 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5808    0.6958    2.2874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1562   -0.8265    1.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3510   -0.9647   -0.0799 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9034   -0.2874   -0.0054 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1175   -0.9222   -0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1160   -2.1707   -0.1907 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4024   -0.2182    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4661    1.1501    0.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7090    1.7740    0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8692    1.0495    0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8281   -0.3139    0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5843   -0.9247   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0228   -0.5551   -1.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4366    2.7669   -0.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9156    1.8268    1.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3109    1.2195   -0.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6047    0.7087   -2.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3687   -0.7138   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0773   -1.9501   -1.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4643   -1.6797    1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4916   -0.1909    0.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3297    1.6436    2.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5528   -1.8268    1.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5287   -0.4823    2.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0862   -2.0588   -0.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5340    1.6875    0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6877    2.8429    0.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8139    1.5684    0.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7261   -0.9380   -0.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5163   -2.0185   -0.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3845    0.1511   -1.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1941   -1.4224   -2.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  0
  9 19  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  6  2  1  0
 18 13  1  0
 19  3  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  6
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  6
 19 37  1  0
 19 38  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END


  Mrv1533004241516522D          

 19 21  0  0  0  0            999 V2000
    2.1787    0.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3941   -0.0001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624    0.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624   -0.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9788   -1.7313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -0.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667    0.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1497   -0.0001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5622    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1497    1.4288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3872    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7997    1.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6247    1.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0372    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6247   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7997   -0.0001    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
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 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>
NP0149669

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2CCC1(O)CC(C2)OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H19NO3/c1-16-12-7-8-15(16,18)10-13(9-12)19-14(17)11-5-3-2-4-6-11/h2-6,12-13,18H,7-10H2,1H3

> <INCHI_KEY>
XJPJWHPAEMZDER-UHFFFAOYSA-N

> <FORMULA>
C15H19NO3

> <MOLECULAR_WEIGHT>
261.321

> <EXACT_MASS>
261.136493476

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.914136235552462

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl benzoate

> <ALOGPS_LOGP>
1.71

> <JCHEM_LOGP>
2.3208183879999997

> <ALOGPS_LOGS>
-1.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.125894068960221

> <JCHEM_PKA_STRONGEST_BASIC>
8.020727048464664

> <JCHEM_POLAR_SURFACE_AREA>
49.77

> <JCHEM_REFRACTIVITY>
71.57990000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxytropacocaine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       4.067   0.476   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.602  -0.000   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.170   1.730   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.966   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.966  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.170  -1.730   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.827  -3.232   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.671  -1.388   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.339  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.671   1.387   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.879  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.649   1.333   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.879   2.667   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.189   1.333   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.959   2.667   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.499   2.667   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.269   1.333   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.499  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.959  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2    7    8                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    3                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   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
1-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl benzoic acid	Generator

Chemical Formula

C₁₅H₁₉NO₃

Average Mass

261.3210 Da

Monoisotopic Mass

261.13649 Da

IUPAC Name

1-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl benzoate

Traditional Name

hydroxytropacocaine

CAS Registry Number

Not Available

SMILES

CN1C2CCC1(O)CC(C2)OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H19NO3/c1-16-12-7-8-15(16,18)10-13(9-12)19-14(17)11-5-3-2-4-6-11/h2-6,12-13,18H,7-10H2,1H3

InChI Key

XJPJWHPAEMZDER-UHFFFAOYSA-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 coca	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Tropane alkaloid
Benzoyl
Piperidine
N-alkylpyrrolidine
Cyclic alcohol
Pyrrolidine
Carboxylic acid ester
Hemiaminal
Monocarboxylic acid or derivatives
Alkanolamine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen 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	1.71	ALOGPS
logP	2.32	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	13.13	ChemAxon
pKa (Strongest Basic)	8.02	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.58 m³·mol⁻¹	ChemAxon
Polarizability	27.91 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

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

57467897

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for hydroxytropacocaine (NP0149669)

MOL for NP0149669 (hydroxytropacocaine)

3D MOL for NP0149669 (hydroxytropacocaine)

3D SDF for NP0149669 (hydroxytropacocaine)

3D-SDF for NP0149669 (hydroxytropacocaine)

PDB for NP0149669 (hydroxytropacocaine)

3D PDB for NP0149669 (hydroxytropacocaine)

SMILES for NP0149669 (hydroxytropacocaine)

INCHI for NP0149669 (hydroxytropacocaine)

Structure for NP0149669 (hydroxytropacocaine)

3D Structure for NP0149669 (hydroxytropacocaine)