NP-MRD: Showing NP-Card for Homatropine hydrobromide (NP0138849)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-06-29 19:19:57 UTC

Updated at

2022-06-29 19:19:57 UTC

NP-MRD ID

NP0138849

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Homatropine hydrobromide

Description

HOMATROPINE HYDROBROMIDE, also known as ak-homatropine or I - homatrine, 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. Homatropine hydrobromide was first documented in 2006 (PMID: 30000723). Based on a literature review a small amount of articles have been published on HOMATROPINE HYDROBROMIDE (PMID: 34084029) (PMID: 26771454) (PMID: 25304219) (PMID: 23303483).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
    0.7611    0.0000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2225    0.7336   -2.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9511    0.2307   -1.0308 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1590    1.2136    0.0092 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6344    1.2468    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0378   -0.1887    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8387   -0.8313   -0.6200 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1094   -1.5995    0.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969   -0.7339    1.1819 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1548   -0.9171    0.5458 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2462   -1.4745    1.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1050   -1.8454    2.3624 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625   -1.6843    0.5128 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4364   -2.3576    1.3853 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2285   -0.4689    0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917    0.7380    0.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2849    1.8550   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792    1.7801   -0.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2070    0.5556   -0.8847 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5275   -0.5557   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4540    0.7037    1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5262    1.8201   -2.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9928    0.1999   -2.8987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2729    0.6879   -2.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8306    2.2275   -0.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7682    1.5479    1.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1961    1.9440   -0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9581   -0.2879   -0.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2595   -0.6350    1.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1468   -1.4851   -1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8365   -2.0649    1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5809   -2.4308   -0.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9996   -1.1213    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3907   -2.4244   -0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4988   -1.9241    2.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5656    0.8730    0.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7861    2.7940   -0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1161    2.6681   -1.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2224    0.4681   -1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0227   -1.5381   -0.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5470    1.3256    1.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1073    0.9553    2.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 21  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  7  3  1  0
 20 15  1  0
 21  4  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  2 25  1  0
  4 26  1  6
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  6
  8 32  1  0
  8 33  1  0
  9 34  1  1
 21 42  1  0
 21 43  1  0
 13 35  1  6
 14 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
M  END


  Mrv1652306292221192D          

 21 22  0  0  1  0            999 V2000
   -0.9969    1.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815    0.7732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0132    1.7001    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6582    1.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6582    0.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0132   -0.1537    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2089    0.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8509    0.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2089    1.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0259    0.7732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3866    0.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0259   -0.6558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2116    0.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6241   -0.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4491   -0.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8616   -1.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4491   -2.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6241   -2.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2116   -1.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6241    0.7732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8651    0.0000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  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  2  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  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
 13 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138849

> <DATABASE_NAME>
NP-MRD

> <SMILES>
Br.CN1[C@H]2CC[C@@H]1CC(C2)OC(=O)C(O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO3.BrH/c1-17-12-7-8-13(17)10-14(9-12)20-16(19)15(18)11-5-3-2-4-6-11;/h2-6,12-15,18H,7-10H2,1H3;1H/t12-,13+,14?,15?;

> <INCHI_KEY>
DWSGTFTVBLXELC-MOTQWOLNSA-N

> <FORMULA>
C16H22BrNO3

> <MOLECULAR_WEIGHT>
356.26

> <EXACT_MASS>
355.078307

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
29.09923160224502

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
1.593867434333332

> <ALOGPS_LOGS>
-1.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.99215218165852

> <JCHEM_PKA_STRONGEST_BASIC>
9.384485571609536

> <JCHEM_POLAR_SURFACE_AREA>
49.769999999999996

> <JCHEM_REFRACTIVITY>
75.80540000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl hydroxy(phenyl)acetate hydrobromide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -1.861   1.919   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -3.325   1.443   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -3.758   3.173   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.962   2.213   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.962   0.673   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.758  -0.287   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.257   0.056   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.588   1.443   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.257   2.831   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.048   1.443   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.722   0.110   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.048  -1.224   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.262   0.110   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.032  -1.224   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.572  -1.224   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.342  -2.558   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.572  -3.891   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.032  -3.891   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.262  -2.558   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.032   1.443   0.000  0.00  0.00           O+0
HETATM   21 Br   UNK     0       9.082   0.000   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   20                                                  
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   13                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
AK-homatropine	MeSH
I - homatrine	MeSH
Homatropin - pos	MeSH
Minims-homatropin	MeSH
Homatropine hydrochloride, (endo-(+-)-isomer)	MeSH
Isopto homatropine	MeSH
Minims-homatropine hydrobromide	MeSH
Homatropine	MeSH
Homatropine hydrobromide, (endo-(+-)-isomer)	MeSH
Homatropine sulfate (2:1), endo-isomer	MeSH
Homatropine, (3(S)-endo)-isomer	MeSH
Homatropine, exo-(+-)-isomer	MeSH
Homatropine sulfate (1:1), (3(R)-endo)-isomer	MeSH
Homatropine sulfate (1:1), (3(S)-endo)-isomer	MeSH

Chemical Formula

C₁₆H₂₂BrNO₃

Average Mass

356.2600 Da

Monoisotopic Mass

355.07831 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

51-56-9

SMILES

Br.CN1[C@H]2CC[C@@H]1CC(C2)OC(=O)C(O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H21NO3.BrH/c1-17-12-7-8-13(17)10-14(9-12)20-16(19)15(18)11-5-3-2-4-6-11;/h2-6,12-15,18H,7-10H2,1H3;1H/t12-,13+,14?,15?;

InChI Key

DWSGTFTVBLXELC-MOTQWOLNSA-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

Not Available

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
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Alcohol
Organic oxide
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Carbonyl group
Hydrocarbon derivative
Aromatic alcohol
Hydrobromide
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

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

4925541

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6419941

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Thomas J, Rajashekar B, Kamath A, Gogate P: Comparison between Plusoptix A09 and gold standard cycloplegic refraction in preschool children and agreement to detect refractive amblyogenic risk factors. Oman J Ophthalmol. 2021 Feb 27;14(1):14-19. doi: 10.4103/ojo.OJO_284_2019. eCollection 2021 Jan-Apr. [PubMed:34084029 ]
Authors unspecified: Homatropine.. 2006. [PubMed:30000723 ]
Fang L, Yu J, Jiang Z, Guo X: Preparation of a beta-Cyclodextrin-Based Open-Tubular Capillary Electrochromatography Column and Application for Enantioseparations of Ten Basic Drugs. PLoS One. 2016 Jan 15;11(1):e0146292. doi: 10.1371/journal.pone.0146292. eCollection 2016. [PubMed:26771454 ]
Sander BP, Collins MJ, Read SA: The effect of topical adrenergic and anticholinergic agents on the choroidal thickness of young healthy adults. Exp Eye Res. 2014 Nov;128:181-9. doi: 10.1016/j.exer.2014.10.003. Epub 2014 Oct 7. [PubMed:25304219 ]
Zuo L, Meng H, Wu J, Jiang Z, Xu S, Guo X: Combined use of ionic liquid and beta-CD for enantioseparation of 12 pharmaceuticals using CE. J Sep Sci. 2013 Feb;36(3):517-23. doi: 10.1002/jssc.201200824. Epub 2013 Jan 10. [PubMed:23303483 ]

Showing NP-Card for Homatropine hydrobromide (NP0138849)

MOL for NP0138849 (Homatropine hydrobromide)

3D MOL for NP0138849 (Homatropine hydrobromide)

3D SDF for NP0138849 (Homatropine hydrobromide)

3D-SDF for NP0138849 (Homatropine hydrobromide)

PDB for NP0138849 (Homatropine hydrobromide)

3D PDB for NP0138849 (Homatropine hydrobromide)

SMILES for NP0138849 (Homatropine hydrobromide)

INCHI for NP0138849 (Homatropine hydrobromide)

Structure for NP0138849 (Homatropine hydrobromide)

3D Structure for NP0138849 (Homatropine hydrobromide)