NP-MRD: Showing NP-Card for Hyoscyamine (NP0001497)

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Record Information

Version

2.0

Created at

2012-09-06 15:16:49 UTC

Updated at

2024-09-03 04:16:45 UTC

NP-MRD ID

NP0001497

Natural Product DOI

https://doi.org/10.57994/0792

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hyoscyamine

Description

Hyoscyamine is a chemical compound, a tropane alkaloid it is the levo-isomer to atropine. It is a secondary metabolite of some plants, particularly henbane (Hyoscamus niger.). Hyoscyamine is used to provide symptomatic relief to various gastrointestinal disorders including spasms, peptic ulcers, irritable bowel syndrome, pancreatitis, colic and cystitis. It has also been used to relieve some heart problems, control some of the symptoms of Parkinson's disease, as well as for control of respiratory secretions in end of life care.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309272007302D          

 21 23  0  0  0  0            999 V2000
 9984.3638 9988.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.2007 9988.2932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9987.8435 9987.6720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9988.5566 9988.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.2723 9987.6720    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9989.2723 9986.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.9858 9986.4364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9988.5566 9988.9097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9987.1318 9988.0992    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9986.6272 9987.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.9363 9988.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.8023 9987.4342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9985.4498 9988.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.2783 9988.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.1876 9989.2474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9991.4146 9988.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.7001 9989.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.9856 9988.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.9855 9988.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.7000 9987.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4146 9988.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  2  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 14  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  9  3  1  6  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 16  1  0  0  0  0
  5 19  1  0  0  0  0
 15  2  1  1  0  0  0
 12  2  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0001497

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1

> <INCHI_KEY>
RKUNBYITZUJHSG-FXUDXRNXSA-N

> <FORMULA>
C17H23NO3

> <MOLECULAR_WEIGHT>
289.3694

> <EXACT_MASS>
289.167793607

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.741089874876113

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.19

> <JCHEM_LOGP>
1.571241016666666

> <ALOGPS_LOGS>
-2.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.145740617562414

> <JCHEM_PKA_STRONGEST_BASIC>
9.385561870758496

> <JCHEM_POLAR_SURFACE_AREA>
49.77

> <JCHEM_REFRACTIVITY>
80.81640000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.52e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-hyoscyamine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8637.4798645.418   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8640.9088644.814   0.000  0.00  0.00           N+0
HETATM    3  O   UNK     0    8643.9758643.654   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8645.3068644.425   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8646.6428643.654   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8646.6428642.116   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8647.9748641.348   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8645.3068645.965   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8642.6468644.452   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8641.7048643.233   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8642.2818645.948   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8640.1648643.211   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8639.5068645.906   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8639.1868644.400   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8640.8848646.595   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8650.6418645.964   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8649.3078646.734   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8647.9738645.964   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8647.9738644.424   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8649.3078643.654   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8650.6418644.424   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1   15   12                                                  
CONECT    3    4    9                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    4                                                            
CONECT    9   10   11    3                                                  
CONECT   10    9   12                                                       
CONECT   11    9   15                                                       
CONECT   12   10   14    2                                                  
CONECT   13   14   15                                                       
CONECT   14   12   13                                                       
CONECT   15   11   13    2                                                  
CONECT   16   17   21                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20    5                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
(-)-Atropine	ChEBI
(-)-Hyoscyamine	ChEBI
(S)-(-)-Hyoscyamine	ChEBI
[3(S)-endo]-alpha-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester	ChEBI
Daturine	ChEBI
Duboisine	ChEBI
L-Hyoscyamine	ChEBI
L-Tropine tropate	ChEBI
Tropine, (-)-tropate	ChEBI
[3(S)-endo]-a-(Hydroxymethyl)benzeneacetate 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester	Generator
[3(S)-endo]-a-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester	Generator
[3(S)-endo]-alpha-(Hydroxymethyl)benzeneacetate 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester	Generator
[3(S)-endo]-Α-(hydroxymethyl)benzeneacetate 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester	Generator
[3(S)-endo]-Α-(hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester	Generator
L-Tropine tropic acid	Generator
Tropine, (-)-tropic acid	Generator
(Leo)-atropine	HMDB
(Leo)-hyoscyamine	HMDB
(S)-(Leo)-hyoscyamine	HMDB
(S)Atropine	HMDB
Hyocyamine	HMDB
L-Atropine	HMDB
L-Hyopscyamine	HMDB
L-Hyoscamine	HMDB
Hyoscyamine	ChEBI

Chemical Formula

C₁₇H₂₃NO₃

Average Mass

289.3694 Da

Monoisotopic Mass

289.16779 Da

IUPAC Name

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

Traditional Name

L-hyoscyamine

CAS Registry Number

101-31-5

SMILES

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

InChI Identifier

InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1

InChI Key

RKUNBYITZUJHSG-FXUDXRNXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD3OD, experimental)	jaewoo.choi@oregonstate.edu	Not Available	Not Available	2023-08-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agrobacterium rhizogenes		LOTUS database
Anisodus acutangulus	Plant	KNApSAcK
Anisodus belladonna	Plant	KNApSAcK
Anisodus luridus	Plant	KNApSAcK
Anisodus luridus Link et Otto.	Plant	KNApSAcK
Anisodus tanguticus		LOTUS database
Anthocercis fasciculata	Plant	KNApSAcK
Anthocercis myoporoides	Plant	KNApSAcK
Anthocercis pannosa	Plant	KNApSAcK
Anthocercis viscosa	Plant	KNApSAcK
Anthocercis walcottii	Plant	KNApSAcK
Anthotroche myoporoides	Plant	KNApSAcK
Anthotroche pannosa	Plant	KNApSAcK
Anthotroche walcottii	Plant	KNApSAcK
Atropa acuminata		LOTUS database
Atropa baetica	Plant	KNApSAcK
Atropa bella-donna	Plant	KNApSAcK
Atropa belladona	Plant	KNApSAcK
Atropa belladonna	Plant	KNApSAcK
Brugmansia arborea	Plant	KNApSAcK
Corydalis yanhusuo	Plant	KNApSAcK
Cyphanthera anthocercidea	Plant	KNApSAcK
Cyphanthera odgersii		LOTUS database
Cyphanthera spinescens	Plant	KNApSAcK
Cyphomandra betaceae	Plant	KNApSAcK
Datura arborea L.	Plant	KNApSAcK
Datura ceratocaula	Plant	KNApSAcK
Datura inoxia	Plant	KNApSAcK
Datura metel	Plant	KNApSAcK
Datura meteloides DC.	Plant	KNApSAcK
Datura quercifolia	Plant	KNApSAcK
Datura stramonium	Plant	KNApSAcK
Duboisia arenitensis	Plant	KNApSAcK
Duboisia hopwoodii		LOTUS database
Duboisia leichhardtii	Plant	KNApSAcK
Duboisia myoporoides	Plant	KNApSAcK
Erythroxylon coca	-	KNApSAcK
Hyoscamus albus	-	KNApSAcK
Hyoscamus aurea	-	KNApSAcK
Hyoscamus muticus	-	KNApSAcK
Hyoscamus niger	-	KNApSAcK
Hyoscamus reticulatus	-	KNApSAcK
Hyosciamus niger	-	KNApSAcK
Hyoscyamus albus	Plant	KNApSAcK
Hyoscyamus boveanus	Plant	KNApSAcK
Hyoscyamus desertorum	Plant	KNApSAcK
Hyoscyamus muticus	Plant	KNApSAcK
Hyoscyamus niger	Plant	KNApSAcK
Hyoscyamus pusillus		LOTUS database
Hyoscyamus reticulatus	Plant	KNApSAcK
Latua pubiflora		LOTUS database
Lycium barbarum	Plant	KNApSAcK
Lycium chinense	Plant	KNApSAcK
Mandragora autumnale	Plant	KNApSAcK
Mandragora autumnalis	Plant	KNApSAcK
Mandragora autunnale	Plant	KNApSAcK
Mandragora officinarum		LOTUS database
Mandragora officinarum L.	Plant	KNApSAcK
Mandragora scopoliae	Plant	KNApSAcK
Mandragora turcomanica		LOTUS database
Mandragora turcomanica Mizger	Plant	KNApSAcK
Mandragora vernalis	Plant	KNApSAcK
Physochlaina alaica	Plant	KNApSAcK
Physochlaina orientalis	Plant	KNApSAcK
Przewalkia tangutica	-	KNApSAcK
Przewalskia tangutica	-	KNApSAcK
Scopolia carniolica	Plant	KNApSAcK
Scopolia japonica	Plant	KNApSAcK
Scopolia parviflora		LOTUS database
Solandra grandiflora		LOTUS database

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
Beta-hydroxy acid
Monocyclic benzene moiety
Hydroxy acid
Piperidine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate (CHEBI:17486 )
Tropane alkaloids (C02046 )
Tropan alkaloids (C02046 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	141 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.52 g/L	Not Available
LogP	1.8	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.52 g/L	ALOGPS
logP	2.19	ALOGPS
logP	1.57	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	15.15	ChemAxon
pKa (Strongest Basic)	9.39	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	5	ChemAxon
Refractivity	80.82 m³·mol⁻¹	ChemAxon
Polarizability	31.74 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