NP-MRD: Showing NP-Card for Atroscine (NP0138837)

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Record Information

Version

2.0

Created at

2022-06-29 19:19:22 UTC

Updated at

2022-06-29 19:19:22 UTC

NP-MRD ID

NP0138837

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Atroscine

Description

Atroscine is found in Anisodus tanguticus, Atropanthe sinensis, Brugmansia arborea, Brugmansia sanguinea, Brugmansia candida, Datura discolor, Datura ferox, Datura inoxia, Datura metel, Datura quercifolia, Datura stramonium, Duboisia hopwoodii, Duboisia leichhardtii, Duboisia myoporoides, Hyoscyamus albus, Hyoscyamus desertorum, Hyoscyamus pusillus, Mandragora officinarum, Mandragora turcomanica, Scopolia carniolica, Scopolia japonica and Solandra grandiflora.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305221921022D          

 22 25  0  0  0  0            999 V2000
    0.0804    0.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3655    3.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7780    2.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5405    3.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3655    1.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1280    2.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2924   -0.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2924    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5405    0.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5405    1.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    0.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1280    1.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0967   -0.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0967    1.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -0.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417    0.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3030    1.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8650    0.2872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3655    0.2872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8905    1.7161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8905    0.2872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4562    0.2872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 18  1  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19  9  1  0  0  0  0
 20 17  2  0  0  0  0
 21 11  1  0  0  0  0
 21 17  1  0  0  0  0
 22 15  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138837

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2CC(CC1C1OC21)OC(=O)C(CO)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3

> <INCHI_KEY>
STECJAGHUSJQJN-UHFFFAOYSA-N

> <FORMULA>
C17H21NO4

> <MOLECULAR_WEIGHT>
303.3529

> <EXACT_MASS>
303.147058165

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.698402603451644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl 3-hydroxy-2-phenylpropanoate

> <ALOGPS_LOGP>
1.40

> <JCHEM_LOGP>
0.8949522950000002

> <ALOGPS_LOGS>
-1.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.145739865848086

> <JCHEM_PKA_STRONGEST_BASIC>
6.953523808607151

> <JCHEM_POLAR_SURFACE_AREA>
62.3

> <JCHEM_REFRACTIVITY>
79.72130000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl 3-hydroxy-2-phenylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0       0.150   1.012   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.282   5.871   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.052   4.537   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.742   5.871   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.282   3.203   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.972   4.537   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.546  -0.851   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.546   1.924   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.742   0.536   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.742   3.203   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.122   0.536   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.972   1.870   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.047  -1.194   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.047   2.266   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.251  -0.234   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.251   1.306   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.432   1.870   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.615   0.536   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -6.282   0.536   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.662   3.203   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.662   0.536   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.585   0.536   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   10                                                       
CONECT    6    4   10                                                       
CONECT    7   11   13                                                       
CONECT    8   11   14                                                       
CONECT    9   12   19                                                       
CONECT   10    5    6   12                                                  
CONECT   11    7    8   21                                                  
CONECT   12    9   10   17                                                  
CONECT   13    7   15   18                                                  
CONECT   14    8   16   18                                                  
CONECT   15   13   16   22                                                  
CONECT   16   14   15   22                                                  
CONECT   17   12   20   21                                                  
CONECT   18    1   13   14                                                  
CONECT   19    9                                                            
CONECT   20   17                                                            
CONECT   21   11   17                                                       
CONECT   22   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
boro Scopol	MeSH
BoroScopol	MeSH
Scoburen	MeSH
Winzer brand OF scopolamine borate	MeSH
Bull brand OF scopolamine hydrobromide	MeSH
Hamilton brand OF scopolamine hydrobromide	MeSH
Hope brand OF scopolamine	MeSH
Hydrobromide, scopolamine	MeSH
Hyoscine	MeSH
Novartis brand OF scopolamine	MeSH
Novartis consumer health brand OF scopolamine	MeSH
Scopolamine cooper	MeSH
Cooper brand OF scopolamine hydrobromide	MeSH
Inibisa brand OF scopolamine hydrobromide	MeSH
Kwells	MeSH
Renaudin brand OF scopolamine hydrobromide	MeSH
Scopoderm TTS	MeSH
Scopolamine hydrobromide	MeSH
Travacalm ho	MeSH
Vorigeno	MeSH
Alcon brand OF scopolamine hydrobromide	MeSH
boro-Scopol	MeSH
isopto Hyoscine	MeSH
Roche brand OF scopolamine hydrobromide	MeSH
Scopace	MeSH
Transderm scop	MeSH
Transderm V	MeSH
Transderm-V	MeSH

Chemical Formula

C₁₇H₂₁NO₄

Average Mass

303.3529 Da

Monoisotopic Mass

303.14706 Da

IUPAC Name

9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl 3-hydroxy-2-phenylpropanoate

Traditional Name

9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl 3-hydroxy-2-phenylpropanoate

CAS Registry Number

138-12-5

SMILES

CN1C2CC(CC1C1OC21)OC(=O)C(CO)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3

InChI Key

STECJAGHUSJQJN-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, 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
Anisodus tanguticus	LOTUS Database	35616633
Atropanthe sinensis	LOTUS Database	35616633
Brugmansia arborea	LOTUS Database	35616633
Brugmansia sanguinea	LOTUS Database	35616633
Brugmansia x candida	LOTUS Database	35616633
Datura discolor	LOTUS Database	35616633
Datura ferox	LOTUS Database	35616633
Datura inoxia	LOTUS Database	35616633
Datura metel	LOTUS Database	35616633
Datura quercifolia	LOTUS Database	35616633
Datura stramonium	LOTUS Database	35616633
Duboisia hopwoodii	LOTUS Database	35616633
Duboisia leichhardtii	LOTUS Database	35616633
Duboisia myoporoides	LOTUS Database	35616633
Hyoscyamus albus	LOTUS Database	35616633
Hyoscyamus desertorum	LOTUS Database	35616633
Hyoscyamus pusillus	LOTUS Database	35616633
Mandragora officinarum	LOTUS Database	35616633
Mandragora turcomanica	LOTUS Database	35616633
Scopolia carniolica	LOTUS Database	35616633
Scopolia japonica	LOTUS Database	35616633
Solandra grandiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (SCOPOLAMINE )

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	1.4	ALOGPS
logP	0.89	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	15.15	ChemAxon
pKa (Strongest Basic)	6.95	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.72 m³·mol⁻¹	ChemAxon
Polarizability	31.7 Å³	ChemAxon
Number of Rings	4	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

FDB023199

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hyoscine

METLIN ID

Not Available

PubChem Compound

5184

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Atroscine (NP0138837)

MOL for NP0138837 (Atroscine)

3D MOL for NP0138837 (Atroscine)

3D SDF for NP0138837 (Atroscine)

3D-SDF for NP0138837 (Atroscine)

PDB for NP0138837 (Atroscine)

3D PDB for NP0138837 (Atroscine)

SMILES for NP0138837 (Atroscine)

INCHI for NP0138837 (Atroscine)

Structure for NP0138837 (Atroscine)

3D Structure for NP0138837 (Atroscine)