NP-MRD: Showing NP-Card for Ecgonine methyl ester (NP0087505)

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Record Information

Version

2.0

Created at

2022-05-11 16:51:31 UTC

Updated at

2022-05-11 16:51:31 UTC

NP-MRD ID

NP0087505

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ecgonine methyl ester

Description

Ecgonine methyl ester, also known as methyl ecgonine, 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. Ecgonine methyl ester is a very strong basic compound (based on its pKa). Ecgonine methyl ester is found in Erythroxylum coca, Erythroxylum novogranatense and Mus musculus. Ecgonine methyl ester was first documented in 1992 (PMID: 1298401). Ecgonine methyl ester exists in all living organisms, ranging from bacteria to humans.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
    4.1204    0.5884    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8568    0.7268    0.2522 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0374   -0.3477   -0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716   -1.4931    0.2399 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7365   -0.1170   -0.7077 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0526   -1.3775   -1.1105 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0436   -2.3391   -0.1052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3358   -1.0703   -1.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0673   -0.0910   -0.7054 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0395   -0.6151    0.7225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7717   -0.0490    1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1740    0.7553    0.1502 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2950    1.1111   -0.6965 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0078    2.2666   -0.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3833   -0.4890    0.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2275    1.1732    1.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8719    0.9933    0.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9111    0.4797   -1.6504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6207   -1.8075   -1.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7669   -3.0141   -0.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1915   -0.5079   -2.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9352   -1.9535   -1.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0844    0.0128   -1.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0629   -1.7067    0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9435   -0.2782    1.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0729   -0.8228    1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0185    0.6020    2.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3804    1.6148    0.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2967    3.1302   -0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8103    2.4846   -0.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3738    2.1406    0.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  1  0
  9 13  1  0
 13 14  1  0
  6  5  1  0
 13 12  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  6
 12 28  1  1
 11 26  1  0
 11 27  1  0
 10 24  1  0
 10 25  1  0
  9 23  1  6
  8 21  1  0
  8 22  1  0
  6 19  1  6
  7 20  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
M  END


  Mrv0541 02231220392D          

 14 15  0  0  1  0            999 V2000
   13.2472  -11.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6712  -12.0423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2737  -12.3393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5874   -8.3478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9815   -9.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1950   -9.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7152  -10.9804    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.4926  -10.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7060   -9.7842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0478   -9.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9617  -10.6450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1748   -7.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8867  -11.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8426  -12.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  1  0  0  0
  2 13  1  0  0  0  0
  2 14  1  0  0  0  0
  3 13  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 12  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  7 13  1  1  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087505

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1C2CCC(C[C@@H]1O)N2C

> <INCHI_IDENTIFIER>
InChI=1S/C10H17NO3/c1-11-6-3-4-7(11)9(8(12)5-6)10(13)14-2/h6-9,12H,3-5H2,1-2H3/t6?,7?,8-,9+/m0/s1

> <INCHI_KEY>
QIQNNBXHAYSQRY-ABIFROTESA-N

> <FORMULA>
C10H17NO3

> <MOLECULAR_WEIGHT>
199.2469

> <EXACT_MASS>
199.120843415

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.816593722450087

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

> <ALOGPS_LOGP>
0.14

> <JCHEM_LOGP>
-0.2131918396666671

> <ALOGPS_LOGS>
0.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.5954100931088

> <JCHEM_PKA_STRONGEST_BASIC>
9.0392885149116

> <JCHEM_POLAR_SURFACE_AREA>
49.77

> <JCHEM_REFRACTIVITY>
51.3384

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.87e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ecgonine methyl ester

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      24.728 -20.641   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      29.253 -22.479   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      26.644 -23.033   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      29.097 -15.583   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      29.832 -18.583   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.231 -17.096   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.468 -20.497   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.653 -19.751   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.051 -18.264   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.223 -18.339   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.062 -19.871   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.326 -14.249   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.788 -22.003   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.573 -23.985   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   13   14                                                       
CONECT    3   13                                                            
CONECT    4    5    6   12                                                  
CONECT    5    4    7    8                                                  
CONECT    6    4    9   10                                                  
CONECT    7    5   11   13                                                  
CONECT    8    5    9                                                       
CONECT    9    6    8                                                       
CONECT   10    6   11                                                       
CONECT   11    1    7   10                                                  
CONECT   12    4                                                            
CONECT   13    2    3    7                                                  
CONECT   14    2                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
Methyl ecgonine	Kegg

Chemical Formula

C₁₀H₁₇NO₃

Average Mass

199.2469 Da

Monoisotopic Mass

199.12084 Da

IUPAC Name

methyl (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Traditional Name

ecgonine methyl ester

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]1C2CCC(C[C@@H]1O)N2C

InChI Identifier

InChI=1S/C10H17NO3/c1-11-6-3-4-7(11)9(8(12)5-6)10(13)14-2/h6-9,12H,3-5H2,1-2H3/t6?,7?,8-,9+/m0/s1

InChI Key

QIQNNBXHAYSQRY-ABIFROTESA-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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Erythroxylum coca	LOTUS Database	35616633
Erythroxylum novogranatense	LOTUS Database	35616633
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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

Piperidinecarboxylic acid
Tropane alkaloid
Beta-hydroxy acid
Hydroxy acid
Piperidine
N-alkylpyrrolidine
Methyl ester
Pyrrolidine
Cyclic alcohol
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organonitrogen compound
Alcohol
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organopnictogen compound
Amine
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Tropane alkaloids (C12448 )

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	0.14	ALOGPS
logP	-0.21	ChemAxon
logS	0.47	ALOGPS
pKa (Strongest Acidic)	14.6	ChemAxon
pKa (Strongest Basic)	9.04	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	2	ChemAxon
Refractivity	51.34 m³·mol⁻¹	ChemAxon
Polarizability	20.82 Å³	ChemAxon
Number of Rings	2	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

HMDB0006406

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023911

KNApSAcK ID

Not Available

Chemspider ID

391939

KEGG Compound ID

C12448

BioCyc ID

Not Available

BiGG ID

2267774

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443844

PDB ID

Not Available

ChEBI ID

708640

Good Scents ID

Not Available

References

General References

Roy IM, Jefferies TM, Threadgill MD, Dewar GH: Analysis of cocaine, benzoylecgonine, ecgonine methyl ester, ethylcocaine and norcocaine in human urine using HPLC with post-column ion-pair extraction and fluorescence detection. J Pharm Biomed Anal. 1992 Oct-Dec;10(10-12):943-8. doi: 10.1016/0731-7085(91)80103-g. [PubMed:1298401 ]

Showing NP-Card for Ecgonine methyl ester (NP0087505)

MOL for NP0087505 (Ecgonine methyl ester)

3D MOL for NP0087505 (Ecgonine methyl ester)

3D SDF for NP0087505 (Ecgonine methyl ester)

3D-SDF for NP0087505 (Ecgonine methyl ester)

PDB for NP0087505 (Ecgonine methyl ester)

3D PDB for NP0087505 (Ecgonine methyl ester)

SMILES for NP0087505 (Ecgonine methyl ester)

INCHI for NP0087505 (Ecgonine methyl ester)

Structure for NP0087505 (Ecgonine methyl ester)

3D Structure for NP0087505 (Ecgonine methyl ester)