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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-23 15:30:42 UTC

Update Date

2021-09-14 15:44:46 UTC

HMDB ID

HMDB0006548

Secondary Accession Numbers

HMDB06548

Metabolite Identification

Common Name

Ecgonine

Description

Ecgonine is an organic chemical and tropane alkaloid found naturally in coca leaves. It is has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance, as are all known substances which can be used as precursors to ecgonine itself. Structurally, ecgonine is a cycloheptane derivative with a nitrogen bridge. It is obtained by hydrolysis of cocaine with acids or alkalis, and crystallizes with one molecule of water, the crystals melting at 198-199oC. It is levorotary, and on warming with alkalis gives iso-ecgonine, which is dextrorotary. It is a tertiary base, and has the properties of an acid and an alcohol. It is the carboxylic acid corresponding to tropine, for it yields the same products on oxidation, and by treatment with phosphorus pentachloride is converted into anhydroecgonine, C9H13NO2, which, when heated to 280oC with hydrochloric acid, eliminates carbon dioxide and yields tropidine, C8H13N.(Wikipedia ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv0541 02231220432D          

 13 14  0  0  1  0            999 V2000
   12.1660   -6.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3306   -5.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2851   -6.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8453   -5.0379    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7389   -5.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4327   -6.5434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8393   -4.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1660   -5.5672    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.7298   -6.4343    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5618   -6.3554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5455   -4.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3628   -4.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1349   -4.1282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  9  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  9  1  0  0  0  0
  1  3  1  0  0  0  0
  9 10  1  1  0  0  0
  2  4  1  0  0  0  0
  8 11  1  1  0  0  0
  2  5  1  0  0  0  0
 11 12  1  0  0  0  0
  3  6  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006548

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2CCC1[C@H]([C@@H](O)C2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H15NO3/c1-10-5-2-3-6(10)8(9(12)13)7(11)4-5/h5-8,11H,2-4H2,1H3,(H,12,13)/t5?,6?,7-,8+/m0/s1

> <INCHI_KEY>
PHMBVCPLDPDESM-RLXKETGRSA-N

> <FORMULA>
C9H15NO3

> <MOLECULAR_WEIGHT>
185.2203

> <EXACT_MASS>
185.105193351

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
18.827638677259596

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.69

> <JCHEM_LOGP>
-3.0901585696393723

> <ALOGPS_LOGS>
0.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.871788470590886

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4801822466094126

> <JCHEM_PKA_STRONGEST_BASIC>
9.69054450259908

> <JCHEM_POLAR_SURFACE_AREA>
60.77

> <JCHEM_REFRACTIVITY>
46.5693

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ecgonine

> <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  C   UNK     0      22.710 -11.495   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.150 -10.392   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.066 -11.495   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      20.245  -9.404   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      20.046 -11.034   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.474 -12.214   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.233  -7.864   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.710 -10.392   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.762 -12.011   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      25.315 -11.863   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      23.418  -9.042   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      24.944  -8.994   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      22.652  -7.706   0.000  0.00  0.00           O+0
CONECT    1    9    3                                                       
CONECT    2    8    4    5                                                  
CONECT    3    4    1    6                                                  
CONECT    4    3    7    2                                                  
CONECT    5    6    2                                                       
CONECT    6    5    3                                                       
CONECT    7    4                                                            
CONECT    8    2    9   11                                                  
CONECT    9    1    8   10                                                  
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

COMPND    HMDB0006548
HETATM    1  C1  UNL     1      -2.335   0.221  -1.262  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.024   0.382  -0.718  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.023   0.949   0.616  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.216  -0.193   1.572  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.083  -1.415   0.717  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.334  -0.873  -0.494  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.090  -0.666  -0.160  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.931  -1.019  -1.330  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.393  -1.422  -2.387  1.00  0.00           O  
HETATM   10  O2  UNL     1       3.316  -0.914  -1.282  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.457   0.720   0.269  1.00  0.00           C  
HETATM   12  O3  UNL     1       2.056   1.445  -0.783  1.00  0.00           O  
HETATM   13  C9  UNL     1       0.357   1.518   0.854  1.00  0.00           C  
HETATM   14  H1  UNL     1      -3.144   0.667  -0.657  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.551  -0.841  -1.521  1.00  0.00           H  
HETATM   16  H3  UNL     1      -2.367   0.765  -2.246  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.781   1.747   0.714  1.00  0.00           H  
HETATM   18  H5  UNL     1      -0.387  -0.246   2.338  1.00  0.00           H  
HETATM   19  H6  UNL     1      -2.147  -0.140   2.147  1.00  0.00           H  
HETATM   20  H7  UNL     1      -2.068  -1.823   0.445  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.452  -2.206   1.170  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.501  -1.571  -1.360  1.00  0.00           H  
HETATM   23  H10 UNL     1       1.365  -1.409   0.644  1.00  0.00           H  
HETATM   24  H11 UNL     1       3.747  -0.662  -0.412  1.00  0.00           H  
HETATM   25  H12 UNL     1       2.263   0.621   1.039  1.00  0.00           H  
HETATM   26  H13 UNL     1       2.618   2.155  -0.346  1.00  0.00           H  
HETATM   27  H14 UNL     1       0.366   2.578   0.465  1.00  0.00           H  
HETATM   28  H15 UNL     1       0.456   1.634   1.970  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    6
CONECT    3    4   13   17
CONECT    4    5   18   19
CONECT    5    6   20   21
CONECT    6    7   22
CONECT    7    8   11   23
CONECT    8    9    9   10
CONECT   10   24
CONECT   11   12   13   25
CONECT   12   26
CONECT   13   27   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2R,3S)-3-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid	HMDB
3-b-Hydroxy-2-b-tropanecarboxylic acid	HMDB
3-beta-Hydroxy-2-beta-tropanecarboxylic acid	HMDB
Ekgonin	HMDB
L-Ecgonine	HMDB
Ecgonine acetate, (1R-(exo,exo))-isomer	HMDB
Ecgonine hydrochloride	HMDB
Ecgonine, (1R-(2-endo,3-exo))-isomer	HMDB

Chemical Formula

C₉H₁₅NO₃

Average Molecular Weight

185.2203

Monoisotopic Molecular Weight

185.105193351

IUPAC Name

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

Traditional Name

ecgonine

CAS Registry Number

481-37-8

SMILES

CN1C2CCC1[C@H]([C@@H](O)C2)C(O)=O

InChI Identifier

InChI=1S/C9H15NO3/c1-10-5-2-3-6(10)8(9(12)13)7(11)4-5/h5-8,11H,2-4H2,1H3,(H,12,13)/t5?,6?,7-,8+/m0/s1

InChI Key

PHMBVCPLDPDESM-RLXKETGRSA-N

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
Cyclic alcohol
Pyrrolidine
Amino acid or derivatives
Amino acid
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Amine
Organic oxide
Organopnictogen compound
Alcohol
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Tropane alkaloids (C10858 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0006548)

Source

Exogenous

Exogenous (HMDB: HMDB0006548)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0006548)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	205 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	178 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1050 g/L	ALOGPS
logP	-0.69	ALOGPS
logP	-3.1	ChemAxon
logS	0.75	ALOGPS
pKa (Strongest Acidic)	3.48	ChemAxon
pKa (Strongest Basic)	9.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	60.77 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	46.57 m³·mol⁻¹	ChemAxon
Polarizability	18.83 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	141.129	31661259
DarkChem	[M-H]-	137.851	31661259
DeepCCS	[M+H]+	142.46	30932474
DeepCCS	[M-H]-	140.065	30932474
DeepCCS	[M-2H]-	173.953	30932474
DeepCCS	[M+Na]+	148.714	30932474
AllCCS	[M+H]+	142.6	32859911
AllCCS	[M+H-H2O]+	138.4	32859911
AllCCS	[M+NH4]+	146.4	32859911
AllCCS	[M+Na]+	147.5	32859911
AllCCS	[M-H]-	140.2	32859911
AllCCS	[M+Na-2H]-	140.8	32859911
AllCCS	[M+HCOO]-	141.5	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ecgonine,1TMS,isomer #1	CN1C2CCC1[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C)C2	1668.1	Semi standard non polar	33892256
Ecgonine,1TMS,isomer #1	CN1C2CCC1[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C)C2	1520.4	Standard non polar	33892256
Ecgonine,1TMS,isomer #1	CN1C2CCC1[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C)C2	2299.7	Standard polar	33892256
Ecgonine,1TMS,isomer #2	CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O)C2	1607.2	Semi standard non polar	33892256
Ecgonine,1TMS,isomer #2	CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O)C2	1578.6	Standard non polar	33892256
Ecgonine,1TMS,isomer #2	CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O)C2	2371.8	Standard polar	33892256
Ecgonine,2TMS,isomer #1	CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C2	1686.6	Semi standard non polar	33892256
Ecgonine,2TMS,isomer #1	CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C2	1653.8	Standard non polar	33892256
Ecgonine,2TMS,isomer #1	CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C2	2108.2	Standard polar	33892256
Ecgonine,1TBDMS,isomer #1	CN1C2CCC1[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C2	1880.3	Semi standard non polar	33892256
Ecgonine,1TBDMS,isomer #1	CN1C2CCC1[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C2	1760.2	Standard non polar	33892256
Ecgonine,1TBDMS,isomer #1	CN1C2CCC1[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C2	2440.8	Standard polar	33892256
Ecgonine,1TBDMS,isomer #2	CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C2	1834.7	Semi standard non polar	33892256
Ecgonine,1TBDMS,isomer #2	CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C2	1820.3	Standard non polar	33892256
Ecgonine,1TBDMS,isomer #2	CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C2	2508.2	Standard polar	33892256
Ecgonine,2TBDMS,isomer #1	CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C2	2128.7	Semi standard non polar	33892256
Ecgonine,2TBDMS,isomer #1	CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C2	2125.3	Standard non polar	33892256
Ecgonine,2TBDMS,isomer #1	CN1C2CCC1[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C2	2349.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ecgonine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-9200000000-48c3b8ee572b2dc52292	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ecgonine GC-MS (2 TMS) - 70eV, Positive	splash10-006t-9132000000-9a8887ca9dce4b08af81	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ecgonine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ecgonine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine 10V, Positive-QTOF	splash10-014r-0900000000-84cf8248e17a8b226247	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine 20V, Positive-QTOF	splash10-0gb9-0900000000-ada9e3b58a4a68bf34fe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine 40V, Positive-QTOF	splash10-0fk9-3900000000-4fe8aa09d75ccea8cb33	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine 10V, Negative-QTOF	splash10-007o-0900000000-c8352412d369827945bc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine 20V, Negative-QTOF	splash10-00dl-0900000000-143c9c6dc9126fa654dc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine 40V, Negative-QTOF	splash10-00dl-1900000000-cb49be4d17eb1921ff3e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine 10V, Positive-QTOF	splash10-000i-0900000000-4a6fc2f9a39f6a7a3d44	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine 20V, Positive-QTOF	splash10-00kv-5900000000-a2ec3ebcb3ee1f393d9b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine 40V, Positive-QTOF	splash10-00dj-9700000000-ac3cdeb9ee66f2c193db	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine 10V, Negative-QTOF	splash10-0159-0900000000-dc9636670e82e30cec7c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine 20V, Negative-QTOF	splash10-007o-1900000000-5cbac175885e0c570c49	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ecgonine 40V, Negative-QTOF	splash10-0089-6900000000-987da97e182a8b3e0ba9	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Endoplasmic reticulum

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

2273742

Wikipedia Link

Ecgonine

METLIN ID

Not Available

PubChem Compound

443003

PDB ID

Not Available

ChEBI ID

708641

Food Biomarker Ontology

Not Available

VMH ID

ECGON

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Valente MJ, Henrique R, Vilas-Boas V, Silva R, Bastos Mde L, Carvalho F, Guedes de Pinho P, Carvalho M: Cocaine-induced kidney toxicity: an in vitro study using primary cultured human proximal tubular epithelial cells. Arch Toxicol. 2012 Feb;86(2):249-61. doi: 10.1007/s00204-011-0749-3. Epub 2011 Oct 8. [PubMed:21983858 ]
Yao D, Shi X, Wang L, Gosnell BA, Chen C: Characterization of differential cocaine metabolism in mouse and rat through metabolomics-guided metabolite profiling. Drug Metab Dispos. 2013 Jan;41(1):79-88. doi: 10.1124/dmd.112.048678. Epub 2012 Oct 3. [PubMed:23034697 ]
Hezinova V, Aturki Z, Kleparnik K, D'Orazio G, Foret F, Fanali S: Simultaneous analysis of cocaine and its metabolites in urine by capillary electrophoresis-electrospray mass spectrometry using a pressurized liquid junction nanoflow interface. Electrophoresis. 2012 Feb;33(4):653-60. doi: 10.1002/elps.201100410. [PubMed:22451058 ]
Brim RL, Noon KR, Collins GT, Nichols J, Narasimhan D, Sunahara RK, Woods JH: The ability of bacterial cocaine esterase to hydrolyze cocaine metabolites and their simultaneous quantification using high-performance liquid chromatography-tandem mass spectrometry. Mol Pharmacol. 2011 Dec;80(6):1119-27. doi: 10.1124/mol.111.074534. Epub 2011 Sep 1. [PubMed:21885621 ]
van Nuijs AL, Abdellati K, Bervoets L, Blust R, Jorens PG, Neels H, Covaci A: The stability of illicit drugs and metabolites in wastewater, an important issue for sewage epidemiology? J Hazard Mater. 2012 Nov 15;239-240:19-23. doi: 10.1016/j.jhazmat.2012.04.030. Epub 2012 Apr 21. [PubMed:22572562 ]
Gonzalez-Marino I, Quintana JB, Rodriguez I, Sanchez-Mendez N, Cela R: Transformation of cocaine during water chlorination. Anal Bioanal Chem. 2012 Dec;404(10):3135-44. doi: 10.1007/s00216-012-6428-2. Epub 2012 Sep 30. [PubMed:23052872 ]
Hantson P, Capron A, Wallemacq P: Toxicokinetics of cocaine and metabolites in a body-packer becoming symptomatic. J Forensic Leg Med. 2011 Nov;18(8):385-7. doi: 10.1016/j.jflm.2011.07.004. Epub 2011 Aug 9. [PubMed:22018173 ]
Saussereau E, Lacroix C, Gaulier JM, Goulle JP: On-line liquid chromatography/tandem mass spectrometry simultaneous determination of opiates, cocainics and amphetamines in dried blood spots. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Feb 15;885-886:1-7. doi: 10.1016/j.jchromb.2011.11.035. Epub 2011 Dec 2. [PubMed:22281234 ]

Enzymes

Enzyme Details

1. Arylacetamide deacetylase

General function:: Involved in hydrolase activity
Specific function:: Arylacetamide deacetylation is an important enzyme activity in the metabolic activation of arylamine substrates to ultimate carcinogens. Displays major serine hydrolase activity in liver microsomes. Hydrolyzes also flutamide, which is an antiandrogen drug used for the treatment of prostate cancer that occasionally causes severe hepatotoxicity. Displays cellular triglyceride lipase activity in liver. Increases intracellular fatty acids derived from hydrolysis of newly formed triglyceride stores.
Gene Name:: AADAC
Uniprot ID:: P22760
Molecular weight:: 45733.28

Showing metabocard for Ecgonine (HMDB0006548)

MOL for HMDB0006548 (Ecgonine)

3D MOL for HMDB0006548 (Ecgonine)

3D SDF for HMDB0006548 (Ecgonine)

3D-SDF for HMDB0006548 (Ecgonine)

PDB for HMDB0006548 (Ecgonine)

3D PDB for HMDB0006548 (Ecgonine)

SMILES for HMDB0006548 (Ecgonine)

INCHI for HMDB0006548 (Ecgonine)

Structure for HMDB0006548 (Ecgonine)

3D Structure for HMDB0006548 (Ecgonine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes