NP-MRD: Showing NP-Card for Emetine (NP0050972)

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Record Information

Version

2.0

Created at

2022-04-27 22:26:16 UTC

Updated at

2022-04-27 22:26:16 UTC

NP-MRD ID

NP0050972

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Emetine

Description

Emetine, also known as emetan or methyl cephaeline, belongs to the class of organic compounds known as emetine alkaloids. These are alkaloids with a structure characterized by the presence of both an isoquinoline and a benzoquinolizidine nuclei. Emetine is a very strong basic compound (based on its pKa). Emetine is found in Alangium longiflorum, Carapichea affinis, Cephaelis acuminata, Cephaelis ipecacuanha , Cephalis acuminata, Cephalis ipecacuanha, Hedera helix , Psychotria burucana, Psychotria ipecacuanha , Psychotria klugii and Uragoga ipecacuanha. Emetine was first documented in 2005 (PMID: 16109351). A pyridoisoquinoline comprising emetam having methoxy substituents at the 6'-, 7'-, 10- and 11-positions (PMID: 17094176).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1572004221603172D          

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M  END

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    6.1579   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204   -1.5395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.2539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204   -2.9684    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 18  6  1  1  0  0  0
 18 17  1  0  0  0  0
 19  7  1  0  0  0  0
 19 13  2  0  0  0  0
 20  8  1  0  0  0  0
 20 14  2  0  0  0  0
 21 11  1  6  0  0  0
 21 12  1  0  0  0  0
 21 18  1  0  0  0  0
 22 15  2  0  0  0  0
 22 19  1  0  0  0  0
 23 16  2  0  0  0  0
 23 20  1  0  0  0  0
 24 11  1  6  0  0  0
 24 22  1  0  0  0  0
 25 12  1  0  0  0  0
 25 23  1  0  0  0  0
 26 13  1  0  0  0  0
 27 14  1  0  0  0  0
 28 15  1  0  0  0  0
 28 26  2  0  0  0  0
 29 16  1  0  0  0  0
 29 27  2  0  0  0  0
 30  9  1  0  0  0  0
 30 24  1  0  0  0  0
 31 10  1  0  0  0  0
 31 17  1  0  0  0  0
 31 25  1  0  0  0  0
 32  2  1  0  0  0  0
 32 26  1  0  0  0  0
 33  3  1  0  0  0  0
 33 27  1  0  0  0  0
 34  4  1  0  0  0  0
 34 28  1  0  0  0  0
 35  5  1  0  0  0  0
 35 29  1  0  0  0  0
 18 36  1  6  0  0  0
 21 37  1  1  0  0  0
 24 38  1  1  0  0  0
 25 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0050972

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(C[C@@]2([H])C[C@]3([H])N(CCC4=CC(OC)=C(OC)C=C34)C[C@]2([H])CC)NCCC2=CC(OC)=C(OC)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C29H40N2O4/c1-6-18-17-31-10-8-20-14-27(33-3)29(35-5)16-23(20)25(31)12-21(18)11-24-22-15-28(34-4)26(32-2)13-19(22)7-9-30-24/h13-16,18,21,24-25,30H,6-12,17H2,1-5H3/t18-,21-,24+,25-/m0/s1

> <INCHI_KEY>
AUVVAXYIELKVAI-CKBKHPSWSA-N

> <FORMULA>
C29H40N2O4

> <MOLECULAR_WEIGHT>
480.649

> <EXACT_MASS>
480.298807776

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
54.91788855198844

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R)-1-{[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl]methyl}-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

> <ALOGPS_LOGP>
4.18

> <JCHEM_LOGP>
4.488257155000001

> <ALOGPS_LOGS>
-5.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
9.108974099165897

> <JCHEM_POLAR_SURFACE_AREA>
52.19000000000001

> <JCHEM_REFRACTIVITY>
139.7507

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.82e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
emetine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       1.485  -0.206   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.055 -10.876   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.805  -0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.485 -10.876   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.035  -4.207   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.255  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.825  -4.207   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.055  -2.874   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.795  -4.207   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.825  -6.875   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.255  -6.875   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.055  -5.541   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.485  -5.541   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.255  -4.207   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.055  -8.208   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.485  -8.208   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       1.485  -2.874   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0       6.105  -0.206   0.000  0.00  0.00           N+0
HETATM   32  O   UNK     0      -0.825  -9.542   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      13.035  -1.540   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.255  -9.542   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      11.495  -4.207   0.000  0.00  0.00           O+0
HETATM   36  H   UNK     0       3.025  -2.874   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.335  -4.207   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.025  -5.541   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0       5.335  -1.540   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   32                                                            
CONECT    3   33                                                            
CONECT    4   34                                                            
CONECT    5   35                                                            
CONECT    6    1   18                                                       
CONECT    7    9   19                                                       
CONECT    8   10   20                                                       
CONECT    9    7   30                                                       
CONECT   10    8   31                                                       
CONECT   11   21   24                                                       
CONECT   12   21   25                                                       
CONECT   13   19   26                                                       
CONECT   14   20   27                                                       
CONECT   15   22   28                                                       
CONECT   16   23   29                                                       
CONECT   17   18   31                                                       
CONECT   18    6   17   21   36                                             
CONECT   19    7   13   22                                                  
CONECT   20    8   14   23                                                  
CONECT   21   11   12   18   37                                             
CONECT   22   15   19   24                                                  
CONECT   23   16   20   25                                                  
CONECT   24   11   22   30   38                                             
CONECT   25   12   23   31   39                                             
CONECT   26   13   28   32                                                  
CONECT   27   14   29   33                                                  
CONECT   28   15   26   34                                                  
CONECT   29   16   27   35                                                  
CONECT   30    9   24                                                       
CONECT   31   10   17   25                                                  
CONECT   32    2   26                                                       
CONECT   33    3   27                                                       
CONECT   34    4   28                                                       
CONECT   35    5   29                                                       
CONECT   36   18                                                            
CONECT   37   21                                                            
CONECT   38   24                                                            
CONECT   39   25                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
Cephaeline methyl ether	ChEBI
Emetan	ChEBI
Emetin	ChEBI
Methyl cephaeline	ChEBI
Dihydrochloride, emetine	MeSH
Emetine dihydrochloride	MeSH
Hydrochloride, emetine	MeSH
Ipecine	MeSH
Methylcephaeline	MeSH
Emetine hydrochloride	MeSH

Chemical Formula

C₂₉H₄₀N₂O₄

Average Mass

480.6490 Da

Monoisotopic Mass

480.29881 Da

IUPAC Name

(1R)-1-{[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl]methyl}-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Traditional Name

emetine

CAS Registry Number

Not Available

SMILES

[H][C@]1(C[C@@]2([H])C[C@]3([H])N(CCC4=CC(OC)=C(OC)C=C34)C[C@]2([H])CC)NCCC2=CC(OC)=C(OC)C=C12

InChI Identifier

InChI=1S/C29H40N2O4/c1-6-18-17-31-10-8-20-14-27(33-3)29(35-5)16-23(20)25(31)12-21(18)11-24-22-15-28(34-4)26(32-2)13-19(22)7-9-30-24/h13-16,18,21,24-25,30H,6-12,17H2,1-5H3/t18-,21-,24+,25-/m0/s1

InChI Key

AUVVAXYIELKVAI-CKBKHPSWSA-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
Alangium longiflorum	Plant	KNApSAcK
Carapichea affinis	-	KNApSAcK
Cephaelis acuminata	Plant	KNApSAcK
Cephaelis ipecacuanha	Plant	KNApSAcK
Cephalis acuminata	-	KNApSAcK
Cephalis ipecacuanha	-	KNApSAcK
Hedera helix	Plant	KNApSAcK
Psychotria burucana	Plant	KNApSAcK
Psychotria ipecacuanha	Plant	KNApSAcK
Psychotria klugii	Plant	KNApSAcK
Uragoga ipecacuanha	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as emetine alkaloids. These are alkaloids with a structure characterized by the presence of both an isoquinoline and a benzoquinolizidine nuclei.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Emetine alkaloids

Sub Class

Not Available

Direct Parent

Emetine alkaloids

Alternative Parents

Substituents

Emetine alkaloid
Quinolizidine
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
Aralkylamine
Piperidine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Secondary aliphatic amine
Ether
Azacycle
Secondary amine
Organoheterocyclic compound
Organonitrogen compound
Amine
Organopnictogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoquinoline alkaloid (CHEBI:4781 )
pyridoisoquinoline (CHEBI:4781 )
Alkaloids (C09421 )
Isoquinoline alkaloids (C09421 )

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	4.18	ALOGPS
logP	4.49	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	9.11	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.19 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	139.75 m³·mol⁻¹	ChemAxon
Polarizability	54.92 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB13393

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001849

Chemspider ID

Not Available

KEGG Compound ID

C09421

BioCyc ID

CPD-14817

BiGG ID

Not Available

Wikipedia Link

Emetine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

4781

Good Scents ID

Not Available

References

General References

Silber TJ: Ipecac syrup abuse, morbidity, and mortality: isn't it time to repeal its over-the-counter status? J Adolesc Health. 2005 Sep;37(3):256-60. doi: 10.1016/j.jadohealth.2004.08.022. [PubMed:16109351 ]
Calzada F, Alanis AD: Additional antiprotozoal flavonol glycosides of the aerial parts of Helianthemum glomeratum. Phytother Res. 2007 Jan;21(1):78-80. doi: 10.1002/ptr.2031. [PubMed:17094176 ]

Showing NP-Card for Emetine (NP0050972)

MOL for NP0050972 (Emetine)

3D MOL for NP0050972 (Emetine)

3D SDF for NP0050972 (Emetine)

3D-SDF for NP0050972 (Emetine)

PDB for NP0050972 (Emetine)

3D PDB for NP0050972 (Emetine)

SMILES for NP0050972 (Emetine)

INCHI for NP0050972 (Emetine)

Structure for NP0050972 (Emetine)

3D Structure for NP0050972 (Emetine)