NP-MRD: Showing NP-Card for Aporheine (NP0138816)

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Record Information

Version

1.0

Created at

2022-06-29 19:18:24 UTC

Updated at

2022-06-29 19:18:24 UTC

NP-MRD ID

NP0138816

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aporheine

Description

Aporeine, also known as roemerine, belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Aporheine is found in Meconopsis cambrica, Papaver dubium, Papaver pilosum and Papaver rhoeas. Based on a literature review very few articles have been published on aporeine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 42  0  0  0  0  0  0  0  0999 V2000
    3.2615   -1.0812    1.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3484   -0.0374    0.9108 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558    1.0413    0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3836    2.1449   -0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9221    1.8833   -0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0298    2.9126   -0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411    2.7104   -0.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8482    1.4031   -0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9341    0.3778   -0.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4150    0.5872   -0.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4282   -0.4668   -0.1286 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9109   -1.8204    0.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5402   -2.0537   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9776   -3.3945    0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3208   -3.6277   -0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2173   -2.6021   -0.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7832   -1.2822   -0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4176   -0.9996   -0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2215    1.5568   -0.4924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6179    2.8744   -0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4275    3.5675   -0.5952 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8671   -1.7646    2.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1422   -0.5629    1.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6926   -1.5950    0.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7514    1.4317    1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9436    0.6245   -0.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7461    2.2642   -1.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6189    3.1011    0.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4298    3.9372   -0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417   -0.3912   -1.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2555   -2.3510    0.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3537   -2.4711   -0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2303   -4.1580    0.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7077   -4.6634   -0.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2814   -2.7830   -0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4847   -0.4848   -0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4696    3.1914   -0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8772    2.9813    0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8 19  1  0
 19 20  1  0
 20 21  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 11  2  1  0
 18 13  1  0
 10  5  1  0
 21  7  1  0
 18  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
 20 37  1  0
 20 38  1  0
 11 30  1  6
 12 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
M  END


  Mrv1652306292221182D          

 21 25  0  0  1  0            999 V2000
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3276   -1.7895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9920   -2.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715   -2.4570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11  2  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  9 18  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  7 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138816

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCC2=CC3=C(OCO3)C3=C2[C@@H]1CC1=CC=CC=C31

> <INCHI_IDENTIFIER>
InChI=1S/C18H17NO2/c1-19-7-6-12-9-15-18(21-10-20-15)17-13-5-3-2-4-11(13)8-14(19)16(12)17/h2-5,9,14H,6-8,10H2,1H3/t14-/m0/s1

> <INCHI_KEY>
JCTYWRARKVGOBK-AWEZNQCLSA-N

> <FORMULA>
C18H17NO2

> <MOLECULAR_WEIGHT>
279.339

> <EXACT_MASS>
279.125928791

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.178237158059787

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(12S)-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0^{2,6}.0^{8,20}.0^{14,19}]icosa-1(20),2(6),7,14,16,18-hexaene

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
3.324645495333333

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.432988948711422

> <JCHEM_POLAR_SURFACE_AREA>
21.700000000000003

> <JCHEM_REFRACTIVITY>
81.79320000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(12S)-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0^{2,6}.0^{8,20}.0^{14,19}]icosa-1(20),2(6),7,14,16,18-hexaene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.478  -3.340   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.852  -4.747   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.320  -4.586   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10    2   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13    9                                                  
CONECT   19    8   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    7                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

View in JSmol

Synonyms

Value	Source
Roemerine	MeSH
Roemerine hydrochloride, (R)-isomer	MeSH
Roemerine, (S)-isomer	MeSH

Chemical Formula

C₁₈H₁₇NO₂

Average Mass

279.3390 Da

Monoisotopic Mass

279.12593 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

2030-53-7

SMILES

CN1CCC2=CC3=C(OCO3)C3=C2[C@@H]1CC1=CC=CC=C31

InChI Identifier

InChI=1S/C18H17NO2/c1-19-7-6-12-9-15-18(21-10-20-15)17-13-5-3-2-4-11(13)8-14(19)16(12)17/h2-5,9,14H,6-8,10H2,1H3/t14-/m0/s1

InChI Key

JCTYWRARKVGOBK-AWEZNQCLSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Meconopsis cambrica	LOTUS Database	35616633
Papaver dubium	LOTUS Database	35616633
Papaver pilosum	LOTUS Database	35616633
Papaver rhoeas	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
Naphthalene
Quinoline
Tetrahydroisoquinoline
Benzodioxole
Aralkylamine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Acetal
Azacycle
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

700036

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

800239

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Aporheine (NP0138816)

MOL for NP0138816 (Aporheine)

3D MOL for NP0138816 (Aporheine)

3D SDF for NP0138816 (Aporheine)

3D-SDF for NP0138816 (Aporheine)

PDB for NP0138816 (Aporheine)

3D PDB for NP0138816 (Aporheine)

SMILES for NP0138816 (Aporheine)

INCHI for NP0138816 (Aporheine)

Structure for NP0138816 (Aporheine)

3D Structure for NP0138816 (Aporheine)