NP-MRD: Showing NP-Card for (-)-Lirinidine (NP0081219)

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Record Information

Version

2.0

Created at

2022-04-29 02:11:10 UTC

Updated at

2022-04-29 02:11:10 UTC

NP-MRD ID

NP0081219

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Lirinidine

Description

(-)-Lirinidine 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. (-)-Lirinidine is found in Annona purpurea , Artabotrys venustus and Papaver orientale. (-)-Lirinidine was first documented in 2013 (PMID: 23270663). Based on a literature review a small amount of articles have been published on (-)-Lirinidine (PMID: 34019754).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
    4.9155   -1.3989   -0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0219   -0.3259   -0.1433 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6633   -0.4493    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9993   -1.6374    0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6512   -1.6724    0.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1161   -0.5075    0.4193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5492    0.7013    0.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9007    0.7313   -0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5852    1.8965   -0.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2535    1.9281    0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273    3.1370   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4628    4.2738   -0.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8240    4.1800    0.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3852    2.9439    0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6168    1.7793    0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3554    0.5483    0.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5471   -0.6862    0.6550 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1072   -1.8143   -0.0171 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9496   -1.5108   -1.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990   -2.8527   -0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1142   -2.9100    0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8654   -1.0815   -0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5191   -2.2419   -0.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0722   -1.6854    0.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5846   -2.5439    0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5620    1.9846   -0.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3637    3.3117   -0.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0250    5.2686   -0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4130    5.0885   -0.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4678    2.9000    0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1248    0.4852   -0.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9999    0.7216    1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6080   -0.9730    1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9978   -1.2703   -0.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0215   -2.4444   -1.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4690   -0.7613   -1.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6840   -3.8407   -0.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6981   -2.5312   -1.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4520   -3.8265    0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5931   -2.9143    1.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
  6 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21  5  1  0
  5  4  2  0
  4  3  1  0
 10  7  1  0
  5  6  1  0
 10 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  9 26  1  0
 17 33  1  1
 16 31  1  0
 16 32  1  0
 14 30  1  0
 13 29  1  0
 12 28  1  0
 11 27  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
  4 25  1  0
M  END


  Mrv1652304292204112D          

 21 24  0  0  1  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    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
    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  1  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
    0.7145   -0.4125    0.0000 N   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  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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0081219

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C2=C3[C@@H](CC4=CC=CC=C24)N(C)CCC3=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H19NO2/c1-19-8-7-12-10-15(21-2)18(20)17-13-6-4-3-5-11(13)9-14(19)16(12)17/h3-6,10,14,20H,7-9H2,1-2H3/t14-/m1/s1

> <INCHI_KEY>
YXVXMURDCBMPRH-CQSZACIVSA-N

> <FORMULA>
C18H19NO2

> <MOLECULAR_WEIGHT>
281.355

> <EXACT_MASS>
281.141578856

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
31.75813284320695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9R)-15-methoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,13,15-hexaen-16-ol

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
3.240175440333333

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.914940297160433

> <JCHEM_PKA_STRONGEST_BASIC>
7.245388714721415

> <JCHEM_POLAR_SURFACE_AREA>
32.7

> <JCHEM_REFRACTIVITY>
84.47040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9R)-15-methoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,13,15-hexaen-16-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   17                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16    7   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19                                                            
CONECT   21   11                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₉NO₂

Average Mass

281.3550 Da

Monoisotopic Mass

281.14158 Da

IUPAC Name

(9R)-15-methoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,13,15-hexaen-16-ol

Traditional Name

(9R)-15-methoxy-10-methyl-10-azatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,13,15-hexaen-16-ol

CAS Registry Number

Not Available

SMILES

COC1=C(O)C2=C3[C@@H](CC4=CC=CC=C24)N(C)CCC3=C1

InChI Identifier

InChI=1S/C18H19NO2/c1-19-8-7-12-10-15(21-2)18(20)17-13-6-4-3-5-11(13)9-14(19)16(12)17/h3-6,10,14,20H,7-9H2,1-2H3/t14-/m1/s1

InChI Key

YXVXMURDCBMPRH-CQSZACIVSA-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
Annona purpurea	Plant	KNApSAcK
Artabotrys venustus	LOTUS Database	35616633
Papaver orientale	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
1-naphthol
Naphthalene
Quinoline
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Ether
Amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
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
logP	2.86	ALOGPS
logP	3.24	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	7.25	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.7 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	84.47 m³·mol⁻¹	ChemAxon
Polarizability	31.76 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00046981

Chemspider ID

717585

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

821343

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Maneenet J, Omar AM, Sun S, Kim MJ, Daodee S, Monthakantirat O, Boonyarat C, Chulikhit Y, Awale S: Benzylisoquinoline alkaloids from Nelumbo nucifera Gaertn. petals with antiausterity activities against the HeLa human cervical cancer cell line. Z Naturforsch C J Biosci. 2021 May 24;76(9-10):401-406. doi: 10.1515/znc-2020-0304. Print 2021 Sep 27. [PubMed:34019754 ]
Nakamura S, Nakashima S, Tanabe G, Oda Y, Yokota N, Fujimoto K, Matsumoto T, Sakuma R, Ohta T, Ogawa K, Nishida S, Miki H, Matsuda H, Muraoka O, Yoshikawa M: Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells. Bioorg Med Chem. 2013 Feb 1;21(3):779-87. doi: 10.1016/j.bmc.2012.11.038. Epub 2012 Dec 5. [PubMed:23270663 ]

Showing NP-Card for (-)-Lirinidine (NP0081219)

MOL for NP0081219 ((-)-Lirinidine)

3D MOL for NP0081219 ((-)-Lirinidine)

3D SDF for NP0081219 ((-)-Lirinidine)

3D-SDF for NP0081219 ((-)-Lirinidine)

PDB for NP0081219 ((-)-Lirinidine)

3D PDB for NP0081219 ((-)-Lirinidine)

SMILES for NP0081219 ((-)-Lirinidine)

INCHI for NP0081219 ((-)-Lirinidine)

Structure for NP0081219 ((-)-Lirinidine)

3D Structure for NP0081219 ((-)-Lirinidine)