NP-MRD: Showing NP-Card for Perlolyrine (NP0045884)

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Record Information

Version

2.0

Created at

2022-03-17 19:44:50 UTC

Updated at

2022-03-17 19:44:50 UTC

NP-MRD ID

NP0045884

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Perlolyrine

Description

Perlolyrine, also known as alkaloid ys, belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. Perlolyrine is a moderately basic compound (based on its pKa). Outside of the human body, Perlolyrine has been detected, but not quantified in, a few different foods, such as herbs and spices, saffrons, and soy beans. Perlolyrine is found in Apis cerana, Codonopsis pilosula , Codonopsis tangshen , Codonopsis pilosula var.modesta , Houttuynia cordata , Ligusticum chuanxiong, Lolium chuanxiong, Lolium perenne , Lycium chinense, Ophiocordyceps sinensis, Panax ginseng , Polygala tenuifolia , Streptomyces spp. and Tribulus terrestris . This could make perlolyrine a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305092D          

 20 23  0  0  0  0            999 V2000
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046   -2.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6895   -1.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475   -2.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800   -2.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1612   -3.5421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800   -1.4117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  2  0  0  0  0
 10  5  2  0  0  0  0
 10  9  1  0  0  0  0
 11  3  2  0  0  0  0
 12  7  1  0  0  0  0
 12 11  1  0  0  0  0
 13  4  2  0  0  0  0
 13 11  1  0  0  0  0
 14  6  2  0  0  0  0
 15 12  2  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17  8  1  0  0  0  0
 17 16  2  0  0  0  0
 18 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19  9  1  0  0  0  0
 20 10  1  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045884

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1=CC=C(O1)C1=NC=CC2=C1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C16H12N2O2/c19-9-10-5-6-14(20-10)16-15-12(7-8-17-16)11-3-1-2-4-13(11)18-15/h1-8,18-19H,9H2

> <INCHI_KEY>
KFUCYPGCMLPUMT-UHFFFAOYSA-N

> <FORMULA>
C16H12N2O2

> <MOLECULAR_WEIGHT>
264.2787

> <EXACT_MASS>
264.089877638

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.588973991252445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5-{9H-pyrido[3,4-b]indol-1-yl}furan-2-yl)methanol

> <ALOGPS_LOGP>
2.66

> <JCHEM_LOGP>
2.119186950333333

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.751026894203264

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.433887143113587

> <JCHEM_PKA_STRONGEST_BASIC>
2.788122435059806

> <JCHEM_POLAR_SURFACE_AREA>
62.05

> <JCHEM_REFRACTIVITY>
75.1638

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
perlolyrine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.393   0.450   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.411   2.235   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.382  -4.651   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.287  -3.405   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.329  -5.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.083  -4.175   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.382  -2.159   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -0.173   0.450   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -2.168  -6.612   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.083  -2.635   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1   11                                                       
CONECT    4    2   13                                                       
CONECT    5    6   10                                                       
CONECT    6    5   14                                                       
CONECT    7    8   12                                                       
CONECT    8    7   17                                                       
CONECT    9   10   19                                                       
CONECT   10    5    9   20                                                  
CONECT   11    3   12   13                                                  
CONECT   12    7   11   15                                                  
CONECT   13    4   11   18                                                  
CONECT   14    6   16   20                                                  
CONECT   15   12   16   18                                                  
CONECT   16   14   15   17                                                  
CONECT   17    8   16                                                       
CONECT   18   13   15                                                       
CONECT   19    9                                                            
CONECT   20   10   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Value	Source
2-(b-Carbolin-1-yl)-5-hydroxymethylfuran	HMDB
2-Dehydrocarbonylflazin	HMDB
5-(9H-Pyrido(3,4-b)indol-1-yl)-2-furanmethanol	HMDB
5-(9H-Pyrido[3,4-b]indol-1-yl)-2-furanmethanol, 9ci	HMDB
Alkaloid ys	HMDB
[5-(9H-beta-Carbolin-1-yl)-2-furyl]methanol	HMDB
Substance ys	MeSH
Yellow substance ys	MeSH

Chemical Formula

C₁₆H₁₂N₂O₂

Average Mass

264.2787 Da

Monoisotopic Mass

264.08988 Da

IUPAC Name

(5-{9H-pyrido[3,4-b]indol-1-yl}furan-2-yl)methanol

Traditional Name

perlolyrine

CAS Registry Number

29700-20-7

SMILES

OCC1=CC=C(O1)C1=NC=CC2=C1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C16H12N2O2/c19-9-10-5-6-14(20-10)16-15-12(7-8-17-16)11-3-1-2-4-13(11)18-15/h1-8,18-19H,9H2

InChI Key

KFUCYPGCMLPUMT-UHFFFAOYSA-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
Apis cerana	LOTUS Database	35616633
Codonopsis pilosula	Plant	KNApSAcK
Codonopsis pilosula subsp. tangshen	Plant	KNApSAcK
Codonopsis pilosula var.modesta	Plant	KNApSAcK
Crocus sativus	FooDB	KNAPSACK
Glycine max	FooDB	KNAPSACK
Houttuynia cordata	Plant	KNApSAcK
Ligusticum chuanxiong	LOTUS Database	35616633
Lolium chuanxiong	Plant	KNApSAcK
Lolium perenne	Plant	KNApSAcK
Lycium chinense	LOTUS Database	35616633
Ophiocordyceps sinensis	LOTUS Database	35616633
Panax ginseng	Plant	KNApSAcK
Polygala tenuifolia	Plant	KNApSAcK
Streptomyces spp.	Bacteria	KNApSAcK
Tribulus terrestris	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harman
Beta-carboline
Pyridoindole
Indole
Indole or derivatives
Benzenoid
Pyridine
Heteroaromatic compound
Pyrrole
Furan
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic molecular entity (CHEBI:69444 )
Indole alkaloids (C09231 )

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	2.66	ALOGPS
logP	2.12	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12.43	ChemAxon
pKa (Strongest Basic)	2.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.05 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.16 m³·mol⁻¹	ChemAxon
Polarizability	28.59 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon