NP-MRD: Showing NP-Card for (+)-Loline (NP0066256)

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Record Information

Version

2.0

Created at

2022-04-28 10:28:09 UTC

Updated at

2022-04-28 10:28:09 UTC

NP-MRD ID

NP0066256

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Loline

Description

Loline, also known as festucine, belongs to the class of organic compounds known as loline alkaloids and derivatives. These are alkaloids with a structure characterized by a saturated pyrrolizidine ring, a primary amine at the C-1 carbon, and an internal ether bridge joining two distant ring (C-2 and C-7) carbons. Different substituents at the C-1 amine, such as methyl, formyl, and acetyl groups, yield various loline species. (+)-Loline is found in Acremonium coenophialum, Acremonium sp., Adenocarpus decorticans, Argyreia mollis, Epichloe coenophiala e19, Epichloe coenophiala e4163, Epichloe festucae E2368, Epichloe uncinata e167, Festuca arundinacea , Festuca ovina, Lolium cuneatum and Lolium temulentum . (+)-Loline was first documented in 2021 (PMID: 34822583). Based on a literature review a small amount of articles have been published on loline (PMID: 35482316) (PMID: 35454243) (PMID: 35109929) (PMID: 34850658).

Structure

MOL 3D MOL SDF PDB SMILES InChI

View in JSmol

Synonyms

Value	Source
(+)-Loline	ChEBI
(1R,3S,7S,8R)-N-Methyl-2-oxa-6-azatricyclo[4.2.1.0(3,7)]nonan-8-amine	ChEBI
Festucine	ChEBI
Lolina	ChEBI

Chemical Formula

C₈H₁₄N₂O

Average Mass

154.2130 Da

Monoisotopic Mass

154.11061 Da

IUPAC Name

(1R,3S)-N-methyl-2-oxa-6-azatricyclo[4.2.1.0^{3,7}]nonan-8-amine

Traditional Name

(1R,3S)-N-methyl-2-oxa-6-azatricyclo[4.2.1.0^{3,7}]nonan-8-amine

CAS Registry Number

Not Available

SMILES

CN[C@H]1[C@H]2CN3CC[C@H](O2)[C@H]13

InChI Identifier

InChI=1S/C8H14N2O/c1-9-7-6-4-10-3-2-5(11-6)8(7)10/h5-9H,2-4H2,1H3/t5-,6+,7-,8+/m0/s1

InChI Key

OPMNROCQHKJDAQ-FKSUSPILSA-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
Acremonium coenophialum	Fungi	KNApSAcK
Acremonium sp.	Fungi	KNApSAcK
Adenocarpus decorticans	Plant	KNApSAcK
Argyreia mollis	Plant	KNApSAcK
Epichloe coenophiala e19	Fungi	KNApSAcK
Epichloe coenophiala e4163	Fungi	KNApSAcK
Epichloe festucae E2368	Fungi	KNApSAcK
Epichloe uncinata e167	Fungi	KNApSAcK
Festuca arundinacea	Plant	KNApSAcK
Festuca ovina	LOTUS Database	35616633
Lolium cuneatum	Plant	KNApSAcK
Lolium temulentum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as loline alkaloids and derivatives. These are alkaloids with a structure characterized by a saturated pyrrolizidine ring, a primary amine at the C-1 carbon, and an internal ether bridge joining two distant ring (C-2 and C-7) carbons. Different substituents at the C-1 amine, such as methyl, formyl, and acetyl groups, yield various loline species.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Loline alkaloids and derivatives

Sub Class

Not Available

Direct Parent

Loline alkaloids and derivatives

Alternative Parents

Substituents

Loline
Pyrrolizidine
Para-oxazepine
Morpholine
Oxazinane
N-alkylpyrrolidine
Pyrrolidine
Tetrahydrofuran
Tertiary amine
Tertiary aliphatic amine
Secondary amine
Azacycle
Oxacycle
Ether
Secondary aliphatic amine
Dialkyl ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.81	ALOGPS
logP	-0.44	ChemAxon
logS	0.3	ALOGPS
pKa (Strongest Basic)	9.28	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	24.5 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	41.4 m³·mol⁻¹	ChemAxon
Polarizability	16.79 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

C00023609

Chemspider ID

16735876

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Loline alkaloid

METLIN ID

Not Available

PubChem Compound

716098

PDB ID

Not Available

ChEBI ID

156448

Good Scents ID

Not Available

References

General References

Panth N, Wenger ES, Krebs C, Bollinger JM Jr, Grossman RB: Synthesis of 6,6- and 7,7-Difluoro-1-acetamidopyrrolizidines and Their Oxidation Catalyzed by the Nonheme Fe Oxygenase LolO. Chembiochem. 2022 Jul 5;23(13):e202200081. doi: 10.1002/cbic.202200081. Epub 2022 May 17. [PubMed:35482316 ]
Froehlich KA, McAnulty R, Greer A: Loline Alkaloid Effects on Gastrointestinal Nematodes. Animals (Basel). 2022 Apr 12;12(8). pii: ani12080996. doi: 10.3390/ani12080996. [PubMed:35454243 ]
Thunen T, Becker Y, Cox MP, Ashrafi S: Epichloe scottii sp. nov., a new endophyte isolated from Melica uniflora is the missing ancestor of Epichloe disjuncta. IMA Fungus. 2022 Feb 3;13(1):2. doi: 10.1186/s43008-022-00088-0. [PubMed:35109929 ]
Croy RG, Sutherland BL, Hume DE, Mace WJ, van Koten C, Finch SC: Animal safety of a tall fescue endophyte (Epichloe sp.) in a perennial ryegrass (Lolium perenne) host. N Z Vet J. 2022 May;70(3):165-176. doi: 10.1080/00480169.2021.2011795. Epub 2022 Jan 27. [PubMed:34850658 ]
Liu M, Findlay W, Dettman J, Wyka SA, Broders K, Shoukouhi P, Dadej K, Kolarik M, Basnyat A, Menzies JG: Mining Indole Alkaloid Synthesis Gene Clusters from Genomes of 53 Claviceps Strains Revealed Redundant Gene Copies and an Approximate Evolutionary Hourglass Model. Toxins (Basel). 2021 Nov 13;13(11). pii: toxins13110799. doi: 10.3390/toxins13110799. [PubMed:34822583 ]

Showing NP-Card for (+)-Loline (NP0066256)

MOL for NP0066256 ((+)-Loline)

3D MOL for NP0066256 ((+)-Loline)

3D SDF for NP0066256 ((+)-Loline)

3D-SDF for NP0066256 ((+)-Loline)

PDB for NP0066256 ((+)-Loline)

3D PDB for NP0066256 ((+)-Loline)

SMILES for NP0066256 ((+)-Loline)

INCHI for NP0066256 ((+)-Loline)

Structure for NP0066256 ((+)-Loline)

3D Structure for NP0066256 ((+)-Loline)