NP-MRD: Showing NP-Card for N-Formylnorloline (NP0066260)

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Record Information

Version

2.0

Created at

2022-04-28 10:30:14 UTC

Updated at

2022-04-28 10:30:14 UTC

NP-MRD ID

NP0066260

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Formylnorloline

Description

N-[(1R,3S,7S,8S)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]Nonan-8-yl]carboximidic acid 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. N-Formylnorloline is found in Lolium cuneatum. Based on a literature review very few articles have been published on N-[(1R,3S,7S,8S)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]Nonan-8-yl]carboximidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212302D          

 12 14  0  0  1  0            999 V2000
    1.0743   -1.8602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4096   -1.3351    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9256   -0.7530    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8416   -0.0226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6977   -0.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7358   -1.2797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9081   -0.7115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5602   -0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3239   -0.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9760   -0.0130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0462   -0.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3027   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  6  0  0  0
  6  7  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066260

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=CN[C@@H]1[C@H]2CN3CC[C@H](O2)[C@H]13

> <INCHI_IDENTIFIER>
InChI=1S/C8H12N2O2/c11-4-9-7-6-3-10-2-1-5(12-6)8(7)10/h4-8H,1-3H2,(H,9,11)/t5-,6+,7+,8+/m0/s1

> <INCHI_KEY>
XKEMMYSNKGUOCT-LXGUWJNJSA-N

> <FORMULA>
C8H12N2O2

> <MOLECULAR_WEIGHT>
168.196

> <EXACT_MASS>
168.089877634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.79620825016937

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(1R,3S,7S,8S)-2-oxa-6-azatricyclo[4.2.1.0^{3,7}]nonan-8-yl]formamide

> <ALOGPS_LOGP>
-1.03

> <JCHEM_LOGP>
-1.0991887673333336

> <ALOGPS_LOGS>
-0.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.619755682437113

> <JCHEM_PKA_STRONGEST_BASIC>
6.946430099241556

> <JCHEM_POLAR_SURFACE_AREA>
41.57

> <JCHEM_REFRACTIVITY>
41.5739

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(1R,3S,7S,8S)-2-oxa-6-azatricyclo[4.2.1.0^{3,7}]nonan-8-yl]formamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  O   UNK     0       2.005  -3.472   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.765  -2.492   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.728  -1.406   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.571  -0.042   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.169  -0.338   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.240  -2.389   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.562  -1.328   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       4.779  -0.385   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.205  -0.968   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.422  -0.024   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.086  -0.027   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.565  -1.536   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    3    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    4   12                                                       
CONECT   12   11    2                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   28    0
END

View in JSmol

Synonyms

Value	Source
N-[(1R,3S,7S,8S)-2-Oxa-6-azatricyclo[4.2.1.0,]nonan-8-yl]carboximidate	Generator

Chemical Formula

C₈H₁₂N₂O₂

Average Mass

168.1960 Da

Monoisotopic Mass

168.08988 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H12N2O2/c11-4-9-7-6-3-10-2-1-5(12-6)8(7)10/h4-8H,1-3H2,(H,9,11)/t5-,6+,7+,8+/m0/s1

InChI Key

XKEMMYSNKGUOCT-LXGUWJNJSA-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
Lolium cuneatum	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
N-alkylpyrrolidine
Oxazinane
Morpholine
Tetrahydrofuran
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	-1	ALOGPS
logP	-1.1	ChemAxon
logS	-0.08	ALOGPS
pKa (Strongest Acidic)	15.62	ChemAxon
pKa (Strongest Basic)	6.95	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.57 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	41.57 m³·mol⁻¹	ChemAxon
Polarizability	16.8 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14488256

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for N-Formylnorloline (NP0066260)

MOL for NP0066260 (N-Formylnorloline)

3D MOL for NP0066260 (N-Formylnorloline)

3D SDF for NP0066260 (N-Formylnorloline)

3D-SDF for NP0066260 (N-Formylnorloline)

PDB for NP0066260 (N-Formylnorloline)

3D PDB for NP0066260 (N-Formylnorloline)

SMILES for NP0066260 (N-Formylnorloline)

INCHI for NP0066260 (N-Formylnorloline)

Structure for NP0066260 (N-Formylnorloline)

3D Structure for NP0066260 (N-Formylnorloline)