NP-MRD: Showing NP-Card for n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]propanimidic acid (NP0302483)

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Record Information

Version

2.0

Created at

2022-09-10 16:06:50 UTC

Updated at

2022-09-10 16:06:50 UTC

NP-MRD ID

NP0302483

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]propanimidic acid

Description

N-[(1R,3S,7S,8R)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]Nonan-8-yl]propanimidic 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-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]propanimidic acid is found in Epichloe coenophiala. Based on a literature review very few articles have been published on N-[(1R,3S,7S,8R)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]Nonan-8-yl]propanimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
    3.8960    0.9474    0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3879   -0.4701    0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0560   -0.5822   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9724   -0.1655   -1.7380 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0841   -1.0452    0.2620 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2013   -1.1629   -0.3400 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8314    0.1751   -0.6867 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2582   -0.3018   -0.9071 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1176    0.7826   -0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1140    1.6683    0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9307    0.8153    0.5891 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2756   -0.2686    1.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2862   -1.5164    0.6936 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4204   -1.4479   -0.1297 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6370    1.0119    1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4629    1.1450   -0.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0923    1.6928    0.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1002   -1.0621   -0.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3597   -0.8362    1.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3960   -0.6183   -2.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2892   -1.8738   -1.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3867    0.7105   -1.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4835   -0.4886   -1.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6650    1.2745   -1.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8760    0.3720    0.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8033    2.4518   -0.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5149    2.0406    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5661   -0.3062    2.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2904   -0.1237    1.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1340   -2.4431    1.1887 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
  3  5  2  0
  5  6  1  0
  6 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8 14  1  0
  8  7  1  0
  7  6  1  0
 14 13  1  0
  7 11  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  4 20  1  0
  6 21  1  6
 13 30  1  1
 12 28  1  0
 12 29  1  0
 10 26  1  0
 10 27  1  0
  9 24  1  0
  9 25  1  0
  8 23  1  6
  7 22  1  6
M  END


  Mrv1652309102218062D          

 14 16  0  0  1  0            999 V2000
   -2.6035   -0.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8496   -0.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1824   -0.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2692   -1.4099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4286   -0.2544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386   -0.7398    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2313   -0.7631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3256   -0.0329    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2047   -0.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800   -0.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7608   -1.3386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1104   -1.8574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4343   -1.2995    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4483   -0.2078    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  4  0  0  0
  3  5  2  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  1  0  0  0
  8 14  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0302483

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N2O2/c1-2-8(13)11-9-7-5-12-4-3-6(14-7)10(9)12/h6-7,9-10H,2-5H2,1H3,(H,11,13)/t6-,7+,9-,10+/m0/s1

> <INCHI_KEY>
DONSVQBFPXNWRA-WPYKOPORSA-N

> <FORMULA>
C10H16N2O2

> <MOLECULAR_WEIGHT>
196.25

> <EXACT_MASS>
196.121177763

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
20.861897170499645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-1.0937734181668315

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.34874894078698

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.292182664541984

> <JCHEM_PKA_STRONGEST_BASIC>
7.508305521208446

> <JCHEM_POLAR_SURFACE_AREA>
45.06

> <JCHEM_REFRACTIVITY>
51.21300000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.860  -0.820   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.453  -0.194   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.207  -1.100   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.369  -2.632   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      -0.800  -0.475   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.445  -1.381   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.298  -1.424   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.475  -0.061   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.115  -0.105   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.629  -1.591   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       3.287  -2.499   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.073  -3.467   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.811  -2.426   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.837  -0.388   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    7   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13    8                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₁₀H₁₆N₂O₂

Average Mass

196.2500 Da

Monoisotopic Mass

196.12118 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H16N2O2/c1-2-8(13)11-9-7-5-12-4-3-6(14-7)10(9)12/h6-7,9-10H,2-5H2,1H3,(H,11,13)/t6-,7+,9-,10+/m0/s1

InChI Key

DONSVQBFPXNWRA-WPYKOPORSA-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
Acremonium coenophialum	LOTUS Database	35616633

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
Amino acid or derivatives
Carboxamide group
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxide
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organopnictogen compound
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	-1.1	ChemAxon
pKa (Strongest Acidic)	5.29	ChemAxon
pKa (Strongest Basic)	7.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	51.21 m³·mol⁻¹	ChemAxon
Polarizability	20.86 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

78439962

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585025

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]propanimidic acid (NP0302483)

MOL for NP0302483 (n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]propanimidic acid)

3D MOL for NP0302483 (n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]propanimidic acid)

3D SDF for NP0302483 (n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]propanimidic acid)

3D-SDF for NP0302483 (n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]propanimidic acid)

PDB for NP0302483 (n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]propanimidic acid)

3D PDB for NP0302483 (n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]propanimidic acid)

SMILES for NP0302483 (n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]propanimidic acid)

INCHI for NP0302483 (n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]propanimidic acid)

Structure for NP0302483 (n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]propanimidic acid)

3D Structure for NP0302483 (n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]propanimidic acid)