NP-MRD: Showing NP-Card for (1s)-4-amino-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid (NP0234277)

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Record Information

Version

2.0

Created at

2022-09-06 16:13:27 UTC

Updated at

2022-09-06 16:13:27 UTC

NP-MRD ID

NP0234277

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s)-4-amino-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid

Description

(1S)-4-amino-2,5-dioxo-7-oxabicyclo[4.1.0]Hept-3-ene-3-carboxylic acid belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. (1s)-4-amino-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid is found in Streptomyces baarnensis. Based on a literature review very few articles have been published on (1S)-4-amino-2,5-dioxo-7-oxabicyclo[4.1.0]Hept-3-ene-3-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062218132D          

 13 14  0  0  1  0            999 V2000
    3.5724    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    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    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    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
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0234277

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=C(C(O)=O)C(=O)[C@H]2OC2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H5NO5/c8-2-1(7(11)12)3(9)5-6(13-5)4(2)10/h5-6H,8H2,(H,11,12)/t5-,6?/m1/s1

> <INCHI_KEY>
YWEJARDWQNOPAX-LWOQYNTDSA-N

> <FORMULA>
C7H5NO5

> <MOLECULAR_WEIGHT>
183.119

> <EXACT_MASS>
183.016772265

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.890225147233403

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S)-4-amino-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid

> <JCHEM_LOGP>
-1.1706636776666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.898328322236704

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.62842790665

> <JCHEM_PKA_STRONGEST_BASIC>
-4.320388092361559

> <JCHEM_POLAR_SURFACE_AREA>
109.99000000000001

> <JCHEM_REFRACTIVITY>
38.8243

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-4-amino-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  N   UNK     0       6.668   3.850   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9   11                                                       
CONECT   11   10    9   12                                                  
CONECT   12   11    2   13                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Value	Source
(1S)-4-Amino-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate	Generator

Chemical Formula

C₇H₅NO₅

Average Mass

183.1190 Da

Monoisotopic Mass

183.01677 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

NC1=C(C(O)=O)C(=O)[C@H]2OC2C1=O

InChI Identifier

InChI=1S/C7H5NO5/c8-2-1(7(11)12)3(9)5-6(13-5)4(2)10/h5-6H,8H2,(H,11,12)/t5-,6?/m1/s1

InChI Key

YWEJARDWQNOPAX-LWOQYNTDSA-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
Streptomyces baarnensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Vinylogous amide
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Enamine
Oxirane
Ether
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Primary aliphatic amine
Organonitrogen compound
Primary amine
Organic oxide
Amine
Organic nitrogen compound
Hydrocarbon derivative
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

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

2313879

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3052006

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s)-4-amino-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid (NP0234277)

MOL for NP0234277 ((1s)-4-amino-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid)

3D MOL for NP0234277 ((1s)-4-amino-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid)

3D SDF for NP0234277 ((1s)-4-amino-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid)

3D-SDF for NP0234277 ((1s)-4-amino-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid)

PDB for NP0234277 ((1s)-4-amino-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid)

3D PDB for NP0234277 ((1s)-4-amino-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid)

SMILES for NP0234277 ((1s)-4-amino-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid)

INCHI for NP0234277 ((1s)-4-amino-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid)

Structure for NP0234277 ((1s)-4-amino-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid)

3D Structure for NP0234277 ((1s)-4-amino-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid)