NP-MRD: Showing NP-Card for n-[(5s)-5-[(1r)-1,2-dihydroxyethyl]-2-oxo-5h-furan-3-yl]ethanimidic acid (NP0233137)

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Record Information

Version

2.0

Created at

2022-09-06 14:37:53 UTC

Updated at

2022-09-06 14:37:53 UTC

NP-MRD ID

NP0233137

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(5s)-5-[(1r)-1,2-dihydroxyethyl]-2-oxo-5h-furan-3-yl]ethanimidic acid

Description

Leptosphaerin belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. n-[(5s)-5-[(1r)-1,2-dihydroxyethyl]-2-oxo-5h-furan-3-yl]ethanimidic acid was first documented in 2017 (PMID: 28196973). Based on a literature review a small amount of articles have been published on Leptosphaerin (PMID: 28398053) (PMID: 35903995) (PMID: 35423499).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062216372D          

 14 14  0  0  1  0            999 V2000
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145   -2.2438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    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
  2  4  2  0  0  0  0
  4  5  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0233137

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)=NC1=C[C@H](OC1=O)[C@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C8H11NO5/c1-4(11)9-5-2-7(6(12)3-10)14-8(5)13/h2,6-7,10,12H,3H2,1H3,(H,9,11)/t6-,7+/m1/s1

> <INCHI_KEY>
XBJZBELDKOKZKH-RQJHMYQMSA-N

> <FORMULA>
C8H11NO5

> <MOLECULAR_WEIGHT>
201.178

> <EXACT_MASS>
201.063722458

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
18.800810203744437

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(5S)-5-[(1R)-1,2-dihydroxyethyl]-2-oxo-2,5-dihydrofuran-3-yl]ethanimidic acid

> <JCHEM_LOGP>
-1.2414421576666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.282644600926076

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.438382928114547

> <JCHEM_PKA_STRONGEST_BASIC>
0.24400905117724592

> <JCHEM_POLAR_SURFACE_AREA>
99.35000000000001

> <JCHEM_REFRACTIVITY>
46.762800000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-[(5S)-5-[(1R)-1,2-dihydroxyethyl]-2-oxo-5H-furan-3-yl]ethanimidic 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  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.608   3.620   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       1.060   3.620   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.267  -1.375   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.109  -2.943   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.014  -4.188   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.290  -0.290   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10                                                            
CONECT   12    7   13                                                       
CONECT   13   12    5   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₈H₁₁NO₅

Average Mass

201.1780 Da

Monoisotopic Mass

201.06372 Da

IUPAC Name

N-[(5S)-5-[(1R)-1,2-dihydroxyethyl]-2-oxo-2,5-dihydrofuran-3-yl]ethanimidic acid

Traditional Name

N-[(5S)-5-[(1R)-1,2-dihydroxyethyl]-2-oxo-5H-furan-3-yl]ethanimidic acid

CAS Registry Number

Not Available

SMILES

CC(O)=NC1=C[C@H](OC1=O)[C@H](O)CO

InChI Identifier

InChI=1S/C8H11NO5/c1-4(11)9-5-2-7(6(12)3-10)14-8(5)13/h2,6-7,10,12H,3H2,1H3,(H,9,11)/t6-,7+/m1/s1

InChI Key

XBJZBELDKOKZKH-RQJHMYQMSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

N-acyl-alpha amino acid or derivatives
2-furanone
Dihydrofuran
Acetamide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Carboxamide group
Carboxylic acid ester
Lactone
Secondary carboxylic acid amide
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Primary alcohol
Organonitrogen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-1.2	ChemAxon
pKa (Strongest Acidic)	5.44	ChemAxon
pKa (Strongest Basic)	0.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.35 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.76 m³·mol⁻¹	ChemAxon
Polarizability	18.8 Å³	ChemAxon
Number of Rings	1	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

9074920

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Leptosphaeria orae-maris

METLIN ID

Not Available

PubChem Compound

10899660

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lin J, Wang R, Xu G, Ding Z, Zhu X, Li E, Liu L: Two new polyketides from the ascomycete fungus Leptosphaeria sp. J Antibiot (Tokyo). 2017 Jun;70(6):743-746. doi: 10.1038/ja.2017.5. Epub 2017 Feb 15. [PubMed:28196973 ]
Dhokale RA, Mhaske SB: Diversity-Oriented Synthesis of Spiroannulated Benzofuran-3-one Scaffold of Leptosphaerin C and Congeners via Aryne Insertion. J Org Chem. 2017 May 5;82(9):4875-4882. doi: 10.1021/acs.joc.7b00606. Epub 2017 Apr 14. [PubMed:28398053 ]
Neville JC, Lau MY, Sohnel T, Sperry J: Haber-independent, asymmetric synthesis of the marine alkaloid epi-leptosphaerin from a chitin-derived chiral pool synthon. Org Biomol Chem. 2022 Aug 24;20(33):6562-6565. doi: 10.1039/d2ob01251k. [PubMed:35903995 ]
Ji Y, Zhou Q, Liu G, Zhu T, Wang Y, Fu Y, Li Y, Li R, Zhang X, Dong M, Sauriol F, Gu Y, Shi Q, Lu X, Ni Z: New protein tyrosine phosphatase inhibitors from fungus Aspergillus gorakhpurensis F07ZB1707. RSC Adv. 2021 Mar 10;11(17):10144-10153. doi: 10.1039/d1ra00788b. eCollection 2021 Mar 5. [PubMed:35423499 ]
LOTUS database [Link]

Showing NP-Card for n-[(5s)-5-[(1r)-1,2-dihydroxyethyl]-2-oxo-5h-furan-3-yl]ethanimidic acid (NP0233137)

MOL for NP0233137 (n-[(5s)-5-[(1r)-1,2-dihydroxyethyl]-2-oxo-5h-furan-3-yl]ethanimidic acid)

3D MOL for NP0233137 (n-[(5s)-5-[(1r)-1,2-dihydroxyethyl]-2-oxo-5h-furan-3-yl]ethanimidic acid)

3D SDF for NP0233137 (n-[(5s)-5-[(1r)-1,2-dihydroxyethyl]-2-oxo-5h-furan-3-yl]ethanimidic acid)

3D-SDF for NP0233137 (n-[(5s)-5-[(1r)-1,2-dihydroxyethyl]-2-oxo-5h-furan-3-yl]ethanimidic acid)

PDB for NP0233137 (n-[(5s)-5-[(1r)-1,2-dihydroxyethyl]-2-oxo-5h-furan-3-yl]ethanimidic acid)

3D PDB for NP0233137 (n-[(5s)-5-[(1r)-1,2-dihydroxyethyl]-2-oxo-5h-furan-3-yl]ethanimidic acid)

SMILES for NP0233137 (n-[(5s)-5-[(1r)-1,2-dihydroxyethyl]-2-oxo-5h-furan-3-yl]ethanimidic acid)

INCHI for NP0233137 (n-[(5s)-5-[(1r)-1,2-dihydroxyethyl]-2-oxo-5h-furan-3-yl]ethanimidic acid)

Structure for NP0233137 (n-[(5s)-5-[(1r)-1,2-dihydroxyethyl]-2-oxo-5h-furan-3-yl]ethanimidic acid)

3D Structure for NP0233137 (n-[(5s)-5-[(1r)-1,2-dihydroxyethyl]-2-oxo-5h-furan-3-yl]ethanimidic acid)