NP-MRD: Showing NP-Card for U43795 (NP0003632)

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Record Information

Version

2.0

Created at

2020-12-09 00:49:38 UTC

Updated at

2021-07-15 16:46:57 UTC

NP-MRD ID

NP0003632

Secondary Accession Numbers

None

Natural Product Identification

Common Name

U43795

Provided By

NPAtlas

Description

2-Amino-2-[(4S,5R)-3-chloro-4-hydroxy-4,5-dihydro-1,2-oxazol-5-yl]acetic acid belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). U43795 is found in Streptomyces sviceus. Based on a literature review very few articles have been published on 2-amino-2-[(4S,5R)-3-chloro-4-hydroxy-4,5-dihydro-1,2-oxazol-5-yl]acetic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117483D          

 19 19  0  0  0  0            999 V2000
   -1.5287   -1.6541   -0.0277 N   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9057   -0.4260    0.5014 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7037    0.7098    0.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733    1.9099    0.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8307    0.5186   -0.6941 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4966   -0.4808    0.1129 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7752   -0.5360   -1.2679 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1714   -0.4847   -1.2958 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6229    0.1599   -0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2998    0.4843    0.1228 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4325    0.5940    0.5243 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1176    1.8562    0.0139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6362   -1.5812   -1.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071   -1.8750    0.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9555   -0.5729    1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2993   -0.3824   -0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9250   -1.4406    0.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6559    0.6248    1.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2431    2.5762    0.6588 H   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  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11  6  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
  2 15  1  1  0  0  0
  5 16  1  0  0  0  0
  6 17  1  1  0  0  0
 11 18  1  1  0  0  0
 12 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003632

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]([H])(N([H])[H])[C@@]1([H])ON=C(Cl)[C@@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C5H7ClN2O4/c6-4-2(9)3(12-8-4)1(7)5(10)11/h1-3,9H,7H2,(H,10,11)/t1-,2-,3+/m0/s1

> <INCHI_KEY>
KUYDILDQEMQBKJ-ZVKPHKKVSA-N

> <FORMULA>
C5H7ClN2O4

> <MOLECULAR_WEIGHT>
194.57

> <EXACT_MASS>
194.0094344

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
16.011308106890073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-2-[(4S,5R)-3-chloro-4-hydroxy-4,5-dihydro-1,2-oxazol-5-yl]acetic acid

> <ALOGPS_LOGP>
-2.33

> <JCHEM_LOGP>
-3.3881015617393975

> <ALOGPS_LOGS>
-0.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.960891652333677

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2986704695815225

> <JCHEM_PKA_STRONGEST_BASIC>
7.908687520621042

> <JCHEM_POLAR_SURFACE_AREA>
105.14000000000001

> <JCHEM_REFRACTIVITY>
37.7346

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.41e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-amino[(4S,5R)-3-chloro-4-hydroxy-4,5-dihydro-1,2-oxazol-5-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  N   UNK     0      -1.529  -1.654  -0.028  0.00  0.00           N+0
HETATM    2  C   UNK     0      -0.906  -0.426   0.501  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.704   0.710   0.093  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.473   1.910   0.389  0.00  0.00           O+0
HETATM    5  O   UNK     0      -2.831   0.519  -0.694  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.497  -0.481   0.113  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.775  -0.536  -1.268  0.00  0.00           O+0
HETATM    8  N   UNK     0       2.171  -0.485  -1.296  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.623   0.160  -0.275  0.00  0.00           C+0
HETATM   10 Cl   UNK     0       4.300   0.484   0.123  0.00  0.00          Cl+0
HETATM   11  C   UNK     0       1.433   0.594   0.524  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.118   1.856   0.014  0.00  0.00           O+0
HETATM   13  H   UNK     0      -1.636  -1.581  -1.050  0.00  0.00           H+0
HETATM   14  H   UNK     0      -2.407  -1.875   0.486  0.00  0.00           H+0
HETATM   15  H   UNK     0      -0.956  -0.573   1.617  0.00  0.00           H+0
HETATM   16  H   UNK     0      -3.299  -0.382  -0.712  0.00  0.00           H+0
HETATM   17  H   UNK     0       0.925  -1.441   0.530  0.00  0.00           H+0
HETATM   18  H   UNK     0       1.656   0.625   1.604  0.00  0.00           H+0
HETATM   19  H   UNK     0       1.243   2.576   0.659  0.00  0.00           H+0
CONECT    1    2   13   14                                                  
CONECT    2    1    3    6   15                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3   16                                                       
CONECT    6    2    7   11   17                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12    6   18                                             
CONECT   12   11   19                                                       
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15    2                                                            
CONECT   16    5                                                            
CONECT   17    6                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2-Amino-2-[(4S,5R)-3-chloro-4-hydroxy-4,5-dihydro-1,2-oxazol-5-yl]acetate	Generator

Chemical Formula

C₅H₇ClN₂O₄

Average Mass

194.5700 Da

Monoisotopic Mass

194.00943 Da

IUPAC Name

(2S)-2-amino-2-[(4S,5R)-3-chloro-4-hydroxy-4,5-dihydro-1,2-oxazol-5-yl]acetic acid

Traditional Name

(S)-amino[(4S,5R)-3-chloro-4-hydroxy-4,5-dihydro-1,2-oxazol-5-yl]acetic acid

CAS Registry Number

Not Available

SMILES

NC([C@H]1ON=C(Cl)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C5H7ClN2O4/c6-4-2(9)3(12-8-4)1(7)5(10)11/h1-3,9H,7H2,(H,10,11)/t1?,2-,3+/m0/s1

InChI Key

KUYDILDQEMQBKJ-ZVKPHKKVSA-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
Streptomyces sviceus	NPAtlas	1126872

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Isoxazoline
Amino acid
Secondary alcohol
Halohydrin
Chlorohydrin
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Primary aliphatic amine
Carbonyl group
Amine
Alcohol
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	-2.3	ALOGPS
logP	-3.4	ChemAxon
logS	-0.76	ALOGPS
pKa (Strongest Acidic)	1.3	ChemAxon
pKa (Strongest Basic)	7.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	37.73 m³·mol⁻¹	ChemAxon
Polarizability	16.01 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

NPAtlas ID

NPA013329

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78437854

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139586789

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for U43795 (NP0003632)

MOL for NP0003632 (U43795)

3D MOL for NP0003632 (U43795)

3D SDF for NP0003632 (U43795)

3D-SDF for NP0003632 (U43795)

PDB for NP0003632 (U43795)

3D PDB for NP0003632 (U43795)

SMILES for NP0003632 (U43795)

INCHI for NP0003632 (U43795)

Structure for NP0003632 (U43795)

3D Structure for NP0003632 (U43795)