NP-MRD: Showing NP-Card for hypoglycin A (2S,4S isomer) (NP0038668)

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Record Information

Version

2.0

Created at

2021-06-20 21:17:45 UTC

Updated at

2021-06-30 00:11:34 UTC

NP-MRD ID

NP0038668

Secondary Accession Numbers

None

Natural Product Identification

Common Name

hypoglycin A (2S,4S isomer)

Provided By

JEOL Database JEOL Logo

Description

L-Hypoglycin A belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. hypoglycin A (2S,4S isomer) is found in Blighia sapida Koenig. hypoglycin A (2S,4S isomer) was first documented in 2009 (Bowen-Forbes,C. S., et al.). Based on a literature review very few articles have been published on L-Hypoglycin A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123173D          

 21 21  0  0  0  0            999 V2000
   -1.1351    3.3465   -0.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1349    2.8318    0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7608    3.0305    1.2656 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7572    1.7521    0.3490 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3379    0.4395    0.9434 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0905   -0.6413   -0.1168 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0501   -0.3007   -1.0268 N   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2199   -1.9893    0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3719   -2.4594    1.5142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2435   -2.6241   -0.0757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5769    2.8311   -1.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5416    4.3170   -0.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5480    3.7581    1.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576    2.9561    2.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5733    1.6624   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5530    0.5572    1.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1390    0.1059    1.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9796   -0.7937   -0.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7667    0.1688   -0.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7210    0.4464   -1.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5249   -2.0117   -0.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  6  1  0  0  0  0
  2  4  1  0  0  0  0
  6  7  1  0  0  0  0
  3  2  1  0  0  0  0
  6  8  1  0  0  0  0
  2  1  2  3  0  0  0
  4 15  1  6  0  0  0
  8  9  2  0  0  0  0
  4  5  1  0  0  0  0
  8 10  1  0  0  0  0
  3 13  1  0  0  0  0
  3 14  1  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  5 16  1  0  0  0  0
  5 17  1  0  0  0  0
  6 18  1  6  0  0  0
  7 19  1  0  0  0  0
  7 20  1  0  0  0  0
 10 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038668

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])[C@@]1([H])C(=C([H])[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C7H11NO2/c1-4-2-5(4)3-6(8)7(9)10/h5-6H,1-3,8H2,(H,9,10)/t5-,6-/m0/s1

> <INCHI_KEY>
OOJZCXFXPZGUBJ-WDSKDSINSA-N

> <FORMULA>
C7H11NO2

> <MOLECULAR_WEIGHT>
141.1677

> <EXACT_MASS>
141.078978601

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
14.531370751647977

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-[(1S)-2-methylidenecyclopropyl]propanoic acid

> <ALOGPS_LOGP>
-2.23

> <JCHEM_LOGP>
-2.1110315690711

> <ALOGPS_LOGS>
-0.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5154022786939834

> <JCHEM_PKA_STRONGEST_BASIC>
9.508615782922254

> <JCHEM_POLAR_SURFACE_AREA>
63.32000000000001

> <JCHEM_REFRACTIVITY>
36.6948

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hypoglycin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.135   3.346  -0.482  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.135   2.832   0.197  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.761   3.030   1.266  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.757   1.752   0.349  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.338   0.440   0.943  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.091  -0.641  -0.117  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.050  -0.301  -1.027  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.220  -1.989   0.556  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.372  -2.459   1.514  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.244  -2.624  -0.076  0.00  0.00           O+0
HETATM   11  H   UNK     0      -1.577   2.831  -1.326  0.00  0.00           H+0
HETATM   12  H   UNK     0      -1.542   4.317  -0.216  0.00  0.00           H+0
HETATM   13  H   UNK     0       1.548   3.758   1.122  0.00  0.00           H+0
HETATM   14  H   UNK     0       0.358   2.956   2.267  0.00  0.00           H+0
HETATM   15  H   UNK     0       1.573   1.662  -0.358  0.00  0.00           H+0
HETATM   16  H   UNK     0      -0.553   0.557   1.576  0.00  0.00           H+0
HETATM   17  H   UNK     0       1.139   0.106   1.616  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.980  -0.794  -0.739  0.00  0.00           H+0
HETATM   19  H   UNK     0      -1.767   0.169  -0.460  0.00  0.00           H+0
HETATM   20  H   UNK     0      -0.721   0.446  -1.647  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.525  -2.012  -0.803  0.00  0.00           H+0
CONECT    1    2   11   12                                                  
CONECT    2    4    3    1                                                  
CONECT    3    4    2   13   14                                             
CONECT    4    3    2   15    5                                             
CONECT    5    6    4   16   17                                             
CONECT    6    5    7    8   18                                             
CONECT    7    6   19   20                                                  
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   21                                                       
CONECT   11    1                                                            
CONECT   12    1                                                            
CONECT   13    3                                                            
CONECT   14    3                                                            
CONECT   15    4                                                            
CONECT   16    5                                                            
CONECT   17    5                                                            
CONECT   18    6                                                            
CONECT   19    7                                                            
CONECT   20    7                                                            
CONECT   21   10                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
Hypoglycin a	Kegg
Hypoglycine a	Kegg
L-Hypoglycin	Kegg
Hypoglycin, (S)-isomer	MeSH
Hypoglycin	MeSH
Hypoglycin, carboxy-(14)C-labeled	MeSH

Chemical Formula

C₇H₁₁NO₂

Average Mass

141.1677 Da

Monoisotopic Mass

141.07898 Da

IUPAC Name

(2S)-2-amino-3-[(1S)-2-methylidenecyclopropyl]propanoic acid

Traditional Name

hypoglycin

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])[C@@]1([H])C(=C([H])[H])C1([H])[H]

InChI Identifier

InChI=1S/C7H11NO2/c1-4-2-5(4)3-6(8)7(9)10/h5-6H,1-3,8H2,(H,9,10)/t5-,6-/m0/s1

InChI Key

OOJZCXFXPZGUBJ-WDSKDSINSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Billia hippocastanum	KNApSAcK Database	22123792
Blighia sapida	JEOL database	Bowen-Forbes,C. S., et al, Magn. Reson. Chem. 47, 1004 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Carbocyclic fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:6248 )
Phytotoxins (C08287 )

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	-2.2	ALOGPS
logP	-2.1	ChemAxon
logS	-0.15	ALOGPS
pKa (Strongest Acidic)	2.52	ChemAxon
pKa (Strongest Basic)	9.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	36.69 m³·mol⁻¹	ChemAxon
Polarizability	14.53 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

C00001372

Chemspider ID

390184

KEGG Compound ID

C08287

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hypoglycin A

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bowen-Forbes,C. S., et al. (2009). Bowen-Forbes,C. S., et al, Magn. Reson. Chem. 47, 1004 (2009). Mag. Reson. Chem..

Showing NP-Card for hypoglycin A (2S,4S isomer) (NP0038668)

MOL for NP0038668 (hypoglycin A (2S,4S isomer))

3D MOL for NP0038668 (hypoglycin A (2S,4S isomer))

3D SDF for NP0038668 (hypoglycin A (2S,4S isomer))

3D-SDF for NP0038668 (hypoglycin A (2S,4S isomer))

PDB for NP0038668 (hypoglycin A (2S,4S isomer))

3D PDB for NP0038668 (hypoglycin A (2S,4S isomer))

SMILES for NP0038668 (hypoglycin A (2S,4S isomer))

INCHI for NP0038668 (hypoglycin A (2S,4S isomer))

Structure for NP0038668 (hypoglycin A (2S,4S isomer))

3D Structure for NP0038668 (hypoglycin A (2S,4S isomer))