NP-MRD: Showing NP-Card for (2s,3r)-2-{[(3-amino-2-hydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxybutanoic acid (NP0164588)

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Record Information

Version

2.0

Created at

2022-09-02 23:29:51 UTC

Updated at

2022-09-02 23:29:51 UTC

NP-MRD ID

NP0164588

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r)-2-{[(3-amino-2-hydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxybutanoic acid

Description

Antimycic acid, also known as antimycate, belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Based on a literature review very few articles have been published on Antimycic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 32  0  0  0  0  0  0  0  0999 V2000
   -4.3751   -0.7198   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9391   -1.1848   -0.0628 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5602   -2.0292   -1.1134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0697    0.0756   -0.0997 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7069   -0.3325    0.0464 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2595    0.4351   -0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0680    1.6398   -0.8709 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6276   -0.0470   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8443   -1.3105    0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1043   -1.8068    0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1591   -1.0066    0.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9564    0.2181   -0.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0625    1.0143   -0.7358 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6777    0.7445   -0.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6019    1.9821   -1.1049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003    0.9951    0.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6910    1.3143    1.8926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7809    1.5079    1.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4003    0.2175   -0.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8229   -0.5610    0.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9318   -1.5259   -0.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8472   -1.6612    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3434   -2.5474   -1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2138    0.5685   -1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3513    2.4640   -0.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9759   -1.8868    0.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -2.7688    1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1549   -1.3960    0.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9671    1.9018   -1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0435    0.7256   -0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8842    2.5792   -1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0201    2.4007    0.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
  4 16  1  0
 16 18  1  0
 16 17  2  0
 14  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  4 24  1  6
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 15 31  1  0
 18 32  1  0
M  END


  Mrv1652309032201292D          

 18 18  0  0  1  0            999 V2000
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  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
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    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  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  2  0  0  0  0
  6  7  1  4  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0164588

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)[C@H](N=C(O)C1=CC=CC(N)=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N2O5/c1-5(14)8(11(17)18)13-10(16)6-3-2-4-7(12)9(6)15/h2-5,8,14-15H,12H2,1H3,(H,13,16)(H,17,18)/t5-,8+/m1/s1

> <INCHI_KEY>
RNUIZVZDCCDCCJ-XRGYYRRGSA-N

> <FORMULA>
C11H14N2O5

> <MOLECULAR_WEIGHT>
254.242

> <EXACT_MASS>
254.090271559

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.572587521208327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R)-2-{[(3-amino-2-hydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxybutanoic acid

> <ALOGPS_LOGP>
0.31

> <JCHEM_LOGP>
-0.11712396669007362

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.707122563292459

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.806492370934985

> <JCHEM_PKA_STRONGEST_BASIC>
4.3045855595768465

> <JCHEM_POLAR_SURFACE_AREA>
136.37

> <JCHEM_REFRACTIVITY>
63.77710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-2-{[(3-amino-2-hydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxybutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.667   4.620   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334   8.470   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    8   15                                                  
CONECT   15   14                                                            
CONECT   16    4   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
Antimycate	Generator

Chemical Formula

C₁₁H₁₄N₂O₅

Average Mass

254.2420 Da

Monoisotopic Mass

254.09027 Da

IUPAC Name

(2S,3R)-2-{[(3-amino-2-hydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxybutanoic acid

Traditional Name

(2S,3R)-2-{[(3-amino-2-hydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxybutanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](O)[C@H](N=C(O)C1=CC=CC(N)=C1O)C(O)=O

InChI Identifier

InChI=1S/C11H14N2O5/c1-5(14)8(11(17)18)13-10(16)6-3-2-4-7(12)9(6)15/h2-5,8,14-15H,12H2,1H3,(H,13,16)(H,17,18)/t5-,8+/m1/s1

InChI Key

RNUIZVZDCCDCCJ-XRGYYRRGSA-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. N-acyl-alpha amino acids are compounds containing an alpha amino acid 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

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Aminophenol
O-aminophenol
Aniline or substituted anilines
1-hydroxy-4-unsubstituted benzenoid
Beta-hydroxy acid
Phenol
Monocyclic benzene moiety
Hydroxy acid
Benzenoid
Amino acid
Secondary alcohol
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxide
Organic nitrogen compound
Amine
Alcohol
Carbonyl group
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Primary amine
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	0.31	ALOGPS
logP	-0.12	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	2.81	ChemAxon
pKa (Strongest Basic)	4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	63.78 m³·mol⁻¹	ChemAxon
Polarizability	24.57 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12306710

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r)-2-{[(3-amino-2-hydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxybutanoic acid (NP0164588)

MOL for NP0164588 ((2s,3r)-2-{[(3-amino-2-hydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxybutanoic acid)

3D MOL for NP0164588 ((2s,3r)-2-{[(3-amino-2-hydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxybutanoic acid)

3D SDF for NP0164588 ((2s,3r)-2-{[(3-amino-2-hydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxybutanoic acid)

3D-SDF for NP0164588 ((2s,3r)-2-{[(3-amino-2-hydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxybutanoic acid)

PDB for NP0164588 ((2s,3r)-2-{[(3-amino-2-hydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxybutanoic acid)

3D PDB for NP0164588 ((2s,3r)-2-{[(3-amino-2-hydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxybutanoic acid)

SMILES for NP0164588 ((2s,3r)-2-{[(3-amino-2-hydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxybutanoic acid)

INCHI for NP0164588 ((2s,3r)-2-{[(3-amino-2-hydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxybutanoic acid)

Structure for NP0164588 ((2s,3r)-2-{[(3-amino-2-hydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxybutanoic acid)

3D Structure for NP0164588 ((2s,3r)-2-{[(3-amino-2-hydroxyphenyl)(hydroxy)methylidene]amino}-3-hydroxybutanoic acid)