NP-MRD: Showing NP-Card for 3-[(1,2,4-trihydroxy-3,3-dimethylbutylidene)amino]prop-2-enoic acid (NP0170709)

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Record Information

Version

2.0

Created at

2022-09-03 06:56:46 UTC

Updated at

2022-09-03 06:56:46 UTC

NP-MRD ID

NP0170709

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(1,2,4-trihydroxy-3,3-dimethylbutylidene)amino]prop-2-enoic acid

Description

SCHEMBL16011117 belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage. SCHEMBL16011117 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 29  0  0  0  0  0  0  0  0999 V2000
   -1.9399   -1.0835    0.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7532    0.4078    0.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5896    1.1303    1.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2763    0.8329   -1.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6311    0.5253   -1.1943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3310    0.7709    0.4887 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0275    0.3820    1.8105 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6492    0.1118   -0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5719    0.3231   -1.6173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6649   -0.7429    0.0978 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6131   -1.3833   -0.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9092   -1.1722   -0.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4646   -0.2664    0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6973   -0.0948    0.4605 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6240    0.4065    1.2269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9436   -1.2271    0.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8928   -1.6203   -0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1274   -1.4982    1.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5754    1.4088    0.8556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0480    2.0429    1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7996    0.4889    2.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7409    0.2167   -1.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1284    1.9016   -1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8251   -0.4199   -1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1790    1.8761    0.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8094    0.0635    2.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7467   -0.9399    1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2684   -2.0681   -1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6260   -1.6914   -1.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7827    1.3189    1.6108 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
  2  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  1
  7 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  0
M  END


  Mrv1533004171519022D          

 15 14  0  0  0  0            999 V2000
    3.3000    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    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
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    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  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0170709

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(CO)C(O)C(=O)NC=CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H15NO5/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h3-4,7,11,14H,5H2,1-2H3,(H,10,15)(H,12,13)

> <INCHI_KEY>
HWKKTJQAKVPKTK-UHFFFAOYSA-N

> <FORMULA>
C9H15NO5

> <MOLECULAR_WEIGHT>
217.221

> <EXACT_MASS>
217.095022587

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
21.279976789701855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2,4-dihydroxy-3,3-dimethylbutanamido)prop-2-enoic acid

> <ALOGPS_LOGP>
-0.74

> <JCHEM_LOGP>
-1.139558375333333

> <ALOGPS_LOGS>
-1.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.630898064060514

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.553141130309593

> <JCHEM_PKA_STRONGEST_BASIC>
-2.786012983644877

> <JCHEM_POLAR_SURFACE_AREA>
106.86

> <JCHEM_REFRACTIVITY>
51.734899999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2,4-dihydroxy-3,3-dimethylbutanamido)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       6.160   4.207   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.160   1.127   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.700   2.667   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.470   4.001   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.850   4.001   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.620   0.000   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       2.310   1.334   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.540   0.000   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  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    6                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₉H₁₅NO₅

Average Mass

217.2210 Da

Monoisotopic Mass

217.09502 Da

IUPAC Name

3-(2,4-dihydroxy-3,3-dimethylbutanamido)prop-2-enoic acid

Traditional Name

3-(2,4-dihydroxy-3,3-dimethylbutanamido)prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

CC(C)(CO)C(O)C(=O)NC=CC(O)=O

InChI Identifier

InChI=1S/C9H15NO5/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h3-4,7,11,14H,5H2,1-2H3,(H,10,15)(H,12,13)

InChI Key

HWKKTJQAKVPKTK-UHFFFAOYSA-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 amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

N-acyl amines

Alternative Parents

Substituents

Monosaccharide
N-acyl-amine
Acrylic acid or derivatives
Vinylogous amide
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organonitrogen compound
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	-0.74	ALOGPS
logP	-1.1	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	51.73 m³·mol⁻¹	ChemAxon
Polarizability	21.28 Å³	ChemAxon
Number of Rings	0	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

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

78108302

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(1,2,4-trihydroxy-3,3-dimethylbutylidene)amino]prop-2-enoic acid (NP0170709)

MOL for NP0170709 (3-[(1,2,4-trihydroxy-3,3-dimethylbutylidene)amino]prop-2-enoic acid)

3D MOL for NP0170709 (3-[(1,2,4-trihydroxy-3,3-dimethylbutylidene)amino]prop-2-enoic acid)

3D SDF for NP0170709 (3-[(1,2,4-trihydroxy-3,3-dimethylbutylidene)amino]prop-2-enoic acid)

3D-SDF for NP0170709 (3-[(1,2,4-trihydroxy-3,3-dimethylbutylidene)amino]prop-2-enoic acid)

PDB for NP0170709 (3-[(1,2,4-trihydroxy-3,3-dimethylbutylidene)amino]prop-2-enoic acid)

3D PDB for NP0170709 (3-[(1,2,4-trihydroxy-3,3-dimethylbutylidene)amino]prop-2-enoic acid)

SMILES for NP0170709 (3-[(1,2,4-trihydroxy-3,3-dimethylbutylidene)amino]prop-2-enoic acid)

INCHI for NP0170709 (3-[(1,2,4-trihydroxy-3,3-dimethylbutylidene)amino]prop-2-enoic acid)

Structure for NP0170709 (3-[(1,2,4-trihydroxy-3,3-dimethylbutylidene)amino]prop-2-enoic acid)

3D Structure for NP0170709 (3-[(1,2,4-trihydroxy-3,3-dimethylbutylidene)amino]prop-2-enoic acid)