NP-MRD: Showing NP-Card for Acetyl-3-hydroxyisobutyric acid (NP0006692)

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Record Information

Version

2.0

Created at

2020-12-09 03:38:46 UTC

Updated at

2021-07-15 16:55:32 UTC

NP-MRD ID

NP0006692

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acetyl-3-hydroxyisobutyric acid

Provided By

NPAtlas

Description

3-(Acetyloxy)-2-methylpropanoic acid belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Acetyl-3-hydroxyisobutyric acid is found in Tolypocladium and Tolypocladium cylindrosporum. Based on a literature review very few articles have been published on 3-(acetyloxy)-2-methylpropanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118303D          

 20 19  0  0  0  0            999 V2000
    3.3908    1.1124    0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3507    0.2926   -0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7164   -0.3922   -1.0274 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255    0.2624    0.4323 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1396   -0.5655   -0.2901 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2515   -0.5479    0.2491 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1041   -1.4712   -0.6067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8163    0.8175    0.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0991    1.7418   -0.2536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1201    1.0588    0.6664 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0361    1.6641    1.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7817    1.8620   -0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2727    0.4568    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5931   -1.5722   -0.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0995   -0.1478   -1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3210   -0.9337    1.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213   -1.0518   -0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2015   -2.4756   -0.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6223   -1.6197   -1.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7489    1.5092    0.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  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
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  5 14  1  0  0  0  0
  5 15  1  0  0  0  0
  6 16  1  1  0  0  0
  7 17  1  0  0  0  0
  7 18  1  0  0  0  0
  7 19  1  0  0  0  0
 10 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006692

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O4/c1-4(6(8)9)3-10-5(2)7/h4H,3H2,1-2H3,(H,8,9)/t4-/m0/s1

> <INCHI_KEY>
MQLMCMRCMGKYFQ-UHFFFAOYSA-N

> <FORMULA>
C6H10O4

> <MOLECULAR_WEIGHT>
146.142

> <EXACT_MASS>
146.057908802

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.27343133947835

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-(acetyloxy)-2-methylpropanoic acid

> <ALOGPS_LOGP>
0.55

> <JCHEM_LOGP>
0.1805306646666666

> <ALOGPS_LOGS>
-0.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.141418749926321

> <JCHEM_PKA_STRONGEST_BASIC>
-6.995517393595405

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
32.771300000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.95e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-(acetyloxy)-2-methylpropanoic 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  C   UNK     0       3.391   1.112   0.633  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.351   0.293  -0.022  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.716  -0.392  -1.027  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.026   0.262   0.432  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.140  -0.566  -0.290  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.252  -0.548   0.249  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.104  -1.471  -0.607  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.816   0.818   0.205  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.099   1.742  -0.254  0.00  0.00           O+0
HETATM   10  O   UNK     0      -3.120   1.059   0.666  0.00  0.00           O+0
HETATM   11  H   UNK     0       3.036   1.664   1.503  0.00  0.00           H+0
HETATM   12  H   UNK     0       3.782   1.862  -0.111  0.00  0.00           H+0
HETATM   13  H   UNK     0       4.273   0.457   0.852  0.00  0.00           H+0
HETATM   14  H   UNK     0       0.593  -1.572  -0.318  0.00  0.00           H+0
HETATM   15  H   UNK     0       0.100  -0.148  -1.325  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.321  -0.934   1.288  0.00  0.00           H+0
HETATM   17  H   UNK     0      -3.121  -1.052  -0.773  0.00  0.00           H+0
HETATM   18  H   UNK     0      -2.201  -2.476  -0.163  0.00  0.00           H+0
HETATM   19  H   UNK     0      -1.622  -1.620  -1.606  0.00  0.00           H+0
HETATM   20  H   UNK     0      -3.749   1.509   0.015  0.00  0.00           H+0
CONECT    1    2   11   12   13                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   14   15                                             
CONECT    6    5    7    8   16                                             
CONECT    7    6   17   18   19                                             
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   20                                                       
CONECT   11    1                                                            
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14    5                                                            
CONECT   15    5                                                            
CONECT   16    6                                                            
CONECT   17    7                                                            
CONECT   18    7                                                            
CONECT   19    7                                                            
CONECT   20   10                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3-(Acetyloxy)-2-methylpropanoate	Generator
Acetyl-3-hydroxyisobutyrate	Generator

Chemical Formula

C₆H₁₀O₄

Average Mass

146.1420 Da

Monoisotopic Mass

146.05791 Da

IUPAC Name

(2S)-3-(acetyloxy)-2-methylpropanoic acid

Traditional Name

(2S)-3-(acetyloxy)-2-methylpropanoic acid

CAS Registry Number

Not Available

SMILES

CC(COC(C)=O)C(O)=O

InChI Identifier

InChI=1S/C6H10O4/c1-4(6(8)9)3-10-5(2)7/h4H,3H2,1-2H3,(H,8,9)

InChI Key

MQLMCMRCMGKYFQ-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, 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
Tolypocladium	NPAtlas	17183517
Tolypocladium cylindrosporum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	0.55	ALOGPS
logP	0.18	ChemAxon
logS	-0.32	ALOGPS
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	32.77 m³·mol⁻¹	ChemAxon
Polarizability	14.27 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

NPAtlas ID

NPA012519

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

14821484

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20194286

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Acetyl-3-hydroxyisobutyric acid (NP0006692)

MOL for NP0006692 (Acetyl-3-hydroxyisobutyric acid)

3D MOL for NP0006692 (Acetyl-3-hydroxyisobutyric acid)

3D SDF for NP0006692 (Acetyl-3-hydroxyisobutyric acid)

3D-SDF for NP0006692 (Acetyl-3-hydroxyisobutyric acid)

PDB for NP0006692 (Acetyl-3-hydroxyisobutyric acid)

3D PDB for NP0006692 (Acetyl-3-hydroxyisobutyric acid)

SMILES for NP0006692 (Acetyl-3-hydroxyisobutyric acid)

INCHI for NP0006692 (Acetyl-3-hydroxyisobutyric acid)

Structure for NP0006692 (Acetyl-3-hydroxyisobutyric acid)

3D Structure for NP0006692 (Acetyl-3-hydroxyisobutyric acid)