NP-MRD: Showing NP-Card for (S)-(+)-2-Hydroxy-3-methylbutyric acid (NP0002797)

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Record Information

Version

1.0

Created at

2020-11-23 19:40:41 UTC

Updated at

2021-08-12 19:52:10 UTC

NP-MRD ID

NP0002797

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(S)-(+)-2-Hydroxy-3-methylbutyric acid

Provided By

BMRB

Description

2-Hydroxy-3-methylbutyric acid, also known as a-hydroxyisovaleric acid or 2-oxyisovalerate, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 2-Hydroxy-3-methylbutyric acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. It was first documented in 2008 (PMID: 17984079). Based on a literature review very few articles have been published on 2-Hydroxy-3-methylbutyric acid (PMID: 18502700) (PMID: 21516781).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 18 17  0  0  0  0  0  0  0  0999 V2000
   -1.3909    0.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2730   -0.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2731   -1.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7272    0.7942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3907    1.7944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8451   -0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7192   -1.7006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2702    0.2622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5198   -0.3112    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0189    1.3815    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5088    1.6766    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147   -1.4526    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5046   -0.5852    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1552   -2.4417    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2732   -2.5595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7273    1.9121    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0835    3.2626    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3881   -0.7380    0.0000 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
  4  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  6
  1 10  1  0
  1 11  1  0
  2 12  1  1
  3 13  1  6
  3 14  1  0
  3 15  1  0
  4 16  1  1
  5 17  1  0
  8 18  1  0
M  END
> <DATABASE_ID>
NP0002797

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H10O3/c1-3(2)4(6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t4-/m0/s1

> <INCHI_KEY>
NGEWQZIDQIYUNV-BYPYZUCNSA-N

> <FORMULA>
C5H10O3

> <MOLECULAR_WEIGHT>
118.132

> <EXACT_MASS>
118.062994182

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
11.776164381367607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-hydroxy-3-methylbutanoic acid

> <ALOGPS_LOGP>
0.10

> <JCHEM_LOGP>
0.4156657033333334

> <ALOGPS_LOGS>
0.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.053181861607996

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.138361788089717

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8921886131871277

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
27.8354

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.15e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-hydroxyisovaleric acid

> <JCHEM_VEBER_RULE>
0

$$$$

View in JSmol

Synonyms

Value	Source
(S)-(+)-2-Hydroxy-3-methylbutanoic acid	ChEBI
(S)-(+)-2-Hydroxy-3-methylbutyric acid	ChEBI
2-Hydroxy-3-methyl-(S)-(+)-butyric acid	ChEBI
2-Hydroxyisovalerate	ChEBI
2-Oxyisovalerate	ChEBI
a-Hydroxyisovaleric acid	ChEBI
L-(+)-2-Hydroxyisovaleric acid	ChEBI
L-(+)-alpha-Hydroxyisovaleric acid	ChEBI
(S)-(+)-2-Hydroxy-3-methylbutanoate	Generator
(S)-(+)-2-Hydroxy-3-methylbutyrate	Generator
2-Hydroxy-3-methyl-(S)-(+)-butyrate	Generator
2-Hydroxyisovaleric acid	Generator
2-Oxyisovaleric acid	Generator
a-Hydroxyisovalerate	Generator
L-(+)-2-Hydroxyisovalerate	Generator
L-(+)-a-Hydroxyisovalerate	Generator
L-(+)-a-Hydroxyisovaleric acid	Generator
L-(+)-alpha-Hydroxyisovalerate	Generator
L-(+)-Α-hydroxyisovalerate	Generator
L-(+)-Α-hydroxyisovaleric acid	Generator
2-Hydroxy-3-methylbutyrate	Generator
(S)-2-Hydroxy-3-methylbutyrate	Generator

Chemical Formula

C₅H₁₀O₃

Average Mass

118.1320 Da

Monoisotopic Mass

118.06299 Da

IUPAC Name

(2S)-2-hydroxy-3-methylbutanoic acid

Traditional Name

α-hydroxyisovaleric acid

CAS Registry Number

Not Available

SMILES

[H][C@](O)(C(C)C)C(O)=O

InChI Identifier

InChI=1S/C5H10O3/c1-3(2)4(6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t4-/m0/s1

InChI Key

NGEWQZIDQIYUNV-BYPYZUCNSA-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, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Not Available

Substituents

Not Available

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	0.1	ALOGPS
logP	0.42	ChemAxon
logS	0.26	ALOGPS
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	27.84 m³·mol⁻¹	ChemAxon
Polarizability	11.78 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

HMDB0062584

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

745606

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

60631

Good Scents ID

Not Available

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Wishart DS, Lewis MJ, Morrissey JA, Flegel MD, Jeroncic K, Xiong Y, Cheng D, Eisner R, Gautam B, Tzur D, Sawhney S, Bamforth F, Greiner R, Li L: The human cerebrospinal fluid metabolome. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Aug 15;871(2):164-73. doi: 10.1016/j.jchromb.2008.05.001. Epub 2008 May 8. [PubMed:18502700 ]
Beloborodova NV, Bairamov IT, Olenin AIu, Fedotcheva NI: [Exometabolites of some anaerobic microorganisms of human microflora]. Biomed Khim. 2011 Jan-Feb;57(1):95-105. doi: 10.18097/pbmc20115701095. [PubMed:21516781 ]

Showing NP-Card for (S)-(+)-2-Hydroxy-3-methylbutyric acid (NP0002797)

MOL for NP0002797 ((S)-(+)-2-Hydroxy-3-methylbutyric acid)

3D MOL for NP0002797 ((S)-(+)-2-Hydroxy-3-methylbutyric acid)

3D SDF for NP0002797 ((S)-(+)-2-Hydroxy-3-methylbutyric acid)

3D-SDF for NP0002797 ((S)-(+)-2-Hydroxy-3-methylbutyric acid)

PDB for NP0002797 ((S)-(+)-2-Hydroxy-3-methylbutyric acid)

3D PDB for NP0002797 ((S)-(+)-2-Hydroxy-3-methylbutyric acid)

SMILES for NP0002797 ((S)-(+)-2-Hydroxy-3-methylbutyric acid)

INCHI for NP0002797 ((S)-(+)-2-Hydroxy-3-methylbutyric acid)

Structure for NP0002797 ((S)-(+)-2-Hydroxy-3-methylbutyric acid)

3D Structure for NP0002797 ((S)-(+)-2-Hydroxy-3-methylbutyric acid)