NP-MRD: Showing NP-Card for 2-Hydroxyisocaproic acid (NP0002704)

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Record Information

Version

2.0

Created at

2020-11-23 19:38:21 UTC

Updated at

2024-09-03 04:18:42 UTC

NP-MRD ID

NP0002704

Natural Product DOI

https://doi.org/10.57994/1480

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Hydroxyisocaproic acid

Provided By

BMRB

Description

D-Leucic acid, also known as D-leucate or delta-leucic acid, 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-Hydroxyisocaproic acid was first documented in 1996 (PMID: 8605029). Based on a literature review a small amount of articles have been published on D-Leucic acid (PMID: 9766851).

Structure

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


     RDKit          2D

 21 20  0  0  0  0  0  0  0  0999 V2000
   -1.6723   -1.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1311    0.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5301    0.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2679   -0.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6669   -0.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1257   -2.1034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2080    0.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4165    1.9687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6902    0.9254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5311   -0.8046    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8913   -1.4389    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2134   -2.4200    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5899    1.7769    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889    2.3181    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9479    0.1382    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9290    1.4603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0514   -1.0221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345    1.2913    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0658   -1.2456    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667   -3.2715    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2314    2.3243    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
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  1
  1 11  1  0
  1 12  1  0
  2 13  1  1
  3 14  1  1
  3 15  1  0
  3 16  1  0
  4 17  1  1
  4 18  1  0
  5 19  1  1
  6 20  1  0
  9 21  1  0
M  END
> <DATABASE_ID>
NP0002704

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t5-/m1/s1

> <INCHI_KEY>
LVRFTAZAXQPQHI-RXMQYKEDSA-N

> <FORMULA>
C6H12O3

> <MOLECULAR_WEIGHT>
132.1577

> <EXACT_MASS>
132.07864425

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
13.706299606781844

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-hydroxy-4-methylpentanoic acid

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
0.7822806383333333

> <ALOGPS_LOGS>
-0.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.276112311717824

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.257807082104199

> <JCHEM_PKA_STRONGEST_BASIC>
-3.801045430820605

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
32.513400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-α-hydroxyisocaproate

> <JCHEM_VEBER_RULE>
0

$$$$

View in JSmol

Synonyms

Value	Source
(R)-2-Hydroxy-4-methylvaleric acid	ChEBI
(R)-2-Hydroxyisocaproic acid	ChEBI
(R)-Leucic acid	ChEBI
2-Hydroxy-4-methyl-D-valeric acid	ChEBI
alpha-Hydroxyisocaproic acid	ChEBI
D-2-Hydroxy-4-methylpentanoic acid	ChEBI
D-2-Hydroxy-4-methylvaleric acid	ChEBI
D-2-Hydroxyisocaproic acid	ChEBI
delta-Leucic acid	ChEBI
Leucic acid	ChEBI
D-2-Hydroxyisocaproate	Kegg
(R)-2-Hydroxy-4-methylpentanoate	Kegg
D-Leucate	Kegg
(R)-2-Hydroxy-4-methylvalerate	Generator
(R)-2-Hydroxyisocaproate	Generator
(R)-Leucate	Generator
2-Hydroxy-4-methyl-D-valerate	Generator
a-Hydroxyisocaproate	Generator
a-Hydroxyisocaproic acid	Generator
alpha-Hydroxyisocaproate	Generator
Α-hydroxyisocaproate	Generator
Α-hydroxyisocaproic acid	Generator
D-2-Hydroxy-4-methylpentanoate	Generator
D-2-Hydroxy-4-methylvalerate	Generator
delta-Leucate	Generator
Δ-leucate	Generator
Δ-leucic acid	Generator
Leucate	Generator
(R)-2-Hydroxy-4-methylpentanoic acid	Generator
(-)-2-Hydroxyisocaproate	HMDB
(-)-2-Hydroxyisocaproic acid	HMDB
(-)-a-Hydroxyisocaproate	HMDB
(-)-a-Hydroxyisocaproic acid	HMDB
(-)-alpha-Hydroxyisocaproate	HMDB
(-)-alpha-Hydroxyisocaproic acid	HMDB
(R)-2-Hydroxy-4-methyl-pentanoate	HMDB
(R)-2-Hydroxy-4-methyl-pentanoic acid	HMDB
2-Hydroxy-4-methyl-delta-valerate	HMDB
2-Hydroxy-4-methyl-delta-valeric acid	HMDB
D-a-Hydroxyisocaproate	HMDB
D-a-Hydroxyisocaproic acid	HMDB
delta-2-Hydroxy-4-methylpentanoate	HMDB
delta-2-Hydroxy-4-methylpentanoic acid	HMDB
delta-2-Hydroxy-4-methylvalerate	HMDB
delta-2-Hydroxy-4-methylvaleric acid	HMDB
delta-2-Hydroxyisocaproate	HMDB
delta-2-Hydroxyisocaproic acid	HMDB
delta-alpha-Hydroxyisocaproate	HMDB
delta-alpha-Hydroxyisocaproic acid	HMDB

Chemical Formula

C₆H₁₂O₃

Average Mass

132.1577 Da

Monoisotopic Mass

132.07864 Da

IUPAC Name

(2R)-2-hydroxy-4-methylpentanoic acid

Traditional Name

(-)-α-hydroxyisocaproate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t5-/m1/s1

InChI Key

LVRFTAZAXQPQHI-RXMQYKEDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-12-21	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-12-21	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-12-21	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-12-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-12-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-12-21	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	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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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	251.31 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	165500 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.522 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	0.5	ALOGPS
logP	0.78	ChemAxon
logS	-0.03	ALOGPS
pKa (Strongest Acidic)	4.26	ChemAxon
pKa (Strongest Basic)	-3.8	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	3	ChemAxon
Refractivity	32.51 m³·mol⁻¹	ChemAxon
Polarizability	13.71 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

HMDB0000624

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022149

KNApSAcK ID

Not Available

Chemspider ID

388986

KEGG Compound ID

C03264

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Hydroxyisocaproic acid

METLIN ID

5597

PubChem Compound

439960

PDB ID

Not Available

ChEBI ID

55534

Good Scents ID

rw1118401

References

General References

Heil M, Podebrad F, Beck T, Mosandl A, Sewell AC, Bohles H: Enantioselective multidimensional gas chromatography-mass spectrometry in the analysis of urinary organic acids. J Chromatogr B Biomed Sci Appl. 1998 Sep 4;714(2):119-26. doi: 10.1016/s0378-4347(98)00233-3. [PubMed:9766851 ]
Chiou AJ, Ong GT, Wang KT, Chiou SH, Wu SH: Conformational study of two linear hexapeptides by two-dimensional NMR and computer-simulated modeling: implication for peptide cyclization in solution. Biochem Biophys Res Commun. 1996 Feb 15;219(2):572-9. doi: 10.1006/bbrc.1996.0275. [PubMed:8605029 ]

Showing NP-Card for 2-Hydroxyisocaproic acid (NP0002704)

MOL for NP0002704 (2-Hydroxyisocaproic acid)

3D MOL for NP0002704 (2-Hydroxyisocaproic acid)

3D SDF for NP0002704 (2-Hydroxyisocaproic acid)

3D-SDF for NP0002704 (2-Hydroxyisocaproic acid)

PDB for NP0002704 (2-Hydroxyisocaproic acid)

3D PDB for NP0002704 (2-Hydroxyisocaproic acid)

SMILES for NP0002704 (2-Hydroxyisocaproic acid)

INCHI for NP0002704 (2-Hydroxyisocaproic acid)

Structure for NP0002704 (2-Hydroxyisocaproic acid)

3D Structure for NP0002704 (2-Hydroxyisocaproic acid)