NP-MRD: Showing NP-Card for 2-Hydroxyoctanoic acid (NP0002799)

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Record Information

Version

2.0

Created at

2020-11-23 19:40:44 UTC

Updated at

2021-08-12 19:52:11 UTC

NP-MRD ID

NP0002799

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Hydroxyoctanoic acid

Provided By

BMRB

Description

(R)-2-Hydroxycaprylic acid belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Based on a literature review very few articles have been published on (R)-2-Hydroxycaprylic acid.

Structure

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


     RDKit          2D

 27 26  0  0  0  0  0  0  0  0999 V2000
   -5.2607    0.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7658    0.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2709   -0.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7761   -0.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7188   -0.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2137   -0.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7086   -0.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5847   -2.0304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325    0.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7132    1.9579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1890    1.5995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1368    1.7026    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3846   -1.2872    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7556    0.3316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8897   -1.4111    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6419    1.5787    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1471    1.4548    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3948   -1.5349    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8999   -1.6588    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6522    1.3309    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8427    1.2071    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5949   -1.7827    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0898   -1.9066    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1544    1.0871    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2034   -0.6595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8174   -2.8852    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3129    3.0943    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  6
  1 13  1  0
  1 14  1  0
  2 15  1  6
  2 16  1  0
  3 17  1  1
  3 18  1  0
  4 19  1  1
  4 20  1  0
  5 21  1  6
  5 22  1  0
  6 23  1  6
  6 24  1  0
  7 25  1  1
  8 26  1  0
 11 27  1  0
M  END
> <DATABASE_ID>
NP0002799

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H16O3/c1-2-3-4-5-6-7(9)8(10)11/h7,9H,2-6H2,1H3,(H,10,11)/t7-/m1/s1

> <INCHI_KEY>
JKRDADVRIYVCCY-SSDOTTSWSA-N

> <FORMULA>
C8H16O3

> <MOLECULAR_WEIGHT>
160.2108

> <EXACT_MASS>
160.109944378

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.190397637118792

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-hydroxyoctanoic acid

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.828967537

> <ALOGPS_LOGS>
-1.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.284148892109581

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.422499319236623

> <JCHEM_PKA_STRONGEST_BASIC>
-3.797528711914386

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
41.767799999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
D-2-hydroxyoctanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

COMPND    NP0002799
HETATM    1  C1  UNL     1       3.706   1.074   0.782  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.005  -0.157   0.255  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.537   0.172   0.028  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.901  -1.091  -0.494  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.580  -0.917  -0.771  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.354  -0.533   0.436  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.815  -0.396   0.088  1.00  0.00           C  
HETATM    8  O1  UNL     1      -3.506  -0.040   1.284  1.00  0.00           O  
HETATM    9  C8  UNL     1      -3.096   0.650  -0.913  1.00  0.00           C  
HETATM   10  O2  UNL     1      -2.711   0.612  -2.092  1.00  0.00           O  
HETATM   11  O3  UNL     1      -3.840   1.764  -0.538  1.00  0.00           O  
HETATM   12  H1  UNL     1       4.671   0.813   1.215  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.020   1.584   1.507  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.867   1.747  -0.083  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.137  -1.019   0.937  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.454  -0.411  -0.738  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.492   0.983  -0.711  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.114   0.503   0.987  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.097  -1.915   0.188  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.376  -1.319  -1.469  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.945  -1.932  -1.087  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.693  -0.266  -1.633  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.313  -1.325   1.234  1.00  0.00           H  
HETATM   24  H13 UNL     1      -1.022   0.435   0.886  1.00  0.00           H  
HETATM   25  H14 UNL     1      -3.238  -1.386  -0.223  1.00  0.00           H  
HETATM   26  H15 UNL     1      -2.892   0.593   1.769  1.00  0.00           H  
HETATM   27  H16 UNL     1      -4.371   1.777   0.313  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7   23   24
CONECT    7    8    9   25
CONECT    8   26
CONECT    9   10   10   11
CONECT   11   27
END

View in JSmol

Synonyms

Value	Source
(R)-2-Hydroxycaprylate	Generator
(R)-2-Hydroxyoctanoate	HMDB
(R)-2-Hydroxyoctanoic acid	HMDB
(R)-a-Hydroxycaprylate	HMDB
(R)-a-Hydroxycaprylic acid	HMDB
(R)-alpha-Hydroxycaprylate	HMDB
(R)-alpha-Hydroxycaprylic acid	HMDB
2-Hydroxy-D-octanoate	HMDB
2-Hydroxy-D-octanoic acid	HMDB
2-Hydroxy-delta-octanoate	HMDB
2-Hydroxy-delta-octanoic acid	HMDB
D-2-Hydroxyoctanoate	HMDB
D-2-Hydroxyoctanoic acid	HMDB
delta-2-Hydroxyoctanoate	HMDB
delta-2-Hydroxyoctanoic acid	HMDB
2R-Hydroxy-octanoate	Generator, HMDB

Chemical Formula

C₈H₁₆O₃

Average Mass

160.2108 Da

Monoisotopic Mass

160.10994 Da

IUPAC Name

(2R)-2-hydroxyoctanoic acid

Traditional Name

D-2-hydroxyoctanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H16O3/c1-2-3-4-5-6-7(9)8(10)11/h7,9H,2-6H2,1H3,(H,10,11)/t7-/m1/s1

InChI Key

JKRDADVRIYVCCY-SSDOTTSWSA-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

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 medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Hydroxy fatty acid
Alpha-hydroxy acid
Hydroxy acid
Monosaccharide
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Hydroxy fatty acids (LMFA01050313 )

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	1.8	ALOGPS
logP	1.83	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.42	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	6	ChemAxon
Refractivity	41.77 m³·mol⁻¹	ChemAxon
Polarizability	18.19 Å³	ChemAxon
Number of Rings	0	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

HMDB0002264

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022934

KNApSAcK ID

Not Available

Chemspider ID

4472285

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6582

PubChem Compound

5312860

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 2-Hydroxyoctanoic acid (NP0002799)

MOL for NP0002799 (2-Hydroxyoctanoic acid)

3D MOL for NP0002799 (2-Hydroxyoctanoic acid)

3D SDF for NP0002799 (2-Hydroxyoctanoic acid)

3D-SDF for NP0002799 (2-Hydroxyoctanoic acid)

PDB for NP0002799 (2-Hydroxyoctanoic acid)

3D PDB for NP0002799 (2-Hydroxyoctanoic acid)

SMILES for NP0002799 (2-Hydroxyoctanoic acid)

INCHI for NP0002799 (2-Hydroxyoctanoic acid)

Structure for NP0002799 (2-Hydroxyoctanoic acid)

3D Structure for NP0002799 (2-Hydroxyoctanoic acid)