NP-MRD: Showing NP-Card for 10-hydroxydecanoic acid (NP0271968)

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Record Information

Version

2.0

Created at

2022-09-08 18:26:00 UTC

Updated at

2025-02-11 15:47:27 UTC

NP-MRD ID

NP0271968

Natural Product DOI

https://doi.org/10.57994/2648

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-hydroxydecanoic acid

Description

10-Hydroxycapric acid, also known as 10-hydroxydecanoate or 10-OH-decanoic acid, belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain. 10-hydroxydecanoic acid is found in Trypanosoma brucei. 10-hydroxydecanoic acid was first documented in 1979 (PMID: 113393). 10-Hydroxycapric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 1839651).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 32  0  0  0  0  0  0  0  0999 V2000
   -4.7791   -0.0214    2.5366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4522    0.5242    1.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1746    1.5934    1.0008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2833   -0.0188    0.7048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0447    0.7664   -0.5686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8724    0.2315   -1.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5730    0.2788   -0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4908   -0.2821   -1.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8552   -0.3205   -0.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0064   -1.1248    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4453   -1.0545    0.8189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9176    0.3411    1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2685    0.2655    1.5420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6257    1.5090    0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4929   -1.0818    0.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4061    0.1288    1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464    0.6202   -1.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9687    1.8491   -0.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0435   -0.8573   -1.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6995    0.8043   -2.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3682    1.2735   -0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7256   -0.3841    0.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5199    0.3337   -2.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1766   -1.3026   -1.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5652   -0.6964   -1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1662    0.7435   -0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8247   -2.2070    0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3350   -0.8349    1.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0823   -1.4582   -0.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6465   -1.6964    1.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9541    1.0014    0.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3318    0.7441    1.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8696    0.3321    0.7620 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 13 33  1  0
 12 31  1  0
 12 32  1  0
 11 29  1  0
 11 30  1  0
 10 27  1  0
 10 28  1  0
  9 25  1  0
  9 26  1  0
  8 23  1  0
  8 24  1  0
  7 21  1  0
  7 22  1  0
  6 19  1  0
  6 20  1  0
  5 17  1  0
  5 18  1  0
  4 15  1  0
  4 16  1  0
  3 14  1  0
M  END

HEADER    PROTEIN                                 10-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-FEB-20         0                                  
HETATM    1  O   UNK     0       6.573   5.335   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      21.243   6.105   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      19.909   3.795   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

Synonyms

Value	Source
10-Hydroxydecanoate	ChEBI
10-Hydroxydecanoic acid	ChEBI
10-OH-Capric acid	ChEBI
10-OH-Decanoic acid	ChEBI
10-OH-Caprate	Generator
10-OH-Decanoate	Generator
10-Hydroxycaprate	Generator
10-HDAA CPD	MeSH
10HDA CPD	MeSH
10-Hydroxy caprate	Generator

Chemical Formula

C₁₀H₂₀O₃

Average Mass

188.2670 Da

Monoisotopic Mass

188.14124 Da

IUPAC Name

10-hydroxydecanoic acid

Traditional Name

10-hydroxydecanoic acid

CAS Registry Number

Not Available

SMILES

OCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C10H20O3/c11-9-7-5-3-1-2-4-6-8-10(12)13/h11H,1-9H2,(H,12,13)

InChI Key

YJCJVMMDTBEITC-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-24	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-24	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-24	View Spectrum

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

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	2024-05-24	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Medium-chain hydroxy acids and derivatives

Direct Parent

Medium-chain hydroxy acids and derivatives

Alternative Parents

Substituents

Medium-chain hydroxy acid
Medium-chain fatty acid
Hydroxy fatty acid
Straight chain fatty acid
Fatty acyl
Fatty acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

medium-chain fatty acid (CHEBI:17409 )
omega-hydroxy fatty acid (CHEBI:17409 )
Hydroxy fatty acids (C02774 )
Hydroxy fatty acids (LMFA01050033 )

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	2.38	ALOGPS
logP	2.15	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
pKa (Strongest Basic)	-2	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	9	ChemAxon
Refractivity	51.41 m³·mol⁻¹	ChemAxon
Polarizability	22.64 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

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

C02774

BioCyc ID

10-HYDROXYDECANOATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74300

PDB ID

Not Available

ChEBI ID

17409

Good Scents ID

Not Available

References

General References

Ichihara K, Yamakawa I, Kusunose E, Kusunose M: Fatty acid omega and (omega-1)-Hydroxylation in rabbit intestinal mucosa microsomes. J Biochem. 1979 Jul;86(1):139-46. [PubMed:113393 ]
Yamada J, Sakuma M, Suga T: Assay of fatty acid omega-hydroxylation using high-performance liquid chromatography with fluorescence labeling reagent, 3-bromomethyl-7-methoxy-1,4-benzoxazin-2-one (BrMB). Anal Biochem. 1991 Nov 15;199(1):132-6. doi: 10.1016/0003-2697(91)90280-7. [PubMed:1839651 ]
LOTUS database [Link]

Showing NP-Card for 10-hydroxydecanoic acid (NP0271968)

MOL for NP0271968 (10-hydroxydecanoic acid)

3D MOL for NP0271968 (10-hydroxydecanoic acid)

3D SDF for NP0271968 (10-hydroxydecanoic acid)

3D-SDF for NP0271968 (10-hydroxydecanoic acid)

PDB for NP0271968 (10-hydroxydecanoic acid)

3D PDB for NP0271968 (10-hydroxydecanoic acid)

SMILES for NP0271968 (10-hydroxydecanoic acid)

INCHI for NP0271968 (10-hydroxydecanoic acid)

Structure for NP0271968 (10-hydroxydecanoic acid)

3D Structure for NP0271968 (10-hydroxydecanoic acid)