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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:41 UTC

Update Date

2023-02-21 17:16:16 UTC

HMDB ID

HMDB0002207

Secondary Accession Numbers

HMDB02207

Metabolite Identification

Common Name

3-Hydroxyisoheptanoic acid

Description

3-Hydroxyisoheptanoic 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. 3-Hydroxyisoheptanoic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-hydroxyisoheptanoic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Hydroxyisoheptanoic acid.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Hydroxyisoheptanoate	Generator
3-Hydroxy-5-methylhexanoate	HMDB, Generator
3-Hydroxy-5-methylhexanoic acid	HMDB
3-Hydroxyisoheptanoic acid	MeSH

Chemical Formula

C₇H₁₄O₃

Average Molecular Weight

146.1843

Monoisotopic Molecular Weight

146.094294314

IUPAC Name

3-hydroxy-5-methylhexanoic acid

Traditional Name

3-hydroxyisoheptanoic acid

CAS Registry Number

40309-49-7

SMILES

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

InChI Identifier

InChI=1S/C7H14O3/c1-5(2)3-6(8)4-7(9)10/h5-6,8H,3-4H2,1-2H3,(H,9,10)

InChI Key

SCAWECGFPWPHAR-UHFFFAOYSA-N

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
Beta-hydroxy acid
Branched fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0002207)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	49 g/L	ALOGPS
logP	0.92	ALOGPS
logP	0.87	ChemAxon
logS	-0.47	ALOGPS
pKa (Strongest Acidic)	4.77	ChemAxon
pKa (Strongest Basic)	-2.8	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	4	ChemAxon
Refractivity	37.14 m³·mol⁻¹	ChemAxon
Polarizability	15.82 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	133.862	31661259
DarkChem	[M-H]-	128.777	31661259
DeepCCS	[M+H]+	136.441	30932474
DeepCCS	[M-H]-	133.438	30932474
DeepCCS	[M-2H]-	170.017	30932474
DeepCCS	[M+Na]+	145.251	30932474
AllCCS	[M+H]+	135.1	32859911
AllCCS	[M+H-H2O]+	131.1	32859911
AllCCS	[M+NH4]+	138.8	32859911
AllCCS	[M+Na]+	139.9	32859911
AllCCS	[M-H]-	133.7	32859911
AllCCS	[M+Na-2H]-	136.0	32859911
AllCCS	[M+HCOO]-	138.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.87 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3666 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.67 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	97.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1313.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	316.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	102.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	179.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	77.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	369.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	383.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	72.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	712.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	312.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1088.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	221.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	279.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	386.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	260.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	128.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyisoheptanoic acid	CC(C)CC(O)CC(O)=O	2398.3	Standard polar	33892256
3-Hydroxyisoheptanoic acid	CC(C)CC(O)CC(O)=O	1125.7	Standard non polar	33892256
3-Hydroxyisoheptanoic acid	CC(C)CC(O)CC(O)=O	1206.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyisoheptanoic acid,1TMS,isomer #1	CC(C)CC(CC(=O)O)O[Si](C)(C)C	1278.5	Semi standard non polar	33892256
3-Hydroxyisoheptanoic acid,1TMS,isomer #2	CC(C)CC(O)CC(=O)O[Si](C)(C)C	1265.4	Semi standard non polar	33892256
3-Hydroxyisoheptanoic acid,2TMS,isomer #1	CC(C)CC(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1337.1	Semi standard non polar	33892256
3-Hydroxyisoheptanoic acid,1TBDMS,isomer #1	CC(C)CC(CC(=O)O)O[Si](C)(C)C(C)(C)C	1506.7	Semi standard non polar	33892256
3-Hydroxyisoheptanoic acid,1TBDMS,isomer #2	CC(C)CC(O)CC(=O)O[Si](C)(C)C(C)(C)C	1498.9	Semi standard non polar	33892256
3-Hydroxyisoheptanoic acid,2TBDMS,isomer #1	CC(C)CC(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1767.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyisoheptanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-8c7785486d2967623f7f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyisoheptanoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00g3-9240000000-a93110d8dcfe7473668c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyisoheptanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 10V, Positive-QTOF	splash10-004i-0900000000-4f0f7b8be6306c19d284	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 20V, Positive-QTOF	splash10-06vi-8900000000-8e494c921862c1c9e4b4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 40V, Positive-QTOF	splash10-0a4i-9000000000-0d359b94f30656d44123	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 10V, Negative-QTOF	splash10-0002-1900000000-80487e4978cb411e9e90	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 20V, Negative-QTOF	splash10-0pdj-7900000000-7d31155a461e6459783e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 40V, Negative-QTOF	splash10-0a4i-9000000000-374bd8812777a5fcac69	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 10V, Positive-QTOF	splash10-015j-9200000000-9e20a8918c8904e28e63	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 20V, Positive-QTOF	splash10-0a4i-9000000000-bdcf82166c5593049c51	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 40V, Positive-QTOF	splash10-0536-9000000000-30891312129a2bd8cddb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 10V, Negative-QTOF	splash10-0002-4900000000-4285cef758491224a36a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 20V, Negative-QTOF	splash10-0a4i-9100000000-fb5953d0f4ec22f2d585	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyisoheptanoic acid 40V, Negative-QTOF	splash10-0006-9000000000-a36d488f6a6b1853e249	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022907

KNApSAcK ID

Not Available

Chemspider ID

168187

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6547

PubChem Compound

193804

PDB ID

Not Available

ChEBI ID

165406

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Annunziata, Rita; Cinquini, Mauro; Gilardi, Amilcare. Optically active 2-(arylsulfinylmethyl)-oxazolines, chiral enol acetate equivalents in aldol-type condensations. Synthesis (1983), (12), 1016-17.

Material Safety Data Sheet (MSDS)

Not Available

General References

Divry P, Vianey-Liaud C, Cotte J: Routine gas chromatographic/mass spectrometric analysis of urinary organic acids. Results over a three-year period. Biomed Environ Mass Spectrom. 1987 Nov;14(11):663-8. [PubMed:2962675 ]
Lehnert W: 3-Hydroxyisoheptanoic acid: a new metabolite in isovaleric acidemia. Clin Chim Acta. 1981 Jun 2;113(1):101-3. [PubMed:7237839 ]

Showing metabocard for 3-Hydroxyisoheptanoic acid (HMDB0002207)

MOL for HMDB0002207 (3-Hydroxyisoheptanoic acid)

3D MOL for HMDB0002207 (3-Hydroxyisoheptanoic acid)

3D SDF for HMDB0002207 (3-Hydroxyisoheptanoic acid)

3D-SDF for HMDB0002207 (3-Hydroxyisoheptanoic acid)

PDB for HMDB0002207 (3-Hydroxyisoheptanoic acid)

3D PDB for HMDB0002207 (3-Hydroxyisoheptanoic acid)

SMILES for HMDB0002207 (3-Hydroxyisoheptanoic acid)

INCHI for HMDB0002207 (3-Hydroxyisoheptanoic acid)

Structure for HMDB0002207 (3-Hydroxyisoheptanoic acid)

3D Structure for HMDB0002207 (3-Hydroxyisoheptanoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra