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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:24:17 UTC

Update Date

2022-03-07 03:17:45 UTC

HMDB ID

HMDB0060486

Secondary Accession Numbers

HMDB60486

Metabolite Identification

Common Name

Mandelonitrile

Description

Mandelonitrile belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Mandelonitrile is an extremely weak basic (essentially neutral) compound (based on its pKa). Mandelonitrile exists in all living organisms, ranging from bacteria to humans.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+)-Mandelonitrile	ChEBI
(R)-(+)-Mandelonitrile	ChEBI
D-Mandelonitrile	ChEBI
Benzaldehyde cyanohydrin	Kegg
(R)-Mandelonitrile	Kegg

Chemical Formula

C₈H₇NO

Average Molecular Weight

133.1473

Monoisotopic Molecular Weight

133.052763851

IUPAC Name

(2R)-2-hydroxy-2-phenylacetonitrile

Traditional Name

(-)-mandelonitrile

CAS Registry Number

Not Available

SMILES

O[C@@H](C#N)C1=CC=CC=C1

InChI Identifier

InChI=1S/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H/t8-/m0/s1

InChI Key

NNICRUQPODTGRU-QMMMGPOBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Alpha-hydroxynitrile
Secondary alcohol
Cyanohydrin
Nitrile
Carbonitrile
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

mandelonitrile (CHEBI:18450 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0060486)
extracellular (HMDB: HMDB0060486)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	MetCCS_train_pos	128.871	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.89 g/L	ALOGPS
logP	0.68	ALOGPS
logP	0.95	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	11.8	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	44.02 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.68 m³·mol⁻¹	ChemAxon
Polarizability	13.55 Å³	ChemAxon
Number of Rings	1	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]+	128.961	31661259
DarkChem	[M-H]-	125.646	31661259
DeepCCS	[M+H]+	128.901	30932474
DeepCCS	[M-H]-	126.098	30932474
DeepCCS	[M-2H]-	162.169	30932474
DeepCCS	[M+Na]+	137.308	30932474
AllCCS	[M+H]+	128.2	32859911
AllCCS	[M+H-H2O]+	123.5	32859911
AllCCS	[M+NH4]+	132.6	32859911
AllCCS	[M+Na]+	133.9	32859911
AllCCS	[M-H]-	125.4	32859911
AllCCS	[M+Na-2H]-	127.0	32859911
AllCCS	[M+HCOO]-	128.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mandelonitrile	O[C@@H](C#N)C1=CC=CC=C1	2163.3	Standard polar	33892256
Mandelonitrile	O[C@@H](C#N)C1=CC=CC=C1	1264.3	Standard non polar	33892256
Mandelonitrile	O[C@@H](C#N)C1=CC=CC=C1	1285.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mandelonitrile,1TMS,isomer #1	C[Si](C)(C)O[C@@H](C#N)C1=CC=CC=C1	1288.9	Semi standard non polar	33892256
Mandelonitrile,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H](C#N)C1=CC=CC=C1	1499.9	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 - Mandelonitrile GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aor-7900000000-63735c13ec334fa809ee	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mandelonitrile GC-MS (1 TMS) - 70eV, Positive	splash10-0100-7900000000-11427484bfb13fd6a7a9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mandelonitrile 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 - Mandelonitrile 10V, Positive-QTOF	splash10-001i-0900000000-8cf5145ba5004cd7bb81	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mandelonitrile 20V, Positive-QTOF	splash10-05o0-0900000000-5e06bfde5bdcc96f3896	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mandelonitrile 40V, Positive-QTOF	splash10-0mmj-9400000000-c916686bb130eeff008d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mandelonitrile 10V, Negative-QTOF	splash10-001i-0900000000-6297236be9bcd46fc863	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mandelonitrile 20V, Negative-QTOF	splash10-003r-4900000000-ed4bbee965e6623f6aa1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mandelonitrile 40V, Negative-QTOF	splash10-004i-9100000000-732942c55dfb450c7cdd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mandelonitrile 10V, Positive-QTOF	splash10-014i-0900000000-ff2f50a1cd0316c3889d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mandelonitrile 20V, Positive-QTOF	splash10-014i-2900000000-e7674fcadf80c742e74d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mandelonitrile 40V, Positive-QTOF	splash10-02t9-9200000000-ee74ae1e15bd8bae8852	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mandelonitrile 10V, Negative-QTOF	splash10-001i-4900000000-6f591a5616423a7c26c5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mandelonitrile 20V, Negative-QTOF	splash10-0059-9600000000-f4b4bc42937e4ce43fd6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mandelonitrile 40V, Negative-QTOF	splash10-0kdi-6900000000-95f96f3606696317faf9	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart 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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00561

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mandelonitrile

METLIN ID

Not Available

PubChem Compound

9548674

PDB ID

Not Available

ChEBI ID

18450

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Cytosolic beta-glucosidase

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
Gene Name:: GBA3
Uniprot ID:: Q9H227
Molecular weight:: Not Available

Reactions

Prunasin + Water → Mandelonitrile + D-Glucose	details

Showing metabocard for Mandelonitrile (HMDB0060486)

MOL for HMDB0060486 (Mandelonitrile)

3D MOL for HMDB0060486 (Mandelonitrile)

3D SDF for HMDB0060486 (Mandelonitrile)

3D-SDF for HMDB0060486 (Mandelonitrile)

PDB for HMDB0060486 (Mandelonitrile)

3D PDB for HMDB0060486 (Mandelonitrile)

SMILES for HMDB0060486 (Mandelonitrile)

INCHI for HMDB0060486 (Mandelonitrile)

Structure for HMDB0060486 (Mandelonitrile)

3D Structure for HMDB0060486 (Mandelonitrile)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions